is it crazy to quit my job to go freelance in 2021?

It’s the Thursday “ask the readers” question. A reader writes:

I am considering leaving my job to build my own business as a freelancer (copywriting / digital content marketing). I’m not ready to quit just yet, but I plan to start building up my savings account and take on more side projects and sign up for a business coaching class offered by a great freelancer I know. I used to think I didn’t have the discipline or the drive to work for myself, but my confidence is growing and I’m starting to think I’ve underestimated myself, especially when I compare my work output and experience to the freelancers and contractors that my company hires.

I also used to be scared by the insecurity of working for myself but, well, I’m 29 and I’ve been through two layoffs (both companies were bought out; one was amazing to work for, one was a nightmare) and am now working for a third company that looked awesome from the outside but has dubious long-term prospects and a terrible management culture. I’ve done the 9-5 thing, and it has not brought me stability. In fact, it has given me anxiety, and ten years ago I never thought I’d be an anxious person.

I’d love advice and stories from readers who have quit their jobs to become freelancers, especially within the last year or so! Is it working out? Did you try it and decide it actually wasn’t for you? What should I know before I take the leap? Am I crazy for thinking that working for myself is my best shot at finally having a stable career?

Readers, what’s your advice?

{ 184 comments… read them below }

  1. Detective Amy Santiago*

    I think the most important thing you need to do before you pull the trigger is build your network. Word of mouth is going to get you much more bang for your back in terms of advertising your services than any other sort of marketing. If you don’t have a solid network of potential clients, it’s going to be far more difficult to be successful.

    1. Web of Pies*

      You can also reach out to clients you work with at your current job after you leave to let them know you’re available (emphasis on AFTER though!). Just make sure to check the contract you’re currently under at your job to see what the noncompetes are…usually they end after a year and you’re free to reach out to clients. I’ve had several reach out to me directly (presumably after they reached out to my old job and found I wasn’t there anymore) and that’s fun because we already have a working relationship.

      1. mediamaven*

        Yeah I would not do that. It’s probably against the contract but it’s also really unethical. Trust me you don’t want to burn bridges with a past working relationship. If they reach out to you that’s one thing, but pursuing them is a really bad look.

        1. merula*

          I strongly disagree! There are so many people without employment contracts that it’s really hard to believe “it’s probably against the contract”, much less that potential clients would presume to know what may or may not be in a contract that may or may not exist.

        2. Web of Pies*

          I actually wrote into AAM about this years ago, and she didn’t have an issue with it! As long as you’re following what’s agreed in the contract it’s not unethical. I don’t think letting a year pass and then emailing a client “hey, FYI I’m available for work if you need!” is going to burn a bridge at all…esp since OP sounds like they want to be an individual freelancer, not start a company where this could be considered poaching.

          1. mediamaven*

            Perhaps unethical isn’t the right word choice. Perhaps it’s ethical but still not a great thing to do. I made a decision similar to this years ago – it wasn’t unethical per se, and I still don’t think I was necessarily in the wrong – but I burned a bridge with my previous employer that burned for a long long time. You really need to decide if that’s ok with you or not.

            1. Web of Pies*

              @mediamaven I’m sorry that happened to you! I think CJ below is right, it’s probably industry- or even company-specific. Some companies are really dramatic about their clients (I’ve worked for a few like that) so that even if you’re acting fully within what you both contractually agreed to, they get into a snit.

              I’m freelancing in a similar field to the LW and haven’t had any trouble with this personally, LW will just have to assess how their employer might react.

          2. Nanani*

            This is vital. A lot of people don’t seem to understand the distinction between a self-employed freelancer and starting your own rival business. Not the same at all!
            (There may be fields where one doesn’t exist and people conflate them colloquially all the time – this isn’t about nitpicking language but to point out that the distinction is real in a lot of fields)

        3. Cj*

          I think it depends on what industry you are in. I’m a CPA, and it is against our ethics rules to do this, even if your non-compete has expired. It’s OK if they reach out to you, though.

        4. I'm just here for the cats*

          I don’t know if this applies to the LW. She says that she is copywriting and digital marketing. I know lots of people who do that just for their company, and don’t have any outside clients.

          For example, a professional development and licensure school I worked for had a marketing team and they did digital marketing just for themselves. They also had copywriters for their print materials. It was just in house.

          If nothing she could see if the company would be willing to give her some freelance work, if that’s something they do.

  2. Web of Pies*

    I say do it! I’ve been freelancing for several years and it’s great. There are lots and lots of freelance agencies you can join if you want to ease into it, the pay rates aren’t as high as you’d get on your own, but if you’re worried about finding work it’s a great supplementary option. Be prepared to not make a ton your first year as you build up a client base and reputation. It’s good practice for saving anyway, since freelance work can be variable. Learn about the taxes (1099 freelancers pay 2x taxes as compared to W2 workers) and save for that accordingly throughout the year.

    One thing that really helped me was picking an annual earnings goal and then dividing by 365 to see how much money I needed to make per day to make the goal. It both helps me stay on track when I feel like slacking, and also allows me to take a break in times when I can see missing a few days of income won’t mess me up.

    1. Reeny*

      I agree with signing up with agencies to help ease in or cover some gaps. There are several creative agencies that specialize in writers, editors, and designers that usually have good relationships with companies who need these types of creatives on the regular. Good luck!

      1. Web of Pies*

        One note on freelance agencies, you might have to join a few. I joined five: two gave me no work ever, one gave me a year of OK work, another gave me OK work but was predatory with their fees (charged a service fee + withheld extra taxes illegally) and one sends tons of work, and it’s a lot like working at a regular agency job. Shop around!

        1. Nanani*

          Oh yes, tax withholding!
          If you have clients in a different country this gets very complicated very fast so do your research ahead of time!

    2. Director of Alpaca Exams*

      A helpful thing for taxes is to take half of every check you get and put it into an account that you DO NOT TOUCH except to pay your quarterly (quarterly! not annual!) taxes. Your effective tax rate may not actually end up being 50%, depending on your expenses and such, but it’s unlikely to be more than 50%, and dividing every payment in half requires very little thought, so it’s an easy habit to get into and a good way to make sure you’re saving at least as much as you need for the state and the IRS.

    3. RabidChild*

      Having an earnings goal is key! I like knowing that I need to work X hours per day to cover expenses, and the rest is profit. Knowing what that is should be linked to actual expenses, so take the time to go through what you spend in a given year on everything–rent/mortgage, clothes, health insurance (a BIG expense these days for Americans), utilities, car, etc. Include any savings you want to incorporate like IRAs for retirement, too. Add it up and you’ll know the minimum you need to earn–and don’t forget taxes (which are a factor of how much you make so it can be difficult to factor in–I use 30% of earnings as a benchmark but that’s in PA).

      Don’t forget that certain expenses become deductible like subscriptions to magazines and memberships relevant to your field, books, office and computer equipment, conferences, mileage to and from client meetings, etc.

  3. So not getting paid*

    No. I have a lot of friends that have done this with success in the past few months. I’m really thinking about it myself.

  4. Kiki*

    I’m in your same boat. I used to freelance, then got a job when I moved, now I want to go back to freelance.
    My advice:
    -take lots of trainings during work hours if you can
    -remember that work you did for your employer is still work you did, so when you describe yourself on your website, don’t say “worked in x field x years” but also list some of those accomplishments/skills closer to how you would if the buys had been your own direct clients. Not lying, but just owning what you did. I feel like freelancers sometimes forget that.
    -If you have any 401k you could consider pulling it, but get tax advice. ie maybe do it in 2022 if you have earned income this year. My friends who opened businesses like shops got business loans. When we do a sole proprietorship we don’t start with a loan. But you need a base amount of working funds.
    -maybe take a part time job. I’m considering working just Saturdays at a salon (my old industry). When I’m freelancing, that would give me maybe $200/week guaranteed money. Also I could quit if I needed to.
    -If you switch to working from home you will probably save money. when i work for myself i make less sometimes, but i cook more, have extra time to shop cheaper, etc
    I do lots of side stuff when I work for myself, like $100 focus groups or product testing, etc

    good luck! as soon as I figure out health insurance I’m joining you!

    1. Carol the happy elf*

      Remember that anything you do while employed at XYZ Llama grooming might actually be owned by XYZ.
      It really stinks, but a friend did a massive project on his own, during his sabbatical year, and found that his university got hold of it, copyrighted the papers, and even got a patent on a procedure. Because he was an employee during the year, they paid him a bonus of $20,000 and used his work for years.
      Now, he knows to have any employment contracts looked over by his lawyer, and has the company rep sign a release for his own work, not done with company time, products, employees, ….Some companies don’t use contracts; that would bind THEM, but they have you sign for the handbook with the caveat that this will apply to any and all future revisions and updates.

      Basically, make sure Rumplestiltskin doesn’t already have adoption paperwork for your unborn baby!

      1. Jessica*

        I think in this case Kiki meant “own what you did as an employee” in the sense of “take pride in it and describe what you accomplished.” Obviously ownership of any projects you completed might rest with the company, but nobody else can “own” the skills that you developed or the accomplishments you achieved while working there.

        1. AcademiaNut*

          Also, if you’re employed at a university in a research or research adjacent position, there may not be a valid work model for being paid to do other projects by a third party while still employed by (and that the patents belong to the university, not you). This is a pretty common setup – there’s similar language in my contract.

  5. mediamaven*

    I left a toxic job about 14 years ago to freelance. I really just wanted a break as I was really burnt out.

    Fast forward my freelance gig is now a multi million dollar company with 20 employees. So I have some perspective.

    The hardest part about being on your own is ensuring that you have a constant stream of business coming in and you get that by having great relationships and connections. Do you have those things? In my opinion you should also be making more money than you did when you worked for someone so make sure your pricing makes sense – accessible for small companies but not so low that people think you aren’t worth it. You are at the perfect age to freelance because you are likely still “in the weeds” with your work but have enough leadership experience that you can speak high level (without knowing your industry). I see very junior people trying it and they can’t make it work because they don’t have a deep enough understanding of the workings of a business beyond tactical execution. I see people with 20 years of experience trying to do it but unable to make it work because they’ve been leading for so long and not serving as producers.

    Make a website and think of a name as quick as possible because you’ll need that to create your business. Also, my big word of advice is to set up a separate bank account for your business! Please do this – you will thank me later! And good job creating a savings – that’s critical. Good luck!

    1. Delta Delta*

      Separate bank account is good advice. I commented down thread, but after reading your comment thought I’d also add that it really helps to create an LLC and keep all the business stuff under the LLC so there’s no commingling and it’s truly separate.

      1. Director of Alpaca Exams*

        At the very least, get a credit card that you use only for business expenses, so you can easily separate them out when it’s filing time.

    2. Nanani*

      You… don’t need a name and a website to be a freelancer. You really don’t.
      You -can- and there may be fields where that’s the norm, but you can be a freelancer taking contract work without starting a business in the legal or financial sense, and you don’t need to Advertise in the broad sense.

      No shade on mediamaven, that business sounds amazing! But many freelancers are not going to start a company because those aren’t the same thing and don’t have to be connected.

      1. mediamaven*

        I disagree just because it helps to have something to point prospective clients too and to house your capabilities especially in LWs line of work. You can even call it Letter Writer Consulting LLC if you want. But it sounds a bit more established and can help pave the way for larger contracts.

      2. RR*

        From the perspective of someone who has to approve the hiring of freelancers: the more you can show you are truly an independent business, the easier it is for us to contract with you. Because my organization has full time staff on hand who do the exact same work as what we also sometimes contract out for, we need to be careful to document that it is not an employee/employer relationship. If you have an LLC (or similar separately incorporated business), your own email domain, your own website, that’s a clearer distinction.

      3. Marcella*

        This probably is industry specific, but I would never hire a freelance creative who didn’t have a website. Especially a freelance writer. I’m sure there are wonderful freelancers without them, but I need to see some investment and a sense of digital skill. If someone can’t be bothered to pay for a domain, put up a basic Squarespace site, and write some copy selling their ability to write copy – that tells me everything.

        1. Splendid Colors*

          Exactly. There are so many free or low cost “build your own website” things these days that there isn’t really an excuse NOT to have one. They have templates and all you need to do is pick one, maybe change out the stock photos, and replace the placeholder text. It doesn’t even cost that much to have your own domain name.

  6. Glomarization, Esq.*

    Before you take the leap, draw up a business plan and a marketing strategy. There’s no real way to tell whether it’s ever a good time to start a business, whether in 2021 or whenever, if you haven’t put the realities down on paper and analyzed them.

    1. Freelance Freetime*

      My personal rule was that I had to start job-searching if I didn’t hit certain metrics in my business plan. In the beginning they were very flexible low-bar metrics, like I had to find paying work every month, but over time they had to ramp up if I was going to consider freelancing a real career equal to my prior job. Putting some rails like this around your goals may help OP.

    2. Nanani*

      Freelancing and starting a business aren’t really the same thing.
      You can be a contractor for other companies and not a “business” in any meaningful sense. You don’t need to be a legally distinct entity. You might decide to go that way, but it’s not automatic in every line of work.

      1. Glomarization, Esq.*

        You’re right. Many people do freelance work without formally starting and running a business. They leave themselves open to more possibilities of legal liability problems than people who don’t do their work through a legal business entity. And without a business plan or some other kind of roadmap that defines and tracks what success means to them, they miss a lot of valuable information about their accomplishments and what they might expect in the future. But there are as many paths to financial and professional success as there are individuals who choose to freelance.

        1. Nanani*

          See to me this sounds like at best, a sales pitch for something I don’t need. Or maybe like those writing advice people who insist that outlines are the only valid way to write even though a lot of writers don’t outline much or at all.

          LW and any other people thinking about freelancing, please don’t be scared off by anyone insisting you need X Y or Z (unless they are an authority on your jurisdiction’s taxes)

          1. Splendid Colors*

            I have run into people claiming you must have an LLC or incorporate to be a legitimate business, or that it will protect you from lawsuits. Neither of those are correct, according to actual lawyers teaching small business classes: Sole proprietorship is perfectly legitimate for a freelancer. And having an LLC may keep you from losing your house or personal assets if you’re sued, but you still have to pay lawyers.

            However, if you have business insurance, THAT will pay any claims against you so you don’t have to go to court. (And a colleague of mine lost his business to identity theft, so he highly recommends paying about $100 a year for a cybersecurity insurance rider.) You probably want to make sure your computers etc. are covered by homeowner’s or renter’s insurance, or insure them with business property insurance, in case of disaster. (A classmate of mine in Paradise, CA lost all her illustration business property in the wildfire and had NO insurance because she was a renter and it wasn’t required. It’s like $12/mo.)

            I have had my own business for nearly a decade, and am still a sole proprietorship because I don’t need to spend $800 on LLC annual fees or muck around with a board that might have bad ideas about products and marketing.

            If you want to have a business name that doesn’t include your last name, you can file a fictitious business name statement with your county–and then you can use that name on your business bank account. But it’s more important to have a separate account for business purposes even if it has your name on it. You don’t need to have an official fictitious business name filed to buy the domain name. You don’t have to trademark your business name unless you think your company will be big enough people would make problems.

            Right now during the pandemic, there is a VERY good chance you can get a free (subsidized) online class to develop a business plan. I am almost finished with one from Renaissance Entrepreneurship Center in the SF Bay Area (need to finish the actual business plan but the class meetings are finished). Check with the SBDC in your area to find out what local groups support new entrepreneurs–whether that means a business plan class or just helping you make sure you meet any local requirements for business “licenses” or home offices, etc. (My city is very persnickety that the annual fees are a business TAX, not a “license to do business.” Whatever. I still fall under the “small enough to be exempt” threshold.)

            But for a freelancer working from home with minimal overhead, no employees, no inventory, probably no plans to convince a lender they’re a good risk–a business plan is a lot less necessary than it would be for a restaurant, a retailer, or a construction company.

      2. RabidChild*

        Agreed. My accountant didn’t think it was necessary for me to have an LLC as a freelancer, though ymmv. I do marketing strategy as well as content writing, similar to OP, and there’s not a lot of overhead other than computer equipment.

        1. banoffee pie*

          Yeah here in the UK you can just register as a sole trader and as long as you pay your taxes you’re ok. You don’t have to start a company (unless you earn over a certain amount of money but it’s quite a lot, you probably wouldn’t have to worry about that for a year or two)

  7. Chc34*

    So I kind of almost did this: long story short, I left my industry to go to (unrelated) grad school but kept freelancing for my old job on the side, then last summer I didn’t get paid as a grad student and also, for obvious reasons, had no social life, so I took on a ton more freelance work and realized it was actually feasible I could do it full time. I dropped out of grad school with that plan, but ended up accepting a remote position in my old industry in the spring. So I can tell you both about what was appealing about it and why I ultimately didn’t end up staying with it.

    1) First, build up enough savings so that if you realize early on that it’s not going to work for you, you have a cushion while you try to find another full-time job (this will depend on your industry and how easily you think you can do this). At the beginning of the year, I decided that I was going to give it until December to see if it worked, and if it didn’t, I would start looking for jobs seriously in January.

    2) The flexibility is both a blessing and a curse. Yes, you can go to the gym/run errands/hang out with friends whenever you want! Hooray! But also . . . you can work whenever you want and there was no time I didn’t feel like I should be working. I found it very, very difficult to set actual boundaries around my work time and constantly took on too much work because it’s a lot scarier to turn down money when your freelance work is your only source of income.

    3) Unfortunatley this jump is a lot easier for people who have, say, a spouse whose health insurance they can go on, because health insurance costs can be REAL depending on what your state offers. When I was looking at plans, I could get one for pretty cheap, but also they came with like $9000 deductibles. So definitely look into how much that will cost you and factor it into your decision.

    4) You’ll have to set aside money for taxes, so calculate those costs as well: I personally take my tax estimate out of every single freelance paycheck I get and put it into a separate savings account so I don’t ever think of that money as mine.

    I took the full-time job that was offered to me because 1) it offered me more money than I thought I could reasonably make freelancing and 2) going back to having benefits, like health insurance and a 401K. But what was nice is that I was only sending in the occassional application for jobs that really interested me, and I had a specific salary in my head for what it would take for me to give up the flexibility of freelancing. And even now, I know that in the back of my head, if I ever decide I want to leave my job, I can probably go back to it.

    I’ll reply with more things if I think of them!

    1. Shira*

      So much good advice here! “…constantly took on too much work because it’s a lot scarier to turn down money when your freelance work is your only source of income.” – This was my experience too. There’s a special kind of difficulty in setting work boundaries when you are your own boss.

    2. Letter Writer*

      Thank you! This is so helpful. I am engaged, and it has definitely crossed my mind I would not be able to leave my job before we get married and I can move to my fiancee’s insurance.

      I also worry about the not setting boundaries around work thing and not actually taking advantage of the flexibility! When I was laid off a few years ago, I felt extremely guilty if I wasn’t constantly job searching or working on freelance projects, even when there were literally no more jobs to apply for.

      1. Chc34*

        Setting boundaries on my time was DEFINITELY the hardest part for me. One thing that helped: I would generally calculate out based on my workload about how much work I needed to get done every day to stay on track for all my deadlines and then would use that to try to estimate whether I had the room to take on more work. When I did those calculations, I specifically did NOT include weekends as available days to work on things. That helped me not feel guilty when I went out and did things on weekends, since I hadn’t planned for any work to get done that day anyway, and it also meant that if I ended up with downtime on weekends and did some work anyway, it was like I was working “bonus” hours that would decrease my workload for the next week.

      2. Nicotena*

        If you are your fiance want to buy a house together in the next few years, this is also something to keep in mind.

      1. Carol the happy elf*

        Yes, but. Even with a part time job, read the employee “Handbook”, which is sometimes more like ancient indenture papers than a contract. They might sneak in wording that even though you are a part-time Turtle Painter (don’t ever do that, btw) with them, they have ownership of your off time side business of Elephant Toenail Design.
        This is a particular bugbear of mine, because someone who taught one subject had his work taken, even thouth it was on something completely different. The university still holds the rights to it, and until it became outdated, they made a LOT of money.

        1. Green Beans*

          Working for a university is really different than most positions, especially if you’re in a (I’m guessing research) position where you can get a university-supported sabbatical. Your friend should have known the intellectual rights agreement he had with the university – this is not unusual or uncommon in academic research, and it only takes an email to start the process to negotiate a favorable outcome once you have something that involves IP rights.

          1. Green Beans*

            (and if he was faculty, this was very much covered in his negotiation process before he signed his contract.)

          2. Gan Ainm*

            Yes and part time in a university is nothing like part time in retail, or similar, which is likely what the commenter was recommending – something you can apply to and start almost with no prep, learn quickly, with set hours (ie you can say max 16 hours per week, or max 2 shifts per week, etc), and no take-home responsibility (you do your cashiering or whatever and you go home and it doesn’t take up any space in your brain the rest of the week which frees you up for freelance), and something you can quit down the road easily without burning bridges, just to have a little steady income
            to fall back on and cushion the transition, and maybe give a little structure to the week. Added current benefit is that everyone is dying for employees in customer service sector del wages are going slightly up, and it will be easy to get something quickly if you want it.

    1. Nanani*

      Yes! Depends on your type of work of course, but you can definitely have a part-time job for someone else and work on your freelance stuff at the same time.

      Taxes will be complicated though. Watch for that. Set more of your income aside than you expect to need for taxes Just In Case.

  8. Delta Delta*

    I’m not a freelancer, exactly, but I can offer some thoughts. I am a lawyer who went from working in a firm to working solo (so, it’s sort of like being a freelance lawyer, I guess). I had some savings so I was able to have a cushion for a while while working on creating the business. Here are some things I can offer:

    1. Make sure you have a plan for how you’ll pay yourself and how you’ll keep money in reserves for taxes. Depending on your state, you may need to pay taxes quarterly or monthly. I’m friendly with a guy who started a small business in CT and has to pay his taxes monthly and he really likes that since it keeps him on-budget.

    1a. Make sure you also have a very good plan for how you’ll keep all your expenses and asset values organized so that when you do your taxes in April it’s not a nightmare.

    2. If you work for yourself, you obviously get to set your own hours/work schedule. This is great, since you’re able to work when you are most effective. It also gives you flexibility to do things during regular business hours. On the other hand, you may find that you work more or that you continue to work a regular 9-5 schedule. You may find your anxiety is less, though, since you’re in control of the workflow and schedule.

    2a. You may find you have more business than you can handle! This may or may not be a good thing.

    3. If you find you don’t love working on your own you can always a) team up with someone else and form a company together or b) go back to being an employee in a structured job setting. That’s also okay, especially if you can bring a book of business with you.

    Good Luck!

    1. World's Most Common Initials*

      I am also a lawyer who went solo from 2020 into 2021. I agree with all of this excellent advice about being aware of taxation issues from the start. I, unfortunately, left a government job without a book of business or needed certifications for certain appointment work, so had some very fallow months early on.

      One thing I will add is to be very careful about letting your self-perception and fear of failure drive you to take on unreasonable workloads. I did this and ended up way more anxious as a result. I am now working on being mindful of not biting off more than I can reasonably chew.

  9. Caroline Bowman*

    I am a freelancer and have been for many years, wrong continent also, so probably no direct comparisons, except to say that, depending on your particular skills and qualifications, you can earn a substantial amount more as a contractor *when you’ve got work*. Obviously that’s always the catch and only you know what sort of genuine safety net you have or could readily mobilise. I have a partner with a steady (decent, moderate) salary and we have 3 dependents, so before I went freelance, I made sure we had 4 months of my usual contribution to our expenses if we changed nothing in our spending, more like 5 if we cut back. As it turned out, it all went brilliantly and from month 2 I was earning noticeably more (taking into account all the usual tax and so on) than before, with far more flexibility and balance. Medical aid, which is also a thing in the US, or so I understand, is via my partner, so that remained unchanged, and of course is a serious thing to consider and to account for. HOWEVER. It totally can be done, and done brilliantly. It just takes careful planning, not rushing and possibly a few months of seriously long hours while you try and spend more time on your side hustles while maintaining your day job.

    So my basic, long-winded advice is; get a very decent pot of savings first, and a game plan that you will follow if things don’t seem to be working out OR are simply taking just that bit longer to do so.

    Best of luck!

  10. ThatGirl*

    I am in a similar line of work, but have decided I do not have the stomach for permanent freelance. So I will share why I decided against it; if these are not things that bother you, then that may be a sign you should go for it!

    – Quite honestly the hustle of building a client base sounds exhausting to me
    – I don’t want to have to figure out my own taxes, worry about my own health insurance or worry about whether I can afford to take time off
    – I like having coworkers who I can commiserate with and share a workload with and a manager who’s got my back
    – I like having a company behind me who gets to worry about logistics, office space, equipment, HR-related things, etc.
    – I like knowing I can turn my laptop off or leave the office and be done with work for the day

    I do know a few people who’ve built their own companies. They wanted flexibility, they didn’t mind handling the logistics of things like taxes and LLCs and had good relationships with people who wanted their services, so it wasn’t as big a challenge to build a client base.

    But here’s a big thing to remember: One of them went back to working for a company after a little while; that’s *always* an option, you’re not locked into freelancing permanently forever if you decide you hate it. You can try it for six months or a year, if your finances permit, and if you love it, great! If not, there are plenty of ways to talk about that experiment without it being a negative.

    1. NYWeasel*

      I was coming into the comments to post about how there are personality/working style factors that feed directly into whether someone feels empowered as a freelancer or if they feel overwhelmed. I’m in the latter camp, but knowing that about myself takes away the regret of not trying to go solo, and lets me enjoy the benefits of my corporate position. For people who are more in the former camp, freelancing can be quite rewarding.

      1. ThatGirl*

        Totally agree, I think personality has a lot to do with it. I’ve never had a problem with stopping work at the end of the day either; if I was solely responsible for chasing down clients and income I’d probably either get lazy or overwhelmed fast.

    2. mediamaven*

      This is all good feedback. I think a lot of people decide to freelance because they think it’s less work. It’s not. It can actually be more work – just different – and you need a heck of a lot of discipline.

      1. WellRed*

        I agree with this and that girl’s comments are on the money for me. No way do I want to hustle my services. I’m a writer not a sales person.

      2. Nanani*

        Discipline and introspection. Figure out what your best working hours are and how that fits into any real-time connection with other people you need to do. You don’t have to replicate the 9-5 in your home office!
        If starting at noon works better for you, or being entirely nocturnal, or whatever, then you can do that.

        You are the only person making sure the work gets done though.

    3. LilyP*

      The “manager who’s got my back” part is also worth really thinking about — as a freelancer you don’t get any of the benefits of a good boss, like someone to be a sounding board for tricky problems, cherry-pick good stretch assignments for you, give you constructive feedback that helps you grow your skills, etc. I think you’d have to take the initiative to find some good mentors and drive your own professional development if you don’t want your skills to stagnate.

  11. A Simple Narwhal*

    I’m interested to hear the responses on this one! I don’t know if I’d ever fully quit my fulltime job, but I’ve considered monetizing a side project and have a lot of similar concerns.

  12. Ali G*

    If you haven’t already, talk to a tax accountant about setting up your LLC (or whatever business unit you will do) and all the steps involved. Many states require you to pre-pay taxes or pay quarterly, since you are doing it yourself. There are lots of weird rules that vary widely so you want to make sure you do it right from the start.

      1. May Flowers*

        Agreed! I came here to say just this. I am someone who made the jump from full-time work to freelance. I quit my job in November 2020 and “opened up shop” in January 2021. Setting up an LLC was the first thing I did, and that’s really helpful when completing all the tax forms needed when working freelance. I’m actually in a similar industry to you (I’m a content writer and editor). I didn’t go through the trouble of setting up my own business, other than setting up an LLC and naming it. I also didn’t set up my own website, or, not yet anyway.

        So far, I have had more than enough work through my network of previous jobs/colleagues and through people finding me on LinkedIn. I’ve actually been turning down work (turned down an offer yesterday). I found that as soon as I told my network that I was hanging out my own shingle, the offers for work started trickling, then pouring in.

        I agree with some of the others that it is key to have your finances figured out before you make the leap. I’m married, and my husband works full-time, so I am on his insurance. Prior to me quitting, we had been living on just one person’s salary for a few years and saving the other person’s salary, so we knew we could live on one income if I struggled with freelancing, and we knew we had a financial buffer as well. Depending on your own financial situation, here are some baselines you could establish for yourself:

        1. It is okay to go x months before you find your first freelance gig
        2. It is okay to earn $xxx for the next x months to determine if the plan is viable
        3. While waiting for the freelance work, trim the budget for various recurring expenses to $$ to keep your buffer
        2. You need to make $xxx (per month/year) to make this work for you

        Good luck with whatever decision you make!

    1. no LLC*

      Also not every one will need an LLC. I have freelanced for years without one. My CPA does not object.

      1. Nanani*

        Ditto. Depends on your field and your actual objective. Freelancing. Is not. Starting a Company.

      2. Splendid Colors*

        The FIRST thing they told us in the Start Smart classes was that YOU DO NOT NEED AN LLC TO START A BUSINESS. Of course someone had already paid a bunch of money to some scam artist offering to set up an out-of-state LLC that didn’t even sound legit…

  13. Cambridge Comma*

    Everyone told me that it would take two years to have a full schedule as a freelancer without investing huge amounts of time seeking work.
    I thought it would be less for me since I had 20 years’ experience and lots of contacts.
    It was fine but I had several months without work here and there (you need savings).
    At the two year point there was a definite gear change. Now I have a full schedule without doing anything.

    1. Lizzo*

      Agree, and I think when this change happens also depends on who you take on as clients early on.

      Example: I have one client who is a nonprofit, and so can’t pay me quite as much as my other clients, but the work is consistent and frequent! (And also interesting and fun.) They are also a great source of referrals.

  14. Marcella*

    Expect a rough few years where you feel like you work more for less money than before. It takes a while to get your rates where it’s a lucrative business.

    Make sure you’re excellent at setting boundaries and talking about money. You’ll do both repeatedly and need to advocate for yourself in a way that is firm and diplomatic.

    Be aware you may have limited visibility into client companies’ financial status. Sudden budget cuts can take you by surprise so don’t get too dependent on one client. To that end, put cut clauses in your contracts whenever possible.

    Finally – join a group for other freelancers in your market. It’s so helpful to bounce rates and expectations off each other and vent about clients.

    1. Shira*

      “Make sure you’re excellent at setting boundaries and talking about money. You’ll do both repeatedly and need to advocate for yourself in a way that is firm and diplomatic.”

      Second this. If you’ve only ever worked as an employee there will almost certainly be a learning curve, but I definitely improved at this over the years!

      1. Lizzo*

        Yes, being able to talk about money without it being uncomfortable is a must! Be fair to the client, but also be fair to yourself and the value of what you bring to the table!

  15. Lurking Tom*

    The one lesson I learned from owning my own business is that health insurance is REALLY expensive. To get on a plan that had the coverage we needed, we paid the same per month for health insurance as we did for our mortgage, to the tune of over $20,000 per year (mind you, this is JUST the premiums, we still had deductibles, copays, etc. to actually USE the insurance). It was a real eye-opener going from having an income and a mortgage to having basically no income at the start and having mortgage*2.

    1. Freelance Freetime*

      Wow, that *is* high. The first year I was freelancing I qualified for a super inexpensive plan – mind you, it was very bare bones and just me. I think this varies widely by state and if you qualify for any subsidies. At least if you’re self employed a portion of the insurance is a write-off.

    2. Ask a Manager* Post author

      I have a health insurance tip for any freelancers living in Virginia. Virginia has a law that if you’re a sole proprietor, you can be considered a one-person business and buy an employer plan (rather than a marketplace plan) and that gets you lower prices than the marketplace plans.

      I think a few other states have this but not many. I had to go through an insurance broker to do this but it was well worth it and saved me a lot of money.

  16. LuckySophia*

    I’ve been “on my own” as a B2B marketing communications writer for many, many years. Best advice I can offer is: at the outset, work your hardest to develop mutually respectful and beneficial (and long-term) business relationships with a few key clients that you genuinely like/enjoy working with. I did that, and found that those clients then enthusiastically recommended me to their colleagues…rinse and repeat. Some of those happy clients changed jobs, and then hired me to do work for their new employers. My business grew organically, mostly through word-of-mouth client referrals. During the pandemic, client budgets were cut…but a couple of “global initiatives” survived the cuts, and I was the person they chose to work on those, because multiple people on those global teams already had solid working relationships with me. So I had my busiest year ever in 2020, and this year is turning out the same.

    As a side note: Some of the best working relationships I’ve ever had were with clients others perceived as “difficult” or “demanding.” But if those clients were smart, and experienced/capable in their field, and demanded as much excellence of themselves as they did of me…we got along swimmingly, and those were some of the most loyal clients I ever had. Conversely…there will always be some client(s) you just don’t “jell” with, or can’t communicate effectively with, for whatever reason….or your “style of working” doesn’t mesh with theirs. If you do a few projects with someone like that, tactfully refer them to someone else and run for the door. Their money will never equal the cost (in creative pain and mental anguish) of trying to sustain a long-term working relationship with people like that. You suffer, the projects suffer, and the clients are never actually satisfied.

    I wish you all the best and firmly believe that you can have a reasonably stable career working on your own.

    1. Letter Writer*

      Thank you, especially for the advice of saying no to clients you do “jell” with! If only I could do that with some of my internal “clients” at my job now.

      1. Splendid Colors*

        Also, I found out the hard way that the clients who try to talk down your rates or your time estimates also end up being difficult to deal with. They will push your boundaries about everything else on the project: they’ll negotiate a low rate, THEN by-the-way want a rush timeline without rush charges, and not stick to the timeline for submitting information or approving drafts. And they’ll keep asking for more rounds of changes that are clearly them changing their minds.

        If you can afford to not get the gig (which is a big IF in the beginning) stand firm with prices and time estimates. If you have other projects running in parallel, be forewarned that they’re likely to screw up your timelines for your other clients’ projects.

  17. Violinrunner*

    Freelance violinist here! I am in a slightly different position because I have always been a freelancer. But I did relocate to a new city last month, which puts me in sort of the same boat. It sounds like you’re doing pretty much what I did to make it work! I decided to move a year ago and spent the last year laying groundwork. Due to so much work becoming remote, I was able to start teaching music lessons in my new city as well as my old city last winter, and build up connections that way. I also have a sister in my new city who is a fabulous connection to have in my field.

    One thing I am just learning myself is, don’t turn down work because you don’t think you’re good enough to do it! Chances are you’re more equipped than you think and as long as you’re willing to work hard and learn you’ll be fine! And don’t be afraid to take on work that isn’t quite what you thought you signed up for! My job in my new city looks a lot different than my job in my old city. But it’s still music work, and still very fulfilling and worthwhile!

    And do ask around. If you have any contacts at all in the field you want to freelance in, talk to them, let them know you’re looking for work, and they might be willing to pass on gigs that they can’t take or don’t want. I definitely know people who will disagree with this, but I will take any gig once, even if it looks terrible/doesn’t pay well/isn’t good quality. The point is to get your name out there and let people know you exist. You can always decline to take any more work from that entity if you decide it’s not worthwhile.

    Good luck! It’s scary making a big change like this, but totally worth it!

    1. Clarinerd*

      Another musician here! I love your point about don’t undersell your abilities. And online teaching definitely has opened up possibilities.

      I’m getting ready to leave my part-time, non-music job that I’ve had for almost 20 years to fully dive into music. It’s scary, but I’m doing it anyway.

      I’ve come to realize that I can’t be split between music and day job. While I’ve done more music work in the past few years that started me down this path, even working just 20 hrs/week is enough to sap my mental energy and make it even harder to compose music/practice my instrument/etc. (on top of doing all the daily life things like dishes and laundry and doctor appointments and other stuff) For those who can stay at their 20-40/week job and still do the side hustle – that’s great! I can’t, and it doesn’t help that I’m really burned out at my day job, which leads to the mental exhaustion referenced earlier. So yeah, I’ve tried doing both, and it’s resulting in neither being great. To get out of my rut at work, I’d have to go full time (NO!). Something has to give, and at 46, I need to give myself a chance to do what I truly want to do.

  18. BatManDan*

    Look to build relationships (not membership-based transactions) with other local business people, especially those that connect with your target market at roughly the same time and space. In your industry, I’d recommend graphic design, web design, printers, professional videographers and photographers. They may not engage you themselves, but they will encounter a never-ending stream of people that need you. If you have built a relationship around “know, like, and trust,” you’ll never hurt for referrals.

  19. redflagday701*

    I’ve worked as a freelance copywriter for about 15 years, and agree 100 percent with what you say about feeling more anxiety when working full time. I actually had a full-time job for about two years in the middle there, when my boss at a freelance gig asked me to come on board. The timing was perfect, because we got better health insurance right before my wife got pregnant, but later on, yep, my whole team got laid off. I wasn’t upset, because while my immediate co-workers were awesome, the company itself blew goats. Anyway, yes, layoffs feel so common and so many companies seem so uninvested in their employees that I’ve never felt like a full-time job was much safer in any way. Those companies usually need to hire freelancers too, and they pay them a premium rate! So I’d rather have one or two reliable anchor clients and the flexibility to switch things up. I’m not saying I wouldn’t go full-time again — and the nice thing about freelancing is that you will get asked to, if you do good work — but it would have to look like a really sweet opportunity.

    As far as advice goes: I have found The Money Book for Freelancers, Part-Timers, and the Self-Employed, by Joseph D’Agnese and Denise Kiernan, to be extremely helpful in figuring out how to manage my finances, particularly its advice to allocate a percentage of each payment you receive to a different part of your budget. You also want to be very careful to take on work that you actually want to do, or at least don’t detest doing, and to charge a worthwhile fee. Every freelancer has gotten themselves into trouble taking on jobs they hate because they were afraid they’d go broke if they turned down an opportunity. There might be situations where you do have to take a gig because you need the money, but usually it just eats up time that could have been spent netting a better gig and leaves you resentful and depressed. On the same note, definitely do not be afraid to charge a high rate — I would say at least $60/hour, even as a new freelancer. About a third of that is going straight to taxes, and $40/hour really isn’t that much once you factor in health insurance and other costs you’re bearing on your own. Undercharging will also turn off the best prospective clients, who will assume you’re inexperienced or not confident about your abilities. (They won’t think they’re getting a great deal; a good client will have a budget and want to spend it on a writer they can trust to get the job done.) Don’t ever take a gig you’ll hate because you feel guilty about declining (I’m speaking from experience here), and don’t undercharge. There is SO MUCH MONEY out there, most of it in the hands of people who do not need that much of it, and it’s fine (and often surprisingly easy!) to take it from them.

    There’s a ton of great advice out there about freelancing, and specifically freelance writing, on the web and in books, and you should seek it out. It takes some strategizing and planning and just plain thinking to succeed, but lots of people do it. One last thing: Do not necessarily pigeonhole yourself as a “freelance copywriter.” Copywriting involves mental organizational skills and emotional intelligence, among other things, that transfer to projects beyond writing as well. And billing yourself as a “consultant” is one of those weird tricks that will make a startling number of clients take you more seriously. You’ve got a lot of room to move! Take advantage of it.

      1. redflagday701*

        Good luck! I hope it goes well and would love to read an update if you feel like sending one!

  20. Sam*

    Some potentially unexpected costs to consider:

    Make sure you know what the cost of health care insurance is, what your deductibles are, what’s not covered. People wrongly assume if they’re healthy now, they’ll always be healthy – make sure you could afford a full deductible payment, an extra prescription medication, or a two-week break from work to recover from an accident/injury/unexpected illness.

    Think about retirement savings as well. What do you have now, if anything? Are you saving for yourself only, or a spouse as well? Do you want to pay for your (potentially future) kids’ educations? It’s often worth it to meet with a financial expert and figure out how much you need to save.

    Explore what government benefits are available to self-employed/freelance workers and whether you want to invest. Depending on where you live, the government may allow you to opt in for pension plans, unemployment insurance, subsidized health care, parental leave, etc. Often these programs are well worth it but you need to start contributing well before you need the benefits, so plan ahead now.

    1. Freelance Freetime*

      Along with this I’d flag mortgage stuff. It’s hard to get a mortgage as a freelancer if your income isn’t consistent (which mine certainly isn’t) – it also made refinancing tricky. I was also hoping to be a foster parent and the application for that basically excluded me because my income was so all over the place. These might be less of an issue if I was more successful during the start-up phase, but I had a pretty slow build.

      1. RabidChild*

        Second this. I co-own my home with my sister and when we refinanced last year, we did it under her name since I only had 2-ish years of freelancing under my belt (I did it for 5 years previously but that didn’t count)

      2. Splendid Colors*

        And even landlords… the manager when I applied to my current apartment pretty much assumed “art/craft business” meant “meth lab” and my Etsy shop was just money laundering. Turns out that is because so many of the people she had NO PROBLEM renting to were meth consumers.

  21. Paris Geller*

    I’ve never freelanced, so might perspective is definitely from the outside looking in, but I have two friends who work part-time jobs and then also freelance, and they really love the balance. They consider their freelance work their primary job, but like having the steady paycheck part-time work brings. Of course the part-time paycheck isn’t a large sum by any means, but it’s enough to get them by when their freelance work isn’t moving as quickly without having to dip into savings. One in particular is lucky that her part-time job has some benefits–they don’t pay for health insurance (which of course is the major expense assuming you’re in the US and use to employer-based healthcare), but they do have a 401k and some paid time off. That might be something you want to consider, at least starting out.

    1. MissDisplaced*

      I think this could be a good way to step into a full time freelance business.
      Keep a part time job for say 20 hours, while you build your business. Preferably, the part time job is something that might lead to contacts or connections for the freelance business.

    2. Director of Alpaca Exams*

      I did the part-time-with-benefits + freelance thing for about 10 years and it was fantastic. Highly recommended.

  22. Mental Lentil*


    * Make sure you really understand the tax implications. A lot of what used to be deductible isn’t any more.
    ** Corollary: If you don’t understand basic bookkeeping, now is the time to learn. Make sure you understand a P&L and a balance sheet.
    * Make sure you know who your target customer base is and how to get in front of them.
    * Watch your cash flow carefully.
    * Get a fully qualified domain name for both your website and your business email.

    1. redflagday701*

      Yes, and MAKE SURE YOU PAY YOUR QUARTERLY TAXES, federal and state. Even if you’re behind and can’t afford the entire amount, the penalties for missing a payment are markedly worse than the penalties for underpaying.

      In my experience, clients won’t mind if you use a Gmail address, and my preference for the Gmail interface is so strong that it’s worth it to me. But you can enjoy the best of both worlds by paying the relatively small charge for a G Suite package tied to your business domain name.

      1. Freelance Freetime*

        I’m always so sad when I hear from friends who didn’t realize they had to pay quarterly taxes until the end of the year :( Set aside approximately a third of everything you make to pay quarterly taxes! In my state, you have to pay state taxes quarterly as well as Federal.

        1. RabidChild*

          In my area, we have local “school” taxes as well which amount to 1% of income. I set aside 30% of every payment so I have it all in savings when the time comes.

          One thing that galls me about US quarterly taxes is that the due dates don’t follow any kind of quarterly calendar logic. Calendar quarters end in March, June, September, and December, so you’d assume taxes would be due shortly after the close of these months, yes? Well, for some reason Q2 and Q3 are due in mid-June and mid-September respectively, which makes no sense to me. It can be particularly hard on cash flow as a freelancer in Q2, when you’ll have just paid your Q1 estimated tax on April 15, possibly some residual tax from the prior year on the same date, then have to pay your for Q2 estimated tax a mere 8 weeks later, when you’ll not have all your billings out much less paid to you. It seriously sucks–so be super diligent about setting that 30% aside so you have a cushion!

  23. Small Medium at Large*

    My experience is some time ago so I can’t speak to the realities of 2021, but I do have a few lessons learned. I was a full-time freelancer from 2006-2010. I marketed myself as a “writer, editor and consultant.”

    1. Do not spend time doing work that doesn’t pay you enough (whatever enough is for you based on market rate for your work and what you need to feel well paid for your work). Doing low paying work robs you of time to do higher paying work or to find higher paying work. This is very hard to do in practice, but is key to building a sustainable business and a network of clients that value you.

    2. You will have to spend time chasing clients to pay you. That will suck. Do not overthink it, just do it promptly, politely and repeatedly until you get paid. If a new client stiffs you, don’t take on more work for them.

    3. Try to work on flat fees for projects rather than hourly when you can because it incentivizes you to work quickly and efficiently so you can take on more work and make more money. I generally only did hourly projects for clients who wanted me to do a lot of fairly regular work and who paid well and promptly. (I did even give a small discount on my hourly rate for a couple of very regular clients.)

    4. Work your network. The people you know who will have lots of connections and send you lots of work may not be the people you expect, so cast a wide net. I had a grad school mentor who I thought would only really know people at his school and wouldn’t be that important a connection since I was a few years out from grad school when I launched my freelance business. He ended up sending me more work and introducing me to more new clients than any other person I knew.

    5. The job boards can be useful but they are often a price race to the bottom. If you’re entirely dependent on meeting strangers online for clients, you will not be well paid.

    1. Small Medium at Large*

      amendment to #5… if you have a very specific highly valued skill that you are fairly senior at, then the job boards might yield better paying clients

    2. Letter Writer*

      Thank you! I have been thinking that project fees make the most sense too, but how do you handle it when a client keeps expanding the scope of the project or asks for more and more revisions. Do you have a very specific contract about what is and is not included?

      1. Ask a Manager* Post author

        You want your initial contract to lay out exactly what you’ll be doing so the scope is clear up-front. You can include things like “up to three rounds of revisions; additional revision rounds will be charged at $X,” etc.

        1. Small Medium at Large*

          Yes, this is what I used to do. I’d include rounds of revision in the scope and then make sure when you deliver, each draft is numbered to match. I’d also generally try to find something quantifiable in the scope like “estimated 600 words” or “three web pages with light copy and multiple images” or whatever so you have something to point to if they ask for a lot more.

  24. Beth*

    Aha, I get to be the first person to link to Scalzi!

    This column is specifically directed to writers, but it applied to ANYONE who wants to make a living doing something creative. To a certain extent, it applies to anyone, period. Just replace the word “writing” with your own field.

    Pay very close attention to items #4, 9, and 10. Also pay close attention to items #5 and 6.

    My own #11: if you are not already a good businessperson, become one. You want to be your own boss, and you want your boss to be good at being a boss — so do it. Study the subject and acquire the skills. The world is full of amazing creative people with terrible business skills who were unable to make a living, while less creative people with adequate skills either succeeded or at least did better. You say you’re taking a business coaching class — that’s a great start, especially if it includes the unromantic skills of taxes, paperwork, planning, budgeting, licenses, etc., as well as coaching and confidence.

    The link:

    The post was written in 2008, and unlike many items on the internet, it has only become more accurate over time.

  25. Teapot Repair Technician*

    I’m a writer who’s been doing “the 9–5 thing” for decades with the occasional side gig, and I think your experience so far is typical. It’s possible to find stability in 9–5 work, but it might take more than three tries. So keep in mind, if you try freelancing and it’s not for you, going back to salaried work is always an option.

    That said, I think your plan is a good one: take side gigs and build up your savings. See how that goes for a while and the decision of whether or not to “take the plunge” will be easier.

    I would recommend you open a separate bank account for freelance earnings and expenses; put in $1000 seed money and watch to see if your balance grows or shrinks. I also have a separate user account on my computer and a separate email address to keep “freelance me” walled off from “personal me”.

    1. Small Medium at Large*

      100% co-sign the separate bank account! I did this when I was a full-time freelancer and then paid myself the smallest salary I could stand to live on from my freelance account to my personal account so that I had a predictable amount to spend each month and it helped me set aside the money for taxes, etc.

  26. pancakes*

    “. . . I’m starting to think I’ve underestimated myself, especially when I compare my work output and experience to the freelancers and contractors that my company hires.” I don’t think “I could be more productive than my coworkers if I gave up my health insurance” is the right frame of mind for making this decision. Nor is “my employer doesn’t seem to put much effort into hiring good freelancers so I bet freelancing is a good way to make a living.”

  27. MissDisplaced*

    My company hires a lot of copywriters and digital content writers and designers. With staff being cut or leaving, there is a need.
    The one thing I would say is to try and build your network of good regular companies to work with before you quit. If possible, sign them on a monthly retainer. The scariest thing about freelance is lack of regularly paying monthly work, and some companies take FOREVER to pay the freelancers. Net 60 or 90 is not uncommon now, and you really don’t want to be waiting around for 3 months to get paid (or you need a good cushion if you do).

    Other than that:
    Healthcare Costs

  28. Lili*

    My long time friend and I actually did just this in Nov 2020 – we started a copywriting and digital marketing agency together. “Agency” is probably a misnomer – two co-owners freelancing together. Things are finally starting to pick up, we just landed some decent-sized re-occurring clients.
    – A business coach is a fantastic idea
    – I would really only leave your 9-5 after you have a strict set of criteria completed: get your business structure set up (lawyer, etc), get your financials set up (bank account, accountant, accounting software), business plan, freelance contract, website and email, corporate phone number, company social media and if possible, one or two small clients. Man, we spent a good two months getting this all set up, doing courses and waiting for banks, etc to process the paperwork. It’s also so much easier to approach a potential client with some success stories than with an empty client roster.
    – It takes 4- 6 weeks to onboard a corporate client, less for an entrepreneur – however they tend to get busy and disappear for random periods of time, then run back with everything on fire. Corporate clients like to do a test project, nail down the terms of the contract and get everyone in the totem pole to approve your sample before they start in earnest – hence the 4 – 6 weeks to start regular work for them.
    – We have one corporate rate structure for small businesses and another for mid-sized clients.
    – Working with another writer is fantastic, I don’t think I could do it alone.

    There’s so much great advice from all the commenters! Good luck!

    1. Letter Writer*

      Thank you and good luck with your business! My company works with entrepreneurs now. I totally get the “everything on fire” aspect!

  29. Anna*

    I’ve been thinking of this. My main concerns are health insurance and retirement savings. I do know some people in my field who do this and the way it works out is that they make a lot more than they would with a full time salary, so even with health insurance/taxes it works out. Following closely!

  30. Maggie*

    I quit my job two months ago to do exactly this — I’m also a writer and content strategist — and I have ZERO REGRETS. I am 100% on Team Freelance! I am much, much happier, and I’m already making as much as I was making at my full-time gig. I’ll probably be making more by the end of the year.

    I gave my boss a month of notice so I’d have that month to reach out to everyone I knew via my current job to let them know what I was doing. I highly recommend this. Tell EVERYONE. You never know where a client may come from!

    I also recommend writing a really positive LinkedIn post about your decision once you’re out on your own. I’ve gotten at least two clients — and counting! — just from the one LinkedIn post that I did.

    Lastly, spend some time thinking about the money. How much do you need to earn? How much do you need to charge in order to earn that? Break it down as many ways as you can think of until you know your numbers cold, and don’t waste your time with low-paying work. There are plenty of people out there who are willing to pay for real value — you just have to find them.

    I took Seth Godin’s The Freelancer’s Workshop and learned a lot from it. I wouldn’t say it’s necessity but I do think it was a great experience — and a few of my classmates have hired me!

    In short, I think you should go for it. Be very thoughtful and planful and make sure you’ve got a safety net and a handful of clients before you leap. Be smart, and you’ll thrive!

    1. Letter Writer*

      This is awesome! I know a freelancer had a really similar experience to what you described! “Tell everyone” is great advice.

      I want to move on from my job, but none of the job postings I see appeal to me. I dread the idea of starting over in another crazy corporate culture, so I think that’s a sign I need to give freelance a shot.

    2. Small Medium at Large*

      Your mention of Seth Godin’s course reminded me. I also liked The Well-Fed Writer back in the day. It may be a bit outdated now but I found it a really helpful way to understand what I was getting into with freelance. I also liked Escape From Cubicle Nation… I think I read excerpts and heard her speak and didn’t read the whole book, but she had a lot of good perspective on the pros and cons of being on your own v. with a traditional jobby job

  31. Documenter*

    Freelancing is great for testing the waters to creating your own full-on small business. It is almost like apartment living as compared to living at home but not owning your own home yet. The biggest psychological change is that it can make you unemployable in the future. After solving problems such as marketing and sales, getting your service delivery down, managing budgets, it can be a hard shift to working for other people again and having to put up with their drama and mismanagement.

  32. So sleepy*

    Sooo I’m kinda commenting from the other side of the coin (I was self-employed but opted to return to the traditional workforce). A few considerations:

    -have you looked into how consultants are hired at your organization? Where I am, you pretty much have to be involved in a particular consulting firm or you won’t get contracts, so you pretty much still work for someone as a consultant and they take a cut of your earnings as well.

    -make sure you are considering all your overhead costs – consulting can seem really lucrative, but keep in mind that you’ll have periods that are less busy and no guaranteed income, so you need to take that into account (as well as other costs such as if you’ll no longer have benefits, unpaid vacation time, etc.)

    -although you may be more skilled than other consultants, keep in mind that a certain amount of your (unpaid) time will be spent actually getting the contracts – meeting with clients, giving quotes, selling them on your services, etc. This can be a lot more time-consuming than you’d expect. This was my least favourite part of running a business. Hi

    -You need to be really self-motivated (it sounds like you are, but it’s worth really examining before you take the plunge).

    Last, it’s worth keeping in mind that the longer you are self-employed, the harder it becomes to return to the traditional work force (between getting stuck in your ways/used to independence, having less references, etc). It can still be a strong selling point to have run a business (and the skill set you develop from it will be incredibly beneficial), but over time it can become more difficult to adjust to working for someone.

    That said, if you think these are all things you can overcome, I’d go for it! There’s something to be said for being entirely in control of your days/time. I have different reasons for leaving self-employment (mainly, I ran the business with my spouse, which sounds fun until you are never apart and neither of you have income during slow periods), but I’d do it again without hesitation if the circumstances were right!

  33. Pete*

    I went freelance again last year during the pandemic (I’m based in Germany) after using up my unemployment following redundancy in my last role.

    It’s surprisingly gone really well. The main lesson I implemented this time around was to think of myself as someone with skills that people needed and that marketing is not a dirty word (I’m a news reporter, editor, and writer). I set up a website ( and started contacting every editor and agency I could. And I think that, combined with a lot of places shedding staff or needing someone who could drop in and do a few pieces each month for them, really gave the freelancing a big push this time around.

    So my advice would be:

    1) Have some kind of marketing plan, even if it’s just an idea of who you’re going to contact and what you’re going to tell them.
    2) Have a clear idea of what your skills are and how much you should charge for them.
    3) Be prepared to work hard.
    4) Have a good idea of what your expenses will be.

    I went freelance again because I didn’t have any other options. But it’s really worked out so far. I hope it works out for the OP, too. Best of luck!

    1. Chamomile*

      I really like Pete’s advice — when my husband got tired of underperforming teammates and poorly-managed projects, we both (financially, emotionally) would’ve managed the transition better with Pete’s 4 points. (I’m a teacher, so I can only cover most of our expenses.) My husband (a software developer) was dismayed by how much time and energy marketing and sales take up, especially if you’re not used to having a lot of front-of-house time/contact with unhappy clients. He started off charging $15 for a product that, 3 years later, is now $200 (and does a lot more) — maybe he knew his own worth, but other people didn’t, so increasing his prices as he gained recognition in his field helped. He lost smaller clients as he gained larger ones– that transition can be hard, but it led him to a more stable income because he just needs a few regular clients. It took time for him to stop obsessing about day-to-day sales, and to look back only at the week or month in general.

      As for stability/anxiety, my husband (already anxious) became MUCH more anxious during the first year that he was on his own, and it’s gotten better (non-linearly) over time. So, maybe setting yourself up with a good therapist, coach, or similar could help you weather the initial roller coaster until your income stabilizes. He also found a decent marketplace health insurance plan that includes behavioral health (like counseling).

      Good luck!

  34. SwampWitch*

    1. Get a solid understanding of how your taxes will work. I’ve owed more than I’ve made some years contracting due to shady hiring and working for crappy companies.
    2. Get a VERY solid 1099 contract of service about your rock solid rates, what happens if someone doesn’t pay you, refunds, what you will and will not do, what is and is not in your purview, who your point of contact is, be clear you’re NOT an employee to be grouched at by a middle-manager in a bad mood (sorry, personal experience) and their responsibility to you and liability. MAKE SURE THEY SIGN IT (again personal experience). Have it reviewed by a lawyer.
    3. Be very solid about your availability and do not waver. I was sucked in to thinking I had to be available 24/7, that I had to jump the minute someone asked me a question to still be kept on the books and paid on time.

  35. redflagday701*

    Question for other freelancers: Do you too read Ask a Manager religiously and sometimes feel a little sad about missing out on bananas workplace situations that would give you a reason to write in?

    1. learnedthehardway*

      I’ve had my own business for over 10 years, and read Ask a Manager sometimes for the education and sometimes for the entertainment value. I’ve learned a lot here about how to manage difficult clients, because one gets bananas situations with clients and sometimes clients have internal bananas issues as well.

      The difference – when you’re not fully dependent on one client – if you have to, you can walk away. I had a good mentor in my early career who wasn’t afraid to fire clients who were abusive / unreasonable, and that example has served me well. I’ve only ever had to fire one client, but I didn’t hesitate when I realized that they were abusive (which totally shocked them, by the way. I don’t think they’d ever been called out like that before.)

      Maybe I thrive on stress, but I have clients I can work with only because I don’t report to them directly – ie. who I would never take a permanent role with – because they are bananas in one way or another. Instead of finding them infuriating or impossible, though, I figure out how to work with them/around them, charge them a premium (my “aggravation tax”), and find the amusement value when they go off the rails in predictable ways.

      Also, one of the things I liked most about being self-employed over COVID was knowing how the business cycle works in my industry. While other people were extremely stressed, I was able to deal with my stress and have some confidence that the industry would pick up again. I started my own business just as the financial crisis was hitting in 2008 – weathered it with the help of mentors who assured me it would be okay, and so this time, was able to do so while helping other self-employed contacts with the same reassurance.

    2. Nanani*

      Yes to the first place, no to the second. I’m quite happy reading about other people’s problems without being there ever again.

  36. Jules the 3rd*

    A close friend and Very Smart Person tried freelancing over the last year. They realized that though they had a great network and were bringing in reasonable accounts and amounts, they really hated all the paperwork – taxes and withholding, contracts… They accepted a job in a consulting group two months ago with a big sigh of relief.

  37. Fernie*

    I have two thoughts to share from someone “client-side”:

    – Most companies I’ve worked for don’t keep content producers or copywriters on staff, it’s true, so there will always be a demand for your services.

    – That said, content and copywriting itself is viewed as a commodity so it will be hard to differentiate yourself or charge higher rates if that’s the main service you provide. If you can add some other services that are more directly connected to your clients’ bottom line, that will help. I’m thinking things like Marketing Analytics, e-commerce content and merchandizing, or full funnel campaign strategy, where you can more easily measure the impact on your client’s revenue.

    All the best! I hope you can send us some updates.

  38. Burnout*

    I am planning to go freelance in the next few months. I am recovering from burnout and from my own self knowledge, believe I will be able to better ramp back up to work if I can pick-and-choose my activities and experiment with what I might like to do (I have skills and a background in multiple areas, and a bunch of possibilities waiting in the wings). The freelance approach may be a medium-term thing before going back to a real job, or it may be a long-term solution. I am luckily in a position where I have both a savings cushion and a partner from whom I can get health insurance.

    Things I am thinking about and doing:
    – Networking — Lunch Club has been a great way to add a bit of randomness into those I meet, though watch the privacy settings
    – How much do I want to work? How can I make sure I maintain a balance that works for myself and avoids further burnout?
    – What people in my network can I get advice from? Can I strengthen those relationships?

    It sounds like you are close to being ready! I’m in the group of do it!

  39. Come On Mylene*

    This is the most perfectly timed, swift kick that I needed. I’ve been dabbling with going freelance, even registered and LLC to do business under in my state. But seeing the OP’s letter, and all the encouraging comments, I’m also going to take the plunge. Thanks!

  40. T. Boone Pickens*

    I hung my own shingle 4 years ago and this is what I’ve learned. For reference, I’m currently still a solo shop although I’m getting to a point where it makes sense to start scaling. My business will gross about $350k/yr for reference.

    First, I spoke with a local CPA on how I wanted to structure my business (S-Corp, C Corp, LLC, partnership, sole proprietorship). Each one has pros and cons so you need to make the determination on what makes the most sense for your individual needs. My CPA helps me with quarterly taxes, handles payroll deposits, helped me pick out a retirement plan and handles my annual tax returns. They’ve been a godsend.

    When I first started up, I made sure to spend a bit more on the front end making sure all my i’s were dotted and t’s crossed. That meant I hired an attorney to handle all my articles of incorporation paperwork, getting the appropriate business licenses, they drafted up my contract proposals, etc. They also keep me on track when I need to do follow up paperwork like filling annual/bi-annual state required reports, board of directors meetings, etc.

    Mediamaven gave the right advice, I strongly, strongly suggest having a separate bank account strictly for business purposes. It makes things so much ‘cleaner’ and you don’t need to worry about co-mingling funds. From a savings standpoint, I made sure to have 3 months of living expenses socked away so that I could fully jump in when I launched my business.

    For retirement plans and health insurance. Unfortunately for health insurance, it’s going to be pretty crappy. My personal experience was I made too much money so any plan I found on the marketplace was really expensive. I ended up getting a pretty bare bones high deductible plan that covers an annual physical per year, but really, that is about it. I’m *knocks on wood* pretty healthy so I’ve never needed to go to the doctor too much. I do have a teledoc option which has been helpful for general aches/pains where I normally would go to the doctor.

    Now, for retirement plans, this has actually been great as you can pick and choose which plan makes the most sense. There are a ton of plans out there and your CPA should be able to provide some insight. If you work with a financial advisor, they should be able to help too. If you don’t have either of those in your network, I’d check with your local SBA and see if they can provide some recommendations. I’m currently transitioning from a SEP IRA to a 401(k) plan as I’m to a point where I can sock away more money for retirement.

    Now, on to the business stuff. I’d caution on trying to take on a variety of work. There are riches in niches. Know what you do really well and focus on that. I do 80% retainer work and 20% contingent and it’s made things much easier from a planning standpoint. Now, before I launched my business I had already been in my space for 5+ years so I knew the lay of the land pretty well and really went solo because I wanted to focus on an even tighter niche. I really focused on customer delight and I think it’s helped me. I keep my customer roster small because I like to underpromise and overdeliver, my business is almost 100% referrals and I like to think it’s because I don’t half ass anything. I try to do the little things, handwritten notes over the holidays, going the extra mile when possible. You need to remember that you are in the sales and service business when you launch your own company and you can never take your eye off the ball.

    Know what you know, and outsource what you don’t. I legitimately burned a year on a website because I thought I could carve out the time on Squarespace to build my own website. Guess what, I couldn’t so I outsourced the work to another company who delivered a product that wildly exceeded anything I could’ve done on my own.

    Whew, this got really long. Good luck!

    1. Freelance Freetime*

      Re insurance, sadly I agree: this was a huge place of privilege for me, in that I was able to accept a crappy state plan because I’m young at the moment and my health is generally good. This precluded a lot of friends who would have otherwise been interested, as their prescriptions and ongoing doctors appointments would have made it impossible to buy a cheap high deductible plan like I did. I hope we can find a solution to this politically, as it’s unfortunate.

      1. T. Boone Pickens*

        Yup, agreed. Now the positive with my high deductible plan is that it comes with a HSA component which is a sneaky nice vehicle to sock away some extra money for retirement as it is triple tax advantaged (tax free dollars, grows tax free, tax free distributions for qualified medical expenses).

    2. learnedthehardway*

      I found it was not affordable to get disability insurance (in Canada) and that it wouldn’t have covered me in many cases anyway (eg. I can work at my job if I had mobility issues, but it would be a real challenge if I was blind or deaf, and those situations were really hard to get coverage for).

      One thing I recommend to anyone is to get “critical illness” insurance – basically, if you have a heart attack or get cancer or have some other debilitating medical condition like that, you get a 1 time, lump sum payout. I never imagined I would need it, but it was pretty cheap and it was a lifesaver when I did get unexpectedly sick, and had to cut back my work by about half for a year to recover. My insurance broker insisted I get it, and I am forever thankful for her for doing so.

      1. Nanani*

        Seconded! I have CI, and on top of being a safety net it kind of doubles as extra retirement money if you get to X age without needing it.

  41. ScreamingFlower*

    I have been really wanting to go freelance (virtual assistant) but I am having such a hard time! I am also scared too. I am tired of working 9-5.

  42. Freelance Freetime*

    So, I have done almost this exact same thing. What I would say looking back on it was that it was the right decision more in a “life is short and you don’t want to live with regrets” way than in a “this was a smart financial decision that set me up for life” way.

    I think it’s really hard in your late 20s/early 30s because you feel like your career should be paying off and sometimes it’s just … not. I’d been working hard for over a decade but none of my jobs seemed to be leading to a place of satisfaction and security, which is quite demoralizing. I was not able to leverage the apparent success I was having and the compliments of my managers into either better paying new jobs or opportunities for advancement in my current job. I did freelancing for two years, kind of trading one set of problems for a new a different set of problems; it was challenging and exciting. Basically, it cured my burnout so that when I got back into a dreary 9-5 where I wasn’t necessarily appreciated, I was more relieved to be there. Sorry if that sounds depressing but it was my experience and I’m glad I tried it.

  43. Heading out the door*

    I’m in the process of going solo. I’m quitting my day job in Dec and had planned on using this time to get ready (training, website, etc) but clients have already found me! None are connected to my day job and I’ve been careful not to violate my non-compete. I’m already making more solo! I can’t quit early, so one of my biggest challenges is to make myself care at work while knowing it’s a better use of my time to build my business. It’s good to plan, and have a backup plan, but at some point you’ve got to just jump.

  44. Little Miss Sunshine*

    Liz Ryan @HumanWorkplace is a big advocate for starting your own business as a freelancer. She has published a ton on Twitter, Forbes, LinkedIn, books, and her blog. Check it out

        1. mediamaven*

          Google Liz Ryan Dangerous – You’ll see a good summary from George Blomgren. I wasn’t able to link it

          1. Lizzo*

            Thanks for the follow up. My main takeaway from that particular article is that he’s a middle-aged white dude who feels threatened by a woman’s ideas that are very different from his, and is in attack mode to try and assuage his fear. Seems to be a big fan of Dale Carnegie, and I probably would’ve enjoyed reading this much more if he’d focused on Carnegie’s advice instead of dragging Liz Ryan through the mud.

  45. Abogado Avocado*

    I have run my own law practice, been part of a large firm, and run a non-profit. They are all businesses, at heart. Yes, you can have great flexibility running your own business — if you understand it is a business that has to pay its way for you — and it — to survive. Therefore:

    (1) Determine your hourly overhead by calculating what it costs to run your business. Include rent, supplies, training, health insurance, your salary and any other benefits (perhaps you’d like some vacation time?), the cost of an accountant, taxes, and total. Divide by 2,087 hours (the number of work hours in a year) or, better, the number of hours you’d like to work in a year (although that will make your overhead rate higher). When setting your hourly rate, you need a number that covers your overhead and allows you some measure of profit.

    (2) There are some services that will do the book-keeping and tax preparation for you. Otherwise, you will need an accountant, as well as a good book-keeping program that you can use to keep track of fees and expenses, and help generate your paycheck (in coordination with the bank that has your business bank account). You also will need a time-keeping program that can generate invoices. If you don’t know what programs you need, talk to the accountant. Remember: it’s a business, so you need the tools to operate the business, which includes billing (and collecting from) clients, keeping track of debits and credits, and ensuring your taxes are paid correctly and on time.

    (3) Learn how to quote a fee and stick to it, and learn how to require a retainer. If this isn’t something you feel you can do, owning your own business probably is not for you. When you work pro bono, do so because you’ve decided to do so, not because someone has failed to pay you. Expect that there will be many people — some family, many clients — who will try to guilt you into working for free or for such a reduced hourly fee that you can’t cover your overhead. Learn to say no to these “offers;” they are not worth it. Knowing your overhead –as well as your worth — will enable you to reject such entreaties.

    (4) You may be tempted to cut corners by those who say they never did any of this when they opened their own businesses, but were successful anyway. Believe them at your peril. Owning your own business can give you great freedom to choose when and how you will work, but only if you earn enough money to pay your overhead, which also means paying yourself.

  46. Willow*

    Build up that savings account with more money than you think you’ll need. There will be clients who are slow to pay (hopefully you won’t get any who refuse to pay), and getting a steady cash flow started may take you longer than you anticipate. A healthy savings account is what will keep you going. I’ve seen freelancers begging for money from friends and colleagues because a client was late and they can’t pay their rent–you don’t want to be that person.

    1. Freelance Freetime*

      Yes sadly in my area of freelance it’s pretty common to pay nothing until the job is done (if I had more pull and my choice of clients, I’d demand at least half up front, but this would be atypical in my field) so in some cases I’d put in 4 months of work without seeing a dime, and then had to wait a month for my final invoice to be paid. I was glad I had robust savings in place. I was only willing to do this because I knew it was government-funded reimbursable money.

  47. Lizzo*

    This will probably be a repeat of much of the advice above, but here is my experience:

    You will be most successful with this if…

    -You can get some clarity on your brand/service offerings that will help set you apart from the competition, e.g. there are a TON of freelancers available out there–why should someone choose to work with you?

    -You can get comfortable talking about yourself and promoting the value of the services you offer. Nobody’s going to do your marketing for you–you’re it!

    -You can build a client base *now* while you still have steady employment. (As others mention, make sure your current employer doesn’t have a “do not compete” clause.) I did this for a more than a decade and it was probably the best thing I could have done as far as being able to launch full steam into a freelance career when I was finally ready to do so.

    -You can figure out some sort of steady income stream to supplement your freelance work, e.g. a retail job. This is also very beneficial for both mental health (you have a steady schedule, you’re required to get out of the house), and potentially for networking (the nature of my particular retail gig allowed me to meet new freelance clients regularly, and management was super supportive about me giving my business card to those folks, though I realize this may be a rare arrangement).

    -You can build a network of people who can *refer* new clients to you. This could be folks who work directly with your kind of freelancer, e.g. marketing folks who are in-house or at agencies; OR other freelancers who can send work your way when it aligns with your expertise or when they are too busy to work with a particular client.

    -You have some sort of financial cushion if you have some lean months. This cushion also gives you some flexibility about who you take on as clients, i.e. saying no to high maintenance, pain in the ass clients who are going to cost you money instead of make you money.

    -You can either make enough money to afford your own insurance, or you are attached to a spouse/partner whose benefits you can take advantage of. Please please please make sure you are taken care of!!!!!!

    -You can offer rates that are competitive but fair for the talent and experience you have to offer. DO NOT UNDERVALUE YOURSELF.

    -You have a plan for growth, but also a backup plan in case you need to go back to a traditional job. (THERE IS NO SHAME IN GOING BACK TO A TRADITIONAL JOB.)

    I’ve got more, but those are the big ones. :-)

    1. Lizzo*

      Oh, also, have a plan to save money both for short term savings and long term savings (i.e. retirement)!!!

  48. some dude*

    My partner did this a while ago and here’s my advice:
    It’s awesome in that you can get a ton of different experience, which can really help you get jobs moving forward. Had she stayed at Day Job she wouldn’t be nearly where she is now in her career.
    Sometimes people can take mooooonths to pay you, so it helps to have savings and a cushion.
    It is very much either pouring or a drought, so be prepared to be crazy busy and then not busy at all. And you constantly have to be hustling for new projects.
    If you work quickly and have a good work ethic and are a good people person, that helps a ton.
    After a while she took a part time gig and then freelanced part time so she had a little more stability.
    She made a little less than Day Job without benefits, so keep that in mind.
    It is a lot of work. She had to invoice, track payments, keep receipts, all that stuff. It’s not all glamour.
    But, again, you can always sign up with a creative firm to get projects and ideally the stuff you do freelance will help your portfolio and help you get new gigs and maybe a new regular job. Especially in creative fields i think having a breadth of experience can be really helpful.

    1. Freelance Freetime*

      Yeah, there are a lot of folks saying clients started coming out of the woodwork as soon as they hung their shingle and they were immediately making more than they were in their old job, but this wasn’t my experience. My goal for the first year was not to spend my savings (basically break even). My goal for the second year was to equal my previous income – which would actually represent a big loss, because of the taxes, insurance, 401K etc. My goal for the third year was to be where I had been at the job I left in terms of take home pay. Have not achieved goal #3 as yet.

  49. Devil's Advocate*

    Gonna play devil’s advocate. What’s your risk tolerance?
    1. You can end up with a crappy “boss” and coworkers with every new project.
    2. You might miss the creative collaboration with coworkers.
    3. Your funds will vary wildly from week to week, month to month.
    4. You’ll have to work DAILY on gaining new clients/projects.
    5. You may find it’s a race to the bottom in terms of hourly rates.
    6. Signing up with agencies is a good move, but… they’ll still be “in charge” and you’ll still be working for a company, not yourself.
    7. Agree that obtaining credit (home, auto) will be more difficult for a few years.

  50. New Freelance Consultant*

    Loving this thread! I lost my job in January 2020 and ended up just sort of…falling into freelance work? I kept looking for a full-time gig and was working contract works in the meantime until I realized that it was really full-time and I could make this work. I’m so far behind in getting my business stuff together because I’ve had a lot of work. Here are my thoughts/advice so far:

    1. As everyone has said, have a nest egg and an exit point. I was very fortunate in that I had planned to purchase a house and had a down payment saved up. I decided that would be fall-back money and I could give this a full year to give it a real shot. In 18 months, I’ve added to that and haven’t had to draw from it to survive.

    2. I wish I could remember where I read this, but she had a great formula for pricing yourself. Determine what annual salary you want to make (this number should include taxes and other expenses you expect to pay) –> Determine how many days/weeks of vacation you want a year, then decide how many hours you want to average per week –> Multiple the avg. hours you want to work by the number of weeks you want to work. –> Divide your desired salary by this number. This is your hourly rate. (e.g. If you want to make $125,000/year with five weeks of vacation, average 30 hours per week, you’d need to charge $89/hour). I then checked my desired number with what market rate is and what my skills are worth. The more I can charge, the fewer hours/weeks I need to work to reach my target.

    3. With all that said, as other commenters have mentioned, per-project based fees or straight retainers are generally preferable. This allows me to get paid “more” per hour if I hustle and get it done. It also helps in that clients don’t get used to a set hourly rate that I later have to raise. Instead, they’re used to me scoping projects and giving them a set amount for the full deliverable. I have done a combination of hourly billing and per-project fees depending on the company and assignment. When I’m scoping a project, I estimate the number of hours it’ll take me and then multiple that by my hourly rate. Now (hard lesson learned), I add another 20% of those anticipated hours to the project scope as I have a tendency to underestimate how long something will take me.

    There’s so many things I haven’t yet figured out – especially the feeling that I *have* to take a job or project. I was just speaking with a client yesterday and she goes “if you have capacity, we’d love to have you shift and work on x, y, z over the next few weeks” – well, I said sure. I don’t have capacity!!! I’ll now be doing work this weekend. So this is a habit I’ve got to break.

    Overall though, I love the flexibility. I’m working fewer hours, on my own terms, and making more money. And I know if work dries up, I can start searching for a full-time gig again because see I have that year’s nest egg :).
    Good luck – you can do this!

    1. Letter Writer*

      This is very helpful, thank you! I also underestimate how long things will take, so I love your tip about adding in an extra 20%.

  51. iglwif*

    So, I didn’t do that in 2021–2021 has its own set of … interesting wrinkles–but I did do it in 2017, and it was an excellent decision!

    Things I learned:

    – The less you burn bridges in the course of leaving, the more likely it is that you can get recommendations and actual work from your former employer(s). I mean, unless they’re jerks.
    – Find out exactly what your current employment contract says about working for or with partner or client orgs after you leave. If there’s nothing in there saying you’ve agreed not to, that can be an excellent source of work.
    – If you have any time at all to spare outside of your full-time job, and if your contract allows it, starting to do a bit of freelance work now can set you up for more later.
    – Plan how to separate your personal and business finances, and then stick to that!
    – If you’re not careful, you can end up working *all the time* so make sure you plan how you’ll take time off, when you’ll get your exercise and outdoors time, etc., etc.!
    – However much you think you’ll need to set aside from each client payment for your taxes, SET ASIDE MORE THAN THAT.

    I have actually ended up in another full-time gig (still remote even pre-pandemic, yay!), but it’s with an organization that I did a bunch of freelance work for first, so that by the time I came on full-time I knew all the people and had seen the place with all its warts, and still wanted to work here.

    1. Freelance Freetime*

      Re: Taxes – Did you set aside more than one-third of what you made? I think it has always ended up being slightly under that in the end, because of deductions. I don’t think I’d say set more than that aside for taxes?

      1. iglwif*

        I set aside ~30% but when you are self-employed, you have to pay your own Employment Insurance and Canada Pension Plan premiums, and I had not accounted for that (I’d been working at the same place since I was 22 and those things just … didn’t occur to me). I ended up owing $10K, and CRA lets you pay in instalments via automatic bill payment with your bank, so nothing terrible happened, but there’s 5% interest and also it just kind of put me in a financial hole for a while. I’d have missed the money a lot less if I’d treated it as belonging to CRA to begin with.

  52. Milly*

    Do it (I *loved* freelancing), but one word of advice: if income insurance is a thing where you are, get it. I went the freelance copywriter route at 30, had a couple of great years, and then had some weird health stuff and no safety net. The irony of that was that I returned to a “real” job just for the health/state benefits I would be entitled to should it be something severe.

    I’m generally okay now, but if I had it to do again, income insurance would be top of my list of essential running costs. It will take a lot of the stress out of self employment.

  53. Nanani*

    I’ve been freelancing since 2014 (so not as recent as you’d like).
    It -will- be scary at first. You might find yourself at a point where there’s too much freelance work to do as a side-hustle but not enough to really support yourself full time, which is exactly why those saving are so very very important.

    Taxes are also tricky the first year or two. Unless you transition from employee to self-employed exactly at the break between two tax years, you will have a year of mixed income (with complicated taxes from your last job plus freelance income) that can be hard to sort out, and it may be more than one full tax year before you are really set up properly for quarterly payments or whatever your local jurisdictions expects self-employed people to do that’s different from regular people who have an employer.

    The taxes will seem very high because you’ll be paying for things that you didn’t before. Look into whether it makes sense to set up business accounts or incorporate or something, and be a small business of one person vs a freelancer. Maybe those are the same where you live, but they might not be and you want to know the tax and legal implications.
    Get a financial planner, tax adviser, something like that.

    Number 2 advice is more for the personal side. Your friends and family might have a hard time wrapping their heads around self-employment/freelancing. You set your own schedule but that doesn’t mean you’re free. You’re not on holiday or retired, obviously. Yet a lot of people who’ve only known set-hour jobs (shifts or 9-5 or school hours or whatever) will not immediately understand that just because you can go run errands in the afternoon and might run into them when doing so, does not mean you’re lounging around all day free to go on spontaneous outings.
    The social reset can be pretty weird when you don’t have outside work hours as the backbone of your calendar.

    Good luck!

  54. anon lurker toph*

    If you don’t already have a mortgage, it is really hard to get a mortgage without W2 income.

    1. Ask a Manager* Post author

      I think this depends! I’ve gotten mortgages twice as a freelancer. They want to see consistent income, and they want a lot more documentation than you’d otherwise need to provide (like cash flow statements and invoices and other stuff). But I did get them.

  55. Susana*

    Do it – but prepare first. Accumulate savings, have a plan for what clients you could get, etc.

    I freelanced twice in my life – both 5-year stints. People said, oh! It’s so uncertain and insecure! But you know what? When I was freelancing, if I lost a client, I adjusted. had I been employed full time by that client and was laid off, I wold have been up the proverbial creek.

    I did just fine both times – and in the second, I ended up making way more per year than I had made at my immediate previous (high prestige, even) job. which meant I negotiated a much higher salary when I took my current staff job.

  56. LMM*

    I did not have the luxury of planning my move to freelance. I was laid off a year ago. But I’ve had a really successful year! If you think you have the network AND you have some money saved – I was very fortunate and did have savings – I say give it a shot. I’m a journalist who had made a move into digital content/copywriting when I was laid off and have moved back into journalism for the most part, because my network was there. I did, however, get a temporary copywriting job from an old boss – echoing those who say don’t burn bridges! It was good money.

    I’ve had really good luck following a few writers who post freelance opportunities in newsletters each week or twice a week and email those out. I found two great editors there, and one of those gave me opportunities that turned into a really amazing job during the Olympics.

    Keep track of your earnings so you know when you need to ask for more money or negotiate more, or if you can afford not to take something (dream world!), and of course for taxes.

  57. Nanani*

    Broader FYI since a few other people are commenting similar things: Freelancing and Starting a Business are NOT the same thing!

    You can freelance as yourself and not a legally-distinct business entity. You can be a freelance contractor for companies that hire a lot of those. You don’t need to open an actual shop or storefront when that’s the case.

    LWs line of work is not mine, but the fact remains that freelance is not actually the same as being a business.

  58. WestOfTheRiver*

    I don’t have advice, but I just want to share that I’ll be bookmarking this question because your letter is MY LIFE DOWN TO THE LAST DETAIL, or so it seems.

    29? Check.
    Done 9-5 and found it kinda anxiety-provoking? Check.
    Currently working for a company where my long-term prospects are limited? Check.
    Not ready to quit, but slowly moving to build up savings and a side-project client list? Check.
    That field being freelance copywriting and digital content creation? Check.
    Slowly starting to gain a sense of confidence in my work, especially compared to other contractors I’ve seen? Check.

    Like… dang. Are you sure you’re not me?

    Anyways, I’ll be watching the answers with great interest.

    1. Letter Writer*

      Hahaha I can’t tell you how many times I read something on AAM and think “is that me? is that my boss?” Good luck!!!

  59. NoBeesOnTyphon*

    I’ve been freelancing writing and editing on the side of full-time jobs since 2007, and had always wanted to go full-time freelance eventually, but thought it most likely wouldn’t happen until we’d paid off our mortgage in a few years. Then I had the absolutely brilliant idea of joining a brand new pre-revenue startup company in January 2020, and ended up getting laid off in September of that year because of the pandemic’s effects on the company’s development plans. It was a bit scary, but it’s turned out really well and I have absolutely no regrets – in fact, I wish I’d had the guts to jump sooner, rather than waiting for a push. I don’t want to ever go back to full-time regular employment.

    It took a few months to ramp up to full-time (and actually I’m having a quiet month right now, but with more work coming down the pipeline for September), but I was able to land my main ongoing client by November, and they’re now about 50% of my workload most months. I did some agency editing work for a few months as a stop-gap until I was able to land enough of my own clients (hated it, was glad to move on, but there are lots of similar companies out there in my field). I ask all my clients for referrals and have got work from secondary and now tertiary contacts that way.

    Ideally I would have started with more money saved up (my husband’s entire industry shut down in the first wave of COVID, and he’d only just gone back when I got laid off), but hey, our expenses are lower than usual during the pandemic. I also figured it was an ideal time to try freelancing because if I end up having to look for a job in a year or two, no-one’s going to worry too much about a perceived resume gap that happened during the pandemic.

    Good luck!

    1. NoBeesOnTyphon*

      oh and I highly recommend reading the book “Solo: How to Work Alone (and Not Lose Your Mind)” by Rebecca Seal. I just finished it last week and am recommending it to every freelancer I know.

      1. NoBeesOnTyphon*

        One more recommendation: The Deliberate Freelancer podcast. It’s all about how to think and plan like a business rather than an individual.

  60. Sharkzle*

    I left my job in April of this year to go full time freelance for graphic design. It’s been the best decision I have made for myself – mind, body, relationships, etc. I get to set my own hours, work for really interesting clients, and I get to work from home. All while only answering to myself and making sure the clients are all satisfied.

    My advice is be realistic about how much “work” you can accomplish each week and keep in mind that work is also writing emails, tracking down leads, and doing client research in addition to the creative stuff. I budget about 20 hours of billable work a week and 20 hours of non-billable (like the aforementioned “work is also…”). Figure out what you’d like your yearly salary to be and do the math to figure out your billable rate. There are a ton of resources out there for this kind of stuff, look ’em up. In addition, start making some freelance friends and get networked up with ’em. Friends in the biz are great, you never know when a designer will need some help with copyrighting or vice versa.

    It’s also been helpful to get linked up with a few creative staffing agencies. It sounds like you’re a few years into your position so it’s likely that you’d be a good candidate for them. They do pay a little less but it’s all W2’d (if you’re in the US) so it’s mostly worth the tradeoff as they do all of the initial legwork.

    If you’re writing in to Ask A Manager about this, you’re probably already a great worker and can handle the switch over. Start saving now, have a good 4-6 months of expenses saved up, the more the better, and take the leap. DO IT!

  61. ToniLeeJordana*

    I’ve been freelancing now for almost 18 years, and while some years have been better than others, overall things have worked out better than I could have hoped.

    My advice: save a cushion before you begin. Definitely put money in another account for tax, as soon as you receive it. Make provisions for your super. Block out holidays in your calendar–the tendency is always to work too much, and mental exhaustion will reduce your productivity and you’ll work more hours to compensate, so it becomes a vicious cycle and you’ll end up getting a job again. Try (not easy, I know) to physically delineate your working space–if you don’t have a room, at least a rug, or a small table, or tape on the floor–and don’t go in that physical area unless you’re working. Budget for sick days–you might not take them, but it’s mentally healthy to know that you can. Consider how you’ll manage your own training and career development needs.

    Overall, I’ve learned to treat myself like a valued employee, with the kindness and respect that I’d have wanted a manager to treat me.

    For me, the decision to begin was difficult because I was earning good money at toxicjob. It was a jump into the unknown! My husband gave me the following piece of great advice which helped me make the decision: Currently you have one employer, providing 100% of your income. You might think this is secure, but it isn’t. You could lose your job any day, for any reason, and then you have no income at all. If you freelance, though, after a period of time building your client list, you might have 10 clients each providing 10% of your income (say). As a freelancer, you’re more secure, not less, because losing one client won’t wipe you out.

    Good luck!

    1. Letter Writer*

      Thank you for your kind advice! You (and your husband) are so right about the income balance – I’ve been wiped out twice for reasons out of my control.

      Also, I love this: “Overall, I’ve learned to treat myself like a valued employee, with the kindness and respect that I’d have wanted a manager to treat me.” I am going to aspire to the same thing!

  62. Katie from Scotland*

    There’s so much practical advice in here already that I won’t add any. But in terms of the “am I just as likely to have a stable career freelancing vs employment” type question, I would say from my own experience that’s as much down to chance in freelancing/self-employment as it is in your choice of employer. I find though that even though my income is way less secure, that’s a worthwhile trade off for the other benefits. One of the key things for me is that my options and opportunities to make changes, find new projects, make money in different ways, get a temp job here and there etc are way better when you’re self employed. So the security isn’t guaranteed by any stretch, but you’ve just got more potential to diversify income streams and avoid being completely without income.
    Keeping a solid savings account, as well as separate tax-related savings, really helps to smooth out the bumps, and sometimes I take on short term close-to-full-time contracts specifically to pay for bigger, less frequent expenses (like a new car or a fancy vacation)

  63. Mrs. Bond*

    I left toxicjob 10 years ago and went freelance. I didn’t have much time to plan but I got a severance package so that kept me afloat when times were lean.

    It’s been great for me, although it took a few years to get a steady flow of work. I find that a combination of working with larger agencies and working with clients directly works well, and usually ensures I have a good stream of work. I’m in a slightly different field (web development), but I’m guessing that a lot of marketing agencies work with contractors in your field as well.

    The advice to talk to an accountant is really important. Make sure you understand your tax obligations in your country. For those outside the US you may also need to be collecting VAT (HST in Canada).

    A few other bits that come to mind:

    – talk to your bank about a business bank account with overdraft protection. This can cover you in case of late invoices/delayed projects.
    – find a good invoicing/bookeeping tool (e.g. Freshbooks, Quickbooks etc.).
    – do not be afraid to talk about money, ask to be paid, and send invoices when you need them. Reasonable clients will be fine with getting an invoice under reasonable circumstances. I used to avoid sending an invoice until I was sure a project was “done” even if there were a lot of delays on the client’s side.
    – Do not work with unreasonable clients
    – Make sure you have a good Scope of Work defined in writing. Something you can point to when the client start’s asking for work that wasn’t in the original plan.
    – If a client promises you lots of work in future, be skeptical.
    – For larger projects, particularly for new/possibly unreliable clients, and/or any project where the client is requiring you to be available in a certain timeframe, ask for a deposit.
    – When discussing timelines, be explicit that the client has to provide feedback/any resources you need within the timelines specified. They have to hold up their end too. And in my experience, it’s almost always client that causes delays.
    – Look for related networking or meetup groups in your area. A local meetup group really helped me to build a network and reputation in my area, but it did take several years to get solid work from there.

    I find it a lot less stressful to be a freelancer (and now I do work for the same organization I worked for at toxicjob!). The stuff that used to stress me out on the inside now does not bother me or affect me. I love the flexibility I have as a freelancer – I can pick up my kids from school some days or go for an appointment in the middle of the day. I don’t have to work with toxic people. The inconsistent income can sometimes be stressful, but it’s never been bad enough that I considered getting a job again. I’m lucky to live in a country where health insurance isn’t a problem.

    Managing workload during busy times can definitely be a challenge. Remember that your priority should be to your existing projects and client service. It’s fine to say no to work, or tell the client you can’t start for x weeks or whatever. That’s better than overworking yourself and providing lesser quality work to your existing clients. For me this didn’t get to be a real problem until about 5 years in. The past year and a half has actually been particularly busy!

    Not having paid vacation is another thing to consider. I now take two weeks off a year, plus some flexibility during slow times.

  64. Pink Geek*

    I tried it and it was not for me. I found finding clients and billing them very stressful. I wanted to just focus on writing code, which is what I do best.

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