5 tough career lessons

When you’re starting out in the work world, it’s easy to think that your career will be straightforward: you’ll find jobs that interest you, work hard, and be rewarded for it. But it’s rarely that simple. Along the way, you’re going to learn some tough lessons about your career. Here are five of the hardest but most common.

1. You have to advocate for yourself; you can’t count on others to do it for you. Too many workers assume that their company will notice their talents and accomplishments and reward them, through raises, promotions, or better assignments. And while this certainly does happen, it’s naïve to rely on it. Instead, assume that you are your own best advocate, and that you’ll need to speak up – whether it’s asking for more money or tracking your accomplishments throughout the year to raise when your performance review comes around.

2. Your reputation matters – a lot. People sometimes wonder why they should work hard and go out of their way to excel at work, when their employer may not show them the same commitment. The reason? You’re not doing it for your employer; you’re doing it for yourself. Building a reputation as someone outstanding at what you do means that you’re creating a safety net for yourself: You’ll have people excited to hire you when you need them to be, former managers clamoring to recommend you and connect you with job openings, and the ability to command more money. Conversely, if your reputation isn’t good, it will become increasingly hard to do the things you want with your career. So it’s key to cultivate and protect your reputation; it’s one of the most valuable currencies you have.

3. A bad boss can ruin the greatest job. You might love your work passionately and adore your coworkers, but if you have a bad boss, none of that will matter. A terrible manager can make your daily life miserable, so it’s crucial to assess your likely management before accepting a job. Don’t get so excited about the work you’d be doing that you miss danger signs about the person you’d be doing it for. Speaking of which…

4. There’s no such thing as a dream job. Or, at least there’s no such thing as a dream job that you can spot from the outside. As much as think you might love a particular job or to work at a particular company, you never know what it will really be like until you’re there. Legions of people have discovered that their “dream job” came with a nightmare of a boss, or awful coworkers, or hours so long they could barely see their family. And feeling that an opening might be your dream job can lead you to miss crucial danger signs during the hiring process – causing you to accept a job that turns out to be nothing like your dream.

5. Your degree might not help you as much as you thought. College and graduate degrees no longer open doors the way they used to, and too many new graduates are surprised and frustrated to discover that even with a degree, they have trouble getting the jobs they want – or, in many cases, any job. Work experience is more and more crucial, and students who don’t start getting real work experience before they graduate are at a significant disadvantage. This is a tough lesson that you can avoid if you plan early enough – and it would help if schools and parents started helping students see this too.

I originally published this at U.S. News & World Report.

{ 45 comments… read them below }

  1. Annie*

    Excellent post! I totally agree about your manager making or breaking your enjoyment in a role.

    Also, excellent advise to those grad students trying to postpone the real world by being a professional student – get out there and start working!

    No such thing as a dream job – totally agree. I’ve come to the realization that I need to stop trying to find that job that I will love doing and never want to do anything else – it doesn’t exist. I’ve decided instead to sell myself to the highest bidder. Sounds jaded but that’s where I am.

    1. Vicki*

      > I totally agree about your manager making or breaking your enjoyment in a role.

      Every time I’ve left a job (not counting short term “contracts”) it was because I had a new manager and things started going downhill. Usually because they didn’t understand what I did (my jobs tend to be internal support and “unusual”) and wanted me to do something else that they understood better.

      People join companies; people leave managers.

      1. Jamie*

        My boss actually said this – that people don’t leave jobs they leave managers. I agree that in some cases that’s true – but people do leave for more money or a more challenging opportunity and it’s no reflection at all on the manager.

        I mean, most of us have a jump number. If someone else is willing to hit that number and there are no glaring red flags many people will leap no matter how much they like working for their boss.

  2. BeenThere*

    Yes so many great points.

    #1 – I didn’t realise this until I read Nice Girls Don’t Get The Corner Office and started asking for things. Yesterday I asked for a higher starting salary and I’m prepared to refuse the position without it.

    #2 – Thank fully I’ve always cared about my reputation, something about growing up in a small town does that.

    #3 – Yes, dream job destroyed by manager that was my first position out of University, I couldn’t leave because I needed to rack up time in the role or my CV would be destroyed. In the end he was forced to resign and most of the team was layed off

    #4 – Job i took after the position in #3 because I needed work and connections knew me turned out to be a dream job. Manager and team made it that way. It’s something I would have never applied for and am still in contact with everyone I worked with.

    #5 – This has always been the case in my home country, the more letters you have after your name with no work experience the less likely you are to get hired. In fact in my field everyone starts paid work in summer breaks while studying as there is a requirement to get 60 days professional experience. In my case I landed such a position at the end of second year and was asked to stay until i graduated. I worked every spare hours I had and it counted way more than my average.

    1. A Bug!*

      Yesterday I asked for a higher starting salary and I’m prepared to refuse the position without it.

      Fistbumps for you! I’ve got my fingers crossed!

  3. PuppyKat*

    This is a great article. I agree with all the points—but especially with #2. People are always watching to see how you handle yourself, how you deal with your work, whether or not you take responsibility for your mistakes, etc.

    Just as in your “outside” life, your work reputation is going to follow you.

    1. Anonymous*

      Absolutely. I learned this lesson the hard way (but in college, so at least I had a bit of a buffer), and it’s incredibly important. People talk, so you have to do your best to make sure they say more positive things about you than negative things.

  4. Martina*

    This post is really helpful to me. I’ve been lucky to have a wonderful job at my college for 3 years (and they let me stay on until i found full-time work). we have a great, dedicated community, a fun and creative environment, and supportive bosses. i just hope i’ll be able to find this again out in the “real world.” i’m trying to be realistic, but don’t want to lose hope/ have very low expectations. Thanks for this post!

  5. FormerManager*

    I totally hear you on #5; my mom is shocked that my master’s degree hasn’t netted me six figures or magically led to a government job. Of course, she has a master’s in education that she’s never used since she left the workplace permanently when I was born 20+ years ago. And she’s absolutely convinced that if anything had ever happened to my dad, her degree would’ve made her a shoe-in for an administrative position in a school despite not having worked since the early 80s (thankfully nothing happened to my dad).

    Fortunately, I have a job that I reasonably like based on my solid history of achievements at other jobs.

    1. Sara*

      I hear this a lot from wannabe stay at home wives/moms who get educated (and usually in more advanced studies like education, medicine, etc) with the intent to never use it…they think it’s their magic ticket to being able to provide for their families in the case of their husbands’ deaths (God forbid of course).

      We all know that right now the job market is so so tough for people with even relevant and up to date experience….that it’s simply naive to think that after being out of the workforce for years you can just jump right back into it.

    2. Anonymous*

      Yep! According to my dad I should be making 100K+ and be management “with your work experience and college degree.” If this were 1975, I could probably have done that. My dad has a union job that he’s been retired from for 20+ years and really has no idea how the world works outside his old job.

  6. JLL*

    #3 and #4 really resonate with me. In my less experienced days, I had at least 2 positions, that if I’d really LISTENED to what they were saying, and really thought critically about what they were asking and explaining in the interview, I probably should not have taken the jobs. Dream companies- “everybody” wanted to work there- but if i’d listened a little more carefully, I would have known my work-life balance was going to be non-existent, that I would have had a boss whose style was almost the exact opposite of what I preferred, and that I would wind up leaving both in less than a year.

    So I guess my add-on is to really listen to what they’re telling you…and sometimes what they aren’t.

    #5 is really hard for some of the older (read: my grandmother) to accept. No way will she ever be convinced that 12 years of solid experience i gained working will ever trump the theater degree i limped towards when i was 20 lol. Even though what I do now is not related to theater at all (not that i’m all that happy about it, but let’s talk about salaries and the arts another day lol), she believes I HAVE to go back and finish, because…she was a professor and academia is its own thing.

    1. perrik*

      Unfortunately, Grandmother has a point about finishing the degree. These days you may not be able to make it past the HR resume screening software if you can’t check that little box saying you have a post-secondary degree. I was at the end of an interview with a hiring manager for a position for which I had the right experience and background. It went so well that she extended an offer on the spot, but then… “What did you get your degree in?” Er, nothing, I didn’t finish. Company policy required a completed 4-year degree. It didn’t matter what your major was, it just had to exist because HR said so, no exceptions. Stupid and short-sighted? Yes. But them’s the rules.

      After I found myself treading water in another job because they wouldn’t take me seriously without the damn degree, I left and completed the damn degree. Sensible hiring managers want to see solid experience, but you still have to get past HR and their checkboxes.

      Lesson #3 is such a universal thing. Even a crappy low-wage job can be made bearable or even good by a talented manager, and vice versa. The only positive thing I can say about one former manager (who replaced a really good one) is that I used several of his poor performance management decisions as case studies for my master’s program. Come to think of it, his poor performance management may be responsible for my current career path. Perhaps I should send him a fruit basket…

      1. Martina*

        Yes! isn’t it true that college degrees are the new high school degrees? i have some acquaintances who say they’re not sure what they want to major in, so they drop out. And I always mention that as long as it’s vaguely related to the jobs you’re applying for, it probably won’t matter. Unless it’s a very specific degree.

        Also, i like that your old manager’s poor performance inspired you. it’s funny how that happens.

        1. AnotherAlison*

          There was a nice HBR blog about this this week: “Stop Requiring College Degrees.” The author quoted an NYT article, noting, “As a recent New York Times story put it, ‘The college degree is becoming the new high school diploma: the new minimum requirement, albeit an expensive one, for getting even the lowest-level job.’ Dental lab techs, chemical equipment tenders, and medical equipment preparers are all jobs that require a degree at least 50% more often than they used to as recently as 2007.”

          The state of things as related to college degree requirements is one of my big pet peeves right now. My sense is we’re on a bubble & this ridiculous won’t go on forever, but having a kid entering college in 3 yrs, I feel like I still have to advise him to play by today’s rules and plan to go to (and finish) college.

      2. Seal*

        An old friend from college dropped out one class short of her finishing her BA. Over the course of 25 years she never got it together to take that one lousy elective she needs to get her degree. She’d tell people that she “studied Sociology” if anyone asked about her degree. I can’t imagine what she’s told employers over the years. Either you have the degree or you don’t; telling a potential employer you “studied” something is not the same thing.

        1. Ask a Manager* Post author

          But isn’t that pretty silly of employers to care? She’s one elective short; that’s basically the degree, minus one administrative requirement. Why should an employer care, especially 25 years later?

      3. glennis*

        It’s true. I have the theatre degree that JLL limped toward – I even probably have her GPA (mine was 2.6). And now, almost forty years later, I am grateful for the fact that I can check that box. Even for a transfer in my own organization, I have to upload a copy of my transcript!

    2. Kat M*

      Right? I’m a child of academics, too, and it really freaks them out that I don’t have a degree. Then I point out that my writing gigs pay far more per hour than my stepmother’s (with an MA in English). That usually keeps them quiet. College degrees are ONLY worthwhile if you know what you’d do with one.

      1. Martina*

        Couldn’t you say, too, that not getting a degree is only worthwhile if you know what you’d do without one? I know that I would have been utterly lost if I hadn’t gone to college, but there are people who can figure it out without a degree and do well (and better a lot of the times.)

        1. K*

          Yeah, I’ve said it before, but statistically a college degree has been a good investment – regardless of what it’s in – for a very long time. That doesn’t mean it’s a good idea to take out six figures (or even necessarily five) of debt for one, but all things being equal – the college graduate is usually going to end up doing better.

          Of course, if you have a solid plan to do something else, that can all change drastically. (Or it can be drastically different in individual cases.) But for a kid who doesn’t know what they want to do, I’m not sure the advice is just “don’t get a degree.” It might well be “get a degree and take advantage of the time your in college to get some work or internship experience in SOMETHING so you have something to point to when you get out.”

  7. ThursdaysGeek*

    I’ve had two wonderful jobs where I loved the work and loved my co-workers, and would have happily stayed until I retired. In one the general manager died, and in the other my great manager retired. Both of those dream jobs quickly turned to nightmares. Managers matter a LOT.

  8. AnotherAlison*

    I definitely agree with #3. I had a bad boss ruin life for me for several years.

    The problem is, I took the job working for someone else, and then the position was restructured and the bad boss was brought in from the outside. I could never have seen it coming.

    I think before you decided NOT to take an otherwise good job because you aren’t sure about the boss, it is worth it to get a better understanding of the corporate culture. In my business, department manager positions tend to be a brief stopping point on someone’s career path, so to not take a job when the bad manager is 4 years into a 5 year tenure might lead to a missed opportunity.

    1. Lora*

      +1 *Raises a cup of tea in solidarity* This just happened to me–the positive, upbeat, work-life balance-y, well-connected, beloved by everyone boss I was hired by is planning to retire and the new guy they brought in…They could have offered me double the salary, I wouldn’t have taken it to work for this character.

      I’ve had four really excellent bosses whom I just adored. One of them made a crummy job completely tolerable, two others made fun jobs abso-friggin-lutely awesome and I’d still be there if it weren’t for corporate takeovers, and then there is the boss who is retiring. *sigh* Oh, Howie…you were my favorite, I miss you so!

      1. AnotherAlison*

        How do they get it so wrong with the new hire bosses?

        I see it all the time. They never want to undo the decision, either.

    2. some1*

      “I think before you decided NOT to take an otherwise good job because you aren’t sure about the boss, it is worth it to get a better understanding of the corporate culture.”

      I agree, but even this means no guarantees. Your organization could get bought by another that has horrible management &/or culture, etc.

      1. AnotherAlison*

        That’s the kicker. There are never any guarantees. That’s why I struggle with this idea because working for a bad boss is completely awful, but avoiding them could cause you to miss out on good opportunities. I didn’t leave under my bad boss, and now I have the second best boss I’ve ever had, although it took a few years. (He would be #1 except he’s on the road a lot and it’s hard to get face time.)

        The good boss came to us from an acquisition made a few months after my bad boss became my boss, so sometimes M&A leads to good things. . .

      2. Lora*

        Yeah, one of my good bosses who did well under the corporate culture that I signed on for, did much worse under the takeover culture. He was the type of person who always gives people the benefit of the doubt and tries to create good things, very positive and upbeat. Takeover company was extremely cutthroat and back-stabby type of culture where the people who succeeded were often the wiliest and most manipulative. He did his best to protect us from the effects of the takeover but it obviously took a toll on him and he was very stressed. Sad, there wasn’t much I could do to help him other than being awesome.

        Re: undoing bad hire decisions, yeah, not sure I understand that. Obviously it is hard to fire someone all the time, but the same companies who don’t want to pink slip a manager seem to have no problem at all telling the lower level people to clean out their desks–even when those lower level people might be so highly specialized in a particular software or skill set that the lower level people would be just as hard to replace as a manager. For example, two jobs ago my employer let go of an expert in running large scale gene sequencers, where there are not exactly new candidates banging down the door or new grads fresh out of college able to do that stuff, but kept a manager who has been responsible for many, many good people leaving in disgust–only to find out they had to hire the sequencer guy back as a contractor for much more money (we’re talking about 6-8X his original salary).

    3. glennis*

      My bad boss really had an impact on me, in two ways. One, she had such a bad relationship with her superiors that it tarred all her subordinates with the same brush.

      And, two, trying to comply with her micro-managing ways, her extreme risk-averseness, her inability to see the forest for the trees instilled similar habits in me, and it’s really hard to un-learn them.

  9. anonz*

    Oh, #3. I left a wonderful job with great co-workers due to an absolutely horrible boss. It was to the point where I got an ulcer and was having panic attacks on an almost daily basis. I loved the work, but the management wound up coloring my perspective so much that for my own health, I had to go.

    Now the staff is down by 3 FTE in the last 8 months, all due to the same person, and upper management is still clueless about why we all left, although myself and at least one of the others cited that person as our primary reason for leaving.

    1. DA*

      I am amazed at how often upper management is completely oblivious to bad lower level managers. They would rather lose entire groups of people than deal with the terrible manager.

      1. Jane Doe*

        I worked at a company where upper management basically played hot potato with bad managers, and by extension, the work group they managed (yes, I worked in one of these). I assumed that the VPs and Directors who fell out of favor with their SVPs or C-level bosses ended up in charge of these groups.

  10. Dan*


    You always write a really good blog, but this is one of your better pieces. Everything you’ve written is so true, and yet for some reason, still must be learned the hard way. You’ve articulated your points quite clearly.

    This is coming from someone who has learned most of those lessons himself.

  11. Sam*

    #5 is so true, but it’s so depressing to watch the cost of a college degree skyrocket while its value nosedives.

  12. Laura*

    Cannot agree more about the bad manager point. I had a boss make my life utter misery for about 6 months (with some help from his chief conniving minion, who was hired by me). Hands down, biggest jerk I have ever worked for in my life. We butted heads from the start, and no one up the management chain would listen to anyone about what a bad decision hiring him had been. His boss was incapable of ever admitting to a mistake, and the person above her (at the C-Level) had some sort of man-crush on this idiot because he had played football for the C-Level exec’s alma mater.

    I was pregnant at the time, which I think is the only thing that saved me. I don’t believe he would have had the cajones to try and fire a 40-year old pregnant woman, and I don’t think HR would have let him. But the minute I was back from maternity leave would have been a different story. I decided I could either voluntarily walk the plank, or wait to be thrown overboard. Thankfully I was able to make a lateral move into another group, doing the kind of work I was ready to start doing again anyway, so it all worked out for the best. It was a pretty awful 6 months getting there though.

  13. Maria*

    Great list. #1 was the hardest and most important lesson I’ve learned, I always thought being a good worker meant I wouldn’t have to ask for higher salaries (they’ll pay me what is fair) or raises… not true. My second “real” job I later learned another candidate was rejected because she asked for 15k or more than I had been willing to accept, and realized I had undersold myself in trusting their offer was fair (I naively hadn’t done my research).
    I’ve run into 3 a few times, unfortunately.
    I wish I knew #5 sooner!

  14. Sara*

    For me the toughest lesson so far has been maintaining a professional attitude, as lame as it sounds. I’ve been examining the issues I’ve had at work over the past few years, and as much as I like to think that I’m professional and was good at what I did….its still hard to swallow that I just may been giving off negative vibes even when I never intended to. I know no one is born knowing anything and we all figure it out as we go along but it seems like others just know what to say/do or rather what NOT to say/do. I just never realized that sometmes the smallest detail that seems like not a big deal could end up having serious consequences. I just recently lost my job (well a temp assignment) over it and I’ll be kicking myself for it until I get another great opportunity like this one.

  15. Waiting Patiently*

    #1 learned the hard way early on about advocating for self but I left that company to “show them” I could do better. Then one day my old big boss called me at the new job asked what would it take for me to come back. And I then had a few aha! moments. First, I was happy that he tracked me down and secondly I could have just asked for a raise and saved myself the extra travel for the new job. Unfortunately, I also had to deal with going back to bad boss, who thought I wanted her job simply because I expressed interest in learning. It was a tough decision because the new employer offered more opportunity and encouragement for growth but the old place just offered more money and me going back to a bad little boss. Naive little me followed the money…

  16. Rana*

    Addendum to #5 – not only is a degree not a guarantee of a good job, if you have too many or the wrong kind, they can actually work against you. Degrees can help, but only if you have experience to go with them.

      1. Rana*

        Yes and no. As I say, the experience is pretty important. From my own limited experience, lack of experience combined with advanced degree (I have a Ph.D. in history) was acceptable only in some pretty limited contexts, such as entry-level faculty jobs. Outside of academia, trying to get an entry-level job with a Ph.D. in anything that wasn’t retail was an uphill battle; people asked me why I was wasting my time, or assumed that I wouldn’t be interested in jobs “beneath” me. What mattered was experience, first and foremost.

  17. Still there*

    I had a group of employees I loved, but an out-of-town boss whose lack of appreciation drove me to the point of putting in my notice. My employees took me to lunch and talked me into staying; one of the things they said that stuck with me was “just ignore [the boss].” It revolutionized my outlook and I am still happily there, almost four years later.

  18. Vicki*

    > There’s no such thing as a dream job.

    So true. The job I held for the longest (6 years and I was laid off) was pretty far from what I would call a “dream job”. But I really liked my co-workers.

    One job that looked perfect at the start (They need me! There’s so much to fix! This is so great!) fizzled in a few months when the person who brought me in left the company.

    The best you can hope for is that you enjoy the work and like your co-workers… or that you can find something else soon.

  19. Erik*

    The point about college is a difficult one to digest for current students because it seems as if they are in a “damned if I do, damned if I don’t” situation. I just read a story on CNN a few days ago about a law firm in Atlanta that will only hire college graduates even for the most menial of tasks, such as their “runner” who carries documents between the courthouse and office for $10/h. They said it was primarily for cultural reasons and that someone without college wouldn’t feel “comfortable” in that environment. But at the same time, we read daily about students racking up $100,000 in debt at the best schools only to have no job at all on the other side, and in many cases because they couldn’t find time for both work experience and taking full course loads. It’s a really tough spot to be in right now.

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