should I leave my family business?

A reader writes:

I need help deciding if I want to stay in my family’s 70-year-old business.

At the moment, I work for my father, and my younger brother is also in the business. We’re a construction firm. I’ve worked at the company since I was 14, doing office work over the summers all the way through college. After getting my degree and working elsewhere for seven years, I came back to the family business and for nearly 10 years have been working my way into more and more of a leadership role.

My dad is my boss, but he is not a good delegator, manager, or mentor. He is a great project manager and knows the industry like the back of his hand and is good at his job, but very much not a teacher or long-term planner. On paper and sort of by actions, I am his heir apparent. But in reality I’m just being given a little bit of everything without any ownership over anything, and its overwhelming.

I am now point on some aspect of almost every part of the company — IT, HR, management,accounting, office management, marketing — and on top of that I keep getting construction projects to manage (I started here as a project manager, and note that none of our other PMs have any other office/admin responsibilities, just me). I keep trying to get out of project management, because it’s hard to prioritize employee reviews or revamping the website when you’re constantly pulled into project issues, which by definition need to take priority because they pay the mortgage. But every time I’m close to finishing out my last project, a really great prospect comes up and we don’t have the staff to handle it, so I end up taking it on and I’m back on the hook for another 9-12 months of PM work taking 50% of my time.

Every time we’ve tried to make a plan for me to take over a specific part of my father’s role or our CFO’s role, it just doesn’t happen. They can’t actually let go. Meanwhile I’m just getting all the mundane stuff put on my plate, like ordering more laptops or figuring out how to run certain reports in our accounting software. These tasks don’t interest me. I want to be big picture, I want to be strategic.

We just had a strategic planning retreat two months ago, which I organized, pulled together the data and agenda for, and facilitated (all of which I really enjoyed). During that retreat, the decision was made that I would go get some financial training and move towards CFO and out of project management. Last week we landed a new 12-15 month project … and guess who is now the PM? We just hired a new PM, guess who is supposed to be training and mentoring him (though I’m not his manager, that’s still my dad)?

I’m so burnt out from the pandemic and trying to figure out how to do my job, what my job even is, and what any sort of pathway towards a job here that I like looks like that I’ve been pretty checked out for the last two months. Yesterday my dad confronted me about that. He asked, “Have you decided construction isn’t for you?” It hurt, and I kind of tried to explain everything above, but I’m really close to just saying, “Yeah, construction isn’t for me, I’m out” and blowing up the last 10 years’ worth of a career I’ve been trying to build here.

It would be so much simpler to be out. But I have a lot of pride in this place, it’s basically another family member, and I love that it’s an ethical company that supports real careers and puts its employees first. But I haven’t been happy here for a while. (I loved putting together and running that strategic retreat … but now all that work feels like a waste of time, because we aren’t doing anything with it.) I feel so stuck, and can’t see any way out besides just blowing it up.

My relationship with my father and brother would be fine if I left. They would understand. The company would figure it out, or it wouldn’t and my dad would have to sell. I don’t know, at some point it’s still just a business, not actually a member of the family, right? I know I have skills that would make this place better, but I feel like they are atrophying after years and years of banging my head against a wall and not getting any sort of direction or plan or mentorship from anyone here, and feeling like all my efforts to develop my role here are just me flailing about.

My passion for this place is gone. Maybe that’s just post-pandemic blues? But I do know I would feel so free if I hit the eject button. I could go back to school, I could find work/volunteer for causes I care about, I could be a more present mom and spouse if I didn’t work here. Maybe that’s the right path, to separate family and work, and just let the chips fall where they may? Note that my spouse also has a full-on career working 60 hours a week for one of the tech giants, so balancing work and family is really hard with both of us having career-type jobs and small kids. And while my income is great to have, it’s not necessary for our financial stability (the same would not be true if we lost my spouse’s income). Any advice would be much appreciated.

Leaving a job is not blowing anything up! People leave jobs. It’s a normal part of doing business.

The reason it feels like blowing everything up is because (a) this is so emotionally fraught for you right now and (b) family. The fact that it’s family ups the emotional fraughtness level 320% and makes it hard to see things clearly.

If this were not your family’s business, just a regular job, and you had spent years being told “yes, we’ll do X and Y for you” and then that never coming to fruition … and not being given real ownership over anything but expected to be responsible for it anyway … and constantly pulled away from the work you want to do (and which they know you want to do, and have told you that you can do!) into the work you don’t want to do … and if mere weeks after receiving specific promises about how your role had changed, you were given a massive project making clear that wasn’t happening any time soon … would you feel so conflicted about leaving?

Frankly, you might. People get conflicted about leaving jobs all the time, even when they’re not working with family. But I bet it would be clearer to you that leaving was more aligned with your interests than staying.

Because leaving is probably more aligned with your interests than staying. Family businesses are hard under the best of circumstances, and these are not the best of circumstances. That’s not to imply anything negative about your dad or other family members; there’s nothing in your letter that indicates they’re anything but lovely people. But the dynamics here — where more and more gets piled on you and your job moves in the wrong direction and you just take it, probably because you want to be helpful and you have generally positive feelings toward the business — are not good for you.

You don’t like the work anymore! You know you’d feel freer if you left. You feel like you’re atrophying. You’re not even worried about a bad reaction from your family if you left (not that that would be a reason to stay, but it makes it harder to separate when you’re worried about that). The only argument you presented for staying was … well, actually, you didn’t even present one! Not one.

Fly free! I predict that shortly after leaving, you will feel enormous relief. (In fact, if you want to test that, do this: Decide in your own head that you’re going to leave, but tell no one yet. See how you feel in two weeks.)

Your family will always be your family, but they don’t need to be your career too.

Read an update to this letter here

{ 172 comments… read them below }

  1. Ms. Frizzle*

    One of my favorite take-aways from Captain Awkward’s blog is The Sheelzebub Principle (I’ll post a link as a reply): If things stayed just as they are, would OP stay for another 6 months? Another year? 10 more years? It’s hard to move on when it feels like things might improve any minute, but it can be helpful to have a plan or deadline for if they don’t (and in this case, unfortunately, it seems likely that they won’t).

      1. Cinderella?*

        Why was I not surprised to read at the very last that the person writing in was female? I really doubt if this was a son that he would be asked to do all of the administrative tasks as well as project management. I think she even says that she’s the only one who has to do this.

        Might be useful to contact Dad and say, you know, I love you dad, and my heart has been totally in this business. But you keep putting essentially secretarial / administrative work on my shoulders probably because I’m the daughter. And it’s really bumming me out that I don’t feel I can have a role in this company because you need to see me more as a gal Friday and less as a construction professional. If you saw me as a construction professional, you would probably respect me enough to give me a singular role at which I could excel and grow. Instead of having me be the admin and secretary and orderer of laptops, on top of doing project management. And then asking me if construction isn’t for me. As opposed to is Administrative work not for me.

        Then see what Dad says. Maybe he doesn’t realize at all that he’s treating you in a typically female sort of discriminatory way. Assuming that you’ll handle all the administrative type stuff and giving you project management jobs on top of that,
        While not doing that to anyone else.

        Now I might be wrong about this dynamic, but it’s what struck me through the whole letter, until I finally got to the last bit where she describes herself as a mom, and my viewpoint was, to me, some degree validated. So I think I might have a kernel of truth here. I mean, give the daughter all the admin work plus project management which is her area, and then when she seems checked out, ask if construction isn’t for her, and not if something else is going on. I can’t imagine asking the son if construction wasn’t for him if they were giving him secretarial / admin work and he seemed checked out.

        Just a possibility. Maybe it’s my usual female discrimination radar going off incorrectly, but those are the bells that are ringing for me.

        1. Ann Nonymous*

          I thought the same thing. I assumed that LW was a male, but finding out that he’s a she put everything into perspective. I completely agree with your assessment.

          1. Jules the Goblin*

            +100. It’s very difficult for me to believe this is not gender-related. Get out, LW — they’ve proved over and over again that they’re not taking you & your concerns seriously.

        2. ThePear8*

          This really stood out to me too, I don’t have any particular advice but it did strike me right off the bat as the role being strongly gendered, that OP seemed to be getting saddled with all the stereotypically “female secretary” work. I think you make a good point that it’s contributing to the issue here because it’s pulling OP in multiple directions handling all the admin work instead of letting her excel at one role

        3. Tedious Cat*

          While it wasn’t confirmed till the end of the letter, I was pretty certain by the end of the second paragraph.

        4. Not One of the Bronte Sisters*

          This is so spot on. Dad needs to seriously consider hiring an office manager. OP might feel better if those tasks were taken away. Maybe not, and maybe she would want to leave anyway, but I think that the position of office manager needs to be created anyway.

        5. Anonone*

          “He asked, “Have you decided construction isn’t for you?””

          I think in the context of OP being a woman, this question really reads as “have you accepted that we’re not going to let you in?”

          I also think that OP might believe she is heir apparent, but is going to get a nasty shock when Dad hands everything over to her brother.

          1. c-*

            Oh, yeah. LW, don’t fool yourself: your brother is the one getting the business after your dad retires, mark my words. They have been roadblocking you for a decade, and now they’re pushing you out (that “have you decided…” = in spite of all your work and feedback, we’ve decided that the problem here is you and we’re hoping you take yourself out to save us the drama when your brother inherits).
            Get out. You are not getting a career out of this. Your dad and your brother don’t see you as an equal construction professional, they see you as a girl lending a hand, and there’s no way you can change that dynamic, because they’re the ones who need to change.
            I’m very sorry. They can be loving family members AND sexist coworkers who prevent you from thriving profesionally at the same time. It sucks, though.
            You put 10 years into this. You gave it more than a fair shake. Enough is enough. You need to look out for your needs. Put in your 2 weeks, take some time to rest, and don’t ever do a smidge of unpaid work for them when they come asking for your help after you’re out.
            I’m very sorry.

        6. Greg*

          Oldest member of the new generation entering a family business here. Male, for what it is worth. And I don’t agree that this is necessarily the case. Without a clear development plan or even corporate structure (as family businesses don’t always do a good job of structuring their companies) I turned into the catchall because, “something, something, development.” Then those tasks were mine. As someone who grew up in the business I had a pretty intimate understanding of how the internal processes in the business worked so it turned out I was really good at what was put on my plate (similar to OP I’d imagine!). Then those were normalized and I did everything I could to automate them and get them off my plate…which just meant, “Oh, let’s give this to him, he did such. a. great. job. with the last one.”

          And I found myself in a similar rut to OP, even going so far as to applying to new jobs. Finally sat my dad down because my brother and cousin (female) were entering into the business and told him what happened to me absolutely couldn’t happen to them. It turned out to be a really good conversation for me as well, but that’s another story. My next project was putting together a family on-boarding plan for new members who want to come in and that has been a net benefit for both the people coming in and the business as a whole.

          As a male, I have no first hand knowledge on how women are treated in the workplace. That is a clear blind spot for me. But as the oldest member of a family business who’s dad has a hard time letting go and struggles being the catch-all for the business in general? Right in my wheel house baby! Family businesses are really complicated animals in their own right and being a family member has its clear benefits and drawbacks. It may be because she is the daughter. But it also might be because she’s the oldest.

          1. c-*

            But the difference here, Greg, is that when you sat your dad down and explained, *he listened* (because you are a man). The LW has explained what the problem is and what needs to be done time and time again, only to be placated with platitudes without seeing meaningful change materialise *for years* (because she’s a woman; trust me, men not listening to us in the workplace because they don’t see us as equal contributors is a very common phenomenon).

            Let’s say for the sake of argument that we know there is absolutely no gender bias here: even in that case, the LW is stuck working for people that don’t give her real development opportunities and who have been making empty promises for years. She feels burnt out and stagnating. She has tried to fix the issue, but nobody is listening. She’s in a position where she can leave this job.
            I say she should go. She’s been trying for a decade: if things are going to change, she’s clearly not going to be the one who changes them.

            1. Greg*

              Well, c-, he listened because his dad is OP’s dad here! Who literally gave my dad control over his dead body. My dad was just doing what he knew and it took me a long time to get the backbone to say something to him. I have plenty of male counterparts that are in the exact same position as OP here. What should I tell them when they call me and ask how they can make the same changes I did?

              I’m not suggesting that OP should stay; there are real issues (that again! I’ve experienced as the oldest member of a new generation in a family business!). I’m also not suggesting it isn’t because OP is a woman but that there may be an alternate My comment is that family business are really tough to navigate as a member of the family (especially as the guinea pig) and that there may be another factor here other than, “She’s a woman so she’s getting screwed.”

              I’m aware that there is a lot I don’t know. I am aware that I am putting this through my lens of experiences. But please note I am not putting a judgement on OP or anyone commenting, and am not shutting down her gender as a possibility, just that there may be nuance.

    1. Keymaster of Gozer*

      The Sheelzebub principle has helped me so, so many times when I’ve worried about what the right thing (for me) to do is.

      It so, so often answers ‘no, I’m not willing to endure this for another x years’

      1. Artemesia*

        50 years ago I ‘invented it’ myself when trying to decide about leaving a marriage. It is a very efficient tool. Without framing it like that I would have hung around, had kids and possibly even be still married to that guy or divorced when it was complicated.

        1. Keymaster of Gozer*

          I wish I’d known it about 25 years ago when a certain bloke was trying to convince me that I had no rights he didn’t give to me.

          (Long ago ex, but escaping from that relationship was the most traumatic moment of my life. I wish I’d got out sooner)

    2. Quinalla*

      Yeah, that is a good one, another I’ve heard on at least 2 different podcasts that is related is asking yourself – how would I feel about/how much will I care about this in 3 hours, 3 days, 3 weeks, 3 months, 3 years, 30 years? Adjust or eliminate some time frames to suit – but I found this very helpful as well!

    3. The_artist_formerly_known_as_Anon-2*

      Yes Ms. Frizzle – see my other post in here regarding my father’s reluctance to leave a failing family business. Then he woke up one morning and said “what the hell am I doing to myself, my wife, and my two (then) teenage kids?”

  2. Xavier Desmond*

    OP, have you thought about asking your Dad if you can step away from the job for maybe 6 months or a year. You say you would be able to manage financially. The time away could give you some space to decide what you want for your future.

    1. Where’s the Orchestra?*

      I said below, what about asking about going part time for a while as a third possibility? That may make it a bit easier to really evaluate if this is the right career for you or not – but without fully leaving work (because frequently is sadly easier to get a new job when you have a current job).

      1. Ins mom*

        And keep part of your work that you like; someone else would be found to pm the new project

      2. Artemesia*

        Part time doesn’t work when the habit of the boss is to keep piling stuff on. I tried that once and the pressure to do more and more is hard to resist and if you do you are ‘not a team player’ or ‘they wondered where you were at 3 pm when the project crisis occurred.’

        A leave might work. I assume a CTJ meeting with Dad has not worked.

        1. WellRed*

          Agreed part time won’t work here. I wonder how clearly OP has talked to dad about all of this. It doesn’t sound like they really have.

        2. Where’s the Orchestra?*

          I’m unclear whether a true CTJ talk has been had with dad though.

          From the letter it sounds like LW more wants to focus on HR and learning to take over finance. Dad may not yet see that as full time work, hence my suggestion of going part time and focusing on just that stuff.

          1. Mr. Shark*

            That’s what I was thinking. I think the LW should sit down, outline exactly what she wants her job to be, outline if she needs to hire someone to take care of the office manager type job duties (since they already have a new PM), and then sit down with dad/brother and lay it all out.
            Tell them specifically, this is what I NEED in order to stay here, or I’m going to have to leave for different opportunities.
            Like you said, I’m not sure if it’s been a hard and fast CTJ meeting, where there is specific consequence if they say no.
            If they agree, and then it doesn’t happen, the LW can leave in 6 months if they want, with no hesitation that they have given every chance for the family to respond and meet their commitments to the LW.

    2. Tara*

      I was going to suggest this, but for a longer time. Say that you’re passionate about the business but feel that you need to learn other ways of working, and learn from experts. Apply for roles in the areas you’d like to be more involved with and see how you go there. Maybe 2-5 years away and you’ll feel you’ve grown, and will be separate enough to go back and negotiate what you actually want in a role? This is assuming you would like to takeover, which is probably something be able to make a better judgment call on with some time apart.

    3. Glitsy Gus*

      This occurred to me as well. You talked about wanting to get more financial training and that the CFO type stuff was really interesting for you. What if you took a leave of absence and went back for your MBA/Finance degree? That way, you get the step back you’re looking for,but you can also keep going down the path that you really enjoyed.

      Sure, things may be really different at your dad’s company when you finish and it still may not be the best place for you, or they may have found someone else, or whatever, but if you can see it more as a “temporary pause” rather than a full on walk-away that may help put things in perspective for both you and your dad.

      1. mf*

        I like this idea a lot. If the OP does decide that construction (or the family business) is not for her, some kind of MBA or Finance degree would help her pivot to a new career in the future.

    4. Working Hypothesis*

      I came here to suggest this. LW, why shouldn’t you tell your dad that you need some time away from the business to figure out for sure whether construction is for you or not, and that you’re planning to go get another job for a year and then reevaluate after that, if that’s okay with him? (You can still go get another job if it’s NOT okay with him, to be clear — you just might not be able to come back. But you’ve said you don’t expect a bad reaction from your dad or brother, and anyway, if you do leave and they don’t let you return, you’re in no worse shape than if you just quit permanently in the first place… which is what you want to do anyway right now!)

      Hopefully, a year away will give you enough distance to know for sure whether you are thriving outside of the family business and never want to go back; or that you miss it and really do want to return; or that you think you want to go back but you’ll need to negotiate specific changes in order to be able to do so, and what those might be. (I’m skeptical that this last one is going to be viable; they’ve already tried to make changes for you but those changes don’t actually happen. But who knows, in a year and with the leverage of being outside of the building, you might figure out a way to make it stick.)

  3. LW*

    LW: Hah, yeah, I didn’t present any reasons for staying did I? I was so wrapped up in bad. So the good: I have free reign to make changes; I can take on improvement projects at will (hey I’m going to upgrade all conference room technology without asking anyone for permission), I can take any enrichment classes I want, I have a lot of flexibility (helps when your boss is the grandfather or your children). But mostly it seems like running a business that helped a couple dozen people build meaningful lives, have good careers, save for retirement, sends some kids through college, go on memorable vacations, and generally lead good lives… that seems like a career worth pursuing… that’s all the good. But I still don’t know that any of it would change Alison’s advice.

    1. Reba*

      You have free rein with some tasks, but not to shape the bulk of your work, right? Not the parts that are most important to you. I don’t think your relatives are doing this to you on purpose, but it seems like a Lucy-and-the-football situation to me. They keep telling you you can change your work, do strategic work, whatever, and there is no follow through.

    2. MissGirl*

      Maybe I’m wrong but I wonder if part of the problem is you’re the daughter. My dad brought in my brothers to his construction company but never brought me in (which did work out better because family business).

      It sounds like they’re giving you the nuts and bolts jobs but nothing with any real teeth. What was the point of that strategic weekend? Are you a default project/office manager but will never have a leadership role?

      1. Who is the asshole*

        Yeah I gotta say, something similar went through my head while reading. If this was not a family business it would sound like one of those jobs where a woman is allowed to keep everything running in an expertly fashion, but never gets the chance to really advance.
        It’s not entirely equivalent, as you are doing project management which in some places is quite a sought-after role. But if you’re trying to get into strategy/management and you’re only allowed to be the hyper-competent office manager/HR/IT, but never take over or change the “meat” of the business… something’s going wrong.

        I’m fully prepared to believe that there’s no ill intent behind it, maybe also a good heaping of people not being able to let go. But…

        You sound like it would be a major relief to stop pushing this boulder up this particular hill, so why not apply to jobs that would allow you to get this management experience in a less emotionally fraught environment?

      2. No Ragrets*

        This. LW, I hate to say it, but I guessed you were female way before reading that part of the letter. I’m sure your dad is wonderful, but probably has some ingrained sexist attitudes he may not even be aware of, and that is shaping your role. You’re doing part-duty as the office admin, picking up the slack, and “allowed” to take on strategic projects that never produce any results. You’re working hard to advance on a dead end street.

    3. LTL*

      Pros and cons lists are all well and good but at the end of the day the question is are you happy in this job. Even with the good, it doesn’t sound like you are. Is there anything on the pros list that you could never give up? If so, can those items be found in other jobs?

      It’s worth job hunting and if you get any bites, you’ll have something more concrete to compare your current job against.

    4. Venus*

      Don’t worry about having left out most of the positive. You make it clear that your father is a good person, and therefore there must be many good reasons to stay. As you say, I don’t think it changes the problems.

    5. Where’s the Orchestra?*

      You said your dad is normally really good about flexibility – what about asking if you can go part-time, without any project management on your plate? From reading your letter it seems that what you really don’t like is managing projects – but you are always there for dad to “give” the project to because it needs done. Would going part time (like while kids are in school working) help make you less available for the projects so better able to focus on the parts of the job that you still enjoy?

      1. Green great dragon*

        I was going to say something similar – it sounds like you’re done, but if not, what would the job have to look like to make you really want to stay – that is concrete things now, not your Dad stepping back/handing over responsibility which doesn’t sound like it’s going to happen soon, whatever they say? What hours? Is it just the project management you want to get rid of, or do you want someone else to pick up the office management, or the accounting, or everything except *x*?

      2. Temperance*

        If she passes on the project management, she’ll just inherit more BS admin tasks. I think she needs to make it super clear that she wants to step up, these are what she wants to do, she’s been wroking towards it, and if not, she’ll look elsewhere.

      3. Artemesia*

        She has already made clear she wants to be CFO and they have ignored that. Is it really a great idea to do only the scut work and not project management. If Dad can’t hear ‘I don’t want to do PM ‘ and he keeps piling that on — how will this work?

      4. e271828*

        There is no way LW would actually be allowed to be part-time. There would always be Something calling them in.

    6. anonymouse*

      Those are good things you can find at another place, considering your skills, education and experience. And they will come with the added bonus of NOT asking you to bring ice to the family bbq.

      1. Keymaster of Gozer*

        Seconded. Okay I’m in a different industry (IT in an engineering firm) but I’d be interested in someone who’s shown considerable ability to handle use about anything thrown at them/likes learning new skills/etc.

        And while I can’t influence anything outside of IT in my area (and don’t want to) I’m pretty much given a lot of trust in HOW I go about it. So long as I don’t violate HR rules/try to purchase million quid worth of software in one go etc.

        The jobs with the freedom exist. With the added benefit my husband/family never gets to see ‘Work Keymaster’.

      2. Small Medium at Large*

        OP, maybe I’m missing where you say it, but it sounds like the options you’re considering are 1) work at this family business or 2) stop working all together. But you sound very employable. Is there a reason that you’re not considering the option of applying for other jobs where you wouldn’t have the family dynamics and you could move into the things you want to do more of and out of the PM work you’re less interested in?

    7. Person from the Resume*

      I’m surprised at Alison’s answer.

      I guess I’m a risk adverse person. And I could tell from your letter that there’s some parts of the job you like.

      I’d suggest you figure out what’s your breaking point. What do you need to change in your duties to stay on and be happy? And then schedule a meeting with your dad and tell him if things don’t change you will leave. You have to prepared to leave. Is it a possibility that you take over as the big boss for your dad who is a “great project manage” but not a great manager or strategic planner.

      I suspect while you continue to be disappointed that the job isn’t what you hoped, I am doubtful you have conveyed had badly you’re disappointed. I think your father doesn’t actually understand how near the breaking point you are. And that the field of construction isn’t the problem, but rather his mismanagement of your duties. Have you ever really pushed back and said “Dad, I can’t be the PM for this new project because I’m already doing all this non-PM stuff. Overwhelm another PM employee for a change because all the non-PM duties take all of of my time and attention”

      1. BPT*

        I’m going to agree with this – maybe you just didn’t mention this in your letter, LW, but have you actually had a sit down talk with your father saying “I need XYZ to stay in this job, and even though we’ve agreed on that many times before, it hasn’t happened. I need you to decide if you would like me to take over those roles now, or if you’ve decide you aren’t going to prioritize me moving into that role, and would rather I leave and find other work.”

        I know you’ve had a lot of conversations with your father, but have you 1) had a real in depth conversation saying that if certain things don’t happen, you will have to leave, and that 2) it isn’t you deciding to leave, it is him deciding that he doesn’t want you to do the job he promised, and so is making the decision that you should look for other work? If you haven’t had a real “face the facts” meeting where you lay out the repercussions of his decisions, I would do so. And I would definitely lay it out like that – you are interested in the role he has promised you. If he has changed his mind or won’t move forward with concrete ways to get you into that role, he has chosen to put you in a position where you have to leave. Put the onus on him and make it clear that you want to stay, but his choices decide whether you will be able to.

        1. Where’s the Orchestra?*

          I think this is valid as well. Have you ever really sat down and kept it strictly work roles and told him what you need to make the job work both now and in the future? It may be worth explicitly having that conversation with the boss.

        2. Troutwaxer*

          I was about to post a very similar response. You need to tell your dad “All this project management is keeping me from learning what I need to really take the reins. The project management goes or I go. Dad, you need to pick one or the other. Me without project management, or me going elsewhere.”

          And whoever wrote “Lucy and the football” above is genius, so I’d use that as part of your communication strategy.

        3. RebelwithMouseyHair*

          Yes, the bit where she nearly said she was done, kind of came across as a moment when she could have had that conversation, but bit her lip instead because she was too mad to be able to speak calmly about what she wants.
          Then again, I get the impression that she made it clear what she wanted at the retreat. Maybe everyone was just humouring her “OP thinks we should go and meditate in the forest and brainstorm how she’s going to take over the company” “OK well so long as there’s wifi, so we can still direct operations”.
          I do wonder whether Dad just can’t let go of his baby… and whether he thinks a girl just can’t cut it as CEO of a construction company.

          (I know this is a grown woman and all, I’m calling her a girl looking through her father’s eyes as it were)

        4. Myrin*

          I wanted to comment something similar but you’ve already said it so perfectly that I’m just going to give this a big thumbs up!

        5. Malarkey01*

          Perfectly said and was going to be my advice. It sounds like you have a solid family business which will be yours, like the eventual work, and not sure the ages here but dad might be thinking retirement semi-soon, and they sound nice non abusive. My last step would be that very clear conversation that you are leaving if xyz accompanied by specific time lines and action plans. If that doesn’t work- you were leaving anyway. However if it hasn’t been clear to your dad yet (and sometimes parents don’t listen to kids in the same way non family does or we can’t be as blunt) this will be a chance to save the job and eventual company for you.

        6. Quinalla*

          Yeah, it seems like he thinks you maybe just don’t like the construction industry anymore – but it doesn’t sound to me like that is it AT ALL. You want to move into a real leadership role, but you haven’t as it is all too easy for your Dad to pile on tasks to you and all to difficult for you to say no. I’d sit down and figure out a plan for offloading tasks from your plate (do you need to hire an admin and another PM? Maybe just the PM?) Maybe it is a 6 month to 2 year plan where you hire and train 2 (or more if needed) people to take on most of the work you do now so you can step into the work you need to be doing more of.

          And talk to your Dad about truly starting to turn over the business to you – it doesn’t have to be all at once, my Dad is a dentist who did a very slow transition from Boss with a dentist under him, to give him more responsibility, to making him a full partner, eventually Dad became the underling, less and less hours and now is going to retire next year. But if your Dad wants to put his company in the best shape to survive him, he has to have a REAL plan to transition out. It can be flexible, long term, etc. but it sounds like he is not really transitioning anything important to you anymore. Succession planning is HUGELY important and your meeting you set up to make you a real CFO sounded like a great idea that immediately fizzled out when urgent things popped up. That stuff is going to keep popping up, so you need a plan to deal with it – new PM/admin staff, someone on staff takes X if it comes in, etc.

        7. LilyP*

          Yeah I think one more come-to-jesus attempt is worthwhile. But if you’re going to stay I really think part of the agreement *must* be taking you off this latest project *immediately*. Not “in a few months”, not “once we get a new PM trained”, not “oh just handle this one last project”, but like, within the next two weeks. What would happen if you gave two-week notice or got hit by a bus? Time to roll that plan out (or let that lack-of-plan unfold and be your dad’s problem) (or actually give two weeks notice!). At some point they have to get used to not having you as a PM so just rip the band-aid off while this project is still young.

      2. EAM*

        I agree with this also. I am wondering if you have ever laid out everything to your father…bluntly. Have you sat him down and explained everything like you did in your letter? If you have and nothing has changed, then I agree with Alison that it is time to move on.
        However, if you have not told your father exactly how you feel or turned down being a PM for another job…I suggest doing that and maybe consider a leave of absence for a while.
        What would happen if you said that you cannot take on another PM job? That you just don’t have the time?

      3. Almost Empty Nester*

        Came here to say that as well. Not sure she’s actually truthfully laid it out for her dad that “if these things don’t change, I’m going to need to leave because this REALLY is not what I want from my career”. He’s already noticed she’s checking out..she needs to use that as an opportunity to have a really frank discussion with him.

    8. mlem*

      You say, “it’s an ethical company that supports real careers and puts its employees first”. Aren’t you an employee? In what you described, I don’t see any putting of *you* and your career over the ease of just dumping ever more tasks on you. Maybe they’ve said they will, but … why hasn’t it happened?

      1. KHB*

        I mean, “not moving into the C-suite” doesn’t necessarily mean “not being supported in having a real career.” There’s not very much in the letter to suggest that LW is being particularly oppressed, especially when you compare it to how she’d be treated at any company not run by her father.

    9. Midwest Manager*

      You said in your letter that the company does right by its employees and is career-supportive. But that hasn’t been the case for you, it seems.

      Since you just hired a new PM, give them the projects you have on your plate and tell Dear ol’ Dad that you can’t accept any others for the next 6 months – so you can focus on these other areas that need your attention. Once they get used to not handing you any new projects, it will be easier to stay out of future projects down the line.

    10. Nanani*

      What’s the real timeline like for a) your dad retiring and b) you being able to actually get a job that isn’t for your dad?

      If you would need to spend years at a low level job in a non-family company before getting anywhere near the work you want to do, where is the breaking point where that makes sense vs waiting for your dad to let go of more work?

      Put real numbers down and see how that affects your feelings.

    11. carlie*

      Have you laid it all, out as clearly for your dad as you did here? To me it reads that you keep asking for more responsibility, but he’s not taking it seriously or noticing that what he is assigning is taking away from what you want. Or he isn’t convinced that you are ready. And he’s trying to be understanding if you don’t want to stay. He might respond better if he realizes how much you want it and how important it is to you. Maybe he gives you the other responsibilities. Maybe you both set up a plan where you go gain more experience elsewhere but then come back to the family business. There might be more options than just stay as is or go.

    12. Can Can Cannot*

      I get the sense that your father is exposing you to all aspects of the company, setting you up to take over. But right now it is overwhelming. But that’s part of owning and running a business — it can get overwhelming. If your dad passed away tomorrow, would you be able to run the business? Is your current work setting you up to be able to run the business? Assuming you are open to running the business, going through this pain today might be necessary. Sure, talk to your dad to see if it can be made less overwhelming in the short term, but if you want this to be your business you will need to accept the pressures of running a business.

    13. Cant remember my old name*

      Quick and simply question. Can you delegate? Can you hire someone to whom you can delegate? This seem like an alignment and a woke load problem, so is there any initiative you can take to realign the tasks that fall under your direct purview and reduce your workload?

    14. Family Business Gal*

      Those are good positives! I think Allison’s advice is predicated on your statement that you don’t like the work anymore, and that you’ve tried as best you can to get the position/work that you want (and that you have been promised!). But it seems to me that you would enjoy the work again if you had the role you want. And, as someone who has worked in her family’s business in a similar capacity, I’m not sure you’ve actually tried as best you can here. How forceful have you been in pushing back against work that shouldn’t be yours?

      For example, what did you say to your dad when he gave you this new PM assignment? Did you say, “No, I won’t do that. We just discussed our planning goals two months ago, and we agreed to move all PM work off of my plate. That’s why we hired a new PM.”? How have you pushed back against the administrative work that is below your level? Have you explicitly said that you will quit if this remains the status quo?

      You have a LOT of leeway to push back and be very direct (even with a parent that has fired, or WOULD fire, their kid — at least in my experience). So, if you HAVE done all of that, then I agree with Alison – leave!! But if you haven’t, I really think it’s worth trying.

    15. Gertrude*

      Has your Dad done any type of succession planning with an accountant / lawyer / banker / personal banker? What’s your Dad’s exit strategy? Sell? Turn over shares to you as a majority owner? I think this is a strategic dialogue that the C-suite and you as his daughter need to be on the same page about.

      I think this question has a bunch of layers: (1) what are your Dad’s plans for the company, (2) what are his specific plans for you, (3) has his history shown that he will follow thru on those plans, and (4) what are your plans/goals for your career. I see lots of family owned businesses run different ways. You know your Dad best and what life will be like with him at the company. I think coming at it from a strategic standpoint of what are his plans for the company is the best place to see if those plans and your plans align.

    16. Tussy*

      When I was in a comparable (but not exactly the same) situation, the best advice I got was from my psychologist who said that I needed to make sure I knew what the leaving point would be and stick to that.

    17. Wombats and Tequila*

      What if you asked your Dad to hire an administrator/office manager to take on stuff like organizing events and upgrading the conference room so that you could do higher level stuff?

    18. Spero*

      Have you gone back to your dad and said, “when you asked me if I was over working in construction I think you’re taking the wrong impression from the concerns I’ve raised. I’m not over working in construction, I’m over working for a company without a defined role. I would work in another construction company that gave me (positives list, clarity of role etc) any day. I wouldn’t work in a company of (list whatever industry he thinks you’re dreaming of) that did (list the problematic management behaviors you’ve highlighted) for a year, much less as long as (list length of time he’s been jerking you back and forth). The only reason I’ve stayed despite (management actions) has been my love for this company and you as my family.”

      Think of it like, you said “I don’t like having cake thrown in my face” and what he heard is “switch to throwing pie in her face” not “cake is great but with a fork please.”

    19. PuzzleObsession*

      What I would suggest is giving your dad this letter, or saying what is in this letter in a direct manner.
      I had some really conflicting views with my dad over my career. It’s not that I would have worked for him, as we’ve got an anti-nepotism stance that has worked well for our family. However, for years my dad could not understand why I would want to go into a field (science) completely different than everyone else in the family, who all run businesses/function as their own bosses. My dad has been encouraging all along, but still tried to sway me with ideas. I thought I had told him as directly as possible. But I hadn’t just come out and said, “dad, when you say X it affects me A, B, C. This is what I’m doing.” So I did that and we had a CTJ. Now, I understand where he’s coming from (he comes up with 500 new ideas before he brushes his teeth)….but he’s completely understanding and keeps the ideas to himself.
      However, if you think this is not a ‘communication’ issue but instead a ‘not wanting to hand over the reins and trust you’ issue, then this won’t help.

  4. ThatGirl*

    You said it yourself, LW: it’s just a business. It’s not actually a family member. I know it can feel more emotionally fraught when family is involved, but truly, family business get sold all the time.

    My father in law owns a construction-adjacent business that’s been in my husband’s family – handed down father to son – for over 100 years. My FIL transformed it from a local shop to a regional power player that’s doing very well. My husband is the oldest son; he has two younger brothers. None of them are interested in taking the business over. They all have different passions and career paths. And it’s fine. My FIL will retire soon, he’ll likely sell the business, and the earth will keep moving. I think my husband’s had a little tiny bit of guilt that it won’t stay in the family, but he also recognizes that he is not the right person to keep things going, and his dad has never once made him feel bad about it – quite the opposite, he’s proud of his sons’ successes in other fields.

  5. Manchmal*

    OP, you left before and came back. That might be an option later, too! When it comes time for your dad to sell, perhaps you and your sibling may decide to buy him out. You may not need to be actively working there between now and then or that to be an option. It may be beneficial for you to gain other experience elsewhere that could help you run the business down the road. Leaving now may not mean shutting the door forever.

  6. Aneurin*

    ” I love that it’s an ethical company that supports real careers and puts its employees first.” Except… you’re also an employee of this company, and it’s not putting you first, or supporting your career. And it doesn’t sound like that’s likely to change, either.

  7. AvonLady Barksdale*

    LW, you are in a great position for a break and a reset! You have experience and transferable skills and a good financial cushion– take a break! I’m so risk-averse I might talk to dad about a leave of absence, but you can also just…quit. Take time for yourself and your immediate family. Go to school or hire a career coach and figure out what gives you the most satisfaction.

    But again: you have skills. You can use them somewhere else, in a different capacity. You have the support to do so, even from the family you’re “leaving.” Go without reservations!

    1. Jaybeetee*

      A leave of absence might be a thought, if LW doesn’t quite want to pull the trigger on leaving outright. It would give LW a chance to breathe, and if her work gets parceled out, it might finally hit her father between the eyes that the job at present isn’t sustainable.

      1. Where’s the Orchestra?*

        That’s a very valid point. I wonder if through the course of time there’s just been so much creep that dad doesn’t realize how much OP is actually doing or what anymore.

        1. Maggie*

          A leave of absence could be just the ticket because the company would have to find replacements for all the different aspects she’s doing (HR, IT, etc.). Once those are managed another way, she wouldn’t necessarily have to pick those aspects back up upon return, which could make all the difference in the world.

  8. Exhausted Trope*

    Wow, what an incredible letter! Interesting problem. OP, it sounds like you have done everything in your power to define your role and to move it in the right direction. Your father isn’t taking your concerns seriously. He’s said things will change and they don’t. I agree with Alison that it’s time for you to fly.
    You mentioned that you have a younger brother. I wonder if you’re being strung along just until he takes over? Just putting that out there.

    1. MMMMMmmmmMMM*

      I wondered this too, sadly. Since OP is a woman, I wondered is small misogynistic things are at play.

  9. Amber Rose*

    If you’ll let me read between the lines a little bit (and I’m sorry if I’m off base) I think what you actually seem to be asking is: Is it a betrayal to leave? If I feel bad/guilty about leaving, does that mean I shouldn’t leave?

    The answer is no. It’s OK to leave! It’s also OK and perfectly normal to grieve that choice even if it’s the right one. That’s your family’s business, a source of great pride and effort and 10 years of your life. 10 years is a big chunk of your life to have invested in it. But sunk cost fallacy aside, if you turn around and walk away now, it’s not because you’re throwing away 10 years and it’s not because you’re throwing away what you’ve worked for. All the skills you’ve learned, all the accomplishments, all the good days, those all still have a lot of meaning and you’ll carry them with you to wherever or whatever you do next.

    Something doesn’t have to last forever to be important.

  10. Red Wine Mom*

    I noticed that you had a strategic planning retreat, and made decisions about changes that would happen. But, was there a plan and pathway for this to happen (including times and phases for things to occur)? I am not a specialist in this in any way, but bringing in a change manager that focuses on family businesses might help move this along, and help your family make decisions that make sense. (One of my friends does this, and she specializes in females moving into the lead role from a traditionally male-dominated, family business. I would think she is not the only one who does this.)
    Good luck with whatever you decide.

    1. Snailing*

      This is a fabulous idea if finances can support it – bring in an external advisor just for a short time to help move this along and it could really be your dream job!

      All of us know, in work and at home and in our lives in general, we get so used to the status quo. We talk about all the things in our lives, work habits, home habits that we want to make better, but we just fall back on what we know – for your dad, that’s you doing PM work. And you accept it because it needs to be done. Talk to him about bringing in a change manager that really know what they’re doing. It will either be the final push you all need to make this happen, or it will be extra clear that you dad and other decision makers are more happy with the status quo, giving you more peace of mind to leave and find a more fulfilling job.

    2. JuniorB*

      I agree completely with engaging a consultant who specializes in management transitions within family-owned businesses. That consultant would discuss with each family member, together and separate, and develop check-ins and milestones.

      I’d want to know how old is Dad, and what is his timetable to retire (or at least relinquish the reins).

    3. KHB*

      I like this idea as well. It sounds to me like Dad isn’t consciously ignoring LW’s wishes or scuttling her plans, but that he doesn’t know how to go from saying “LW is going to become CFO” to actually making that happen. I was thinking of sitting down and putting together a timeline (“As of X date, LW now longer has any PM responsibilities; as of Y date, she’s going to enroll in Z financial class…”), but if there are consultants that specialize in exactly this kind of thing, that’s even better.

      Inertia is such a powerful force in family dynamics. It can be so hard for parents to go from seeing their offspring as subordinates to seeing them as equals. (I’m 43 and my brother’s 40, and our parents still call us “kiddos.”) In a business setting, it must be even harder.

    4. PuzzleObsession*

      Amazing idea! I completely agree. By finding out if your dad is even willing to entertain the idea and talk to a consultant, it may help clarify things also.

  11. LTL*

    I’m not sure if this is a concern (I might be misreading the letter), but it’s worth noting that your career up til now won’t go to waste if you leave the company. Your work experience and skills sound like they would be good assets in a job hunt.

    1. Lily Rowan*

      AND maybe going elsewhere to build the skills she wants to use in the family business will be valuable to the family business down the road. She could leave now and still take over the business when the time comes.

    2. Rachel*

      Completely agree! OP, you would be a stellar hire for someone building a business – you know a little bit of everything and can get things done, and are eager to learn new fields and take on responsibility.

      Maybe part of the leave of absence everyone is suggesting (and I support!) could be doing some part time consulting or volunteering with a startup so you can fully realize all the ways you are experienced, and see how much value others see in you that your father takes for granted.

  12. SentientAmoeba*

    OP Have you sat down and been clear to your Dad about how burnt out you are? Because it doesn’t sound like you’ve had that talk, just kind of danced around it or only said something when you backed into a corner.
    What would happen if your company turned down a client because they didn’t have a PM to manage it instead of you sucking up and doing it? The company isn’t going to go out of business right?
    As Allison said, how would you deal with this if it wasn’t a family business?

  13. Snarkus Aurelius*

    I’m the youngest and a woman in a very sexist, patriarchal family. I intentionally didn’t take up my family’s business because I knew I’d never, ever be taken seriously.

    Furthermore, my parents have said over and over again that they want to pass on the business, but it also never comes to fruition. They say they want to let go, but when my siblings and I try to set up and take over, they’ll do something to undermine it. My dad will call a management firm and undo the deal we just made or he’ll call customers and claim we weren’t authorized to do what we were supposed to. He intentionally causes chaos and confusion over the business he started. My mom has cried, begging me to take over, and I’ll remind her that’s not what they want. They’ve had plenty of opportunities to give it up, but she stands idly by while he causes problems. So nope.

    Plus no matter how much I know or can do, I’ll always be the youngest. I’m still a five year old, tripping over my shoelaces and being bullied in school. My family will never, ever see me differently even though I’ve made national news with my work. That’s fine! It can be left in my brother’s hands. He can deal with the hot mess.

    If you read this website, you’ll see this is a very common theme in family businesses. Parents say they want the next generation to carry on, but they don’t seem to mean that. I’m not sure why.

    Jiro Ono is 95 years old. His sons have been waiting to take over the family’s sushi restaurant, but because he hasn’t stepped down, one of his sons had to start his own restaurant. I suspect Jiro will continue to work until he dies.

    1. LTL*

      I suspect that parents want the family business to be their legacy, carried on by their kids and descendants after they’re gone. But they also don’t want to let go while they’re still here and don’t seem to realize that these two things are at odds with one another.

      1. Snarkus Aurelius*

        This is a great explanation combined with parents not seeing their kids as fully functioning adults.

        I came home under the impression I was going to draft a strategic plan for the next year, but I found out my parents just wanted me to pick up trash and mow the lawn. I was like, “No, I will hire someone to do that. I’m here to talk business with you.” All I got was a lecture about hiring someone because I was too lazy and snotty to do manual labor and I’ll tank the business with excessive expenses.

        Okay then!

        1. Nanani*

          Because free labour is totally not exploitation when it’s demanded of a relative! (read as snarkily as possible)


    2. anonymath*

      Yep, am family-business adjacent and people have a really hard time letting go. Not work stalling your life for.

    3. MassMatt*

      I have known a few friends/family members in the position of supposedly taking over a small business because the founder wants to retire and perpetually seeing that can kicked down the road. One managed to force the issue by holding a retirement party for the owner who had already sold her the business but kept coming in to work, despite deteriorating so badly her work was terrible and driving clients away. Another kept being told they would inherit the business “next year” but the owner would do things like hire staff without telling them and saying “it’s my business, I’ll do whatever I want” when questioned about it. That guy left after several years of such treatment, that was several years ago, and the owner is still lamenting that they “can’t retire”.

      I think when someone founds a business it’s an emotional thing and their identity and self worth is wrapped up in it even more than a typical career, and it’s hard to let go of.

      LW the items that stand out to me is that you are expected to train someone while not managing them, and want to do more strategic planning etc and less mundane work such as ordering computers etc. But have you expressed this in words? You say your dad confronted you about being burnt out and not caring—were you able to make it clear that it’s because you are doing too much x and not enough y? You seem to be saying you are burnt out from doing too much x but your dad seems to think you are burnt out from the industry altogether.

      I doubt suggestions here to go PT a or take a leave of absence will be effective in getting the LW’s job duties to change. Maybe getting an office manager to handle mundane stuff and having it be explicit that this is about freeing up more of your time for managerial/CFO responsibilities will help.

      1. Snarkus Aurelius*

        The last straw for me was when I found out my parents had a hefty offer for their business, and they’d been sitting on that information for A YEAR and didn’t tell me. A year! But my brother knew.

        When I asked my mom how I was supposed to help and advise her when she doesn’t tell me very important things, she said, “I’ll do whatever I want. I don’t report to you. It’s my business, and you’re still my daughter. If I say it’s not your business, it’s not your business.”

        So I quit. She wants her “baby” to come back to family meetings though. I told her I didn’t think those meetings were “my business.”

        1. disconnect*

          “That’s right mom, I’m your daughter, not your employee. Good luck with your business!”

    4. Artemesia*

      I know a family where the son worked for years for a pittance and his family scraped by while Mom and Dad paid themselves well, ‘because this will be yours some day.’ Then they retired and sold the business because ‘we need the money for retirement.’ So there he was at 48 fairly unemployable and without a job. If there isn’t a contract and gradual transfer of the ownership, there is no security in a family business. The patriarch may never retire or may sell the business or may get in a snit and fire the son or daughter who finally stands up for themselves.

  14. anonymouse*

    Did you talk to your brother about scope creep in his position?
    Does he get to do what he signed up for or does he get used as a catch-all for office admin/employee support/technology support, too?
    One last thing to try is talking to him. What works? How does he get to focus on what he wants to do/push back on Dad, without being told “I guess you just don’t like it here.” Does he just not care that these things will fall through? Does he realize your dad will do them, or hire someone to do them if he doesn’t? Or does he think as well, that it’s work that is more suited to you because reasons .
    Or will he tell you, “Yeah, Dad hates/tends to…so I tell him, I need X and then hire/call/delegate myself.
    Might be worth a try. That is, if you want to stay, but on your own (or more your own) terms.
    I’m not saying stay, I’m just suggesting one last ditch effort to assuage your own mixed feelings about leaving.

  15. KHB*

    It struck me that you mentioned the pandemic a couple of times in your letter, even though it doesn’t seem to have much connection to the other specific issues you raise. If it seems to you like any significant part of what you’re feeling is related to how things right now are still very much Not Normal, it might not hurt to sit tight for a couple of months and revisit how you’re feeling later. The pandemic is going to end eventually.

  16. The Starsong Princess*

    What would happen if you said no? No, Dad, I’m not managing this project as it’s not what we agreed. I’m going to do the work we agreed. Dad will have to figure it out, he’s the boss. Your dad doesn’t treat his other employees like this – just you. If he threatens to fire you, say ok but you are still not doing two jobs. See what happens if you start insisting he keeps his end of the bargain.

    1. Brigitha*

      This is exactly what I’m wondering. It’s great to make plans, but in order to re-train people away from dumping all the extras on you, you’re going to have to enforce and then re-enforce boundaries for a while before things start running how you’d like. I’m super curious what those conversations are like and if you feel comfortable putting your foot down.

    2. Little Pig*

      I have the same thought. Could OP have just turned down the latest project?
      This smells like OP has trouble making and enforcing boundaries. It’s hard in the best of cases, and extra hard when family is mixed in. Working in a different environment, where the boss isn’t also your dad, might be helpful in learning how to draw boundaries professionally.

  17. Jaybeetee*

    One thing I’m curious about, is it sounds like you have a decent amount of authority/flexibility/control over projects – if your dad is bad at delegating, are you in a position to be able to do so? Can you decide to pass project management tasks to other people?

    My comments are not intended to convince you to stay if you don’t want to stay. But if you’re torn, it might be worth mulling over some possible solutions to the problems.

  18. Forrest*

    >> it’s an ethical company that supports real careers

    Except yours!

    >>I kind of tried to explain everything above

    Is this “kind of tried” because you’ve explained it lots of times before, and none of it ever stuck, so you’re burned out on trying to explain? Is it because it’s really hard to explain this stuff to your dad? Is it because you know you’re not super happy but this letter is the first time you’ve articulated it?

    I’m not clear on whether you’ve had this frank, “I am considering leaving the business unless XYZ happens” conversation with your dad. If you’ve gone past that point, that’s absolutely fine! You get to decide when you quit, and you don’t owe them that conversation. But given how much you care about the business, do you want to do that? Do you want to arrange a meeting with the CEO and the CFO, lay out, “We specifically agreed that I was going to be transitioning away from PM and towards CFO. That hasn’t happened, which is why I’m reconsidering my position in the company”?

    You are allowed to leave without doing this, but you’re also allowed to address this head-on, and make sure you’ve got all the information you need before you make a big decision!

    1. MassMatt*

      I’m wondering what “kind of tried” means also. Too often people think they are being clear about what they want and when pressed, it turns out they never said anything explicitly at all. Sighs, eye rolls, passive-aggressive comments, shifting body weight, interpretive dance—these are not effective ways to communicate, especially in a difficult conversation.

    2. Purple Jello*

      Exactly! You need to decide what needs to happen for you to want to stay. You need to clearly articulate that, and give them a timeframe for it to happen. If it’s already too late, or they can’t or won’t agree to your terms, well there’s your answer.

  19. anonymath*

    Maybe it would also work to leave for now — and consider buying out your dad, or something like that, when he’s really ready to let go. Sometimes it’s better to go sharpen your skills elsewhere and be able to return as the hero rather than continue as the one who does the glue work who keeps things together (and thus isn’t as glorious). It’s not fair at all, but coming in with shiny unknown potential can be more compelling to people than being a known quantity who people know does good work.

    Good luck, in any case!

    1. Kiki*

      I also wanted to come in and mention the concept of glue work and note the gendered aspect of this. I think it’s a relatively common phenomenon that women end up picking up a lot of work that would otherwise fall instead of having clear boundaries in their role. I feel like folks who end up in these sorts of catch-all positions are more prone to burnout as well because there it’s impossible to be fully “done” at your job because there will always be something new to drop. It’s also really difficult to get the proper appreciation for your work and feel like your career can truly grow– your role is just always expanding and ultimately you end up stretching yourself so thin things break through. And then you are held accountable for those breaks but folks don’t think to remember you really shouldn’t have been stretching to catch those things in the first place.

      Here’s an article about glue work that is directly about software engineering but really applies to everything:

  20. The Crowening*

    If you really just aren’t enjoying it and can’t realistically see a way to make sticking around feel worth it, from a professional satisfaction standpoint, and it’s just the warm feelings/pride and family connections giving you pause, you can try framing it something like this: I have loved working alongside family in this business that takes so much pride in its quality of work and its quality as an employer; I can be grateful to have been able to enjoy the parts I’ve really enjoyed; and I can continue to be proud and supportive even if I am no longer there.

    And if a leave of absence is something that interests you, with the door still propped open, give that a try. But if you do decide to leave, and focus on some of those other things you mentioned – causes you believe in, being more available for kids’ needs, etc. – those are warm-fuzzy reasons to leave. Couple those reasons with “this has been a really hard decision because I believe so strongly in this company and have so enjoyed my time here” etc., and that’s a very positive way to frame your departure.

  21. Marcy Marketer*

    I see both sides of things… as a family business/small business, sometimes you have to do the unglamorous ad hoc jobs. You can’t ask regular employees to give their heart and soul for the business because it isn’t their business… it’s yours! It can’t be all strategy all the time. How many years did your dad PM while trying to move the business forward? Is he still PMing?

    And also, your dad is still here, and he still wants to work full time right? So if you managed the project managers, what would he do? Is there a role for him that would be meaningful while still allowing you to increase your scope?

    At my job, not for my dad (he sold his business cause neither child wanted it), everyone wants to do strategy. No one wants to do the work. There are very few companies where they can afford to have someone just do strategy, and for those jobs that can afford it, the people who do strategy usually take a long time to see their strategic recommendations make an impact, if they ever do. So I guess I just worry that you wouldn’t be happy anywhere.

    Then again, maybe you want to take over the business, and your dad is dangling that carrot, and he is actually going to have a really hard time letting go of the reins. Maybe! I don’t know him but it didn’t seem like it was at that point from your letter.

    Maybe ask him, just like he asked you. “I’ve talked to you about how I want to change the company’s direction, but I’m getting the sense you’re not fully sold on my ideas. What’s holding you back? What’s worrying you? What do you think wouldn’t work, and why?”

    1. Troutwaxer*

      I was thinking a little more about this, and if your dad is really going to hand you the business you should be shadowing him about 90 percent of the time. Going with him to business lunches and meetings, getting introduced to the regular customers, playing golf (or whatever) with the people he wants to cultivate, etc. You can’t do any of that while you’re PMing.

      1. Artemesia*

        I saw nothing in the letter to suggest that Dad was going to transfer the business to her — and there is a son in the mix who doesn’t appear to be doing AA work. She needs to get things clear with him and do what works for her long term.

    2. MassMatt*

      You are reminding me of the famous “ no one will hire me to be their idea man” letter from a new grad years ago. But I think LW is far more practical than that, it sounds as though there is lots of stuff that she would like to do but she gets stuck training (but not managing!) a new hire, and ordering laptops. This catch-all type of job may come from always being reliable and taking on jobs other people are not able to do, but the danger is carving out a role for yourself that you don’t actually want in the long term.

      I knew someone who was a paralegal and kept the fact that she could type really fast/well a closely held secret. As in, if a document absolutely had to get retyped for a close deadline, she would say “I know someone who can do it” and literally lock herself in a windowless room where no one could see or hear her doing it. She did not want people bringing their typing to her, and understandably so. This was decades ago but no doubt the stereotype of a woman in the office having secretarial duties still lives on today.

      1. Marcy Marketer*

        Lol yes that “idea man” letter is exactly the vibe I was feeling when she was talking so much about strategy. Of course we ALL wish we could do strategy for 90% of our work days with no distractions!

        I went and reread it after reading all the comments worrying she was experiencing gender based discrimination and I definitely caught some additional nuances on that second read.

        I’m also really colored by my own family business experience where my dad (the owner) continued to do HR work and random admin work and accounting work and sales and when a whale of a client came in, he would PM the on boarding of that one, and the website needs redoing so he’s working with the designer…. A lot of stuff that he could just not trust to others/ or that couldn’t be done by others and had to do himself. If he had a trusted child taking on a leadership role in the company and he passed her work he would have done himself but now that she’s here he can share some of the load, to me that’s just how a small business is. But if it’s a situation of her landing all the small fry tasks to stay busy, that’s obviously not great. Or if they’ve talked about her taking specific items off her dads plate that he seems reluctant to let go.

      2. Where’s the Orchestra?*

        From reading the letter it sounded like LW wants to focus on like HR and Finances – and how often have we heard about the dysfunctional small/family businesses that are a mess because of no professional HR or Finance division. It could be the case that dad just doesn’t understand how time consuming and important this stuff is – because he’s slightly more old school construction company.

  22. Alton Brown's Evil Twin*

    This seems like a good time for an outside succession planner (your accountant may be able to recommend someone).

    OP did all the stuff for the strategic retreat, and there was at least a halfhearted plan, so it’s not like OP’s dad is blind to the big picture. But maybe by having a third-party to ‘blame’, you could make it stick next time.

  23. nnn*

    Another factor to throw into the pros and cons list is whether your family might actually be better served if some family members don’t work for the business, thereby providing the family as a whole with a diversity of income streams?

    Obviously this isn’t a deal-maker or deal-breakers (and you’re allowed to make career decisions without having to consider the financial security of your family of origin!), but it is one factor.

  24. JuniorB*

    One topic which may or not be a concern to you: what is the plan to pass on the business, presumably to you and your brother? If you leave, would this affect what your dad leaves to you on his passing? It sounds like your dad wouldn’t hold it over your head. But no matter what, you shouldn’t spend the next two to four decades being frustrated.

  25. ComingUpRoses*

    Worth a mention and consideration – there are some gender dynamics at play here. Gender dynamics + family dynamics = a complex situation. While reading your letter, I guessed within a few sentences that you are a women. It is a sad fact that women take on “unpaid” labor in BOTH home and career. You are on the receiving end of both of those. Even if you are properly paid for your extra duties, they likely fall into “non-promotable tasks.”

    Maybe I am totally off base, but worth considering what your brother’s role looks like? Does he take on extra tasks like you? Is he expected to? Does he feel like you do? Is this apart of a life long dynamic? It’s clear from your letter that you love your dad and your brother, but even loving families can’t escape gender/family dynamics. This may be a hard topic to broach with your dad, but if you are at all interested in sticking it out, I’d sit down with him and lay it out. Good luck! Dads are the best, but sometimes have a hard time letting their daughters grow up :) Even their adult daughters with kids

    1. AndersonDarling*

      I’ve known a handful of people in family businesses and in each case, the “boys” were valued members of the company while the “girls” got fancy titles but were always forced to do office management/HR/secretary work. The sons got leadership roles, while women got empty promises.
      I’d remove the family-business part from the equation and just make my decision based on what would I do if I invested 10 years into a business where I was repeatedly handed empty promises. I would leave, no question.

    2. jenni o*

      this is EXACTLY what I was thinking as well. Gender and family dynamics seem to be in play here. As others have said, setting clear boundaries and scope creep also seem to be an issue. People will do to you what you allow them to unless you tell them otherwise. If after setting boundaries and having clear conversations with your family about what you need to be doing to stay, and nothing changes within 3-6 months, then it is time to move on. It might be they have an epiphany in a year and realize they want you to come back with different responsibilities, or they may not until your dad is ready to retire. Either way, a serious talk is in order.

    3. Dust Bunny*

      My grandfather had a family business. My mom worked there all through her teen years while her brothers’ school sports careers were considered too important to interrupt, but it was her brother who inherited the business when my grandfather’s health started to give out. Her brothers still can’t picture that she knows more about how my grandfather ran it than they do!

      (She did resent that her own sports–she was voted “most athletic” in high school, too–didn’t get the same consideration but, decades later, she’s decided she’s glad she had to opportunity to do so much with her dad, and that he didn’t just give her easy jobs because she was a girl. He did, at least, give her serious work.)

  26. Bananaphone*

    Here’s a PM project for you! NOPE. Not doing it. Give it to the PM you hired. No is a complete answer.

    1. MassMatt*

      Well, the answer may be much more complicated if the person asking/assigning the work is your boss. In most cases, you cannot just say “no” to your employer the way you can some stranger or colleague. In this case maybe there’s an entree given there has been some sort of discussion on a change in her role but in general this is not a case for “no is a complete sentence”.

  27. JelloStapler*

    This is so hard, Mr. Jello is in a family business and has considered leaving a few times due to various issues. Family + work is a difficult mix!

  28. The Man, Becky Lynch*

    The dangerous part is here is that your passion is gone. Without passion, the business will suffer even more than if you leave it.

    It sounds like you need multiple new full time people. Construction has been booming and expanding, so it’s not hard to imagine. You hired the new PM, which is great. It sounds like with the mundane stuff you’re dealing with, you need an office manager or perhaps just another assistant to deal with buying laptops and stuff that’s just cluttering your plate. If you cannot get them to hire some new people, you’re going to keep this mess up. It’s a growing pain and learning curve going on at the same time. So you should take a step back and see what is best for you and in the longer run, the family business.

    It’s all about letting you learn the grittiness but you’re getting lost in the fine details that have to get done day to day, instead of the scope of the entire company and it’s on going, constantly evolving needs.

  29. Coast East*

    I know a few others have brought up the male dominated industry vs OP being a woman already, but that *is* what sticks out to me here. I hope its not the case for OP but it reminds me of those “saving family restaurant” episodes where the sister takes on all business/financial/HR/legal work and looks like an heir apparent on paper but the family ends up planing on giving the business to the brother because “thats the way its always been done.” Would a sit down with an attorney or planner and actually confirming OP becomes the business leader help with the ambiguity and give everyone a sense of forward momentum/something to work towards? It seems not having confirmation that the business will be passed on as assumed is playing a part in this. Good luck OP!

  30. pingback*

    If you feel like you need to explore a chance of staying, make your dad do succession planning courses. I work for an association in the construction industry and that is a BIG education piece for us. it’s a very common issue in this industry. (not saying you *should* stay… you do what’s right for you)

  31. I edit everything*

    I think you should leave, and build upon the foundation you have from working for your father. You love the strategic stuff, so maybe think about an MBA, or look for a job with another company, in a strategic role. It’s not blowing anything up, it’s just making the next move. And maybe when your dad starts to slow down and finds it necessary to learn to delegate (you don’t say how old he is or how close to retirement), you can go back with all your new experience and knowledge. He will have gotten along without you–he’ll already have enough project managers to handle the work, he’ll be used to not having you there to pick up the small stuff. And it will be easier to set boundaries. If he tries to give you something that’s outside your job, you say “I’m going to hand that off to So-and-So, who’s better positioned to handle it.”

  32. learnedthehardway*

    I think that you would benefit from working with a career coach to help you determine A) what you WANT to do, from a functional perspective, and to B) develop a career plan to get you where you want to go.

    You have good experience, but it sounds like you’re more interested in the financial or HR or general business management aspects of your family’s business than in the project management side. However, you’re not getting to do either the training or the work effort that would help you to progress to taking over that side of the business.

    The question is, though – is that really what you want to be doing, or do you just happen to enjoy it more than project management of construction projects? A career coach can help you figure that out.

    I do think it would make a lot of sense for you to leave the family business – once you figure out exactly what you want to do, and what you need to get there. In fact, I think you NEED to leave the family business for at least a few years – get outside perspective, learn best practices in other companies, focus your career on what interests you.

    You might come back to the family business in future – eg. when the current CFO retires – but if/when you do come back, come back with the experience and credentials to take on the role you want to take, at the level you want to take, and to not get stuck doing construction project management and administrative work that isn’t of interest to you.

  33. Kate*

    I was rather surprised by Alison’s answer!

    This line stood out to me: “But every time I’m close to finishing out my last project, a really great prospect comes up and we don’t have the staff to handle it, so I end up taking it on and I’m back on the hook for another 9-12 months of PM work taking 50% of my time.”

    I read this as, “A great prospect came up, and since no one else can take it, I took it on myself.”

    You’ve mentioned several times that you are flailing, but have you actually said, no? Have you clearly said, no, I will not order laptops, we need to hire someone to do this? No, I will not take on this project, even if it means losing revenue in the short term? This sounds much more like a situation where a company is too busy fire-fighting to stop and realize they need to hire more staff, even if it’s messy in the short term.

    Training and mentoring another PM seems, to me, like a GOOD sign – because once you’ve trained him, your capacity is freed up, exactly like you want it to be!

    1. Mannheim Steamroller*

      Problem is that once OP has trained the new PM, her brother will likely be given the role that she wants.

      1. KHB*

        There’s nothing in the letter to suggest that that’s even a possibility, let alone at all likely. But even if it is, LW may still be able to ward it off through clear and direct communication, as many comments have suggested.

    2. SpecialSpecialist*

      I second this. Have you tried protecting your time/talents and delegating things to other people who are better positioned to handle them?

      Learning how and when to delegate is very hard, but feels sooooo good when you finally grasp it. I had to learn the fast during the pandemic that I couldn’t keep being an individual contributor at the high level I was used to once I became the director of my own department.

      Nothing makes you come across more as a boss and a leader than being able to successfully delegate work to others. It’s not just about getting someone else to do your work. It’s very much about being able to identify the people who can get the work done well.

  34. Mannheim Steamroller*

    [“After getting my degree and working elsewhere for seven years, I came back to the family business and for nearly 10 years have been working my way into more and more of a leadership role.”]

    But your dad refuses to let you fully take on said leadership role. Take that at face value and leave again.

  35. Sparkles McFadden*

    It’s easy to get very attached to jobs/workplaces even if it’s not a family business. The problem here is that you alone cannot change the dynamic, and the same thing will happen over and over again.

    I worked for the same company for three decades but I changed jobs every four years or so because of this exact dynamic. Each boss would dump more and more work on me because I would get it done. Each boss would say “Yes, I know I am giving you extra work and it’s boring, thankless stuff that’s not really your job, but it’s just to get us through this busy time.” Then we’d work out a strategy to stop that from happening and before you know it: “Oh, could you please just do these few extra things to free up Fergus? He seems overwhelmed.” Now…I maybe I could have said no to that stuff but I always figured “It’s work and my job is to take care of the stuff my boss gives me to do” plus I’d get greater compensation for all the extra work. I’d switch jobs when the “compensation commensurate with my extra effort” stopped. Eventually, the boss dumping work on me would consider all of the extra things to be “normal stuff I did” and there was no way to change that perception, so I’d find something else.

    So, LW, I think you need to find something else. You won’t be “Blowing things up.” You’ll just be doing something else that will fit in better with your home life and make you happier. Since it is a family business, you may come back to it in the future in a different point in your life.

  36. Twenty Points for the Copier*

    I don’t know the age/career stage of everyone involved, but it sounds to me like something really common in my industry. The previous generation has picked out their replacement* and thinks they have a succession plan in place, but refuses to step back. Typically, this eventually leads to the so-called successors leaving rather than waiting around 5, 10, 20 more years than planned to step into the role they want and have been promised.

    Since you mention a lot of things you like that have to do with the autonomy of being a decision-maker in a small business and since you feel these are good people, I think you need to sit down and map out the succession, making it clear that if there are not concrete steps (equity ownership path, change in responsibilities, father and CFO stepping back to make room for the next generation), then you’ll need to move elsewhere. If no plan is put in place and changes are not being made (it doesn’t need to go from 0 to 60 all at once, but it needs to start going SOMEWHERE almost immediately), then at moving on.

    *I know a lot of people have mentioned sexism as a reason for this, but I’m taking OP at her word that she is the natural successor and not her brother.

    1. KHB*

      “I don’t know the age/career stage of everyone involved”

      LW says she’s been working for 17 years since she finished college, so that makes her about 39, give or take. So her father is likely somewhere in his 60s or 70s. So it’s definitely not too soon to be formulating a concrete succession plan, even if Dad isn’t ready to step back completely just yet.

    2. RebelwithMouseyHair*

      Yeah, Prince Charles has been waiting his entire life to become King of England, and is likely to wait another 10-15 years more. Maybe that’s worth waiting for. It’s not like there are any more glamorous royal roles. CEO of a family business though? There are millions of businesses out there. Also, leaving to work elsewhere could mean acquiring more skills that you can bring back to the family business once Dad finally steps down.

  37. Professional Merchandiser*

    The advice to decide in your head you’re leaving and then sit on it for a bit is good advice. After listening to me complaining for months about my supervisor and dithering about whether I wanted to keep working, my husband told me to either resign or quit belly aching. (He put it a bit cruder than that, but that’s what he meant.) I thanked him and told him that was good advice and I would think it over. He even suggested a target leave date. This was in April and I mentally decided June 30 would be my last day. I felt so free!! I didn’t tell anyone for about a month, I just sat with the decision so if I changed my mind no harm no foul. Well, I did decide and put in my notice in a timely manner and Wednesday is my last work day.

    1. Sparkles McFadden*

      Sometimes, the end result of looking to see what’s out there is deciding to stay put.

  38. Bird Lady*

    LW, your letter reads to me like you have already made up your mind and know what you want, but are needing some permission or absolution for the guilt you are feeling about leaving. Since there are so few tangible reasons to stay, what is keeping you there? As a perennially guilt ridden person who tends to submerge her own needs and wants “for the greater good,” my advice is to get super real with yourself and write it down on paper – your needs and wants, your must haves and deal breakers. Get clear with what you are willing to do and how long you are willing to do it. What is your bottom line? Make it a promise to yourself and choose a deadline for how long you will continue to work on this, and then share with your father. Ask that he work with you to either finally fix your position or plan an exit strategy within your deadline. Your happiness matters, best of luck. :-)

  39. The_artist_formerly_known_as_Anon-2*

    YES it’s fine to leave a family business.

    Back in the 1960s – my father, law degree and all, was working in his family’s retail business at the urging of his parents. The difference was ……

    THE BUSINESS WAS FAILING. So much so that my parents had to take out a second mortgage – to pump money into the business that was bleeding cash. No money AT ALL in the house. While we lived in a decent home, we rode around in junk cars, couldn’t take vacations, and one week – we had our telephone shut off and we ate a canned ham for the duration. Apparently his brothers/parents were operating on “good faith” because the Depression only hit them badly for a year or two, this will turn around, right? NO — American retail was changing, rapidly –

    Finally Dad put his foot down and told his brothers – he was seeking a new career (education) and he was giving his brothers ONE YEAR and that’s it. And in doing so he was putting us – my mother, sister, and me AHEAD of the extended family. Before the year was up – his brothers decided to close the business – go out of business. After that—

    – Dad was a happy guy, no longer an ogre – at age 43.
    – We knew how much money was going to come into the house, we could manage
    – he had a new career, with an upward path
    – We went from driving rolling junk to late-model used cars
    – It transformed him, and all of us.
    – I also had a happy life going forward, without those complications.

    He also came to the realization that I was not “prep school” material bound for Ivy League – but I’d do jes’ fine in a public high school (which I enjoyed vey much and was the greatest thing that happened to me at that time) and other colleges… it all worked for all of us. And two of his three brothers found success in the same line of business on their own — one did not but his wife had enough income so he didn’t live badly.

    Had he stayed in that store – it would have killed him. He retired as a school principal and administrator at the age of 65 and enjoyed a 30 year retirement , and had an antiques and collectables business until his passing four years ago at 95.

    I choose not to imagine what would have happened to all of us if he rode out the retail store until bankruptcy took it down.

    LW shouldn’t make/take this decision lightly – but it’s HIS life – you only have one trip on this ball that goes ’round the sun, and lives lived for other people can be unfulfilling and miserable. There IS an apparent difference between LW’s situation and my Dad’s – his family business is apparently doing well.

    But still – living one’s life for him/herself and immediate family is not something necessarily shameful, or disgraceful.

    1. The_artist_formerly_known_as_Anon-2*

      Or HER family business, as the case might be. Same thing…

  40. Beth*

    At one of my prior employers, the rule of thumb was that if you wanted to move up to a different position, you had to leave the company, work that position somewhere else, and then come back to the first place and re-start at the new, higher level.

    That place was dysfunctional as anything (they claimed to prefer to “hire from within”, but only if the person left and returned, as described). But the actual process can have its advantages. You sound as if you have a killer resume and impressive experience. If you do leave, you might have the option to return at some future point on your own terms, with the clout to make the changes stick.

  41. Aphrodite*

    I am going to read the comments after I post this because while reading the original post I somehow thought the OP was male too. It was only when she noted her gender that I realized the whole reason for it might come down to that one factor. You, OP, the are lone female therefore you get the more female-ish jobs in addition to the other ones. I suspect this is all unconscious but its “hidden-ness” is the biggest thing holding you back precisely because it is not seen. Your father and your brother have to see it and acknowledge it first, to recognize that it may well lie behind their actions or inactions, and take deliberate, conscious actions to battle it in themselves before anything can change. That, I think, should be the break it-or-leave it factor here. Can they see it? Are they willing to see it? And are they willing to fight to change their own biases?

    1. The_artist_formerly_known_as_Anon-2*

      It might, but that’s presumptuous. The youngest sibling often gets treated as the “kid brother” or “kid sister”… and there’s sometimes no escaping that.

  42. Dancing Otter*

    You said they just hired another project manager, yes? Right now, training that person is an added responsibility on you, but what about once they’re trained? Won’t having another PM mean less PM work for you? Maybe your father IS trying to move you into company management and administration.

    Does the company have any succession plan? A disaster recovery plan? What is the legal structure of the company? Who inherits under your father’s estate plan? If, God forbid, your father had a sudden severe illness or died, who would be in charge? What happens when he wants to retire or cut back or even just take a good, long vacation? It’s not morbid: every company should have contingency plans.
    Knowing some of these plans might influence your decision, I think. Other commenters have mentioned the “X and Son” mindset of some company owners. Do you expect to become the owner or part-owner, or will you end up working for your brother after making the family business your whole career? Would you be content with that?

  43. Phil*

    My family had a business too, founded in the 1890s by my great grandfather and which I was meant to run after my father and grandfather. I, too, never had a school vacation because I had to work and learn the business. As soon as I became an adult I ran as fast as possible as far away as I could-metaphorically, the place I ended up working was half a block from the family business location.
    It was only after serious therapy I learned why I ran.

    1. The_artist_formerly_known_as_Anon-2*

      Yeah, Phil….

      My father was looking out for me, and perhaps my sister, and perhaps my only male cousin — when he got out of the family business. AND he did the right thing then, and for our futures.

  44. anastaziad*

    I didn’t read all the comments, but I have heard of executive coaches that work specifically with family businesses that I think could really help make with making this work for the OP. It’s not nearly as toxic or broken as many family businesses and as long as daddy would be willing to cooperative, they might be able to develop and execute a real succession plan.

  45. goducks*

    The LW says she’s the heir apparent, even on paper. I assume that means in a will or other legal document? If so, she has a lot of leverage here, even more than the leverage she already has by the fact that the boss is her dad, and as she puts it, the grandfather of her children, which means she can spend a lot of capital that the rest of us cannot with our bosses without repercussion. She mentions she has a lot of autonomy within her role, she just doesn’t get the new role she wants. She should expend capital in a few ways, if she wants to stay and take over the business long run, because she can. The rest of us can’t refuse to take on a project and keep our jobs, she probably can. And should. While holding one of her children, if possible.
    It sounds like her dad does actually want her to take over, but in typical fashion of a guy who starts his own business, just is bad at letting go. She needs to remind him point-blank that if she’s to take over one day, he needs to do certain things. He needs to make a formal succession plan, with help from an outsider. He needs to make formal her inheritance of the business, if it’s not already. He needs to get a hobby or other outside interest to start letting him imagine life on the other side, so he doesn’t feel so compelled to hang on tightly and will be more willing to let go. She has all the leverage in the world to insist on this, if her father truly wants her to take over one day. Because she can walk, and his plans will fall apart, and possibly he won’t have the relationship he wants with her. Parents want to make their kids happy, the LW says he is flexible with her because she’s his daughter. I think he will listen.
    Because, I don’t know that the LW will be happy trading the freedoms she has for what the rest of us get. She has eternal job security, provided the business stays afloat. She has the ability to get favors, to speak her mind whenever she wants. She has the long-term ability to do whatever she wants, when the business becomes hers. Walking away from that isn’t just walking away from a job, it’s walking away from a future that can be whatever she wants it to be.
    If she truly doesn’t want to get the business some day, fine, leave, that’s always an option. But if she does want it, and just doesn’t like how it’s going right now, she has a lot of ability to insist on change. Way more than she’d ever have working for someone else.

  46. Librarian in a Library*

    You’ve worked there since you’ve been 14! It can be really helpful to see how things work in other places to get more examples of what to do or not to do. Maybe you’ll come back and run the company someday, maybe not. But being stuck like this is not great for you so go out and see how things are at other places. Good luck!

    1. Cheerfully Polite Grey Rock*

      OP does mention that once they got their degree they worked elsewhere for seven years before returning to the family business, so it sounds like they do at least have some outside experience.
      I agree that the OP should definitely have a very clear talk with her father regarding succession planning, the steps that need to be taken to get there and the timeline this will happen in. If they refuse and just keep dragging their feet, then finding a job elsewhere that involves the skills that OP wants to grow into would likely be a great career move regardless of whether they plan to return to the family business later.

  47. bryeny*

    Alison’s probably not wrong that leaving is your quickest path to a happier working life. But if you want to make another attempt, try floating a plan with dad-boss that will get you where you want to be in the family business. Maybe something like this:

    1. Find and sign up for the first phase of the financial training you were promised, perhaps on a schedule that starts in the fall. (I’m assuming this won’t be a full-time commitment, but if it will be you might have to adjust some of the steps that follow.)
    2. Figure out how much time it will take to train the new PM to take over most of the day-to-day work on your new big project and make that your primary focus.
    3. Prepare your father for the likelihood that the above will mean TURNING DOWN PROJECTS. (Sounds like he might have a hard time doing that — lots of business owners do.) Tell him if he takes on work that significantly interferes with your plan, you’ll start looking for another job. Make sure he understands that you want to stay, but after years of broken promises this is the last chance to keep you. You’re very interested in construction, you’re just not interested in being taken for granted and treated badly.
    4. Hire someone, perhaps an office manager, to take over as much as possible of the HR, accounting, and keeping-the-office-stocked-with-paper-and-laptops work.
    5. Deliver frequent plan updates to your dad. Partly to make sure he understands that this is serious, partly to keep him focused on the desired outcomes.

    The goal is to get enough off your plate that you can devote time to your financial training, serve as a resource/backup for the new PM, supervise the office manager, and still have a life. If dad won’t agree to a plan — this one or a better one — that will get you where you want to be, polish up your resume and start networking. Good luck!

    1. RebelwithMouseyHair*

      I get the impression that the strategic retreat was supposed to perform that function, and it fell through, because Daddy was just humouring his little girl with that lark.

        1. bryeny*

          If she leaves the odds of that go up, but there’s no evidence in the letter that her dad’s planning that now. She says surprisingly little about her brother, in fact — just that he’s younger than she is and he works there too.

  48. Accountress*

    OP, you say it’s a company that puts employees first, but it seems to me you’re coming in last. Talk to your brother, sit down with him and your dad, and ask straight up why you keep getting put off.

  49. Tedious Cat*

    Good luck to you, LW. Your father has been lucky to have you, but he needs to put his money where his mouth is. I hope we will eventually get an update from you, and I hope it will be a happy one regardless of where you end up.

  50. TardyTardis*

    Why do I feel that the brother is the Heir Apparent all along and the LW is/was being taught to be the Perfect Helpmeet Behind the Throne? Maybe I’m repeating something already said, but this is what it smells like to me.

  51. CountryLass*

    I think it would be worth sitting down with Dad, and giving him this letter to read. Maybe he doesn’t realise all of this is going on, or how you are feeling about it.
    Structure the meeting like you did the strategic one you loved doing; get the agenda, bullet points and what-not, and commit to having a plan of action laid out by the end of the meeting, to be actioned within a certain timeframe. And be prepared to be honest with him, and say that if things don’t change, then you will have to seriously consider if this is the right place for you at the moment, and work out what is best for you and your family.

    If you go in there prepared to hand in your notice unless there is a change, you may be surprised at the amount of power that attitude gives you. Work out exactly what it is you want, and when you want it done/started by. If you know that the decisions cannot be made that day, then have another meeting set up before you finish, where the decisions can be made or given.

  52. bopper*

    Another thought is to have a “come to Jesus” meeting with your father.

    Tell him you want to do the strategic side of things but are not getting the opportunities despite being told you would. Your ideal situation would be to be doing strategic work at the family business. But now your apparent choices are be a PM at the family business or look elsewhere for strategic work. You don’t want to be a PM…so what is your father’s plan if you no longer work for the company? Who would be his heir apparent? When would that be?

    Or maybe he may be happy with you working elsewhere for a while and when he really is ready to retire you come back.

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