I've worked for a very small consultancy firm for just over 2.5 years now - I've thoroughly enjoyed working here, and still do. My line manager is the Managing Director who owns the company.

Recently, however, and purely for personal development reasons I've decided to move into self-employed consulting/contracting. It's taken many months to get to that "Right, I'm doing it!" stage, but I'm now at a point where my CV is attracting attention and I'm keeping a very close eye out for the right opportunity.

Now, as is standard practice, I've kept this very much to myself and haven't felt bad doing so because I simply don't know WHEN the time will come. I'm hoping sooner rather than later, but like I say, I still like my job and if it takes months rather than weeks then so be it.

This hasn't been a problem, but my MD messaged me the other day (We're often in different places in the country) and told me he wants to have a meeting with me to discuss my career within the company. Now, in bigger companies these are just paper-shifting exercises and I've never had a problem just cruising through them and saying the right thing, but there are some facts that make me uncomfortable with this:

  • I may leave sooner rather than later, making it very obvious I knew during this discussion
  • I believe my boss actually cares and wouldn't have asked to speak to me otherwise
  • That said, there are no different job opportunities in this company. I can't become more senior and I can't earn anywhere near what I think I can self employed. This is purely to discuss what exactly my current job entails and what things I'd like to be involved in.
  • The company has been very good to me and while looking out for oneself is important, there's a line where it becomes selfishness and being ungrateful
  • My specialism is a small world and the chances of interacting in future are high. Additionally, I really don't want to burn my bridges here and would gladly work with or for them in future.

But I also feel that going in and being truthful won't end well for me at all. At the moment, being conservative with the truth seems to be the lesser of two evils but I wonder if there's a better way that I'm missing?

  • 2
    I took a chance, and told my boss. We agreed a long notice period and I left on great terms and continued to do occasional consultancy for them
    – Dan
    Commented Feb 12, 2020 at 14:27

8 Answers 8


At the moment, being conservative with the truth seems to be the lesser of two evils but I wonder if there's a better way that I'm missing?

Let's review what you have stated:

  • You have already made a mental decision to leave
  • You are planning to become self-employed
  • But you haven't yet decided when to make that move
  • You might leave soon (but then again, you might not)
  • You see no long-term future at your current company
  • Your Managing Director wants to discuss your career within the company

Since you don't have a definite date in mind yet, your only real choice is to have the meeting with your Managing Director, and keep your future plans to yourself until the dates and plans are absolutely clear.

It's possible the meeting will yield something interesting that might delay (or even change) your self-employment plans. Perhaps a new position has opened up, perhaps there is now a viable future that you will want. More likely, it will just be a general "let's talk about stuff" periodic discussion.

Whenever you come up with an actual date for your departure, you will of course give the standard notice. And if you leave very soon, you can always say something along the lines of "I'm sorry I couldn't be more open about this earlier, but I'm sure you understand that these sorts of things change rapidly." This type of bad timing situation happens now and then. If you tell them soon after you know your definite timeline, and you handle your notice period professionally, they will almost certainly understand.

While it is awkward for you to have this discussion with your Managing Director now, this is one of those professional situations that occur from time to time. You cannot really announce "I'm going to leave soon, but I don't really know when." What if your plans change and you decide that you really want to stay?

Don't sweat it. Be "conservative with the truth" here. Treat this meeting as you would have treated it before you started your mental self-employment planning.

  • 7
    This is the correct answer, I think and the one that I'll be following. Thank you for taking the time to articulate it.
    – Dan
    Commented Nov 18, 2013 at 13:10
  • 1
    I'll add too, that you may learn something about yourself, how to interact with others, business, etc. It's a great opportunity to open up and just absorb and look for ways to make yourself better. Since you are leaning towards leaving, you have the added benefit of being able to not take things too personally. Commented Nov 18, 2013 at 17:30
  • I don't really see why you need to be "conservative with the truth" - what do you have to loose by telling him?
    – Blitz
    Commented Nov 18, 2013 at 18:04
  • 13
    +1 I think the importance of keeping an open mind until a final decision is made cannot be under-stated. If the business was considering having to lay you off, they would not say "hey, we like having you here...might have to lay you off though, but maybe not...you might work here for ahwhile, or maybe we'll fire you tomorrow. We'll see!" The assumption is that you will stay where you are until things change - and everyone knows things change. If you decide to leave you just give an honest, "I've really struggled with this decision, and I've loved working with you, but I have to try..."
    – BrianH
    Commented Nov 18, 2013 at 18:17

If "your CV is attracting attention" it might have caught the attention of your MD. If it's posted on social media this is no big deal, if it's posted on a freelance or job board then perhaps it is.

There's a saying that once a spouse has decided to divorce then they don't fight anymore - they're on their way out - why bother? Similarly, your manager might have noticed the kind of contributions that suggest long term interest in the company or plans for advancement aren't forthcoming. Over time, one might want to know why the initiative seems to have dropped off.

It's also possible (probably likely) that they are working a deal and need to know if you're up for a new challenge. Thus all you know is what is currently on your plate, they might have something new in mind which is invisible to you until they discuss it.

If you're not ready to give them notice, may as well keep your cards close to your chest. However, look at the patterns of your behavior to see if you're dropping clues. You don't have to say anything for someone to know.


I think you can be honest about your feelings without necessarily giving the impression that you are looking to jump ship as soon as the opportunity arises.

He wants to discuss your career within the company. You feel there is no real long-term future for you within the company. It would be perfectly reasonable to bring this up (tactfully) during this meeting. Let him know how happy you are with everything, but honestly bring up your concerns. It may be that he tells you you're right and there isn't much more they can offer you, he may tell you they don't think you're worth more, he may try to offer what incentives he can (even if they aren't the ones you're looking for), or he may surprise you with a real opportunity to move down the path you're wanting to travel.

You don't have to say "This looks like a dead end and I'm awaiting my chance to leave." You don't have to even bring up that it's a possibility. If he directly asks you if you're planning on leaving, you can tell him you'd really rather not because you like the company, but that somewhere down the road you need to advance your career. Let him know your concerns about the company as-is. If you end up leaving in a few weeks or a month, when you give your two weeks' you can tell him honestly that it's because of the concerns you already brought up and you see better opportunity on your own.

Edit to add: I think the biggest issue that can come up with this is it gives the employer a chance to delay you with false hope. If they get the feeling you might start looking elsewhere if you don't have some hope of career progression, they may try to give the impression that you can still advance in the company, even if they can't/won't actually make good on that hope. You just have to keep in mind that you need to see real, substantive action from management on your behalf with regards to advancement rather than just lip service.

There is always a chance that a manager might use this as an excuse to claim you are disloyal or not a company player -- just remember, in this case, you have shown no disloyalty and are doing everything you can to try and give your company the information they need to keep their relationship with you strong. If somebody in your management chain tries to use this against you it is because they were already hostile towards you. Voicing your concerns about your career path is something you should do anyway, even if you aren't leaning towards leaving. A good employer should be trying to constantly keep track of the professional goals of their employees, and addressing any issues they are reasonably able to address to help their employees succeed.

  • Any caveats to this approach? This is the one I like the most, but I am not all that experienced.
    – user606723
    Commented Nov 19, 2013 at 16:27
  • 2
    Biggest caveat from my experience (with employers I've been less close with) is delay -- I'll add to the answer
    – PeterL
    Commented Nov 19, 2013 at 16:30
  • With your new edit, I'd give this one a second +1, if I was able to... Commented Nov 20, 2013 at 11:03

Working as a start-up manager myself who is in a similar opportunity than your boss probably is, I can only tell what worked for me and my employees: We talk to each other. I've had two cases where an employee was set to leave, but was kind enough to let me know. And at least in one occasion I could make something work out for him and us, and he's now in a very valuable position.

In another case, I've had very good relationships with employees that then, after years of working together suddenly tell me that they are leaving. After just having been through a whole personal development process.

If you're set to leave, leave. But when your boss wants to know where you stand at the moment, let him know where you are. He probably won't fire you outright (why would he) - but he might give you an easier start by giving you a chance to work for your old company part time. And in the end, he will feel trusted by your choice of telling him and not taking the cowardly way out.

  • whoever downvoted, please explain - i'd like to learn and get better
    – Blitz
    Commented Nov 18, 2013 at 18:36
  • 12
    I didn't downvote, but I would guess its for your last line ...telling him and not taking the cowardly way out., is the reason for it. Holding personal decisions close to home, is never the 'cowardly' way out. Ultimately you would like to think that all bosses care enough about their employee's that they wouldn't get vindictive or angry when an employee says they are thinking of leaving. However, that is not the case. Employer's do feel hurt or angry or vindictive a lot. So the best advice is almost always to hold your cards close till you really know what you're doing.
    – Ryan
    Commented Nov 18, 2013 at 20:39
  • 2
    +1 This manager's point of view is valuable. Even if not telling your MD that the resources he's about to invest may go to waste isn't a "cowardly way out," it's important to realize that it may feel that way to the manager. Especially if it's a person who does care about you. Yes, being frank has its risks, but it also has large potential benefits, like building character and trust.
    – Lars
    Commented Nov 18, 2013 at 21:54
  • too bad if someone downvoted that answer based on the line 'the cowardly way out', because in some cases a boss may feel not telling exactly that way. No telling opens some risks, telling open some other risks for future relationship, both are probably low in the situation as described but both exists.
    – kriss
    Commented Nov 19, 2013 at 11:21

This is purely to discuss what exactly my current job entails and what things I'd like to be involved in.

You have a good rapport with your boss and feel he really cares then he should be asking the right questions. It's not your fault if he doesn't. He should know there's no room for you to advance and should be asking if there is anything else they can offer.

You're a consultant. Isn't going on your own a fairly common career path? Your boss should be aware of this. It's in some people's nature to want to be on their own and no company should expect excessive advanced warning about your desires unless they have a strong track record of knowing employees will leave and not getting in their way. Otherwise, you have to play the game and protect yourself.

Part of being a good manager is having some idea if something is wrong and undertanding the circumstances (no room for advancement) that influence your employee's careers. Maybe he needs to get creative and find ways for people to advance in the company without moving up in the corporate hierarchy.


It sounds like you have a great relationship with your manager and being frank would probably work out well. It will give you a chance to talk about where you are going and by being frank you may actually get an opportunity you might not otherwise get (like more control over your work or ownership opportunity).

Once you have something you won't want to give that up to stay, so talking before you have done something may actually get you more.

  • So many benefits, and the worst thing that can happen is a month or two without a job. IMO the advantages of this approach overwhelm the disadvantages. +1
    – Vorac
    Commented Nov 25, 2013 at 13:05

You say that you can't get more senior in your current company and that you cannot earn near as much as somewhere else. Don't you think your boss knows that? And if that's so, don't you think that your boss knows that you will be moving on at some point?

You don't say what kind of negative consequences you anticipate, but these real or imagined consequences seem to be the only motivation for keeping your plans to yourself. I will argue, that you have nothing to fear, if you really have made up your mind that you want to leave at some point in the future.

My reasoning is this: worst case scenario, your employer is disappointed and let's you go immediately. Likelihood? Very unlikely, I would say. From a manager's perspective it makes no sense to fire a good employee (unless they have to for other reasons). Do you know how difficult it is to find and hire good employees? Ever considered how much time and money it costs to get them up to speed?

What puts you in an even better position, is that you are dealing with the company owner. She (or he) is an entrepreneur and knows exactly what it feels like to want to build something for yourself.

Also, some food for thought: So you want to be self-employeed, maybe even build your own company and have employees of your own. Ten years from now, one of your best employees comes to you and tells you, something along the lines you described yourself. What will you do then?

Whatever you decide, you have no moral obligation to tell your employer about your future plans if you don't want to. Many employers will not let you know in advance when they decide to let you go (others will).

  • 2
    Hi @Stefan and welcome to Workplace.SE. Your answer, elaborate as it is, feels more like a comment, than an actual answer to Dan's question. Could you re-word it to be less open-ended? "How to answer" might be worth taking a look, too.
    – CMW
    Commented Nov 19, 2013 at 11:49
  • Hi @CMW, thanks for pointing that out. I had thought about submitting my answer as a comment at first, but after looking at the other answers, I felt that my reply would have a similar quality. To be honest, I don't know how to re-word it to make it "more like an answer" without completely re-writing it (and frankly, I just don't have the time for that). Should I delete my answer instead?
    – Stefan
    Commented Nov 19, 2013 at 13:23
  • @Stefan You can do it which ever way you want. Take the time to re-word/re-write it later, delete it, encourage suggestions for edits.
    – CMW
    Commented Nov 19, 2013 at 13:53

One thing that hasn't been covered is that the career development might make staying more attractive. Not necessarily forever, but perhaps for a few years. In fact, this might be a retention offer.

Editing on the advice of DarkCygnus:

1) I assumed that this advice is also intended for posterity. People in the far future (like the 2020's) will come by and read it.

2) My statement stands that this might be an offer worth taking, for the two stated reasons.

  • 3
    This reads more like a comment than an answer. It also doesn't address the actual question asked. This is a 6 years old post, and an answer was already accepted. Could you consider enhancing and editing your answer, in case you have something new and relevant to suggest to OP?
    – DarkCygnus
    Commented Feb 11, 2020 at 19:32

You must log in to answer this question.

Not the answer you're looking for? Browse other questions tagged .