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I have read through similar questions about not burning bridges, but most of them reference a scenario where the applicant wants to: "Retract acceptance" or "reject offer". My question deals with actual parting of ways after beginning work.

So, in the form of an example:


Person X and Person Y recently met through a mutual colleague.

X and Y got along really well and decided to attempt working together. Y has been working freelance and is seeking to expand his business by bringing X into the picture.

X received a decent offer from Y and they decided that they will "give it a try". The structure is in the form of contractual work.

After spending a little time on the actual work (work-place training mostly), X has realized that he isn't enjoying the work at all and that it deviates from his preferred "stack" (a "stack" is a term used in programming to define the "set of tools" a programmer uses), as well as preferred "work".

X is also concerned that Y may have higher expectations than can be reasonably assumed (this being Ys first hire, Y may be unaware of how long it takes to up-skill an employee).

Lastly, X is worried that he may get "locked in" to this type of work for a long duration, as Y has been doing it for quite a few years, although Y has mentioned that they may branch out into other (interesting) projects.


Based on the example:

  • How can X strategically decline/leave working with Y without offending Y to a point where they can no longer participate in any future mutual opportunities?

Points to keep in mind are:

  • This is Ys first hire
  • Y may not be used to workplace rejection
  • X and Y share mutual interests in certain fields
  • X and Y have what one would call a "professional friendship"
  • The issue concerning "not enjoying the work" is besides the point, as the actual question is about parting ways amicably
  • It can be assumed that this isn't an academic exercise. Concerning the second question, I can neither confirm nor deny it. – Joe Oct 8 '14 at 16:34
  • and now that it is fixed, I'll delete my comment (including this one, after giving you a chance to see it). – thursdaysgeek Oct 8 '14 at 17:48
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How can X strategically decline/leave working with Y without offending Y to a point where they can no longer participate in any future mutual opportunities?

I guess I don't understand the conundrum here. These sorts of work arrangements sometimes work out, sometimes not. Just be conversational, and be honest. Sooner or later you always need to move on.

Unless there is a contract between you and your friend which specifies details regarding break-up, you simply tell Y something like:

"Sorry, Y. I've come to the conclusion that this isn't work I enjoy. It's different from the "stack" I prefer, and the "work" I prefer. I also suspect you need a higher skill level than I possess.

I've given it a good try, and really enjoyed working with you, but I feel like I need to move on."

If asked, you might choose to expand on your answer a bit.

You could give Y a reasonable notice period. You could also offer to help find and train a replacement, but you aren't obligated to do so.

If you have a contract, your actions/strategy must be guided by the terms of that contract.

In the real world, the "Y" folks are sometimes reasonable, and sometimes not. Sometimes people will choose to reject future mutual opportunities no matter what you or X or anyone else says. In the real world, you do your gracious best, deal with the consequences, and move on.

  • Thanks for this answer. Is there an alternative for " ... really enjoyed working with you, but I feel like I need to move on." Although it may seem like the situation is being thought over too deeply, the choice of words is vital to ensure that person Y does not feel "outdone" by person X. – Joe Oct 8 '14 at 17:46
  • can we plausibly assume that even if the perfectly worded job decline is given, it may not matter that a "bridge" can be preserved, if person Y feels let down by any rejection at all? If that is the case, I suppose person X should carefully approach the situation and then just "leave it at that". – Joe Oct 8 '14 at 17:56
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1 - if it's feasible, start with the problem, not the resignation.

If any of these problems could be dealt with and dealing with the problem would cause you to stay, start with stating the problem without resigning.

  • Ask for a time to touch base on how ramp-up is going
  • State the problems w/out blame:
    • I don't enjoy this stack as much as I hoped I would, is there any opportunity to change to a stack like this?
    • I'm really worried that I'm disappointing you in the time it is taking me to ramp up. What's your take?
    • I'm afraid I don't have a long-term interest in this type of work - do you think the business will continue heading in this direction? If so, I don't want to take more of your time and money when you could get a candidate that wants to continue this work more than I do...

If he changed 2/3 - for example, told you to work in whatever stack you like, and reassured you that you were doing a great job... would you still want to quit? If not, try this first.

2 - If you really need all 3, and you tried #1 already - then when the answer to the 3rd bullet is "nope, I think we'll have keep with the strategy of this type of work as the business goal, at least for the medium term", ... then your answer is - "OK, how can we plan me out of the business while finding a way to mean the near term commitments you've made to support both our salaries - I don't want to leave you in the lurch, but this isn't a good long term fit for me."

That's a much gentler version of "I quit, here's my notice" that respects that this is a friend with a super-small business and an abrupt end date may be very harmful.


If you also had problems that were deeply personal and potentially insulting ("I hate that you snort every 3 minutes while sitting next to me, I can't work like this") - then you may just want to move to step 2 with the "this isn't a good long term fit for me, how do I leave without screwing you over?" and get out.

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