How to leave when your boss (of a small business) seems desperate to keep you?

Question

I work in a small company in the US - myself, my boss, and a marketing intern. I have worked at the company for four years, marketing intern for 8 months. It is an independent software dev shop. We make software for other companies.

About 3 months ago, I mentioned to my boss that I was leaning towards leaving, because I had been there for a while and I didn't see much potential for future growth (and that it might limit my future career) and I also wanted a change of scenery. I had been thinking about this change for quite a while (about a year).

My boss offered me a decent raise which for the time being I have accepted, though I expressed my reservations about the job at the time. He seems to feel this has made everything fine and even discussed how we'd be working together years later. However I still feel that there's not much growth potential, and I honestly think (based on different salary websites, recruiters, and job listings) I could probably get a higher offer than I was given.

Considering it is a small business and this feels as much like a personal matter as a business matter - how do I amicably cut ties? It doesn't help that I do the majority (I would say 90ish %) of the coding for the company so I feel like if I move on, he won't have anyone to pick up the burden (he can code, but he's always busy with business stuff) at least in the short term. Do I just come out and tell him I want to leave and give him some time in advance (say a few months), despite the raise? Obviously I wouldn't leave until I actually have a job in hand, but considering my field and the demand, I don't feel that will be very difficult.

Answer 1

I came in to the same position you are in. I was hired to replace the dev who started with the company and did 90% of the coding, including building the software from the ground up.

The boss had him get me up to date with the code base and put me on a project to get me familiar with it.

The dev who left is very good frienda with everyone still, and he is available for input whenever we need it, though depending on the difficulty, for a price.

You may find a similar situation beneficial to your boss and you as well.

Hand in your resignation and in the terms state something along the lines of(thanks to @JohnHC and @toadflakz for helping me clarify):

1. Hire a dev to replace you, similarly skilled but not necessarily as skilled.
2. Pause adding new features to product and only do bug fixes or finish already started features before you leave.
3. Get the new dev familiar with the code base, possibly having him/her do a small feature request that wont take too much time.
4. Once the new dev is up to date, you are free to leave.
5. If you still care about the boss and are friends, you could suggest being available for consultation and anything that takes more than X hours to do should be paid at X rate.

Of course this is all up to you and is merely a suggestion.

Answer 2

Pitch the idea of a second coder in the business. Remind your boss that while you have no plans for leaving in the immediate term, you could get hit by a bus tomorrow and his business would be in a very bad spot. This makes the business more resilient to you leaving for whatever reason and reduces the likelihood that your leaving will be taken as a personal attack.