My experience has been that when you are looking for a job working for other people after being self-employed is that the boss thinks you were "self-employed" -

My experience has been that when you are looking for a job working for other people after being self-employed is that the boss thinks you were "self-employed" - you have to get over this idea (in the mind of the hiring manager) that being self-employed is just a euphemism for being unemployed. Some things you can do: Write about technical projects you did for your company... write them up a little like they were different jobs, formatting wise. At least in the sysadmin world it really helps to make sure you include the keywords for the tools you used in those projects. Remove the apology for the lack of experience... if you can list good projects you did for fractals, you won't need to apologize or plead, it will show what you were doing. One way of thinking about it, depending on what sort of job you are applying for, is that you are trying to re-cast your experience at your company as employee work. I mean, I technically have been an employee of prgmr.com for the last decade. That's absolutely true, and the IRS can verify, even though I have also been majority owner for most of that time. Most technical jobs don't actually care that you are 'entrepreneurial' - they care about your technical abilities, so recast on that, if you are applying for an employee job. Fundamentally? that's the problem with trying to get employee work after working for yourself. You need to convince your boss you actually were doing something during your period of self employment - that you weren't just unemployed. The next problem, of course, is convincing the boss that you will focus on their company and not yours, but in my experience, that comes up after they are already interested. You need to be prepared for the question, though; I've definitely bombed some interviews because I was not.