I know this firsthand. I recently retired after 35 years as a Civil Engineer (I took a brief detour 5 yrs in with an Astrophysics degree). I piled up 14 yrs of Civil Service at the beginning and end, but 9 yrs in started my own business that I ran for 6 yrs, then off and on for another 15. In the mid-90s there was a construction recession that hurt (& wife went off benefits, which are what self-employment really lacks), I started interviewing, indeed many treated self-employment like years of no-employment (even though it was quite challenging and skill-sharpening). In '97 I was fielding two offers, one let me work for him and consult with my own business on the side (a rare and great deal actually). The next several years I made a lot of money doing this, eventually back to running my business full time from '02 to '07. I tell my boys (both computer programmers) to work for someone else, learn as much as they can, cultivate a niche, then be in and out of self-employment (its a great thing when your kids are young and your spouse works). The problem is those "non-competition" clauses everyone now has to sign. Honestly though, many businesses love a former employee that can help them with less rules to follow. My career very mottled, had to be on my toes, but I wouldn't trade it for anything.