This reminds me of some research I've seen supporting this effect. I can't remember the exact study but basically a large factory shut down putting a lot of people out of work, who were then offered free schooling to learn a new trade. After some number of years they looked back on those individuals and the ones who took the free training had actually done worse on average than the ones who had turned it down.

The effect seemed to be just what you're describing. Even though most of the non-schooling group got worse jobs to start, they had several years of lead time to build experience and get pay raises which ended up being more valuable than the certificate or degree the other group got.