There's a truism about employee attrition that says employees don't leave bad companies, they leave bad bosses.

Basically, a bad boss is a push factor, something negative that makes you want to change.

A pull factor, is something positive that attracts you to leave. You may have a good boss, but an even better boss with better money is available to you at another company.

My path to going 1099 was mostly motivated by push factors. I wanted to get out of the nonsense of employee life. I didn't perform well in hierarchical organizations, or just in organizations generally. I didn't like doing performance reviews. I also wanted more control over my time.

The quickest path to getting away from these problems was to go 1099. Getting another job would have given me more of the same, but perhaps with more money.

Your motivations for wanting to go 1099 may be different than mine, but I'd pay special attention to the push factors. It may give you more options or eliminate certain possibilities.

If your only push factor is you feel you're getting underpaid, you can simply get another job.

If your primary push factor is a bad boss, you could just switch teams.

You don't have to go 1099.

Generally speaking, reducing sources of unhappiness matters more than adding new types happiness.

Going 1099 addressed a bunch of push factors for me, which is what made it attractive. It was probably the best career move I've made to date.

But if there were other paths to getting more autonomy and money, I don't think 1099'ing on federal government projects would have been my first pick.

So focus on coming up with ways to address your push factors or reduce the things that make you unhappy, this will impact your quality of life far more than adding new things that you want.