What exactly do you hate?

by Dale Davidson March 18, 2026

When I converted my job into a 1099 gig, a lot of my stress went away.

This was because I

Increased my income
Took Fridays off
Only answered to myself and my client

The actual day-to-day client work was easy and I worked with a fun team.

But, what if I hated the actual client work?

Going 1099 would have certainly helped, but the project would not have been sustainable and I would have had to find a new gig.

If you don’t like the actual work you’re doing now, you will need to solve that problem in addition to the 1099 problem.

It’s easy to attribute our frustrations to the wrong thing.

If you have a bad client, and you go 1099 thinking that will make you feel better about the client, it won’t. At least, not for long.

If you don’t like the actual technical work you’re doing, going 1099 but doing the same type of work won’t make you happy. You need to go 1099 and find work you enjoy.

Sometimes going 1099 IS the solution though. If you like the work, you like the clients, but you just don’t like working for anyone else and think you should be better compensated, going 1099 is the right way to do it.

Be honest with yourself about WHY you feel frustrated and address the real problem.

Want the full playbook? Check out Going 1099.