Seasons of 1099 life

Different life seasons brings different moods, vibes, and desires.

When I was a teenager, I was into skateboarding and flirting with girls.

In my twenties I was in my "wander years" after a failed Navy career and trying to figure out what I should do with my life.

Now in my thirties I'm focused on my family and putting down roots.

1099 life has its own seasons.

W2 Stage - You're a little dissatisfied and feel stuck. You're curious about working for yourself but aren't quite sure how to pull it off.

The First 1099 Gig - You're super excited you're working for yourself! You're making a lot of extra money and have more free time. You're learning a lot about the mechanics of business. Life is good.

End of your first 1099 Gig - You're worried the first gig was a fluke and not sure if you have the ability to get a second gig. You really don't want to go back to a job.

The Second Gig - It's not a fluke! You did it! Maybe you got a higher rate and can pad your savings account.

The Third+ Gig - You're getting bored. You're confident you can find work for yourself but you wish you didn't have to do client work anymore.

What's Next Phase - You're trying to figure out what is next for your career. Should you get out of the industry? Should you hire employees?

The Next Thing - You've found something that gets you excited. A hobby, a new business pursuit, a new relationship. The 1099 gigs you have facilitate the next thing. You have more resources and more time to fund your excitement.

Life isn't static and your attitudes and feelings about your 1099 work will change over time. If you know it's coming you'll feel less anxious about it.

Want the full playbook? Check out Going 1099.