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I'm Dale, the author of Going 1099

Pick your problems

Published 20 days ago • 1 min read

Every career path has upsides and downsides.

The upsides are usually obvious.

  • If you work in investment banking, you'll get rich.
  • If you're a teacher, you get summers off.
  • If you're an entrepreneur, you control your destiny.

The downsides are less obvious.

  • If you work in investment banking, you'll work 100 hours per week and maybe even find out you hate it.
  • If you're a teacher, you'll have to work another job during the summer to pay the bills.
  • If you're an entrepreneur, you control less than you think and have to deal with obstacles every day.

It's the same thing with staying W2 vs 1099. You're probably aware of the problems of W2 and the benefits of going 1099.

But the problems of going 1099 are important to acknowledge.

  • You have to take full responsibility for yourself (can be scary).
  • There is more admin work (though maybe less than you think).
  • You can have months go by in between projects.
  • The work itself doesn't necessarily become more enjoyable.

Everyone wants the benefits of going 1099, but I think it's more important to consider the problems first and see if they are something you can live with to get the benefits.

I still think it's worth it, but you may come to a different conclusion.

So pick your problems wisely.


If you're interested in learning how to get your first solo 1099 federal sub-contract, check out my book:

Going 1099: How to become a solo federal sub-contractor and gain control of your working life, earn more money and unlock more free time

I'm Dale, the author of Going 1099

Going 1099 is a book that teaches you how to become a solo federal sub-contractor and gain control of your working life, earn more money and unlock more free time. I wrote it because quite a few people have asked me how they can become a 1099. I figured it was best to write a single book that I can send them and that I can share with others who are interested. This newsletter goes out Monday - Friday and covers topics that will help you succeed in starting and maintaining successful 1099 career.

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