Lessons from self-employment


A reader recently sent me the following article from an entrepreneur/career coach and the lessons he learned from self-employment.

10 Lessons I’ve Learned From 10 Years Of Self-Employment

Listicle articles are usually low quality but I related to quite a few of these.

In particular:

  • Discipline Trumps Talent
  • Progress Takes Longer Than You Think
  • Things Can Always Be Better. . . And Worse

These lessons apply to your solo 1099 federal sub-contractor work.

  • You don't have to be the smartest guy to be a solo 1099. You just need to take a few more risks and be consistent in your efforts.
  • Getting your first gig, subsequent gigs, doing paperwork, networking, and negotiating all take longer than you'd like it to
  • Going 1099 is not the best thing in the world. But it's not the worst. The autonomy and extra income you get are great. Not being billable for a long time sucks. You're always in a position where there is something better and worse.

Working for yourself is a unique experience. It's good to hear from others who have been there before. This article is an honest and refreshing perspective on what it's like.


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.

Read more from I'm Dale, the author of Going 1099

Rocky was a 1099 If you're a decently skilled employee in the government contracting world, there is no reason you shouldn't be able to go 1099. The main differentiator I've seen between people who claim they want to go 1099 and the people that actually do it, are that the people who pull it off are just a little more aggressive (assuming they are equally skilled, in desirable fields, etc.). The successful ones "pester" their network a bit more, negotiate a bit harder, and push to go 1099 for...

Offering half a muffin can often be helpfulvia X When you're trying to go 1099, you're largely focused on what you want. Imagining getting what you want is highly energizing and motivating, so it's easy to focus our energies there. But it's important to focus on what you can do to help others. For example, when you network with people, see if there are ways you can assist them. Maybe they have a friend looking for a job in your field, and you can meet them for coffee and make an introduction...

Treat Yo Self ... to non-billable funvia Reddit One of the fun parts about going 1099 is find opportunities to increase your billable rate. My own billable rate progress sent from something like $85 -> $100 -> $110 -> $115 -> $160 ->$180 per hour over an eight year period. Those early rate increases made a big differences. Actually all of them made a big financial difference. But the thrill of bumping up your rate wears off quickly, and then you're left with figuring out how to make your work...