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

Move faster than this to impress your clientSource The government is slow. Like real slow. Its employees are slow, and so are a lot of contractors. If you can just be a little faster, you'll look impressive. For example, I just started onboarding onto a new project and the account set up process has many steps requiring annoying phone calls to the help desk and submitting various forms. A normal pace for a contractor is to stretch this out over a week. I did most of this in a day. The client...

I maybe wouldn't gift a sweater at your next meetingSource One of the unintended benefits of writing my book is that it gives me a fun talking point when I'm networking for my business. For example, I met with a couple yesterday who run a small contracting business and I gave them a copy of my book as a small gift, which led to an interesting discussion about why and how they started their own business. I'm opposed to spending too much time on formal marketing activities when you're trying to...

Government's reaction to your pitchSource I have a friend who is living in Romania and is interested in going 1099. Obviously, Romania is not a center of a US government contracting and he doesn't plan to move to DC soon, so I was not optimistic he'd be able to pull it off. But, he did mention he did have a few friends who work at the US embassy there, so here's what I advised him to do: Ask his friends if they know of any contractors working either at the embassy or on behalf of the embassy...