Lessons from self-employment

by Dale Davidson March 18, 2026

A funny cartoon showing an impatient entrepreneur who can't wait for his business to succeed. The cartoon features a stick figure entrepreneur standing next to a tiny sprout emerging from a pot labeled 'My Business', looking down at it with a giant magnifying glass, showing an expression of impatience. The entrepreneur is tapping their foot rapidly, looking at a watch on the other wrist, which is set to 'Now!'. Speech bubbles coming from the entrepreneur say, 'Grow faster!' and 'Success, where are you?'. Beside the pot, there's a watering can labeled 'Hard Work' and a bottle of 'Instant Success Fertilizer' that looks suspiciously unused. In the background, a calendar with pages flying off illustrates the passage of time, with 'Day 1', 'Day 2', 'Still Day 2?' written on them. The style is exaggerated and humorous, highlighting the entrepreneur's unrealistic expectations and impatience for immediate success.

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.

Want the full playbook? Check out Going 1099.