Things I’ve learned about myself as a 1099

by Dale Davidson

Here’s what I learned about myself due to my 1099 experience:

  • I hate being assigned work; I like generating the work
  • I can turn a dull task into an interesting one if I figure out how to do it in a novel or creative way
  • I like money, but I like my time more
  • I can only be on a project for a year or two before I get bored
  • My weakness is that I think the grass is greener, so I start unrelated new projects for the novelty when I should really be leveraging my current work
  • I’m not great at nor super interested in managing people
  • I don’t take criticism very well
  • I don’t take setbacks very well. I thought I did, but I’ve never had that many of them so it just felt like I did
  • It’s important to me to be contrarian, to feel like I’m “cheating” in some way to get away
  • I am a decent writer, at least, compared to many other people
  • I actually do think of the big picture and it’s not complete BS when I talk about strategy
  • Conversely I am not interested in details
  • I can be sloppy in my work, particularly when I’m more eager to finish a task than to do it well
  • My laziness and discipline can co-exist. Disciplined for things that matter to me. Very lazy about things that don’t
  • I do value fun colleagues at work. I’m not as much of a solo/loner type as I thought
  • My ambitions are greater than my ability. I can't do more than one or two important projects at a time while spending time with the family, being fit, etc
  • I'm a routine guy, not a spur of the moment type.
  • I don't hate the government contracting industry as much as I thought. I just don't like being the one to do the billable work.
  • My ego is dependent on being contrarian. If I had a "normal job" I'd feel depressed, not because it's bad but because I'm attached to a contrarian identity
  • I can be arrogant and look down on government bureaucrat types
  • I am motivated by money, but mostly when there is a smaller chance of a big payout, not when there is a guaranteed chance of a smaller payout (hiring someone and make $40k vs. raising my rate and working more)
  • Helping one of my 1099 readers and selling a book feels way better than solving a government client problem and billing an hour

What do you think you'll learn about yourself if you went 1099?

Want the full playbook? Check out Going 1099.

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