The 1099 Lottery

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A good party conversation topic is the classic, "How much money would you want or need to quit your job and never work again?"

The question usually comes up when the Mega Millions pot hits some ridiculous number.

Most people have some X number of millions in mind that allows them to live their current life, pay for kids colleges, help other family members, and do some fun stuff.

But the question becomes more interesting if you think of different thresholds.

For example, how much money would you need to

  • Not feel bad about your finances
  • Feel secure about your finances
  • Feel happy about your finances
  • Be able to quit a job you hate and not work for a while
  • To work on your current side projects full time
  • Fly international business class once per year
  • Always fly international business class
  • Give more to charity
  • Buy your dream house
  • Invest in another business

Then you can actually run the numbers and see how much you'd actually need.

What's even more interesting is how much of your meaningful financial thresholds are rooted in a net worth number, versus a time freedom number.

For example, if you want to work on your side projects, do you actually need a X million in the bank? Or can you take a 1099 gig and just work part time, freeing up some much needed time.

I don't think going 1099 will get you rich right away. But you can, in short order, cross a couple meaningful financial and time thresholds.

Saving an extra $100,000 over two years and then going down to part time hours can dramatically increase your happiness.

It's not winning the lottery, but the odds of achieving those results are much higher than winning Mega Millions.

Want the full playbook? Check out Going 1099.