From getting fired to going 1099

by Dale Davidson
A funny cartoon for the subject line 'The Art of Turning 'You're Fired' into 'I'm Hired'—By Myself!'. The scene depicts a stick figure standing in an office with a box of personal items, just having been told they're fired. In the next frame, the same figure is shown setting up a home office with a triumphant smile, placing a 'CEO of Myself Inc.' nameplate on the desk. The transition is comically swift, with the figure tossing the box into the air in excitement as they embrace their new role. The background includes a confused former boss peeking through the office window, scratching their head in bewilderment. The style is exaggerated and humorous, emphasizing the quick pivot from job loss to self-employment in a playful and lighthearted manner.

I have a colleague at work who I met last week at a team happy hour.

She works for the prime, but she mentioned that until the a year prior, she had been working for herself as a 1099 for 20 years.

Naturally, I wanted to know how she became a 1099.

A few interesting tidbits:

  • She worked as a PeopleSoft developer at DoD for a sub-contractor (I think it was Booz)
  • Booz wanted to "green" the contract and basically replace more expensive, older folks with younger, cheaper folks to boost profits
  • She was on the chopping block and would have to find another project
  • The prime was not happy with this and invited her to stay on as a 1099
  • She ended up working for herself until this job because it had good benefits
  • She'll likely go back to becoming 1099 soon

Because of her competence, good relationship with the prime, and her willingness to take a risk, she was able to have a long and successful 1099 career. She turned a challenge into an opportunity.

I'm not sure what the benefits story is, perhaps a project fell through and this W2 job was the best short term option to pay for benefits.

What's funny is she said couldn't stand having to accrue PTO and will go back to becoming a 1099.

I've seen a bunch of folks go 1099 by accident.

However, you can do it deliberately.

You don't need to wait until you're on the verge of getting fired.

Want the full playbook? Check out Going 1099.

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