Move fast and pay penalties

I recently got a notice from the DC Office of Tax and Revenue saying we were late to pay them and we now owe them $500.

Not fun!

The reason we were late was because I set our filing/payment schedule to quarterly instead of monthly for one of our DC employees that we hired.

So yes, I screwed up, and now I have to pay $500.

But, I did it in service of getting an employee hired and wanted to make sure we could start him quickly. If I had waited until I became an expert at researching DC business regulations, I might have lost $5,000 in profit to save the $500.

Mark Zuckerberg of Facebook/Meta fame liked to say "move fast and break things" as a way to set a high tempo while acknowledging this will lead to mistakes and errors. It was worth it to him to because the value of moving fast exceeded the cost of anything they broke.

If you let small fees and potential penalties get in the way of you taking action sooner, you'll kill your momentum and greatly reduce the chances of you successfully getting a 1099 gig.

So adopt the mantra of "move fast on paperwork and pay small penalties." You'll be the Mark Zuckerberg of solo 1099 sub-contractors.

Want the full playbook? Check out Going 1099.