I write a lot about risk mitigation in my book.

It’s easy to romanticize the epic quit stories of now-successful entrepreneurs.

But for most people, just quitting your job before you have something lined up will only really feel good in the moment.

So I advise that anyone considering going 1099 make sure to have savings, validate their value in the job market, cultivate a good relationship with their current client and professional network, and then make a concrete plan to find their first 1099 gig.

But, even if you follow all that advice, you’ll never reduce the risk or uncertainty to zero.

For example, when I went 1099, I knew my gig would get three more months of funding, and was pretty confident it would get extended further, but didn’t know for sure.

I did it anyway.

However, there ended up being a gap in funding of about 4-6 weeks where I wasn’t working.

It wasn’t the worst situation ever. I hung out by the pool for a month. But losing a month of income didn’t feel good.

I won’t even go into the time I spent over a year without billable work due to dumb security clearance issues + COVID.

That felt horrible and hit the wallet hard.

But I don’t regret going 1099.

If you’re looking to get your risk and uncertainty level down to zero before you make the leap, you’ll never do it.

The key is to mitigate the risk to an acceptable level.

You’ll still feel a little queasy in the stomach, but the more you learn to live with that feeling (conditional upon being a smart risk mitigator), the more likely you are to succeed.