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I'm Dale, the author of Going 1099

You’ll never eliminate risk

Published 17 days ago • 1 min read

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.


If you're interested in learning how to get your first solo 1099 federal sub-contract, check out my book:

Going 1099: How to become a solo federal sub-contractor and gain control of your working life, earn more money and unlock more free time

I'm Dale, the author of Going 1099

Going 1099 is a book that teaches you how to become a solo federal sub-contractor and gain control of your working life, earn more money and unlock more free time. I wrote it because quite a few people have asked me how they can become a 1099. I figured it was best to write a single book that I can send them and that I can share with others who are interested. This newsletter goes out Monday - Friday and covers topics that will help you succeed in starting and maintaining successful 1099 career.

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