Is 1099 solo federal sub-contracting the right path for you?

I never thought I'd be in the government contracting business.

In fact, my original plan from high school was to go to college, become a Navy SEAL, and then become a CIA case officer.

I went to college, got into SEAL training, and then promptly dropped out of SEAL training.

Then, I had no idea what I wanted to do.

After doing a stint teaching English in Cairo and then trying to start my own travel related business, I ended taking a job that required a security clearance with, a government contractor. This paid better then my business, which paid negative $1000/year.

Then I eventually ended up in government human capital consulting where I happened to get moderately good at data analysis (ahem...Excel pivot tables).

When I had some leverage, I persuaded my employer to keep me on as a 1099 for the same client and project and since 2015, I have been working for myself as a government sub-contractor, now with a partner and a few employees.

Is this the right path for me? I don't know. It is better than a job, but not what I want to be doing for the rest of my life.

So is it right for you?

Hard to say.

I wouldn't go into it if you're not already in the government contracting world. Too boring and bureaucratic.

But, if you have the right risk tolerance, want to make more money, gain more autonomy, and have more free time, it's a good move if you're stuck in a job at as a government contractor.

Once you have more money, autonomy, and free time, you can explore other things you want to do with your life.

My wife and I are figuring out how we can move back to Portland, OR (where she is from) in a few years. It would be almost impossible to continue doing 1099 federal sub-contracting there, but because I have more money and autonomy when compared to being an employee, I have more flexibility to figure it out.

Maybe I take a few months off of project work and rent an AirBnB there to scope out some opportunities. It would be hard to do that as a W2 employee.

Going 1099 is a good path to take for the right person. Is it the final path?

Probably not.


If you have questions feel free to reach out to me directly at I can also add you to my informal mailing list in case I have updates or news or whatever.


I wrote a book about becoming a 1099 solo federal sub-contractor. I cover in more detail why you should or shouldn't go 1099.

You can read more about it here:

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


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