I'm Dale, the author of Going 1099


Published about 1 month ago • 2 min read

There's a great chapter in the book, The Art of Gig that describes the phenomenon of "sneakoffproofitis."


"The problem is, as a free agent, you are your own boss, and you’re likely a bad boss, unable to relax, and driven by fretful anxiety about lining up the next gig. That would be bad enough, except that you’re also an omniscient bad boss. You know all your own tricks and nothing is hidden from you. You can’t sneak away from yourself. You have sneakoffproofitis.

Here’s what sneakoffproofitis looks like. Your bank balance looks healthy for the moment. You have enough work lined up so the cash flow looks good for the next few months. You’ve only committed a modest fraction of your hours—say ten a week—to deliver that work. You’re temporarily cash rich and time rich. It’s a sweet situation, right? So why is it so hard to take your time/money surplus and do something interesting with it?

The thing is, fun things are only fun when you sneak off from things that feel like work to do them. There is a certain creative freedom that is unleashed when you’re using up free time that feels like it is stolen from commitments towards necessary work. The courage demanded by the time theft fuels boldness in the sneak-off activity. This is funny because the idea of time theft is only well-defined for robotic labor where you are paid to execute a production algorithm, with a clear relationship between time and output. It is incoherent when applied to knowledge work where there is only a weak correlation between time spent at work and the quality/quantity of output."

Rao, Venkatesh; Witherell, Grace. The Art of Gig, Volume 1: Foundations


It's funny that as soon as you have some actual ability to take time off to do fun stuff as a 1099, you don't actually take it.

We've become so conditioned by the oppositional relationship to a boss or employer that we don't know what to do when that relationship is gone.

As a solo 1099 in the government world though, you probably have what looks like a full time job, so you can still trick yourself into thinking that you are stealing time or reveling in some sort of way.

I recommend taking the random Wednesday off or bugging out early on Friday to take a nap.

It may seem silly but it's a small way to enjoy the new work setup you've created for yourself.

You'll get more comfortable with "stealing" time for yourself and be able to focus on more meaningful projects than napping (if you so choose).

So beware of sneakoffproofitis, particularly if you are an anxious ambitious type.

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.

Read more from I'm Dale, the author of Going 1099

There are no golden parachutes at a small companySource: The downsides of working for a large company like Booz Allen, Deloitte, Peraton, etc. are known. They can be bureaucratic and often make you do extra work outside of your billable hours. Small companies generally have a different set of pros and cons. In the government contracting world, you may be able to negotiate some very 1099-like terms with a small company. You might be able to negotiate an hourly rate or high...

about 15 hours ago • 1 min read

Gig timing is somewhat random Here's how long it took to get my 1099 gigs: Gig 1: 2.5 years of working as a W2 at a government contracting company then I converted my job. Gig 2: 2-3 months after my first gig ended (due to clearance issues; agreement was made within the first few weeks of my previous gig ending). Gig 3: 2 months after my second gig ended. A client introduced me to the PM at a prime maybe 6 months prior to that. Gig 4s and 5: 2 years after my third gig. I took some time off,...

1 day ago • 1 min read

Buying stocks on RobinHood is basically like playing roulette In 2010, I was getting out of the Navy and stashed in an office with nothing to do for a while so I looked into "investing." You know what stock I bought? Blockbuster and Palm Pilot. I made money, then lost more money, to the tune of a few thousand bucks. I'm glad I lost that relatively small amount of money at a young age, because it turned me off from stock picking. --- I read an article that described a dramatic increase in the...

3 days ago • 1 min read
Share this post