1099 freedom

by Dale Davidson March 18, 2026

A cartoon showing the difference between an employee and a self-employed freelancer. The cartoon is split into two panels side by side. On the left panel, an employee is depicted in a small, cramped office cubicle, surrounded by stacks of paperwork, looking longingly out of a small window. The employee is dressed in business attire, with a clock on the wall showing the end of a long workday. On the right panel, a self-employed freelancer is shown in a spacious, sunny home office, with a laptop open and a comfortable chair. The freelancer is in casual clothes, with a pet cat lounging nearby, and a cup of coffee on the desk. The freelancer is smiling, working at their own pace with a window open to a beautiful garden view. The style is humorous and exaggerated, emphasizing the freedom and flexibility of the freelancer compared to the restricted and monotonous life of the employee.

Nassim Taleb is one of my favorite authors/thinkers.

In his book, Skin in the Game, has has a chapter called "How to Legally Own Another Person."

Skin in the Game: Hidden Asymmetries in Daily Life (Incerto)

Here are some gems from the chapter:

"In short, every organization wants a certain number of people associated with it to be deprived of a certain share of their freedom. How do you own these people? First, by conditioning and psychological manipulation; second, by tweaking them to have some skin in the game, forcing them to have something significant to lose if they disobey authority—something hard to do with gyrovague beggars who flout their scorn for material possessions. In the orders of the mafia, things are simple: made men (that is, ordained) can be whacked if the capo suspects a lack of allegiance, with a transitory stay in the trunk of a car—and a guaranteed presence of the boss at their funerals. For other professions, skin in the game comes in more subtle forms."

"People who are employees for a living don’t behave so opportunistically. Contractors are exceedingly free; as risk-takers, they fear mostly the law. But employees have a reputation to protect. And they can be fired. People you find in employment love the regularity of the payroll, with that special envelop on their desk the last day of the month, and without which they would act as a baby deprived of mother’s milk."

"True, a contractor has downside, a financial penalty that can be built into the contract, in addition to reputational costs. But consider that an employee will always have more risk. And conditional on someone being an employee, such a person will be risk averse. By being employees they signal a certain type of domestication.

Evidence of submission is displayed by the employee’s going through years depriving himself of his personal freedom for nine hours every day, his ritualistic and punctual arrival at an office, his denying himself his own schedule, and his not having beaten up anyone on the way back home after a bad day. He is an obedient, housebroken dog."

How to Legally Own Another Person (Medium link to the article)

Taleb is obviously being a bit hyperbolic.

But he makes some good points about being an employee:

Companies want employees to be dependable. That's the only way the business can grow
Paychecks are addicting
Being an employee requires regular acts of submission to the organization

Going 1099 in the federal contracting space is a small act of rebellion.

Your day-to-day to will look a lot like a normal job. But you'll get a taste of what it's like to earn money outside of a W2 paycheck.

You'll get a little taste of freedom.

And even with all the risks and potential downsides, for some, it will be impossible to go back to W2 life.

Want the full playbook? Check out Going 1099.