🔐 The Price of Freedom

Dre Baldwin
3 min readNov 29, 2023

I speak to many entrepreneurs every week. Some in direct conversation; others in DMs and texts.

The #1 desire amongst them: Freedom.

“I don’t want a boss telling me what to do.”

“I don’t want to play office politics anymore, pretending to like people who I hate / hate me.”

“I want to have the resources (money, time, calendar space) to do as I wish, WHEN I wish.”

The problem is, their current situation does not provide such freedom. As a matter of fact, the current situation is causing the opposite circumstance.

May I share with you why this is the case? It’s easy to address when you understand this…

People who say the above things are employed. About 61% of working-eligible adults are employed. Employment is a good idea; it comes with the quasi-security of a biweekly paycheck.

But, there are no perfect scenarios in life, only trade-offs. That security is not free.

The price of security is freedom. In exchange for that guaranteed paycheck, you trade in your freedom.

Your freedom to do what you want to do.

Your freedom to not like that bitch from the marketing department.

Your freedom to tell your boss what you really think about him.

Your freedom to jump in that political conversation on Facebook and say what you really believe.

The tradeoff of your security is that your options are limited. Moreso, your options are often dictated to you, either explicitly or implicitly, by the person who signs your checks (or the threat of what this person may do if you get on their bad side).

The alternative is to flip the equation around: Give up all your securities in exchange for full freedom.

No guaranteed check.

No one to defer to when things aren’t working.

No safety net (other than one that you create and maintain).

Then you’re free to do as you wish, with no restrictions.

In reality, we each choose a mix of both freedom and security.

You follow legal rules to stay out of jail.

Adhere to social rules to be polite and not cause unnecessary conflict.



Dre Baldwin

The Discipline to Produce Your Best On Your Toughest Days. It ain’t for everybody. #TheThirdDay Creator of #WorkOnYourGame. DreAllDay.com