Your Business Advice Drove Me Back to a Life of Crime

A woman peeking out between the bars of a prison cell - much like the experience of being trapped by bad business advice.
In my 20s and 30s, I broke into things.

I viewed padlocked fences, spiked wrought iron gates and rules about trespassing as “suggestions.” I broke into hotels in St. Martin, monasteries in Rome and burned-out abbeys in the wild Irish countryside.

Come to think of it, it’s a miracle I’ve never been shot.

I broke into these places because the reasons I was supposed to keep out weren’t any good.

It’s past curfew.

I’m sorry, did you say curfew?

You missed check-in.

I’ll see you in the morning then, as I stroll out of the room I let myself into with the keys I found in your office drawer. And I may have helped myself to a beer for my trouble.

It’s dangerous.

For amateurs, yes.

~

I’m not a fan of rules, you see.

For most of my life, if I was “supposed” to do a thing, chances were good you’d find me exerting a disproportionate amount of energy doing anything but. The opposite was also true. When my high school boyfriend announced he’d never date a girl with facial piercings or a tattoo, guess what I went and did immediately. I mean, what is this . . . the 1800s?

It took me two decades to finally figure out why I’m built this way, why rules chafe me and Keep Out has such an irresistible allure.

Freedom. I want it. 

This desire permeates everything about how I move through the world — coloring outside the lines, insisting on being my own boss, craving the open road. And rules — especially arbitrary ones — stand in direct opposition to this life goal. 

Freedom, in fact, is what finally prompted me to retire that 30-something rebel and take a legit crack at this online entrepreneur thing. Coach, content creator, influencer, course builder — I didn’t care what it made me; I just knew I wanted it.

Passive income — AKA making money while you sleep — is a pretty seductive promise. A lot like how Do Not Enter means there’s a 92% chance something juicy is on the other side of that door.

What I didn’t expect, in my need to learn everything about how to get a slice of that freedom, was that I would become the most rule-abiding citizen on earth. I consumed content on all the business advice under the sun, and because I had no frame of reference, I took it all as bible. I did this willingly — as if I were a stranger to thinking for myself. Instead, I followed the online gurus and business coaches down their dark alleys, nodding like a bobblehead.

When they insisted I must be in all the places, all the time, I obeyed. I melted down on a camping trip when Instagram refused to post my painstakingly-crafted content at the exact time of day proven to make you go viral! My best friend sipped wine and stoked the fire, shaking his head.

But seriously, what is this madness? 

I was once told by an “expert” to charge $3000 for a course I currently — and rightfully — sell for $157. Yet another told me that breaking the pace of my podcast would destroy my listener’s trust. My podcast would die. Everyone I loved would die. I might as well set my life on fire.

I believed all of them. I went from being rebellious in the name of freedom to slaving my way through a list of everybody else’s “shoulds.” The list got so long, it buried me. My life caught fire anyway. 

And it sure didn’t look anything like freedom.

It turns out there’s something fiercely hopeful about looking around at the ashes of your former life. When you have nothing left to lose, you can rebuild using only the materials that feel good. I recommend you never get to that point, but sometimes that’s what it takes to remember who you are.

That’s why I’m going back to basics. I’m listening to my own voice again. The voice of a woman willing to go first. The would-be cat burglar who doesn’t actually take anything except a stand against your stupid rules. (And that one beer).

I’m rallying the troops, too. Let’s all stop “should-ing” on ourselves. Let’s forgo bending to someone else’s agenda and chasing our tails in pursuit of metrics we’ll one day wake up and realize we don’t even care about. Let’s let the reclamation of our own freedom be the permission some soul on the brink of burnout needs ASAP to save her own life.

So To Whom it May Concern, I see your rules, your standards, your markers of success, and I raise you the startlingly few fucks I have left to give. I’m not sure where I even got these fucks, to be honest. I used to be so free.

But I’m becoming that girl again who sees Beware as an advisory for clumsy people and asks for forgiveness, not permission. I’m going to do what feels good from now on, and your Success Framework isn’t it. I may not be climbing any spiked gates; these days, my particular flavor of freedom — a hammock, a killer pinot and no agenda — comes with a slightly lesser likelihood of breaking a hip.

But if the reason I can’t come in is a stupid one, you best believe I’ll be right over.

Your Turn

Tell me about a rule you’re ready to unburden yourself from. Let’s make a list of “Commandments,” then burn it to the ground. 🔥🔥🔥

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