Isn’t It About Time For You To Get A Divorce?

Look, I don’t want to poke my head where it doesn’t belong, but isn’t it about time for you to get a Divorce?

I mean it. File the papers. Split the assets. Walk away from something you once loved.

And sure, maybe you should divorce your spouse. If they're toxic, unsupportive or making your life smaller, that's a conversation for another day and a stiff drink.

But probably not your spouse. (I hope not!)

I'm talking about something in your life that you once chose, once committed to… Something that was the right call at the time.

A business. A strategy. A relationship. A way of working. Maybe even the person you've been pretending to still be.

Something that used to fit. And doesn't anymore.

Here’s the thing…

You don't divorce something you never valued at some point.

You can't. If it never mattered, you just leave. No paperwork. No grief. No story worth telling.

Divorce means you picked this thing. You built around it. You told people about it. You made it part of who you are.

And now it's bleeding you dry.

But you stay. Because you remember when it worked.

Because you're afraid of what people will say. Because walking away from something you chose feels like admitting you were wrong.

You weren't wrong. You just stayed too long at a table that stopped serving you.

Been there, more times than I can count.

Back in 2016 I started a coffee company called “Stiletto Coffee”

A brand built for women, fronted by my Brazilian wife Kenia who grew up on a coffee farm. The name hit me like a bolt. I could see the whole thing. The aesthetic, the bags, the logo, the mission. Ten percent of profits to women's charities.

I fired every consulting client I had.

Read that again. I fired paying clients to go all in on a business I'd never tested and had no experience with

The branding was money (admit, that’s a cool bag and logo). The website was sharp. The copy was dialed. And I worked 12-hour days with the kind of conviction that only comes from being completely in love with your own idea.

Sales came in.

Profits didn't.

I was losing $4,000 a month the business. Living off savings. And every morning I woke up and told myself the same thing: just push harder. Figure it out. Build the plane while you fly it.

My pride had me by the throat. I couldn't shut it down. What would people think? I'd announced this thing to everyone. I'd burned my consulting income for it. Quitting wasn't an option because quitting would mean I was wrong.

So I kept grinding. Like a dog with a bone that stopped having any meat on it months ago.

Then I had lunch with my good friend Roland Frasier. Roland's brilliant. One of the sharpest business minds I know and as close to a mentor as I've ever had.

He asked how the coffee business was going.

Me: "Not great. Negative four grand a month. Making sales but no profit."

Roland: "You working with any clients right now?"

Me: "Nope. Living off savings."

Roland paused. Then he asked a question stopped me cold...

"If Stiletto Coffee was a consulting client paying you $5,000 a month, but they had no marketing budget and needed half your time... would you take them on?"

I opened my mouth to answer. Then closed it.

Roland just sat there grinning.

I just sat there… not grinning.

He was right. I wouldn't take that deal from anyone on earth. But I was giving myself an even worse version of it and calling it commitment.

I shut it down that day.

Here's the part that still gets me.

I didn't feel loss. I felt like I'd been holding my breath underwater for six months and someone finally pulled me to the surface. My chest opened up. My head cleared. I could think again.

Then the dam burst (and boy did it feel good!)

Within 24 hours, a colleague I hadn't spoken to in years texted me asking if I was still consulting. I quoted him fifteen grand for a two-day engagement. He said yes. To earn fifteen thousand in profit from coffee I would have needed a miracle and a time machine.

Two weeks after that, I reconnected with Jesse Itzler, an astounding entpreneur, bestselling author, married to the founder of Spanx Sara Blakely…

…he hired me as his strategic marketing advisor and I helped him build his brand.

None of it. Not a single dollar, conversation or opportunity. None of it was possible while I was “married to a business that wasn’t working.”

Every ounce of time, creativity and attention was committed to something that had already told me, repeatedly, it wasn't working.

I was paying alimony on a dead marriage. Voluntarily. Every day.

And this has happened many times in my life. (But now I know how to recognize when I need a divorce).

So let me turn this on you…

Who What are you still married to?

…Not because it's working but because you said "I do" and your pride won't let you file the papers.

• Maybe it's the strategy you keep resuscitating even though it flatlined months ago…

• Maybe it's a revenue stream you keep alive out of obligation…

• Maybe it's the way you spend your days, doing work that made sense three years ago but now just fills time…

• Maybe it's a version of yourself you've outgrown but haven't had the guts to bury yet.

Could be a person. Could be a business. Could be a belief about what you're supposed to want.

You know what it is. You've known for a while.

Every day you stay, you're paying. Not in dollars that show up on a bank statement. In energy. In the creative bandwidth you don't have for the thing that's trying to reach you. In the future that's sitting on the other side of a decision you keep putting off.

Here's what I learned the hard way.

Nature hates vacuums and it fills them with something else.

But you have to create the vacuum first. Nothing new can walk through a door that's already blocked by something dead.

The day after I buried Stiletto Coffee, opportunity found me. Not because I got lucky. Because I finally had room to be found.

Now there's another side to this.

The other side of divorce is knowing what to marry next.

What actually deserves your full commitment. Your discipline. Your exclusivity. The kind of commitment where you cut off outside options because you're that certain.

But that's a different conversation.

Today, just sit with one question.

What should you have walked away from a year ago?

The honest answer might be the most valuable thing you do this quarter.

Wait… not done.

I can’t leave you hanging without a little AI-Assisted help. After all AI can make finding patterns really effective.

That’s why I created this free “The Divorce-Your-Demons” prompt you can copy paste into the AI system you use most (ChatGPT, Claude, Gemini… etc) and help you find the thing(s) you need to divorce…