2 Lessons Every Entrepreneur Needs to Hear

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Hey pal,

It’s been a good-weird few weeks for me.

At the risk of repeating myself, I have a 14-year-old product strategy business called, New Haircut.

New Haircut and I have a long and sordid history together, which I can summarize in two sentences: A decade ago, it was my darling. The past few years, my albatross. To the point that it brought on overwhelming burnout.

Last year, I parked New Haircut. I stopped marketing and sales. Ceased all client work. I shuttered the company.

In October, I went all in on Profit Ladder. I had all but written off New Haircut. That chapter of my life seemed closed.

Then the strangest thing happened. Prospective clients started reaching out for New Haircut services. That’s not the strange part. What’s strange is that I’ve been saying ‘yes’ and enjoying the work again.

I share this story with you because of the two underlying lessons I wish I’d understood when first becoming an entrepreneur.

Lesson 1: Passion and profession

I started New Haircut because I felt like it was my time to create something.

My passion sprung less from the work, and more from the notion that I’d get to build my own dream (not someone else’s). In that sense, I suppose I would have been passionate about any business I created.

So I followed the path most do. I built a business selling the same work I’d done as an employee. I opted for the assurance of doing what I knew.

In time, the raw passion of being a business owner lost its luster. Building New Haircut had become a job. Except, as my passion waned, so did my income.

Eventually, with little left in the tank to run the company, I parked it. It was the right thing to do. I had fallen out of love.

And if that were the entire story, the lesson would be the same clichéd advice we’ve ben fed a million times: Do what you love.

But sometimes, with enough time and distance, the things we fall out of love with, have a way of returning to us.

These past few weeks, New Haircut business opportunities have re-emerged, in growing numbers. Instead of feeling weary and cynical about them, I’m curious and energized. Grateful, even.

I think, the love and deep purpose from my work with Profit Ladder, have refilled my tank. So much so that I have fresh eyes toward New Haircut.

Yesterday, I ran a workshop for a team of executives at a major US pharmaceutical company. I taught them how to choose the right problems to solve. And while I’ve run similar workshops dozens of times, I killed this one (in a good way). Knocked it out of the park — from our very first planning meeting, to the wrap-up of the workshop itself.

If you’ve played sports, I was locked in. It felt like I couldn’t miss.

Before I got out of their offices, I had emails and texts from the team. They thanked me for such an informative, fun, and engaging session. With an invitation to return for follow-on work.

I say this not to brag, but because of how surprised I’ve been by this re-opening to New Haircut. I think the romantics within us yearn for work we’re hopelessly in love with. But I’m learning that it’s more about finding balance between your passion and profession — an ‘and’ not an ‘or.’

And so I think the advice we’ve been given is incomplete. It’s not do what you love. It’s do what you do, on your way to finding what you love.

As for me and New Haircut, I plan to continue saying ‘yes’ to the right work. Because while I’m still figuring out monetization for Profit Ladder, the New Haircut revenue is a sight for sore eyes.

Cash is fuel. It enables us to be patient. To give more, longer. To earn trust. And to build remarkable things that people adore and appreciate.

Thing is, none of these New Haircut opportunities would be on my doorstep, had I not grown the company’s flywheel.

Speaking of growth…

On to lesson two…

Lesson 2: Good things take time

I’ve talked a lot about building flywheels within our businesses. That is, perpetual loops we build, to grow and monetize our business. Loops that don’t require our incessant hustling, selling, and fulfilling. Repeat.

Flywheels invite our customers in the door, deliver value, and win their business by earning their trust.

I spent years building all of these components of New Haircut’s flywheel: