Designing Your Ideal Role as an Owner

I have found, in my short time on earth, that there are people in our orbits who take it upon themselves to teach you a singular lesson. Something they’ve taken from how they lived and want to make sure you, as someone they care about, learn that lesson the easy way. My Dad’s best friend and roommate from college was one such person.

They went to a prestigious university, and he excelled at Math. Excelled even by this institution’s vaunted and accomplished student body’s standard. Over the years, he followed a winding journey and built a career for himself in custom woodworking. Hand-made cabinetry and doors if I’m remembering correctly.

He used to joke that he was the world’s greatest underachiever. Not because there’s anything less-than about being a woodworker or working in the trades … but because he had the potential to do, and be, something else. Use a gift he had, a talent, that was unique and exceptional.

But he was a passenger on the sailboat of life. He just sort of went with the flow, didn’t direct his course, and took what came his way. He was excellent at his profession, but he sort of fell into it. It wasn’t something he aspired to or dreamed of. It was something that happened to him. And he was regularly trying to impress upon me that I should not live my life this way.

That I too was exceptional in some way and shouldn’t let the tides wash me away.

It took me a while to internalize this lesson. Some people never do.

But my takeaway is that you should always choose. Whenever possible, have a say in what happens to you. Live life on your own terms. Fight for agency.

We started talking about freedom last week, and that’s what this means to me.

Nowhere above did I talk about taking vacations or living a care-free life. That’s not what freedom is. Freedom is the ability to choose. And sometimes you choose to step away, or take a break, but the choice is the thing itself, not the action.

This has always been an underlying theme in how I think about business and how I work with owners. Early on, your business demands everything from you. Later, it demands that you give certain things up. At each stage, your role changes whether you design it or not.

Stage 7 is the first time you get to design it deliberately.

There are many ways you can show up in your business (and this isn’t an exhaustive list by any means):

• The Strategist – sets direction, makes key decisions
• The Rainmaker – focuses on relationships and growth
• The Expert – stays close to the work they love
• The Builder – creates new initiatives, systems, or offerings
• The Steward – optimizes, protects, and maintains the business

One is not better than the other. They’re basic archetypes or roles to help you think through the opportunities available to you. Think of them less as strict boundaries for you to play in, and more clay for you to mold something out of. And this is where it becomes a strategic decision.

The role you choose to play determines how decisions flow, where risk concentrates, how adaptable the business is, and what options remain open to you long-term. Your presence, or absence, shapes how the business behaves when you’re not in the room.

That’s why this stage isn’t about “what do I feel like doing,” but about designing a role that fits both the business and the life you want it to support.

Here are some questions to help bring that into focus:

• What decisions do I want to own personally?
• Where do I create the most value?
• What drains me that no longer needs to?
• If I stepped away for 30 days, what should wait for me?

There are no wrong answers. It may be that what you really want your role to be, is one where you’re not there anymore. That’s not good or bad. And similarly, you may decide you want to lean in and take the business to another level or start a new one. Success isn’t one or the other. It’s having the choice.

Getting to stage 7 likely involved resisting the urge to let the waves take you, fighting for agency over what the business became and your role in it, charting your journey in search of your dreams. Now that you’re here, all that work pays off. Your ship is seaworthy, it’s strong, it’s fast and it can take you wherever you please.

You are the captain and now is your time.

What will you choose?