Why Turning Pro Is a Mindset Every Legacy Leader Needs

Hi there, friend — 

Thinking in centuries requires a different mindset. 

One that doesn’t just reject the quick win — but learns to love the long game. 

That’s why Turning Pro by Steven Pressfield hit me so hard. 

It’s a book about work. But not just any kind of work. 

Meaningful work. Enduring work. Legacy work. 

The kind of work we do in family businesses. 

The kind of work that stretches across decades, not quarters. 

Reading it made me want to crank Thunderstruck by AC/DC and run through a brick wall — but also sit in stillness and ask myself the deeper question: 

Am I showing up like a pro? 

Because most people don’t. 

Most people coast. 

They consume instead of create. 

They fear the grind instead of leaning into it. 

They wait for permission. 

They resist the pain. 

Pros show up. 

Day after day. Brick by brick. 

That’s what Pressfield teaches. 

And it’s a message every family business leader needs to hear. 

Here are my 3 biggest takeaways: 

1. Distraction is the Default 

We live in a world that rewards urgency, not meaning. 

Noise over depth. Metrics over mastery. 

And distraction is the easiest way to stay an amateur. 

The pro learns to sit with discomfort. 

To do deep work. 

To stay focused when the world wants you scattered. 

If you’re leading a multigenerational business, this isn’t just helpful — it’s essential. 

Because distraction builds nothing. 

But focus compounds. 

2. The Work Is the Path to Self-Discovery 

Your work isn’t separate from who you are. 

It’s how you become who you are. 

Whether you’re sweeping floors, leading teams, or painting murals, approach it with care, courage, and service, and that work becomes art. 

Pressfield reminds us that our work can be an act of devotion. 

And that the best version of ourselves doesn’t show up when conditions are perfect. 

It shows up when we do. 

3. Just Outlast Them 

Most people won’t last. 

They’ll burn out. 

Give up. 

Switch paths. 

But when you’re playing a 40-year game — when you’re building for your kids or your grandkids — persistence becomes a strategy. 

You don’t need to be the loudest. 

Or the flashiest. 

You just need to keep showing up. 

Because if you do … 

You outlast. 

I’ve read Turning Pro several times. 

And every time, it sharpens me. 

It reminds me that becoming the best version of ourselves isn’t automatic. 

It’s a discipline. 

That courage is required. 

That legacy is a practice. 

And that how we work matters just as much as what we build. 

If you’re tired of playing short-term games — and ready to lead from a place of grounded, quiet strength — this is your book. 

Onward, 
Matt