My Business Owned Me (Until I Made One Decision)

Let’s rewind to 2017.

I’m taking my first extended trip with my family, and I’m nervous.

Could I really do this while owning a business?

Sixty-three days in Italy. We had booked the villa 18 months before. Grabbed the flights as soon as they were available, so it would become real.

I got strategic. How would I prepare? What would need to be delegated and what would I need to do before I boarded that flight if I was going to be free.

Free to be present.

Free to be playful.

Free.

After we land, it takes me two and a half weeks (and a lot of Aperol Spritz) to finally start enjoying the trip.

One drunken evening, I book Elton John tickets for the family.

We make plans to visit Venice.

I stop eating Paleo and checking Slack daily.

I did it. My business finally stopped owning me.

If you’re reading this right now, you know what I’m talking about. So if you’ve ever felt like your business owns you instead of the other way around…

If you’ve ever felt guilty taking time off because your business can’t run without you…

And if you’ve ever caught yourself saying “I’ll enjoy life once the business is stable,” this story might change everything.

The Moment Everything Shifted

For two weeks I was stressing out about what was happening with my business back home.

Then, the Italian culture finally gets ahold of me.

I slip into the life of siesta, drinking a morning Cappuccino, and finally start to feel more present.

Swimming.

Long dinners.

Pizza one day, gelato the next.

No plan. No agenda.

Wake up and have breakfast and let our imagination kick in.

Maybe see wonderful Siena, or the leaning tower of Pisa, and enjoy Florence.

My business had been my purpose, that warm fuzzy blanket telling me my value. P&Ls, balance sheets, compliments, and creation.

Who am I if not my business?

Seems shallow.

But it was habitual.

Daily routines. Meetings. Coaching. Speeches.

Becoming a Writer (Finally)

It was in Italy that I finally became a writer. I mean, I was an author of multiple books before. But I didn’t write for enjoyment or learning, only for business.

Ghostwriters. Deadlines. And a grind.

Yet, there I was, in a beautiful villa, awake for hours before my family.

Working out with my sandbags I traveled with…having the maid wonder if I was in the military—lol.

My hard charging Striver ways had to be set aside.

(Got some ‘striver’ in you too? Find your Money Persona in our quiz here – it’ll not only help you make better financial decisions, but LIFE decisions too.)

We would go to the town square of Capalbio. It seemed the entire village was there.

Playing cards.

Kids playing tag.

Almost no phones.

We had captured a different world, or it captured us. We warped back in time, to find a slice of the divine.

To be at peace.

To consider quality of life.

Getting to know my kids better.

Not just morning and night like at home, but in the field of battle (that’s what we called playing the hearts card game), long dinners, and plenty of walks.

The Value of Quiet

For someone accustomed to the daily grind of business, this was as foreign to me as the streets of Italy.

Nobody to impress or manage. Just time with my thoughts, with my family.

Most people reserve these experiences for when it’s too late.

In retirement.

When the kids have moved out and gone. When they have their lives and are too busy (learning from how we operated).

There is immense value in quiet.

In moments of boredom.

Time to ponder, to think, to develop our lives.

No longer confined by the hustle of the world, but by the intent of our deeper desires.

These thoughts are rarely considered in a business or financial meeting.

What meaning does money have if never spent, if never enjoyed? What about money is important? Net worth? Why?

Coming Home, Everything Changed (for the better)

This incredible experience brought about a renaissance.

Within weeks of returning, I did my first open mic. Comedy was always something I wanted to do but never created the space or time for it. This led to one of the best 5-month periods of my life. Engaging my youngest son to join me and open for my comedy special.

Rehearsing on walks with my wife, testing jokes with my kids, and writing almost every day. Magic.

The value of hobbies.

Of truly quality time instead of rushing from moment-to-moment.

I came home a changed man.

Permanent delegation.

Consideration of what a life I wouldn’t want to retire from might look like.

Within a year, we bought our family cabin to bring a version of Italy home.

River walks.

Morning espresso.

Time without a phone.

I took lessons with my wife on how to tie flies and started to fly fish.

And learned to shoot a bow. Hobbies that were fulfilling and led to happiness.

There were no earnings attached or money to keep score. It required money to buy things, take the trip, and have the life, yes. But money without experiences is stored potential. And for many, becomes an obsession of growing a net worth without growing a life.

It didn’t stop there. I even went to Intelligentsia and learned to be an amateur barista for family and friends. Finding satiating experiences that lead to connection and conversation.

Money: Asset or Enemy?

Money can be a catalyst or can hold us captive. It can facilitate connection or can corrupt our quality of life.

Not having it means less options. Being obsessed with it can condemn us to a life of a pauper even if we have millions on paper.

Money. Is it an asset and ally or an enemy.

When we confuse money with love we lose. When we use it as a way to add value, to our lives, it serves us.

After selling my business, I lost certainty. What was next. The regular cash flow wasn’t rolling in.

Uncertainty is a culprit of misery and robs our mind of abundance. We’re more likely to play not to lose than to win.

I found myself there in 2023. Uncertain. Stressed. Heavy.

My scarcity mindset kicked in. Should I just work harder and do less that fulfills me? I knew this wasn’t the way. It was tempting. I could make it work, but at what cost?

Connection is hard to find in busyness. Connection gets lost in routine or gobbled up in production.

Yet I knew better. I knew that we win when we play.

Building a Life You Love

And yet, in starting a new business in 2024, I had slipped again. I become too serious. Addicted to my routine. Busy. Productive sure, but with less laughter.

But this time I was armed with a new awareness, a new philosophy. To change the way business is played. I’d have to let go of my past habits that served me financially but limited my life.

This time, it would require me to be intentional about time. About creating the space to recover, to relax, and to see reward in leisure.

When quality of life is at the forefront, we create differently. When it’s an afterthought, it’s lost. Thinking we will change, but sacrifice becomes our identity.

We tell ourselves it’s temporary, but life doesn’t magically get less busy. It requires mental fortitude. A different path. A better way.

What would it take to build a life you love; the one you never want to retire from?

Who would you invest time with? What would you do day-to-day? How could you celebrate the wins along the way.

Create the space for the things that don’t matter to your finances, but matter to your happiness.

This year, when I mapped out my Life Blueprint, I added date nights.
I booked trips in advance.
I set alarms to pick up my guitar and added it to the calendar.

Because without intention and space, it gets lost. What systems would serve my best life? What would lead to fun-filled days along the way?

What’s Your Italy Experience?

What is your dream life?

And what would you have to solve to create that life now, not someday?

For me, that’s things like:

• Four cabin weekends with my high school and college friends.
• A few weeks in Hawaii with family and friends.
• Visiting my parents weekly.
• Hosting brunches at our house as well as the Super Bowl.
• Sunday breakfast with the family.
• Daily coffee and convo with my wife.
• Creating the space, putting it in the calendar.
• Working out with my friends and my wife and son.

To bring it forth not just on paper, but by calendaring it.

And in business, delegating more.

• Hiring the best people.
• Doing more by committing to less.
• Focus.
• Learning to say no or not now.
• Creating quarterly themes to do a deeper dive.
• To do the things that create more value and more freedom as I grow.
• Embedding in communities to offer our services.
• Obsessing on how to improve my videos so I can be home while making an impact and serving those that I never even meet or won’t afford my firms services…yet.

My theme this year: Commitment and consistency. In my personal and professional life. Having space to enjoy people, enjoy my hobbies, and enjoy life.

I could have a bigger net worth if I didn’t fund my comedy special, but I would have missed out on one of the most special times of my life. I could have kept the business I sold even though it no longer spoke to my soul. That would have been playing not to lose.

Instead, I know I’ve already won. I’m writing this now. I have a family that I love and that loves me. I have gratitude for the life I have and the gifts I’ve been given. I get to choose the next step. Who I work with. When I work. What work I do.

You’ve Already Won

No matter where you are now. No matter what you’re going through. It only takes one idea, one relationship or one insight to improve.

Who would you have to forgive? Start with yourself.

Maybe you aren’t behind, you just had to learn, you had to prepare.

Who you are is not what you do. But what you do next can bring you closer to happiness, fulfillment and creating an exciting, compelling future.

What’s your Italy? What is your ‘impossible’ game?

The one you would dedicate your life to. The one where you learn how to be resilient and resourceful. And allow others to support you along the way.

Be inspired. Live inspired. Live the life you love.