Freshly Brewed Blog

Reflections on My First Year

“Modern capitalism is a pro at two things: generating wealth and generating envy. Perhaps they go hand in hand; wanting to surpass your peers can be the fuel of hard work. But life isn’t any fun without a sense of enough. Happiness, as it’s said, is just results minus expectations.”

~”The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness” by Morgan Housel

I made the decision to leave Patterson Dental Company in the summer of 2014.  I didn’t know what I wanted to do or where the decision would take me, but I decided that I wasn’t going to finish my work career with the company.  All too often we tend to get wrapped up in the ending of one thing to a point that we fail to realize the beginning of something else.  I’m guilty of that…consistently.

Little did I know that the start of my entrepreneurial journey in January 2017 would be the beginning of a period marked by some of the highest of highs and lowest of lows of my entire career.  

Little did I understand that I, myself, as a man of my mid-forties to early fifties, was also about to enter a phase of life marked by angst, frustration and struggle – none of which are “accretive to value.”  

Fast forward to late 2023, and I was burning out.  In 2024 I was burned out.  I needed a break.  Doing more of what I was doing, only faster and at a greater level of volume, was creating perilous results.  I longed for a reset.  My world was off its axis because succeeding at business meant losing at life.  And I knew it.  I felt it.  Every additional dollar I earned didn’t mean that much.  In fact, it started to feel like a step in the wrong direction.  

The trend was no longer my friend.  

As I stare down the barrel of 2026, I can honestly say I look forward to what I hope will be the best year of my life – work, family, friends, altruistic endeavors…all of it.  What happened?!  Am I completely delusional?  No.  A deranged optimist hyped up on caffeine?  Never.  A self-absorbed narcissist?  Uh, could you repeat the question…

No, honestly what happened was 2025.  2025 happened to me – and I happened to it.  

I did a decent job of journaling and writing notes in my day planner. Here’s what I learned along the way…

“Experience is not what happens to you; it’s what you do with what happens to you.” ~Aldous Huxley

We’re all the product of our experiences, but it’s up to each of us to take inventory and make sense of them.  If we can make sense of these experiences, then we can share them; we can teach them.  And maybe others can benefit from them.  

If others can benefit from our lived experiences, then we can each be the catalyst to accelerate someone else’s learning curve.  We can be the exponent in their equation.  I’m sick of reading about “exponential growth curves” and “the hockey stick phenomenon” and “coefficients of virality.”  I don’t live in a world of “tech bros” and most of my audience doesn’t either.  My audience is a collection of successful entrepreneurs who are operators at heart.  Most happen to own healthcare practices.  And all of them control their own destiny.  

If I can make sense of my experiences, then I can share wisdom that accelerates their success.  I can be the exponent to their equation.  

I am the product of my experiences: experience as a young member of a family business; experience as a young executive in a publicly traded company; experience as a co-founder of two successful start-ups; and experience as a consultant and strategist.  

As 2024 came to close, I saw it as the end of something.  I was wrong.  As 2025 comes to a close, I now know it was the beginning of something greater.  2025 will go down as culmination of my lived experiences with a better understanding of the crucible moments along the way.  

In the world of solo entrepreneurship, we are artists with a blank canvas; acrobats with no safety net.  Some days I feel like Alex Honnold climbing El Capitan without a safety rope.  [if you don’t know the reference, try to watch the movie “Free Solo” without soaking yourself in sweat.]

Every morning, we confront fear, uncertainty and doubt while we try to avoid draining the tank of our most valuable resource: our confidence.  Then we get to repeat the process tomorrow.  After almost a year of battling against what Stephen Pressfield calls “The Resistance,” I can confidently say the following:

I’ve earned the right to be here.  

Not exactly the most humble thing I’ve ever written, but it’s borne out of understanding – not arrogance.  I’ll close the loop on this sentiment at the end.

“Every day is all there is.” ~Joan Dideon

I was highly intentional that 2025 would be a year of no goals and no expectations.  I had spent the last decade hopping from one pressure cooker to the next.  The last thing I wanted to do was become my own worst enemy on day one.  If I’m being honest, I also wasn’t exactly sure what the business was going to become.  I needed to give myself time and space to figure that out.  In short, I needed to evolve.  

I’ve always enjoyed the “creative side of business” so this creative process felt natural to me.  I jokingly tell people that I went from being a strategist to an artist overnight, but that’s actually pretty accurate.  I spent time reading.  I spent time listening.  I spent time walking.  I spent time wondering.  I spent time reflecting.  I spent time thinking.  

And then I started spending time writing.  Many of you enjoy my podcast because you say that  I am able to break down complicated concepts and make them easier to understand.  I try to be organized and logical in certain ways on the podcast, but it’s still me speaking extemporaneously and, for the most part, unscripted.  Writing adds an element of discipline and structure to what I deliver.  In an odd way, that’s very liberating to me.  

I was also highly intentional about not scheduling something every hour of every day.  I wanted to leave time and space to allow for spontaneity and free thinking.  This might’ve been one of the biggest “unlocks” for me in 2025.  It made me slow down to appreciate every day as truly my own.  The value of my time is incalculable for one reason: it’s truly my own.  

Indeed, every day is all there is.

“The four freedoms for an entrepreneur are the freedom of time, money, relationship and purpose.” ~Dan Sullivan, Founder of Strategic Coach

I had been a follower of Dan Sullivan since my father gave me one of his books on tape (back in 1995), called “How the Best Get Better.”  After I exited my Corporate America gig, I figured I was ready enough to call myself an entrepreneur, so into Strategic Coach I dove.  His “Four Freedoms” is one of the first principles you learn in the program, so I reverted back to it with a vengeance early on this past year.  

Freedom of Money

As I referenced previously, I felt like I honored the “time freedom” part extremely well early on and with a high degree of intentionality.  I was also in a place where money was not going to be a driver of my decision-making process.  We had paid off our home mortgage a few years ago and have no debt, so I had built somewhat of a “moat around our family” (financially-speaking).  I didn’t need to chase dollars – at least not right away.  I was reasonably confident that I could build income over time that would eclipse our monthly family expenses, but I didn’t need to do that in month number one.  

I frequently advise people to “build up a war chest of cash before you make any personal transition” because having cash relieves some pressure.  More importantly, it buys you time.  I’m happy to report that my advice to myself, in fact, worked.  

There’s one more critical lesson I learned on the “freedom of money” piece: once you get past covering your monthly expenses, “freedom of money” is relative.  

Like many of you, I’ve had “a number” in my mind about what I felt was the amount of money I needed in the bank to be wealthy.  I thought long and hard about this as I was in the process of flaming out in 2024.  I would suggest that you do the same.  What I realized was that my number wasn’t actually mine – it was a function of someone else.  It was comparative.  It was relative.  We live a very good life and we’re starting to take Elizabeth on bigger experiences.  And we’re going to have to fly commercial to get there.  I’m OK with that.  

The other stark reality is that I’m not built for something called “retirement,” so the likelihood is that I’ll be earning some level of income for a very long time – not because I have to, but because I want to.  Being able to do work that serves others is winning.  Freedom of money right now is simply that “my earn rate exceeds my burn rate.”  And I’ll soon get to devote my time to endeavors that don’t require compensation.  

Freedom of Relationship 

I jokingly told a lot of people early on that I was “an army of one and an H.R. Department of none.”  And I started quickly believing that to be the case.  I also turned the corner on the humor of it and made it into a full commitment – to both myself and the members of the program.  

Another lesson learned from 2025 is that there’s brilliance in simplicity.  The value proposition of the business that I’m building starts with the fact that it’s actually not a business at all.  Don’t tell Dan Sullivan this, but I’m not building a “self-managing company.”  I am the business and the business is me.  People join the program because of the experiential wisdom I have to teach them.  My commitment to them is that there will never a subordinate coach or anyone else who will come between me and them.  My relationship with each and every one of them is direct.  It’s also personal.  Honestly, this is the part that I love the most.

Successful relationships are about collaboration; never transaction.  I’ve been blessed by a handful of people who are nothing short of incredible.  Their experience and qualification are exceeded only by the generosity of their time.  You know you’re playing a different game when someone simply asks, “How can I help?” without the expectation of anything in return.     

Freedom of Purpose

We all want our work to matter.  We all want it to have meaning.  The lesson I learned in 2025 is that the meaning that our works takes on isn’t bestowed by someone else; it must come from within.  Put another way, if you want it to mean something, it first must mean something to you.  I don’t know if I’ve ever felt a greater connection to that statement than I do today.  

I thought long and hard about the distinction between “meaning” and “purpose.”  No one will ever confuse me with Plato, but I think the difference lies in the fact that purpose is often found in work that serves others.  I think this is why I’m so committed to the simplicity of my business model and my direct relationship with my members.  It’s because I genuinely feel like I’m serving them in some beneficial way.  Many of you in this audience have that sense of purpose because of the clinical outcomes you create, but I now know how much I’ve lacked that in my work.    

“I only control the effort; not the result.” ~Ryan Holiday

I’m not a very good sales rep.  I’m pretty bright and I certainly believe in the merits of what I do, but I don’t want to convince someone to join my coaching program.  I made a commitment to myself at the beginning of the year that I’d have ample runway to create something that people wanted to be a part of.  It’s the biggest bet I’ve ever placed in my life because it’s a bet on myself.  Could I create something that would be worthy of someone’s time, attention and investment?  

One of the critical adjustments I made very early on may seem like verbiage, but it isn’t.  I decided that I wanted nothing to do with “content creation.”  Instead, I decided that my success or failure would ride on “thought leadership.”  

Content creation is pablum.  It’s click bait tied to keywords for SEO and a Google search ranking.  Content creation is short-form for short attention spans and it’s designed to “maximize marketing conversion rates” in your “lead gen funnel.”  

I want no part of that.  The speed at which artificial intelligence can generate short-form blog posts is exceeded only by the rate at which it compromises trust.  I don’t write blogs.  I write long-form essays that are authentic.  And the thought leadership I strive to share has been hard earned.  I can’t control how it resonates with you, but I can control the effort I put into it.  

“To make a living as an artist,…musician, author…or entrepreneur, you need only a thousand true fans.” ~Kevin Kelly

A thousand seems like a lot.  

I love this essay from Kevin Kelly (“1,000 True Fans”) and I’ve referenced it before.  Again, it’s brilliant in its simplicity.  The reason I go back to it so often is because it keeps me out of the “boom or bust” mindset.  I’m not chasing people to be in my program and I’m not in a rush to get there.  I’m not even sure where “there” is.  

Kelly’s focus is on doing the craft.  It’s the art.  It’s pride of authorship.  It’s in the time it takes to be unique.  I do often look at would-be competitors in my space, but they all look the same.  I want the people in my program to say that “it’s like nothing they’ve ever been a part of before.”  That’s a very high bar, but I accepted the challenge early on.  I think the lesson learned here is that if you choose to set the standard incredibly high, then you yourself become the standard.  There is no competitor.  

“How you do anything is how you do everything.” ~Zen Buddhism 

Peter Drucker was the Dean of the Business School at the University of Southern California and was regarded during his time as one of the preeminent “thinkers” in the world of Management and Leadership.  I read a ton of his stuff during my MBA studies at “the other USC.”  

Drucker had a way of creating clarity and one of his many quotes was: “If you weren’t already in the business, would you choose to enter it?  And if the answer is ‘no,’ then what are you prepared to do about it?”  A sledgehammer on competitive strategy, if there ever was one.  In the 1990s, Andy Grove used it to move Intel out of the memory chip business and into the microchip business in one of the boldest moves in Corporate America history.  [read “Only the Paranoid Survive” for more on that…]

I took Drucker’s quote to heart, but from a slightly different perspective.  I’ve been part of numerous coaching programs and have worked with several business coaches during my decades, so I spent some time going through a thought exercise where I asked myself: “I just joined the best coaching program I’ve ever been part of.  What makes it so special?”  

In a world of five-star ratings, I’m aiming for a six.  

My philosophy here is actually one I’ve shared with several clients thought the years, which is: “Everything you do either adds to or subtracts from the brand, patient experience, etc.”  Given that, we should all make a concerted effort at “surprise and delight” when it comes to the customer experience.  

“If you want to create a ‘Happiness Habit,’ then focus on four categories: Faith; Family; Friends; and work that serves Others.” ~Arthur C. Brooks

Entrepreneurs fight a constant battle between financial success and personal happiness.  For far too many of us, these seem to be mutually exclusive.  They’re not.  Arthur Brooks is a thought-leader in the realm of “happiness” and his writing is backed by solid research and extensive science…which is perfect for an analytic like me.  His book, “From Strength to Strength,” was THE catalyst that started my climb out of the depths of that “phase of life marked by angst, frustration and struggle” that I referenced earlier.  

One of the primary reasons I made the change that 2025 became was because my time and my purpose were mostly controlled by others, and because my results and my outcomes were too often compared to others.  Are you living your life or someone else’s?  Think about it for a minute…I mean really, TRULY living your life.  I faced the mirror knowing that I wasn’t.  

For a person who has built a life and a career that grew from one success to another, it’s a pretty ruthless conversation to have with yourself.  There comes a point where you just stop believing the lie that you’ve been telling yourself.  Again, to draw upon the Drucker quote: “what are you prepared to do about it?”  My answer was to be fully accountable for the changes I needed to make.  

Faith

Lucy and I made the decision to leave the church (and the denomination) where we were married and where Elizabeth was baptized back in 2023 because we felt it wasn’t congruent with our beliefs.  It’s probably one of the biggest changes I’ve ever made in my life, and I didn’t fully understand it at the time.  We joined a new church in the late fall of 2024 and Lucy has since taken on a “full-time role with part-time pay” working for the Founding Pastor.  I can see a new light in her eyes brought upon by this role, and I’m thrilled for her.  Clarity of purpose has a way of revealing that.

For me, I had to confront the question: “what do you believe, and why do you believe it?”  It would be trite to say that involves some soul-searching.  Honestly, this wasn’t a personal exploration I was looking forward to – at least, not at first.   I won’t share all of the details, but I will just give you this initial conclusion: when you have confidence in your understanding of faith, hope and belief, the self-imposed pressure of life dramatically abates.  I spend 30 to 60 minutes almost every day reading passages of scripture and faith.  You’d be alarmed to see how much of what’s found in today’s self-help books was written thousands of years ago.  

Family

I travel for work now when I want to; not because I have to.  When I’m home for dinner, I’m more “present” with Lucy and Elizabeth because I’m no longer worried about things I can’t control.  I feel like there’s a greater quality of the time I get to spend with each of them and for us as a family.  Granted, Elizabeth has no appreciation whatsoever for what I do professionally and constantly asks why I can’t hold down a steady job.  

There’s a saying that every parent can relate to when it comes to raising children: “The days are long, but the years are short.”  It’s incredibly true.  I’m confident I’m making the most of the time I have with my family.  

Friends

I’ve referenced the number of times I’ve relocated to take on greater roles.  Those have all be massively beneficial to me in terms of my professional development; however, they’ve been incredibly challenging when it comes to friendships I chose to leave behind.  I say “I chose” because I now have to own that.  I have a handful of dear friends in my life, but very few of them live in Charlotte.  It’s up to me to reinvest in those relationships and make them each a priority.  Yeah, “Cocktails over Zoom” aren’t the same thing as being next to someone in person, but it’s a start.  

Work that Serves Others

The members of the Next Level Executive program hear me talk incessantly about “building a business that’s congruent with the lifestyle you want to lead that doesn’t cannibalize yourself or your family in the process.”  This is the essence of what I call “Entrepreneurial Leadership.”  Winning in business happens when you can combine Entrepreneurial Leadership with purpose.  For some reason, I now feel more connected to the people in the program than I have others with whom I’ve worked in the past.  Maybe that’s due to the phase of life that I’m in or maybe that’s due to the other three aspects that Brooks references being in overall greater alignment.  Oddly, I’m not going to spend any time trying to figure it out.  

Putting a Bow on 2025

There’s a great story told by the author, Kurt Vonnegut, about a party given by a billionaire on Shelter Island.  Vonnegut informs his friend, Joseph Heller, that their host, a hedge fund manager, had made more money in a single day than Heller had earned from his wildly popular novel “Catch-22” over its whole history. 

Heller responds, “Yes, but I have something he will never have.”

Vonnegut replies, “Yeah?  What’s that?”

Heller says, “Knowing that what I have is enough.”

I made the statement earlier that I felt I had “earned the right to be here.”  The word “earning” connotes some level of achievement, but that’s not what I truly meant.  

The changes I started making in 2024 were cast against another phrase Arthur Brooks attributes to some of his work with the 14th Dalai Llama, Tenzin Gyatso, when he states: “we need to learn to want what we have, not to have all we want, in order to create stable happiness in life.”

For me, “earning the right to be here” is a statement born out of walking away from aspects of life defined by others.  It’s an understanding of what I think truly mattes in my life and a renewed, relentless commitment to wanting what I have – not having all I want.  

As I look into 2026, I feel like I have greater congruency in my life than I ever have before and my work brings me a level of fulfillment that I’ve always longed for.  

Maybe that’s what Heller meant by “knowing that what I have is enough.”

Go grind some beans.

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Picture of  Perrin DesPortes

Perrin DesPortes

I help healthcare professionals build and lead financially rewarding group practices.

I am happily married with an 11 year-old daughter and two dogs at home... which is one too many. In my spare time, I am an avid cyclist; enjoy cooking and reading; and love good red wine and strong coffee.

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