The Road He Died On
Walking the little visitor center leading into the gravesite of Meriwether Lewis, I learned he killed himself on the Natchez Trace at the young age of 35.
We'd spent a couple of weeks staying at a campground nestled along the Natchez Trace Parkway — one of the most beautiful stretches of road in this country, for the record — when we went to visit the gravesite of Merriweather Lewis. My oldest had been reading about Lewis and Clark for almost our entire 1.5 year journey. She'd walked through Jefferson's home at Monticello. She'd connected him to the maps, the journals, the whole mythology of the expedition. So when we pulled up to the gravesite along the Trace, it meant something to her. To all of us actually.
What I didn't expect was the broken column.
That's the symbol they chose for his grave marker. A life cut short. He was just 35 years old. At 35, I had just had my first child and I was just starting my first business. I was just starting to piece together my life.
I learned a lot on what was essentially a very short visit. After the expedition — after Lewis and Clark mapped a continent and came back as national heroes — Lewis was appointed Governor of Louisiana Territory. A desk job. A bureaucrat's life after years in the wilderness. Washington started questioning the expenses he'd submitted from the expedition, threatening him with personal liability for debts he'd taken on in service of the country. Jefferson — his mentor, the man who sent him — expressed disappointment that Lewis still hadn't finished the written account of the expedition after three years.
He couldn't get the journals done. He couldn't manage the governor's office. He was drinking heavily. By some accounts, he was using opium. People close to him were worried. He had accomplished things that would echo through history and he could not find his footing in the life that came after.
On October 9, 1809, he stopped for the night at a small inn on the Natchez Trace — the same road we were camping alongside. Right by the building where my family learned all of this history. At this place, the innkeeper's wife, Mrs. Grinder, heard him pacing and talking to himself. Then, she heard pistol shots. He staggered out in the early morning hours asking for water, asking for help. She was too afraid to open the door. He died just after sunrise.
Jefferson, who knew him better than most, said it plainly: Lewis had suffered from deep depression since youth. That it ran in the family. That the darkness was constitutional, not circumstantial.
The broken column and the story stayed with me for my 6.5 hour drive a few short days later. It’s still with me.
The CEO Shift — Go Deeper
THE CEO SHIFT
You Didn't Build a Business. You Built a Job That Follows You Everywhere. If every decision still runs through you, this is the piece that names why — and where to start fixing it.
FOUNDER MATH
The Three Numbers Every Founder Should Know (And Almost Nobody Does) Gross margin. Net margin. Contribution margin. If you can't pull these in five minutes, this one's for you.
We Are Wired for the Gap
Dan Sullivan calls it the Gap. It’s the distance between where you are and where you think you should be - against some ideal that keeps moving no matter how close you get.
Lewis didn't measure himself against where he started. He measured himself against what he hadn't finished. The journals still unwritten. The debts still mounting. The governorship going sideways. The expedition — the actual, extraordinary, historic expedition — barely registered. It was already behind him.
And he measured himself against everyone else’s definition of success. Jefferson, Washington, his partner, the public…they all had their thoughts around what it would look like for him to be successful. He couldn’t live up to them or handle the questions. I don’t know if he’d ever really thought about what his own definition might be.
This is what most founders do. We see the successes of others or we set unrealistic goals or we experience small setbacks and that becomes our yardstick. We fail to focus on all that we’ve really accomplished. We fail to focus on what we’ve learned and on where we’re going. We fail to see how much better we are for how far we’ve come and how that can shape our future. And we fail to truly define what success would look like for us, beyond revenue or what’s been ingrained by others.
I start every client engagement asking for four definitions of what the future would look like to help these founders map out what success looks like for them: the vision, their ideal role, the client experience and the metrics (which is not always money — sometimes it also shows up as free time). Then, every Friday, I also ask these same clients to send me three wins from the week. Any size. No minimum. Just gains — things that moved, things that held, things they did. It sounds small. It isn't. It's a weekly practice in not dying on the gaps. To not realizing the same end as Merriweather Lewis on the Natchez Trace.
If you want to work on this in real time, with a room full of founders who are asking the same questions — join me live every month. I host a free, one hour training for those who want to build their business a little differently. Details are below.
The Friday Wins Practice — One Habit That Changes the Whole Lens
Here's the full version of what I do with my clients. You can start it this week. You can share with your clients if you have them.
Every Friday, before you close your laptop:
Write down three wins from the week. Not goals you didn't hit. Not things still on the list. Wins. Things that moved in the right direction — even slightly. A conversation that mattered. A system that held. A client who renewed. A boundary you held for the first time.
Then send them to someone. A peer, a partner, a coach, a group. The act of sending is the act of accountability. It closes the week with evidence instead of a running tab of what's unfinished. And it allows others to celebrate with you.
Do this for four weeks and watch what happens to how you see your progress. Not because things will suddenly get easier — but because you'll start measuring from where you started instead of against a finish line that keeps moving.
This is the Gain, not the Gap. It's Dan Sullivan's concept and it is one of the most practical reframes I've encountered for the founder brain.
One thing to add: do it with your kids. I've started doing a version of this with my daughters at the end of each week on the road. What did you learn? What did you do that was hard? What are you proud of? They are eight and eleven. They are already learning to live in the gain.
What I Learned From My Dad
My dad helped grow a company from $20 million in revenue to over $1 Billion. He did it from hotel rooms and red-eye flights and Sunday night departures while we stayed home with my mom.
He didn't do anything wrong. He did it the way he was taught — the way most of us are taught. That working harder and building bigger is the definition of getting it right. His parents were not wealthy when he was born. He didn't grow up with much. He wanted more for us and he went out and created it for himself and his family.
But I grew up watching him “succeed” at an enormous scale… and be largely absent doing it. This success came at a cost, but I don’t think he was present to it at the time of creation. Time is a tricky thing. It’s our only irreplaceable asset. Yet, often we give so much more weight to money.
My dad came out to visit us on the Trace. He bought my daughter a new guitar. Music is a shared passion of theirs and he wants to encourage her as much as possible. They have a really special connection. He also went to the Opry with us. He is trying — really trying — to be present with my girls in a way he wasn't able to be with me. There is no blame in that. I see him clearly. I love him and love this stage of where he is at with me and my family.
What I do know is that I am building something different. On purpose. And that the impact of all those years shows up in my past-informed present.
That night at the Opry, the performers that wrecked me were not the most famous. They were the ones who were the most grateful to be on that stage. You could feel it come through the speakers. Gratitude is not a concept — it is a frequency. A vibration. It charges a room differently. And I have been actively working to reconnect with mine for years now. It does not come natural to me. It is something I have to actively work on…all of the time. (I fell in love a little with a band made up of a bunch of dudes that probably should’ve long ago retired. They were so full of energy and so happy. It was probably one of the most energetic performances of our night, oddly enough. See the photo above.)
I get to do work I love. I get to travel this country with my husband and my daughters. I get to watch my kids learn history by standing at a grave on the Natchez Trace instead of reading about it in a textbook.
I am not measuring that against what I haven't built yet.
That's the practice. And for this and so much more, I am thankful.
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“You can’t map the journey, if you don’t know the destination.”
One Shift at a Time,
Christy Cox
“Taking the road less traveled.”
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