🧭 Lessons on Health, Choices & Commerce (Part 1)

How a personal wellness journey illuminates smarter business decisions and better leadership practices.

If you’ve followed some of my earlier posts, you know I’m on a health journey. It’s not just about losing weight or chasing a number on a scale. It’s about being a healthier version of myself — mind, body, and spirit.

An AI sketch of an early morning walk on the Portuguese Coastal Route - Camino de Santiago

I’ve set three goals. First, to simply feel better — about myself, and just… better. Second, to walk the Camino de Santiago along the Portuguese Coastal and Literal routes next summer or fall — roughly 280 kilometers over several days, carrying everything I need on my back. And third, to fit into my “little black suit” — a tailored Isaia made for me years ago in Napoli.

I am feeling better. There’s more work to do, but I’m building up strength and stamina. The Camino is starting to come into view — and I recently wore that little black suit on stage at the Retail Rebels Conference in New York. Progress.

Hiking the Isle of Kerrera, Scotland, on the way to Gylen Castle

A Familiar Road, a Different Mindset

This isn’t my first time taking my health seriously. As I approached 50, I began running 5Ks, got hooked on the runner’s high, lost a significant amount of weight, and felt great. But I ignored an old injury — the same one that once kept me out of the U.S. Navy.

Eventually, pop. It sidelined me.

I did need the time to heal, but slowing down — literally — gave my mind the chance to take over, and that became my excuse to stop.

Fast-forward a few years, and by the end of last year I was at my heaviest. Not feeling good — physically or mentally. But this time, instead of calling it an excuse, I called it what it was: acknowledgment. The truth was uncomfortable, but necessary.

Every month I had waited to “get back on track,” I fell a little further behind. The same thing happens in business — when companies lose momentum, make a few bad calls, and decide to “wait until next quarter.” That hesitation compounds. The climb back becomes steeper. The best time to turn things around is always sooner than you think.

The midpoint break during my weekend hikes - Astrea Coffee

Know Your Limits — and Build from There

One of the first lessons was acceptance. I’m not in my 30s or 40s anymore. My heart might want to move fast, but my body knows better. The trick isn’t denial; it’s alignment — choosing activities that work with your capabilities, not against them.

That’s true in business, too. We fail when we build strategies around who we wish we were, not who we are. You can’t transform until you take an honest inventory of your strengths, weaknesses, and available resources. From there, you can build stamina — or scalability — over time.

“Take care of your body. It’s the only place you have to live.” — Jim Rohn

I talk to people in the industry all the time who say, “We can’t because we don’t have…” Maybe that limits the number of steps you can take — but you can still lace up and start moving forward.

Eventually, the skies will clear (shot at Lollapalooza)

Start Now. Conditions Will Never Be Perfect.

There’s never a perfect moment to begin anything. Waiting for the weather to warm up, the right shoes to arrive, or the stars to align only delays progress.

In early January, I decided enough was enough. No new gear. No perfect timing. Just me, my sneakers, and one loop around the neighborhood. That simple start was everything.

Organizations fall into the same trap — waiting for the “perfect” data, funding, or alignment before acting. Progress doesn’t come from perfect conditions. It comes from starting small and learning fast.

“In any moment of decision, the best thing you can do is the right thing… the worst thing you can do is nothing.” — Theodore Roosevelt

Decision Delays Are Silent Sabotage

A major turning point for me was recognizing how indecision was sabotaging me. I’ve seen it in life and in leadership — the false comfort of waiting. We convince ourselves that time will bring clarity, but more often it just removes good options.

When you hesitate, opportunities expire. By the time the decision is made, you’re left with what’s left — not what’s best. I’ve seen that pattern in business far too often.

Strong leaders make timely, informed choices and refine as they go. Weak organizations wait for certainty and lose ground — or worse yet, become paralyzed by indecision and an inability to take risks.

The perfect scenario likely doesn’t exist. And if you think AI will somehow deliver risk-free decisions — don’t count on it. Knowing when and how to decide is critical, even when the decision is simply to get moving.

Eating for fuel most days allows me to indulge - like the cinnamon buns at Fitzbillies in Cambridge, UK

Food as Fuel — and as a Mirror

For me, one of the poorest decision areas was food. Not because of junk or volume, but because of speed and timing. The classic end-of-day spiral: you’re tired, you haven’t meal-planned, and you end up foraging aimlessly before giving up and ordering takeout.

That changed after a conversation with Ron Thurston on our podcast. When asked about his favorite meal, he said he viewed food as fuel. It clicked.

I still enjoy food — deeply — but I began to separate moments of enjoyment from moments of fueling.

Now I plan my week. I cook once on Sundays: simple, consistent, nourishing. Chicken, mashed cauliflower, vegetables, and a small dessert. No nightly debate. No stress. No waste. And ironically, the budget’s healthier too.

“Discipline equals freedom.” — Jocko Willink

The business parallel? Pre-decisions eliminate bad decisions. Plan the fundamentals in advance so creativity and flexibility can focus where it actually matters.

Sometimes timing is everything, sometimes it doesn't pay off (Blue Angels, photo at the Oceana Air Show)

Just-in-Time Doesn’t Work for Everything

Too many of us live — and lead — by just-in-time decisions. We think delay buys flexibility. In reality, it erodes discipline.

Who wants to waste time sitting in the train station for an hour or longer when you can lounge in more comfortable surroundings and arrive just before departure? The trick is knowing which trains run on schedule — and which ones don’t (and yes, leaving a bit of room for agility).

In business, plenty of decisions can and should be made early — assortment structures, campaign frameworks, resource allocation. Lock in the constants so you can focus energy on the variables that truly need real-time judgment.

280 kilometers...carrying just this Osprey backpack (48L)

Curation — of Bags and Assortments

My upcoming Camino walk is teaching me a lot about curation. Everything I carry, I feel — every pound, every kilometer. What I pack has to be essential, multipurpose, and intentional. So much so that I took the advice of an expert at REI and DOWNSIZED my pack.

I’m getting better, but not perfect. I still overpack — a reminder that editing is hard work.

Yet it’s also the key to freedom.

Retail is no different. As a former buyer (and forever a merchant), I know the temptation to chase variety.

At Brooks Brothers, our custom division offered 2,500–3,000 fabric options. Yet our top ten — yes, mostly navy and gray — drove the majority of sales. Simplicity, not excess, fueled efficiency and profit.

You see this in retailers across Europe and Asia — more curated assortments, less noise.

A recent GlobalData study showed that over the last decade, the share of consumers wanting broader selection is down -9.4 %, while those preferring more curated offerings has increased +7.3 %.

“The best way to choose what to keep and what to throw away is to take each item in one’s hand and ask: ‘Does this spark joy?’ If it does, keep it. If not, dispose of it.”  — Marie Kondo. 

Curation is strategy. Whether in a backpack or a business, what you choose not to carry matters as much as what you do.

Lessons to Be Continued…

This journey isn’t over — not personally, and not professionally. The further I go, the more parallels I find between health, discipline, and commerce.

Next time, I’ll explore what endurance, balance, and recovery have to do with leadership and growth.

For now, I’ll keep walking — and learning — one intentional step at a time.

✍️ Thank you for reading this post on A Sweet Blog, where I connect lessons from commerce, creativity, and curiosity — and occasionally, the road itself.