As we enter the Year of the Horse, I find myself reflecting on the lessons of my childhood, thinking less about media cycles and more about reading long-term life cycles.

I grew up on a farm where horses and horse racing were constant topics of conversation around our dinner table. Life there was seasonal, rhythmic, and honest. You learned early that nothing naturally grows in a straight line, and nothing performs at its peak forever.

My father was a breeder and trainer of thoroughbred racehorses. My oldest brother was a jockey and later became a gifted trainer himself. Working alongside them both taught me lessons about development, timing, and restraint, lessons that would quietly shape how I later thought about leadership, business, and scale.

(Playfair Race Course Spokane, Washington 1993. #5 “Happy New Year” for the Win!

Owner and Trainer – Wayne Dobson / Jockey – Tom Dobson.)

On the farm, there was no room for shortcuts. Each horse had a natural progression. A two-year-old might show raw speed, but that did not mean it was ready for serious competition. Push too hard, too early, and you risk injury that never fully heals. Hold back too long, and you miss the narrow window where strength, confidence, and readiness align.

The craft was not just in training. It was in anticipation. Knowing what the horse was ready for next. Knowing which races to enter, which to avoid, and when restraint was the smarter move.

When that judgment was right, we won races.

When it was wrong, the damage was often permanent.

Years later, building and scaling businesses across Asia, I began to see the same pattern, just with people, capital, and organizations instead of animals.

Businesses Have Life Cycles, Whether We Admit It or Not

Every business moves through predictable stages. Not identical timelines, but recognizable phases. Birth. Survival. Acceleration. Complexity. Maturity. And eventually, renewal or decline.

Most leaders understand this concept intellectually. Fewer lead as if it is true.

The mistake I see repeatedly, at both the founder level and the board level, is applying the right action at the wrong stage. It is the equivalent of running a two-year-old in a race meant for a seasoned five-year-old, or keeping an aging horse on the track long after its body is telling you it is time to stop.

In business, that shows up as:

• Scaling headcount before unit economics are stable

• Installing heavy governance too early, or far too late

• Pushing growth when coherence is breaking down

• Hanging on to a business model because it once worked

These are not intelligence problems. They are anticipation failures.

Inflection Points Are Where Value Is Made or Lost

Most businesses do not fail suddenly. They drift.

Inflection points are moments when the rules quietly change. What worked before begins to create friction. Problems shift from normal to abnormal, recurring in new forms, and eventually to pathological if ignored.

The danger is that many of these moments do not feel dramatic. Revenue may still be growing. The brand may still look strong. But underneath, stress is accumulating.

In my experience, the most dangerous phase is what I call the teenage stage of a business, often around years five to seven. Cash flow improves, confidence rises, innovation is everywhere, but discipline begins to erode. Founders pull back without putting proper systems in place. Boards see performance and assume health.

This is where anticipation matters most.

Just as with a racehorse, the question is not, “Can it run?” It is, “What kind of race is it ready for, and what would applying the wrong strategy cost you later?”

(Ebony Merit for the Win at Emerald Downs June 11, 1994)

The Zone of Maximization Is Designed, Not Accidentally Reached

In horse racing, there is a period when everything aligns: physical strength, mental readiness, experience, and confidence. That is the zone of maximization. You do not stumble into it. You earn it through years of properly sequenced development.

Businesses are no different.

The zone of maximization is when:

• The organization knows who it is and who it is not

• Leadership decisions are clear and distributed appropriately

• Culture reinforces performance rather than compensating for weakness

• Systems support people instead of constraining them

This is where durable value is created, and where many businesses mistakenly try to push even harder, often triggering decline.

Strong leaders know when to press. Great leaders know when restraint is the smarter move.

Anti-Fragility Comes From Culture, Not Control

One of the hardest lessons I learned, both in business and on the farm, is that you cannot control complex systems into strength.

You can only design them to respond well to stress.

Anti-fragile organizations do not avoid pressure. They benefit from it. They surface problems early. They do not punish bad news. They decentralize judgment while anchoring around clear principles. Under stress, they get clearer, not louder.

Culture is what determines how an organization behaves before leadership has time to react. And culture, like training, must be intentional and stage-appropriate.

Too much control too early creates fragility. Too little discipline too late creates chaos.

Where AI Fits, and Where It Does Not

Today, AI is accelerating everything. Learning, execution, and feedback loops. That makes anticipation more important, not less.

AI does not replace leadership judgment. It compresses the time between signal and consequence. In fragile cultures, that means mistakes happen faster. In anti-fragile cultures, learning compounds more quickly.

Used well, AI helps leaders see earlier what used to take months to surface. Used poorly, it simply amplifies existing dysfunction.
The tool is neutral. The culture is not.

Knowing When to Push, and When to Let Go

One of the hardest decisions my father ever made was knowing when a horse was done racing. Not because it was not valuable, but because its value had changed. The role shifted from competitor to breeder, from performer to contributor.

Businesses face the same moment.

Knowing when to exit, reinvent, or let a business unit age gracefully is not weakness. It is wisdom. Undefined patience is not strategy. Time is not neutral.

Final Reflection

Growing up on a farm teaches you humility. You do not argue with seasons. You do not bully biology. You work with cycles, not against them.

Leadership is no different.

The road ahead is rarely a surprise. The signs are usually just ignored.

Great leaders, and great boards, do not react faster.

They anticipate earlier.

And that anticipation is what carries organizations into their true zone of maximization.