My Passion: Sailing, Risk and The Courage to Set My Own Course

By Stuart McCulloch, TAB Franchisee, Farnborough & Farnham

I love to sail yachts.

On the surface, that might sound like a hobby – a pleasant way to spend time on the water. But for me, sailing has become much more than that. Sailing represents freedom, responsibility, risk, perspective and, perhaps most importantly, choice. And a powerful reminder that if you don’t set your own course, you’ll drift.

Myself on the tiller off the Normandy Coast

Where It All Began

I grew up in Scotland. My parents were not sailors. They grew up with no boating background at all. But by supporting each other to build their architecture business, they created opportunities for myself and my two younger brothers that shaped us profoundly.

Our childhood was outdoors. Hillwalking. Climbing. Scout camps in Switzerland. Canoes, windsurfs and a 10-foot wooden Mirror dinghy that the three of us sailed on Scottish lochs. We became experts at loading roof racks and trailers and heading north for the weekend.

I did get out on a few yachts in my teens and early twenties, but only as a passenger.

The moment that changed everything came after 9/11. Holiday plans had to change and I booked myself onto a Day Skipper course in the Canary Islands.

My son Euan taking control of the wheel in Greece 

From Support Boat to Skipper

Getting my first qualification opened the door to chartering yachts. My wife and I began sailing with our children as part of flotillas in Greece and Turkey. There was comfort in having a lead boat helping with route planning and docking, because docking in front of an audience can be stressful.

Those early years were magical. Swimming in quiet coves. Lunches at anchor. Evenings with other crews sharing stories.

As the children grew, so did the level of responsibility. We chartered a bareboat in Croatia with another family. There were nine of us onboard with two weeks to plan our own route. No lead boat. No safety net.

Anchoring is always better than a marina, but as skipper, the pressure is real. Have you set the anchor properly? Will you wake up exactly where you went to sleep? When you are responsible for your family and friends, the weight of decision-making sharpens your thinking.

When I launched my TAB business in 2018, sailing took a back seat. Cash flow was tighter. Holidays were more modest. That is part of building something meaningful. You make trade-offs.

Then a good friend, the same one who introduced me to the franchise opportunity, bought a boat called Tally Too, with a long-term dream of sailing around the world. That gave me the chance to build more miles and experience.

Since then, I have taken my Yachtmaster theory, gained my VHF licence and I am working towards my practical Yachtmaster. I have raced to France four times. Sailed Portsmouth to Dublin. Cork to Portsmouth. Competed in the Scottish Islands Peaks Race, finishing third by just two minutes. Sailed through the Western Isles. I am currently planning a trip from Jersey in May.

Each trip builds competence. Each mile builds judgement.

TAB member sailing trip on the Solent

The Culture of Risk

One of the things I love most about sailing is the community.

Sailors, in my experience are people who are comfortable with a higher level of risk than most. Not reckless, but willing. Willing to head into open water. Willing to trust their preparation. Willing to make decisions with incomplete information. That resonates deeply with me as a business owner and as a TAB facilitator.

Running a business is not risk-free. Growth is not risk-free. Leadership is not risk-free. The question is never whether you can eliminate risk. The question is whether you are prepared, aware and decisive enough to manage it.

Sailing reinforces that mindset constantly.

Action. Reaction. Self-Awareness.

What sailing gives me personally is the direct connection between action and reaction. Trim the sail and the boat responds. Adjust your course and you feel it immediately. Ignore something and it escalates. There is no hiding on the water.

One moment stands out. We were mid-English Channel crossing a shipping lane. A tanker was about two miles away and we would pass comfortably ahead. Suddenly there was a bang and the boat heeled violently. We struggled to stand.The tanker was still approaching.

No one panicked. Alastair, the skipper, assessed calmly. Counterintuitively, the solution was to hoist another sail. It corrected the balance and restored control.

What that moment reinforced for me was this. When pressure hits, your emotional response is a choice.

In business, I have felt that same lurch. A sudden financial challenge. A difficult personnel decision. A setback that was not in the plan. Earlier in my career, I might have reacted emotionally. Sailing has taught me to pause, assess and then act decisively.

It has taught me that I am more comfortable with responsibility than I once realised. That I actually enjoy the weight of decision-making when I am prepared. And that courage is not loud. It is calm.

The Reality of Commitment

Pursuing sailing is not effortless.

Finding a place on a boat is not always easy. Buying one is exceptionally expensive. But the bigger challenge is not financial. It is alignment.

If I buy a boat one day and pursue the ambition of sailing around the world, it cannot just be my dream. My family have to buy into it. Are they coming with me? Are they happy for me to be away for extended periods? These are real conversations, not romantic notions.

Boat ownership is responsibility layered on responsibility. Maintenance, time, money and shared expectations. It mirrors business ownership in many ways. If the people around you are not aligned with the journey, it becomes much harder.

My daughter Jodie in her favourite sleeping place (when their was no wind)

Perspective at Sea

There is something extraordinary about being in the middle of the Irish Sea at night with no phone signal. During the Scottish Islands Peaks Race in May, the sky never truly went dark. The sense of isolation was incredible.

The world continues whether we are watching it or not. That perspective is grounding. It builds resilience. It shrinks everyday stress.

Sometimes, though, the best moments are simple. A ham baguette and a beer in a rocky cove with my wife and two children. No noise. No agenda. Just presence. Success is not always dramatic.

Arriving in Dublin on board Tally Too after crossing from Falmouth in 32 hrs

Planning It, Or Losing It

One of the most practical lessons came not at sea, but in a TAB peer board. A fellow facilitator shared how he balances his time between France and the UK. His secret was a full-year visual planner.

Seeing the entire year mapped out allowed me to commit properly to a summer of racing. If you do not plan it, it does not happen.

Too many business owners say they will pursue their passions when things settle down. I have been guilty of that thinking myself.

But things rarely settle. You have to design space for what matters.

The Queen joining TAB members for her Platinum Jubilee in 2022

Looking Ahead

I have an ambition to buy a boat and sail around the world.

I do not want to look back and think I waited too long or played it too safe. Whether that voyage happens or not, I know this. I will not drift into it accidentally. It will require planning, courage, alignment and the right crew. Exactly like building a successful business.

If sailing has taught me anything, it is that you cannot control the wind, but you can choose how you respond to it. And perhaps that is the real lesson for any business owner.

Set your course. Surround yourself with the right people.Be willing to take measured risks. And do not wait for perfect conditions.

If you would like to explore how TAB can help you grow your business while still making space for the things that give you energy and perspective, I would love to have that conversation.

After all, the right crew changes everything.

Stuart McCulloch

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