We’ve all experienced it — making ill-advised decisions. Then comes retrospect, that sharp and humbling reminder that we could have done better. It lands like a punch: the clarity of hindsight illuminating where we went wrong. If only we’d had a clear head in the moment. Often, the culprits behind these stumbles are stress, pressure, and anxiety. These forces creep in subtly and cloud our judgment — not just in business, but in every aspect of life. I’ve lost track of how many times this has happened to me over my career.

I don’t believe poor decisions can be avoided entirely — we’re human, after all. But we can put things in place to reduce their frequency and impact. Years ago, my former boss, Neil Johnston, a Senior Director at one of the world’s top five engineering firms - Halcrow, introduced me to a book that changed how I think under pressure: “Think Like a Winner” by Yehuda Shinar. Clive Woodward famously used its tools to lead England to the 2003 Rugby World Cup. One of its standout techniques is T-Cup — an acronym for Thinking Correctly Under Pressure.

It sounds simple. But in practice, it’s a discipline. The ability to think clearly when under duress — or to get others to lose their clarity — is half the battle in high-stakes situations.

The First Lesson: The Netherlands

Back in 2008, as a young leader on the rise, I’d just been promoted to European Business Manager by Neil Johnston and my good friend and mentor Peter McDermott. I was managing a multi-million-dollar portfolio across infrastructure projects, with the business concentrated in the UK and Ireland but active in several European markets — Bulgaria, Poland, Turkey, and France — and maintaining advisory links with the EU.

In my previous role while employed by Atkins, I had built relationships in the Netherlands and observed the lucrative fees for advisory work. Determined to make an impact at Halcrow, I pitched and won Board approval for a Dutch market entry plan. It was a proud moment.

But I was over-eager. I pushed too hard, chasing a foothold in the Dutch market at any cost, to the detriment of the rest of my European portfolio. I was too focused on the Netherlands and did not support well enough the rest of the portfolio. The business development costs for entering the NL market were racking up. We eventually landed a high-margin contract — the best margin in our group, in fact — but it wasn’t enough to sustain operations. We exited the market soon after. Looking back, I see it clearly: I wasn’t thinking correctly under pressure. My ambition to deliver something bold clouded my judgment about feasibility. I’d chosen pride over pragmatism.

That failure became a turning point. I internalised the core principle of T-Cup. I used it in later ventures across Europe and Southeast Asia, achieving far better results — because I knew how to slow down and think straight when it counted. Perhaps, the biggest lesson was knowing when to let go of an opportunity and move my focus to the next one.

The Second Test: The Fishing Port PPP

In the latter part of 2013, I had co-founded my first startup, Frontier Law and Advisory, with my close friend and “brother from another mother” Stanley Boots. We specialised in infrastructure law and technical advisory services for projects in transport, energy, and utilities.

But by early 2014, we were running low on cash. A major client — one of Southeast Asia’s largest toll road developers — had signed a deal but hadn’t paid yet. Then came an unexpected opportunity: a PPP project for a fishing port, funded by Rockefeller Foundation and Bloomberg Philanthropies, coordinated through a group called EKO. The client found me on LinkedIn, impressed by my PPP experience and location in the Philippines.

It was a rare project — no one globally seemed to be working on PPPs for fishing ports. Stan and I scoped a small proposal (~$25k in fees), thinking we’d help them explore options, then expand later. We thought small would be quicker, and our cash flow desperately needed quick.

But something felt off. At 11 PM in Vietnam, the night before the deadline, I turned to Stan and said, “We can’t send this. It’s not what the client wants.”

We were exhausted and under immense pressure. But we knew we had to think correctly under pressure.

We asked the client for an extra 24 hours to revise the proposal. They weren’t thrilled, but agreed. We reworked everything — a comprehensive PPP framework, deep research, detailed advisory — and submitted a new proposal for $250k, ten times our original fee. We knew it was a bold move. But it was also the right solution.

They accepted.

A year later, they hired us again — for an additional $220k. The work was intense, but the outcome validated our instincts. That night, we didn’t chase what was easy. We chased what was right.

Today: Tech Startup, Higher Stakes

Now I lead a venture-backed AI startup — Silta Finance — focused on infrastructure. We help some of the world’s largest multilateral banks assess and finance multi-million-dollar infrastructure projects across energy, transport, water, health, and more.

Our technology ingests large volumes of documentation and uses AI to assess project readiness, risk, and ESG alignment. It’s used to guide complex investment decisions for projects that can reach into the hundreds of millions. We’re not a large team, and we don’t yet have the safety net of diversified revenue streams or global scale.

Every decision matters. One poor call can cost us dearly.

To counteract that, I’ve built a board that embraces radical candour. We don’t sugarcoat. We don’t let each other walk blindly into bad calls. We speak plainly — even when it stings. It doesn’t guarantee perfection, but it creates a space where we can pause, challenge assumptions, and think clearly together — especially when the pressure’s on.

T-Cup isn’t just a personal mindset — it’s something we actively use as a leadership team. We regularly reference it in internal conversations, especially when we’re up against a tight decision or a situation that feels emotionally charged. Whether we’re navigating a complex negotiation, closing a contract, or raising funds, the principle is the same: slow things down, remove ego, and sharpen the thinking.

We also seek out external perspectives. On particularly difficult or high-stakes decisions — pricing strategy, investor term sheets, key hires — we bring in advisors we trust. People who aren’t caught in the noise but know how to interrogate assumptions and test logic.

And before a big decision, I’ve developed a ritual: I give the solution time to breathe. I don’t rush into yes or no. I let it marinate — in my mind and in conversation. I hit the gym. I sleep on it. I talk it out with people who aren’t involved in the situation, just to hear it in my own words. And eventually, the right path usually becomes clear.

Thinking correctly under pressure isn’t passive — it’s a discipline. One that takes intention, process, and time.

What You Can Do

If you’re a founder, executive, or anyone in a high-pressure role, remember this: T-Cup is more than a concept. It’s a mindset you practice.

• Surround yourself with clear thinkers who will challenge you without ego.

• Don’t isolate under pressure — that’s when you need perspective the most.

• Use mentors as sounding boards. They’re removed from the emotional chaos and can help you see clearly.

• Be prepared to pause — even when the clock is ticking — to ask: Is this really the best move? Or just the fastest one?

When the pressure rises, your thinking must slow down — not speed up.

Because in the end, clarity is the competitive edge.

Remember: T-Cup. Think correctly under pressure.

And when you can’t do it alone, make sure you’re not alone.

If you’re a founder or startup operator navigating pressure, uncertainty, or big decisions — I can help. I work 1:1 with early-stage teams through business coaching, strategic planning, and enterprise negotiation.

📩 You can reach me directly: bensheppardxyz@gmail.com