Instead, he taught me lessons I still lean on today. He introduced me to performance management, quality control, and KPI frameworks. We tracked everything—from incident response times to lane availability and road closures. I wasn’t fascinated by the roads themselves, but by the systems behind them. What do you need in place to keep something this complex running smoothly? What does “good” even look like? And how do you measure it?

We also tackled continuous improvement—finding ways to reduce costs, streamline processes, and deliver better outcomes. That lit something up in me. Not just “How does this work?” but “How could this work better?” I loved that question.

Honestly, I learned more in that year than in all of university. Uni taught me about people, teamwork, rugby, and resilience. But Optima taught me about business. It gave me my first real glimpse of the world I wanted to help shape.

And it led to my first full-time job.

Misfit to Momentum

My first job after graduation was with Atkins, a major global engineering consultancy. I joined the Birmingham office with the grand title of Business Analyst—a title that sounded impressive, but didn’t quite match the day-to-day. What I actually did was feasibility studies for traffic control centres and “outstations”—the behind-the-scenes infrastructure that keeps motorways running: signal control, traffic light systems, lane switches. The UK’s Highways Agency was rolling out a new system, and I was part of the implementation team. On paper, it all seemed like a good fit. In reality, it wasn’t. Atkins had expected an engineer. What they got was a business management graduate with undiagnosed dyslexia, who hated writing long reports and had no interest in becoming a civil engineer. I was a square peg in a round hole, and it showed. I didn’t enjoy the work, didn’t feel at home, and started to wonder whether I had a future in the industry at all.

That’s when I met Ian McClellan—known to everyone as Tiny. At six foot six and twenty-two stone, the name was pure irony. A former super-heavyweight boxer in the police and a second-team Bath rugby player, Tiny had presence—but also real emotional intelligence. He was a brilliant mentor. My captain. And he saw something in me that I hadn’t yet learned to value. Not my ability to engineer, but my ability to communicate. Coordinate. Lead. He recognised that I didn’t need hand-holding—I needed trust and autonomy. And he gave it to me. When a new international project came up, Tiny put my name forward. It was a joint initiative between the UK and Dutch governments, involving Atkins and a Dutch consultancy called Grontmij. The programme—PIMM—was a three-year pilot designed to exchange best practices in highways and waterways management.

Just like that, I was on a plane. Every Monday morning, I’d catch the red-eye to Schiphol. From there, I’d take a train to wherever the week’s meetings were—Utrecht, Zwolle, Haarlem, or somewhere else. And every Friday night, I’d fly back home. It was exhausting. But it was also exhilarating. The Dutch made a deep impression on me. I loved their clarity, their directness, their confidence. The way they presented ideas with such simplicity and logic. They were collaborative, professional, and refreshingly pragmatic. The project itself gave me the kind of exposure I never expected so early in my career. I was in meetings with senior government officials from both countries. I was helping shape ideas, share frameworks, troubleshoot systems. I was learning what worked, what didn’t, and why. And above all, I was being trusted.

Tiny kept guiding me from a distance. He understood how to get the best out of me—and how to keep me grounded. As a fellow rugby player, he had no problem knocking me down a peg when needed. But he also lifted me up. That project changed my trajectory. When it came to an end, so did that chapter of my career. But it left me with a clear sense of what I didn’t want: I didn’t want to be an engineer. I didn’t want to just manage projects. I wanted to understand businesses. Influence them. Improve them. I wanted to learn the craft of management consultancy.

The Consulting Costume

I entered the market with a boldness that only youth and blind optimism can explain. I applied for jobs well beyond my experience—and somehow, I landed one at EC Harris, a prestigious consultancy with a sparkling new office in London’s King’s Cross. It looked like Google. Colourful chairs. Open-plan spaces. Breakfast stations. It felt modern, elite. The interview process was tough—three rounds, including a partner-led workshop—but I got through it.

I thought I’d be based in Birmingham. Wrong again. It was London. Early trains, long days, and a culture that hit me like a wave. Everyone wore pinstripe suits and bright ties. On Fridays, it was beige slacks with yellow or pink shirts. They all spoke in this consultant dialect I didn’t understand—refined vocabulary, clipped sentences, poised body language. And none of it was accidental. In my first two weeks, we were put through intense onboarding—NLP-infused training covering everything from how to sit, how to speak, how to run a workshop, to how to design slides that could command a boardroom’s attention.

Just as I was starting to find my footing, I got a call from my manager. He was in Dubai.

“We want you to come out and join us. You’ve got international experience, right?”

“Yes,” I said, “I’ve worked in the Netherlands.”

That was enough.

Within days, I was on a plane. I spent around six weeks in Dubai working on some of the most spectacular projects in the world. The programme management office I joined was overseeing something like 72 billion dirhams’ worth of infrastructure and building developments. The pace was relentless—the longest hours I’ve ever worked. Days and weekends blurred together. It was intense, full-on, and ultimately a fantastic experience. It toughened me for the entrepreneurial life still ahead.

All the projects I worked on at EC Harris were like this. I was in the management consulting team, delivering high-stakes work in tight six-week windows. Long days, late nights, and frequent weekends were the norm. During that time, I learned every management consulting tool under the sun. Most days were spent running workshops with Post-its: mapping transformations, building RACI and RAID matrices, conducting stakeholder 360s, developing charters, and running two-day project setup sessions. That period became my real MBA—taught by some of the best consultants in the business, including one I remember in particular: Michael Mould. I’m still grateful for the experience. It straightened me out as a professional.

But it also wasn’t for me.

As a management consultant, I had to follow protocols set by others—strictly. There was little room for innovation, no autonomy, and that made me feel trapped. I missed the freedom I’d had in the Netherlands. The drinking culture, the intensity, the sheer number of hours—it all caught up with me. I was burnt out. I hadn’t been near a gym in months, which was completely unlike me. For anyone with an entrepreneurial spirit, being in an organisation that doesn’t allow room to breathe or build can be suffocating. It was a difficult cultural fit.

I still didn’t know I wanted to start my own company at this point—but I was gaining the skills I’d need to do it. My international experience was growing. My perspective was broadening. The pieces were slowly coming together.

From Trust to Takeoff

It started in an Indian restaurant in Birmingham. I’d just stepped off the train from London, knackered and desperate for a change. I’d been introduced to Peter McDermott, a Global Director at a company called Halcrow, and he agreed to meet me for a curry—something that, as it turns out, became a recurring theme in our friendship. Over dinner, I told him about the work I’d been doing at EC Harris and Atkins. He told me about Halcrow. We got on instantly. He was, and still is, a lovely chap. Today I call him a close friend and mentor. Honestly, he’s like a father to me.

The very next day, I was in Derby meeting John Harding and Jeff White for a job interview. It went really well—Peter had already suggested Halcrow hire me. Halcrow was a people-first, employee-owned business. It couldn’t have been more different from EC Harris, an LLP, or Atkins, a publicly listed company. I loved it immediately. It was entrepreneurial. It gave me space to breathe and thrive. That said, I needed mentoring in those first six months. Peter McDermott and Adrian Baxter helped me recalibrate—I’d been operating at a different pace and intensity, using that strange management consultant vocabulary. But once I settled in, the promotions came quickly: senior consultant, Head of Business Development Europe, PPP expert, Regional Director for Highways and Transport in Southeast Asia.

Everyone was supportive. The work was high quality. The culture was quality over margin—which is rare. Usually, margin speaks loudest. Halcrow was different. The talent across the business was phenomenal. Especially in Scotland—Alan Guthrie, Bob Diffin, Donald Bell, Peter McCracken, Neil Johnston. The list goes on. These guys were instrumental in my development. Most importantly, they trusted me. I felt safe, supported, and knew they had my back—which is exactly the kind of space I now try to create for the founders I coach.

As it happens in this world, Halcrow had caught the attention of a US firm, CH2M Hill, and acquisition was on the horizon. Around that same time, one of my best mates, Richard Burditt—an adrenaline junkie—convinced me to join him on a charity bike ride from Ho Chi Minh City, Vietnam to Phnom Penh, Cambodia. We trained every weekend. I got into fantastic shape. I’d only been to Asia once before—Singapore and Malaysia—but it had stayed with me. I knew I wanted to go back.

Before I knew it, we were in Vietnam. It was monsoon season, and the streets of Ho Chi Minh were flooded. On day one I saw a guy on a motorbike suddenly disappear under the water—he’d fallen into an open manhole. His red helmet popped up quickly, and he was fine. But the message was clear: the need for better infrastructure was obvious. The ride was extraordinary—through jungles, small towns, endless scenery. We ate fried tarantulas, grasshoppers, and goodness knows what else. One moment stood out. A 12-year-old girl tried to sell me bananas. I politely declined. Richard burst out laughing. “What are you laughing at, baldy?” I asked. He told me to look down. There was a tarantula on my chest. I was bricking it. I looked at him and said, with a quiver in my voice, “I don’t know what you’re laughing about—there are two of them on you.” I looked back at the girl. She smiled and said, “Sir, will you buy some bananas?” I bought several. She removed the spiders. A sales tactic I’ll never forget.

I didn’t want to leave. Vietnam had me. The people, the culture—it all pulled me in. I knew then I wanted to live there. In Europe, infrastructure is just another project. But in emerging markets, it changes lives. The sense of impact was overwhelming. When I got back to the UK, I met with Adrian Baxter—my boss and a lovely old chap—and pitched the idea of relocating to Vietnam. Halcrow had an office in Hanoi. Adrian’s response was classic: “Well, old boy, we don’t have any projects there. So if you want to go, you’ll have to win something.” Fair enough. I said I’d find something.

A few months later, a World Bank opportunity came up—a feasibility study for a 220km expressway. By now, I’d embraced feasibility studies. I was also aware of my dyslexia. This was pre-AI, so my hack was to listen back to what I’d written and fix the sentences. It meant I wasn’t the fastest, but the quality of my work had improved dramatically. I’d started to enjoy it. A bid team was assembled, led by me and Richard Frost, supported by Rob Holmes and others. We worked tirelessly, submitted the bid, and months later—we won. I was over the moon. I went straight to Adrian: “We won the Vietnam deal!” Adrian replied, “Fantastic, old chap. Excellent job.” Me: “So I’m going to Vietnam?” Adrian: “No, old boy. We want you here helping out in Europe.”

It was a gut punch. I had massive respect for Adrian—he was instrumental in my growth—so if he wanted me to stay, I’d stay. Plus, I still loved my job. Peter McDermott had given me a great role overseeing our European business portfolio, reporting to Neil Johnston. It was fun work. But the gods had other plans. A few months into the Vietnam project, the client wasn’t happy. They wanted the people who wrote the bid to be on the ground. So myself and Richard Frost got the call. We were heading to Vietnam. I was ecstatic.

Then, a week before departure, another twist: “Hello, old boy. We’d like you to move to the Philippines instead. It’s a bigger office and you can commute into Vietnam as needed.” I had no idea where the Philippines was. I actually thought it was in South America. Eventually, I found it on a map and off I went. When I arrived in Manila, I met my new boss, Mic Yaxley. Great bloke—of course he was, he was Halcrow. That culture ran strong across all 5,000 employees. I loved that about the company. Mic told me to leave my stuff in his office, pack a small bag, and head to Hanoi for a few days.

Picture: Rob Holmes (right) and I (left) in Hanoi, Vietnam

About a year later, I returned to Manila. The Vietnam project had been rocky from the start and required constant care to keep both the Vietnamese government and World Bank happy. It was a steep learning curve: new country, new culture, new client. Our small team was left to figure things out. It was deeply entrepreneurial—limited resources, no global support, high expectations. Meanwhile, CH2M’s acquisition of Halcrow was going through. People were scared. Morale dropped. Focus vanished. It was a shitty experience, and it ended badly. CH2M would itself be acquired by Jacobs a few years later.

But I was happy. I was in Vietnam. I had more autonomy than ever. I was beginning to truly lean into my entrepreneurial itch. When the project wrapped, I moved back to the Philippines. The national slogan at the time was “It’s more fun in the Philippines,” and they weren’t wrong. The people were warm, kind, and relentlessly positive. I got to work with amazing private sector clients—Metro Pacific Investment Corporation with the brilliant Rodrigo Franco, Ayala, Aboitiz, First Balfour with my long-time friend Tito Fernandez. By then, I was a transaction advisor, helping structure PPPs in road and rail. Interesting work. Great clients. I was promoted to Southeast Asia Regional Director for Highways and Bridges.

But not long after acquiring Halcrow, CH2M decided they didn’t want operations in Southeast Asia—a short-sighted move, given Halcrow had offices in Vietnam, Thailand, Malaysia, Singapore, and South Korea. In just three months, my role went from growing a regional business to shutting it down. I wasn’t having it. I was determined to show them why these offices should stay open.

Vietnam was hit first. South Korea soon followed. The Philippines was next. I had to act. Two major projects were up for competitive tender: CALAX (the Cavite–Laguna Expressway) and the Cebu–Mactan cable-stay bridge. My plan? Win them both. Each had an initial nine-month feasibility study, followed by a competitive government tender. If successful, we’d secure major detailed design contracts—years of work. I figured: win these, and Halcrow Philippines survives for at least three more years. Time to buy ourselves a runway.

With massive support from my friends in the UK highways and bridges team, we put together compelling proposals and won both projects. I’d successfully kicked the can down the road. I got some pats on the back. Then I got told: “Well done. You’ve proven yourself. But we’re still closing the office.”

I was furious. I’d already delivered major contracts in Europe. I didn’t need to prove anything. But more than that, my entrepreneurial instincts—my desire to grow something—were being ignored. This wasn’t the Halcrow I’d joined. That company was gone. In its place was something else, and I didn’t fit into it.

It was time to leave.

It was time to become a Founder.

The Next Chapter

This chapter ends where something new begins.

In Part 3, I’ll share the story of how I started my first startup in Southeast Asia—what we built, what we got right, and the many lessons we learned the hard way. From partnerships to pivots, fundraising to failure, it was the beginning of a whole new education. One I’m still living.

And if any of this resonates—if you’re a founder navigating big decisions, an operator looking for clarity, or someone simply feeling the pull to build something of your own—I’d love to help.

As a business coach, I work with founders around the world to make sense of the messy middle: go-to-market, deal structuring, growth strategy, negotiation, and the personal resilience that underpins it all.

If that sounds like something you need, I’d love to hear from you: bensheppardxyz@gmail.com

See you in Part 3.