Playing the Long Game: Milestones and Motivation
Every agency has its moments – the ones where things feel like they might completely fall apart. In this week’s note, I’m sharing the story of a critical incident that, at the time, felt like the beginning of the end. But with a bit of distance, it turned out to be the turning point that shaped how we grew and, eventually, how we exited.
It was 2014 and we were just starting to find our feet as an agency. A small but growing team. Some solid client wins under our belt. Things were starting to feel like they might actually work.
Then one night, everything went offline.
Ironically I was visiting a data centre when my phone started lighting up. Ping after ping. Every single site we hosted had gone down. All of them.
Back then, we had our own dedicated server with a reputable hosting company. It was pre-cloud and the trend was still to have dedicated machines for hosting. But that night, the entire thing failed.
It was one of those heart-sinking moments. Not because of the technical failure itself - things break, that’s life. But because of what it represented. We prided ourselves on reliability and service. And in one sweep, it felt like that was gone.
We got things back online within 16 hours, but the concern stayed with me much longer. That incident became one of the most important moments in our journey. It forced us to take a hard look at the type of business we wanted to be.
In the short term, we upgraded our infrastructure. Moved to cloud hosting. Built in more resilience. Our clients were thankfully very reasonable and kind. But the more significant decision was this:
How do we stop this happening again? Not just technically, but strategically.
That question led us directly to Shopify. Because we realised our value wasn’t in managing servers or patches or uptime. Our value was in strategy, design, UX, and conversion. Shopify could take care of the infrastructure - and we could focus on what we were actually great at. And if there was some kind of major incident, well that wouldn’t be all on us.
That curveball - as stressful and painful as it was - forced the pivot that shaped everything that followed.
When we made the decision to become an eCommerce-first agency and focus just on Shopify, we had to trust our gut to some extent. Trust that our sense of where the market was going, what we thought people wanted (and needed) was right.
We knew we were doing good work and we had conviction in where we wanted things to go, but at that point we didn’t have much proof that customers felt the same. We needed someone to back us. And a few months later, someone did.
I still remember that pitch really clearly. Driving off the motorway to a small Lancashire town where there was, like many places these days, a giant industrial park with a set of modern warehouses. The client ran multiple websites and was open-minded about their future tech stack - they wanted to innovate and to not do things in the same way as before.
But the real challenge wasn’t just selling ourselves. It was selling the platform we specialised in. Back then, Shopify wasn’t the safe, default choice it is now. In the UK, it still felt new and a platform mainly for very small businesses, not brands who worked with some of the largest businesses in the UK. So the pitch was two-fold: first, why us? And then, why Shopify?
We told our story and shared our experience of running our own eCommerce business. We explained why we believed in Shopify as a platform, where it was heading and why it made sense for their business. And to their credit, they bought into it. That first big ‘yes’ wasn’t just a project win - it was a moment of validation. The kind of validation you need early on to believe that the path you’ve chosen might actually work.
It was our biggest project to date. Bigger budget, more complexity, data migration, great design. It gave us something we could build on and something we could talk about to win future deals. And it gave us confidence in our plan - that our vision to back Shopify was a thing.
Momentum
We were focused on delivering the project and doing it well - because we knew there was potential for more work with that client if we did a great job and it would help us to open more doors by having a great case study.
So we kept things simple: do great work, use it to win more work, and let the plan emerge.
It wasn’t until later that we started shaping a much more structured view of the business - monthly revenue goals, more team growth, proper market positioning. But this first win was the thing that gave us permission to start thinking more ambitiously.
The Daily Battle
Any agency leaders know all too well that agency life is noisy. There’s always something demanding your attention. Deadlines, client questions, production issues, staff changes - you name it. And every single one of those things can pull you away from the bigger picture if you’re not careful.
That’s one of the hardest things about growing an agency. Your job, as a founder, is to hold the vision. To create the space to think about where you’re going and why it matters. But doing that requires separation - not just physically, but mentally. And in the early years, that’s incredibly hard.
I was still in everything. Client support, tough phone calls, urgent emails. Not because I didn’t trust the team, but because I felt responsible. I wanted to support them. To back them up. But over time, I realised I was becoming the bottleneck. I was trying to protect the team, but in doing so, I was getting in their way.
The change came when we built a stronger management layer and I learned to step back (a little at least!). To let go. Not of responsibility, but of control. That’s when I could start carving out proper time to work on the business - not just in it.
Building the Rhythm
Eventually we got better at creating structure around our vision. We held strategy workshops with external facilitators - the kind of sessions that let you zoom out and reset. They helped us reflect, ask better questions and see where we needed to go next.
And then we’d translate that into something more tangible for the team. Annual kick-off sessions and clear & consistent messaging in team meetings. I’d often find myself repeating the same story - this is what we’re here to do, this is why it matters - and while it felt a bit repetitive at times, it was always intentional.
Because when new people joined, or when things got tough, it was those reminders that helped keep everyone anchored. Over-communication, maybe. But I went with the notion that I’d rather be too clear than too vague. And that if you didn’t tell someone the story, then they’d create their own version (which would probably be wholly inaccurate!).
Getting Through the Dips
There were plenty of rough patches. Projects that we didn’t win. Difficult clients. Losing great people. Every agency has them. And as a founder, you need a lot of resilience to deal with them.
For me, there were three things that helped:
Clarity - having a clear vision meant that even when things got hard, I could zoom out and remind myself why we were doing this.
Support - having people around me I could talk to candidly, without having to pretend everything was fine. Not performative positivity - real conversations.
Patience - allowing things to breathe. Not reacting emotionally. Letting time do its job. Most of the time!
I’ll be honest - I didn’t always get it right. And there were moments where I felt like I was winging it. In reality, I couldn’t have known everything - eCommerce and digital is, and was, a story that is always being written. But that’s part of it. The trick is not to let the hard weeks shape your strategy. Take a breath, take a step back, and keep moving forward.
Advice I’d Give Myself (and You)
If I could go back to that first major milestone - the moment we won that first big Shopify project - I’d say this:
Back your plan. But look for validation early.
That one win gave us confidence. It proved our hypothesis. And that external validation allowed us to commit more fully to our direction.
Playing the long game means seeing the agency journey as a series of steps - not all of which you can predict. The clarity of your mission is what keeps you steady. And while AI and tech have made some things faster and more tactical, building a business still takes time.
You need strong foundations. Clear principles. And a willingness to evolve.
So if you’re reading this wondering where to start, here’s something simple: Pick one milestone that matters to you - just one - and work backwards from it.
Not a 10-year vision. Not a massive goal. Just one signal that would tell you you’re heading in the right direction.
Then go after it. Test your assumptions. Use the result as fuel for the next step.
Because that’s how the long game is played. One step at a time - with a clear sense of what matters most.
And if you need someone to help you to figure it out, well, give me a call.
PS: Looking to grow your eCommerce agency? We support ambitious founders through both our Agency 360 growth programme and as a Board Advisor. We’ve been there, done that and got the t-shirt (so to speak) having started, scaled and exited one of the first Shopify Plus agencies in Europe.