Welcome back to A Writing Life, our series of monthly articles written by long-time 26 member and contributor Rob Self-Pierson.
Like many of us, Rob straddles the line between commercial and creative writing. Each month, we’re inviting him to share the trials and triumphs of a writing life – and what he learns along the way.
It’s April and Rob’s training for a charity bike ride. He reflects on what cycling can teach us about building a career as a writer…
Have I mentioned that I’m cycling to Paris this July?
I love cycling. Like walking, it soothes my mind and helps bring clarity to my writing.
But that’s not the reason I’ve signed up to ride 300 miles from London to the French capital. I’m doing it for Donald (pictured above) and Gwen. You can read their stories and donate (yes please thank you) here.
In loving tribute to my uncle and my friend’s dear daughter, I decided I’d write about cycling this month. As I pootle around the lanes of Essex, thoughts come and go on the breeze. But what to share? Where to connect cycling training and my writing life?
Aha! Inspired by those LinkedIn posts that keep loading at the top of my feed, I’ll call this piece Three Surprising Reasons Why Cycling A Big Ride Is Like Building A Career As A Writer For Brands.
Right, helmet on, jacket zipped, metaphor ready. And off we go:
Reason 1. You’ve got to keep pedalling
I’m hearing a lot of industry troubles. Design Week, a welcome design world resurrection, keeps featuring stories about struggling agencies. Fellow writers and design partners are experiencing cagier clients, fewer projects and smaller budgets. It’s tough out there.
Unflappable business guru Warren Buffet is pointing us to Kipling’s ‘If’, telling us to keep our heads. I suggest this: keep pedalling.
I went freelance in the fallout of the 2008 financial crisis. First year I made just enough to pay rent and eat. Giving up was tempting. But I kept pedalling. In 2020, following a trade mark dispute, I rebranded my studio as Covid tightened its grip. Marketing budgets were being slashed. Businesses were reneging on contracts. And I wasn’t even ranking on Google. As headwinds whipped, I kept pedalling.
I’ve learned that when you keep turning those pedals, you reach somewhere. Not always where you intended to go. Oftentimes, actually, a place more interesting and more rewarding.
Reason 2. Every hill climbed tests your resolve
Some projects are a constant uphill slog. They’re the times you need to keep pedalling. As mentioned, an unexpected destination can be your reward. So can the intense feeling of overcoming.
Let me tell you a story. Many years ago, I was asked to write a brochure. Some extra writing was added to the scope late, and I was too inexperienced and intimidated to argue that I’d need more time and money to do it. So, I went ahead and drafted the line.
The brochure got signed off quickly. But of course the extra line didn’t. Draft two. Draft three. Phone call. Interview. Draft four. And five. Start over. Day rate silly now. Nails nibbled. Hair falling out.
But I didn’t give up, as tempting as it was. Instead, as the hill got steeper, I clipped back in, stood from the saddle and climbed even harder than before. I focused on the gains – like a new determination and understanding of fairness; and in craft, the ability to see when a sentence needs rewriting from scratch. My beads of frustration dripped away until the extra line eventually got signed off.
The line soon appeared on billboards around London. That felt good. So did explaining to the client why their next project wasn’t for me. Getting to the top of that hill had taught me lessons in resolve.
Reason 3. Saddle sore is real – but the pain’s worth it
You’ve got to spend a lot of time in the saddle to make a success of your brand language business. Late nights, weekends working when others are playing, long trips across the country/city/world.
It’s easy to get sore, dedicating all those hours. It’s also easy to believe it’s less effort for others, especially today with social media presenting so many ‘overnight successes’. Look at the others, gliding by on their carbon fibre frames, in their highest gear, grinning. Why am I putting in so much effort? Why’s it so simple for them?
I repeat: you’ve got to spend a lot of time in the saddle to make a success of your brand language business. Whoever you are. You’ve got to do pro bono. Work under people you doubt. Learn from them as much as you learn from those you admire. You’ve got to sit in, dig in, feel your skin blistering, get obsessed with progression, set and beat targets, fail and go again, ride till you can’t stand no more.
Then you’ll be a man, my son. I mean then you can enjoy looking back from the finish line, appreciating all you’ve achieved. Before you get back in the saddle and go again the next day. And the next day…
Together we go
I enjoyed that. Applying a constraint to my personal language play. I’m reminded how it stretches my writing, similar to a great brand language brief. This really is my time to learn and grow.
Have a go yourself. Choose your subject and metaphor. Write your headline. And see where the ride takes you. I’ll be back here in May.
Onwards,
Rob
If you’d like to share in response, message Rob via Max at 26. Also, find out more about Rob or connect with him.


