December 10, 2025

Life as the underdog

By Robert Woolf

It became a bit of a running joke when I was younger that I only ever got a “promotion” when I left a job. The person stepping into my role would suddenly get a huge pay rise to “fill my boots” – it was annoying.

But the truth is, I never spoke up. I left it until the exit interview and no one really knew how I felt until it was too late. It was the same in sport, my first love.

I was genuinely good at most sports growing up (football and running mainly) but I never pushed myself forward. At Plymouth Uni, I’d often start on the bench despite being one of the best players in the team. I didn’t hang out with the lads, basically.

In one match, I came on for a half-hour cameo in a close cup game, scored a hat-trick. We won 4-1. Next week? Back on the bench. As always.

I didn’t say anything, of course. Instead, I expressed my frustration by rainbow-flicking the captain at training. He got mad with me which, in hindsight, was fair enough. I was showing off instead of being honest about my feelings.

A similar pattern followed me into rugby coaching 20 years later. When I started helping with my son’s rugby team, I spent a whole year as the “Chief Cone Officer” (responsible for picking up cones) before the head coach discovered I’d actually played semi-pro and knew the game pretty well. He too was annoyed.

In all these situations, I don’t blame anyone else. I should have been more forthcoming. My two sons are the same: they might start in the third team but will often finish in the first. Quiet confidence runs in the family.

But that’s the thing, we do have confidence. Loads of it. We’re just not great at projecting it. We try to let our ability speak for itself while simultaneously hiding it from people.

That’s also how I was initially ignored for the A-team in gig rowing when I first moved to Cornwall, even though I could pull sub-7 on the erg (a time only one A-crew rower could match). I didn’t tell them, so how would they know? They later discovered!

It’s the same with pool too. I consistently surprise people by beating them even though I pretend to be a total amateur. I suppose I’ve never looked like a pool player or a rugby player or someone with a 6:39 erg PB.

And honestly, it’s probably the biggest reason I’m not more outwardly “successful”. It’s definitely the biggest reason Made Open isn’t more recognised. In most industries, you need that outer confidence that signals authority. Otherwise you rely on people noticing you which, generally speaking, they don’t.

In 30 years, I’ve only spoken at a few events. It’s not that I turn down invitations, I simply don’t get many.

But there are definitely perks to being the underdog. You can move through the world quietly. You can get on with the job without your ego being dented.

In fact, I quite like it. Because when you’re good at something and you reveal it quietly, the trust you earn afterwards feels genuine. And being humble helps.

(Though I’m not always humble at home!!)

Anyway, in short, I know what I’m good at. Countdown numbers round? Step aside, Carol. Pool? Darts? Rugby? Football? Tennis? Once upon a time, I could do it all.

None of it has much real-world value but it’s all part of who I am.

The self-certified underdog.