Ive been thinking about my career and how lucky I’ve been, how I always seemed to be In
the right place at the right time, when opportunities came up.
One thing I realised whilst reflecting,
I’ve Spent Very Little of My Career in My Comfort Zone.
Here’s my take on that…
Most people spend their careers trying to find comfort.
I spent mine running from it.
Not by design. Not because I had some grand philosophy about growth and discomfort. But
because life kept presenting me with opportunities that were bigger than my experience, and I
kept saying yes anyway.
My career didn’t begin in a boardroom. It began in a bakery.
As a young boy I worked alongside my Grandad (Papa), learning things no business school
teaches, the value of hard work, what real responsibility is, what it means to serve people
properly, and that showing up matters even when you don’t feel like it.
Then at eighteen, I found myself running it.
I wasn’t ready. I know that now. I probably knew it then. But sometimes life doesn’t consult
your confidence levels before handing you responsibility. You either step up or you step back.
I stepped up. And in doing so, I learned the first great lesson of my career: responsibility has
a way of forcing you to grow faster than comfort ever will.
The Leap I Had No Business Making
At twenty-five, I made a decision that made very little logical sense. But huge sense
emotionally.
I left the bakery and walked into a sales role.
There was just one problem. I had never sold anything in my life.
Not a product. Not a service. Not even an idea. Everything about sales was foreign to me, the
prospecting, the rejection, the art of asking for business without flinching. I had no track
record, no training and no safety net.
What I did have was a work ethic second to none and a willingness to be bad at something
while I got better at it.
And I got better.
Because here’s what nobody tells you about stepping into the unknown: the discomfort is
loudest at the beginning. Push through that early noise and something shifts. Competence
starts to build. Confidence follows. What once felt impossible starts to feel like yours.
Leading Before I Knew How
Before long, another opportunity arrived. A promotion into national sales management.
Once again, I had no experience of doing the job.
Overnight I went from selling to leading, responsible not just for my own results but for a
team spread across the country. I had to learn how to motivate people I hadn’t hired, manage
performance I couldn’t always see, and take accountability for outcomes far beyond my own
efforts.
It was uncomfortable. It was stretching. It was exactly where I needed to be.
The Biggest Leap of All
At thirty-five, I started Midshire from scratch.
If you’ve never built a business from nothing, it’s difficult to describe what that feels like.
Every decision is yours. Every mistake is yours. Cash flow, hiring, winning customers,
retaining them, there are no colleagues to defer to, no processes to hide behind, no one else’s
name above yours on the door.
It is the ultimate comfort zone eliminator.
Over the years that followed, Midshire grew steadily, eventually reaching a turnover of £35
million before being acquired by a multinational.
From the outside, perhaps it looks like a clean, well-executed journey.
The reality?
Every single stage required stepping into something I hadn’t done before. Something
uncertain. Something that didn’t feel comfortable at the time and wouldn’t feel comfortable
until I’d done it long enough to make it mine.
The Pattern I Only Recognised Looking Back
The moments that defined my career were never the ones where I felt fully prepared.
They were the moments I said yes before I was ready. The moments I took the role, made the
call, started the company, and figured it out as I went.
That’s the pattern. And it’s the lesson I now share with every business owner I coach:
Growth and comfort rarely travel together.
If you’re waiting to feel completely ready before you take the next step, the promotion, the
pivot, the business, the bold decision, you may be waiting a very long time.
Because readiness, in my experience, isn’t something you feel before you act.
It’s something you build by acting.
The opportunity you’re hesitating over? It won’t wait until you feel qualified. It won’t arrive
on a day when the timing is perfect and the risk feels manageable.
It arrives now. Messy, uncertain, slightly too big for where you currently are.
And that,
if my career has taught me anything,
is precisely the point.
Step into the discomfort. That’s where everything worth having is built.