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'It’s easy to underestimate the power of having someone on your side'

By
Simon Dennet
Career stories
Image of a man standing against a brick wall
What did you want to be when you grew up?

Like many people, I had no clear vocation or passion, but I was always interested in entrepreneurship. I loved problem solving and overcoming the odds, and I always had a deep rooted confidence that I’d be able to do something interesting. As a bit of an introvert, I never saw myself as a high profile self-made business leader, but I knew I liked the idea of being accountable to myself.

What's most surprised you about where your career has taken you?

That the slightly nebulous role I interviewed for at a ‘music industry disruptor’ with an office in a damp South London basement would transform my career. I took the job and ended up staying for over ten years, while the company grew from a plucky start up to a huge success with a big valuation. I became one of a handful of decision makers, and spent five years working in New York City. It was an incredible ride. Not a bad return for an hour in a dingy basement!

What are you most proud of in your career so far?

Balancing the success and growth story of the organisation with my own values and integrity. High growth companies are often seen as being aggressive or competitive, but that wasn’t my experience, thanks to the founding team who had really high moral integrity. I can honestly say I made progress without ever being an a***hole or consciously stepping on someone else. I am very proud of that.

What's the biggest career mistake you have ever made?

So if I have one regret it’s that I stayed too long at that organisation. I had an amazing run, but following a return to London from New York a few years ago, I felt the company had grown to the point that it no longer held that special magic for me. I’m tremendously proud of the role I played in that growth but I wish I’d tapped out before the emotional connection diminished for me.

When are you at your best?

I thrive when I’m collaborating with others trying to solve hard problems as a team; I love being surrounded by smart people who bring interesting and diverse perspectives. I've always suffered from imposter syndrome., those voices in your head that tell you that you're not good enough or don’t know as much as the person next to you, but working closely with others has been a tonic for self-doubt. Sharing ideas and experiences, and solving problems together has helped overcome those feelings of insecurity.

Who's been on your side?

I've been lucky enough to have people to turn to at each stage of this journey. They've all played different roles; from encouraging me to share my opinions, to challenging my thinking and advising me on where to focus next. They were pivotal in making me see myself differently and pushing me to achieve something specific. It’s easy to underestimate the power of having someone on your side, or to think you’d have got there anyway, but in reality it’s transformative.

What's the best bit of career advice you’ve given others?

Be proud of your fundamental self and your values. They are non-negotiable. If they do not fit with your work environment, make a change. Never contemplate trying to be something you are not.

Knowing what you know now, what advice would you give to your younger self?

It is hard to notice when you are gradually becoming unhappy at work. Build a repeated, scheduled habit of testing your happiness. When you notice a sustained change, act on it.

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