Never a good time

There is a good time to take risks in your career. But it’s not when you might expect.

In my early career, I had several opportunities to move from my reliable, pensionable employment into riskier roles in startups and rapid-growth companies. Invariably, I declined all of these opportunities.

Looking back, the success-to-failure ratio of these opportunities is about 1:1. Some of them completely tanked, others went on to become major successes (including one that had an almost 9-figure exit). The one constant is that the people involved have all gone on to success since. Every single one of them.

In April 2014, I left my role as Head of Technology for CoreHR, a position I had grafted for almost seven years to attain. I left Core to join Vearsa (previously ePubDirect) as their CTO. It was my first real taste of risk. What made me finally take the plunge? Two things:

  1. They had a great team. Gareth Cuddy is an inspiring founder, Aiveen Hyland is an impressive COO and they had a wealth of experience across the board in finance, sales and marketing.
  2. I knew I wanted to start my own business soon, but I wanted a taste of a volatile startup before I made the leap. Vearsa was a challenging environment, and it was the ultimate preparation for launching my own company.

My timing was seen by some as borderline lunacy. My first child, my daughter Lily, was born in February of that year. I took a 25% paycut for the role, and would get a tiny amount of equity should I stay longer than a year (which I didn’t).

Fast-forward to February 2015, and I handed in my notice at Vearsa, having decided that now was the time to do my own thing. In April 2015, I started Array Software, a consulting company. Vearsa were my first customer, and I had enough work to keep me busy until August from the start.

My second child, my son Jamie, was born in June 2015. In August, I finally decided to stop doing consulting work and go full-time on my startup, Subwoofr. I managed to convince Simon Cogan, my co-founder, to join me. Again, people thought I was completely insane (I’m pretty sure it was the same for Simon). Two kids under two years of age, zero income and now I’m not even doing consulting work anymore? Did I fall and hit my head?

Maybe I am completely mad, but for me there is never a better time to take a risk than when everything depends on it being successful. If I had a cushion to fall on, an easy plan B, a fallback strategy that would allow me to fail gracefully — this would lead to me having less drive to succeed than I do right now. I need to win, I don’t have a choice. I need Subwoofr to work. My family’s future depends on it. I’m not a millenial or twenty-something who can just move on to the next thing if this opportunity doesn’t work out. If this doesn’t work, the dream is over and I’m back looking to work for someone else. What better motivator for success is there than that?

So for me, there is a good time to risk. And that’s the time that 99% of people think is the worst time to take a risk. The time when failure is not an option.

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