The Hard Road

Learning to choose the smartest option, not the toughest one.

The first time you get on a bicycle, you soon fall off. The second time? Probably a similar story. But at some point, the action becomes natural. Your mindset shifts. You think to yourself, “that’s right — I was always riding bikes!” Mastery of that skill takes time and effort, but the rewards are great.

Discomfort is a necessary by-product of change. To become comfortable in a new role, you’ll have to step outside of your comfort zone. This is true for anything that’s worth striving for. You’ve got to find the resolve to battle through it, until you’re comfortable enough with your abilities to wonder how you ever struggled in the first place.

There’s real value in pushing yourself into a space where you feel that discomfort. I’m a big believer in extending myself, to see how far I can go; to discover what I’m capable of, and what I’ve got in me.

There’s a difference, though, between taking the hard road and the smart road. In the past, I’ve generally favoured the former. Over a decade ago, aged 23, I knew that, if I wanted to achieve my goals and ambitions, I had to move on from my previous strategy of investing in real estate, and spend time learning about scaleable businesses.

I willed myself into that situation. I kept pushing and pushing. I didn’t know much, but after looking at a few options in a range of industries, I told myself that Mandalay — then named Weighmaster — was my entry point. Yet I never envisaged that it would be as challenging as it ultimately has proved to be. For the first two or three years with this company, I felt completely out of my depth. I felt complete inadequacy. Plenty of people — likely more sane than me — would’ve pulled back, given up, or rationally exited due to the obvious failure and challenges that needed to be overcome in order to make a success of the venture.

That period challenged every aspect of my psyche: my relationship with money, with others, and with my own identity. I put on lots of weight. I nearly went bankrupt (more than once). It was a weathering and transformative process, but eventually, I started to understand the environment. The learning period was a lot longer than I’d desired and I’d never wish that journey upon anyone.

That mindset can lead to problems if it becomes ingrained, however. For much of my career so far, my natural response to a challenging situation has been to start jogging down that hard road. To will myself into it and know that I will reach the other side.

My level of comfort and resilience in tough situations — particularly in business — is pretty high, because I’ve been a bit of a masochist. Over time, I’ve built up a reference chest that shows I can survive tough situations. I’ve proven to myself that I can work hard. As a result, I feel a level of self-assuredness that others might not.

But I’m still learning to shift my mentality toward jogging down the smarter road. It’s a major behavioural change. I constantly need to stop and remind myself of the need to be a wiser judge of my time and energy than Simon, aged 23. Although the hard road still beckons, it doesn’t necessarily mean it’s always the best option.