Don’t Follow Your Passions, Retire Regularly and Develop Laterally

Much to my surprise, almost every week someone reaches out to me for career advice. I find this amusing, and humbling, as I consider my career to be remarkably non-linear.

Over the course of my career I’ve worn many hats: a plumber, a dishwasher, a ski-instructor, a bartender, an accountant, a management consultant, a skipper, a waiter, a gardener, a delivery boy, a marketer, an auditor, a laborer, and for the most part of the last decade, a chief executive and founder.

We’re not told this, but the choices we make about our careers are among the most significant decisions we’ll ever have to make in our lives. Sadly, we also aren’t taught much about what’s important — which often leads us to make bad career calls.

Through my own pitfalls, choices and experiences, I’ve been fortunate to learn some of the principles to a successful career and life. Many of these ​‘lessons’ I share might seem unconventional and go against the grain of what we’ve been told about traditional career paths.

But I hope that at least one will inspire you to embrace the often complex yet impactful decisions we have to make throughout our professional lives.