Don’t follow your passions, retire regularly and develop laterally: An 11-step guide to success

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. 

1. Make your career a three-legged stool

You should hope for a career that ‘supports your life goals’, ‘gives you energy’ and ‘plays to your strengths’. In that exact order.

Miss one of those legs? And the stool (you) falls over.

Don’t centre your life on career goals. Your career is there to advance your life. Your life is not there to advance your career.

2. Don’t listen to anyone who tells you what you ‘should do’ — including yourself 

Ninety-nine per cent of career advice is terrible. While well-intentioned, it is often founded on personal biases. You should weigh any advice by a simple fact: people typically have greater confidence in what someone else should, rather than what they should do. 

Further, ‘what you should do’ is too complex a question.

Often, when our mind is confronted with something complex, we default to the simple or the known. ‘I studied law, therefore I should be a lawyer.’ I hate to think of the talent that has been lost due to our minds’ shortcomings.  

Instead, change that question up. Focus on understanding what gives you energy and what takes your energy, and how you can do more of the former. You’ll end up in a pretty good place. 

 3. ‘Who’ matters more than ‘what’ in work 

Many people join companies because they love the product, the market, the industry, the salary or the perks. Ultimately, none of those things matter.

It is the ‘who’ that defines life’s journey. It is the ‘who’ that teaches you and the ‘who’ that invests in you. It is the ‘who’ that inspires you to be the best possible version of yourself.

Every day, I would choose to work with brilliant, inspiring people, than have, say, an office ping pong table. 

4. People leave bad bosses, not bad companies

After your parents and your spouse, the bosses you have are the people who are likely to have the greatest impact on your success. Don’t waste your time on B-grade bosses.

What makes a good boss?

First, you can learn from them. Second, they genuinely care about your success.

5. Always learn more than you earn

If you believe ‘work’ is selling your time for money, you will be tempted to put more weight on compensation and less on personal growth. In the short term, this is great. In the long term, it’s a disaster. 

Compensation is diluted by tax and lifestyle over time. While knowledge quietly compounds in all aspects of your life.

Worse still, compensation leads you to compromise on all the important attributes in your career. This may be small at first, like staying at a company you don’t like to get that next promotion on your CV.

But ultimately it leads you to fall into the ‘income trap’ — stuck in a career you don’t like because changing would be too disruptive to your lifestyle. 

Some of the best career decisions I have made have involved taking big pay cuts.

6. Work + life = balance 

Much of what we’ve been taught to believe about careers is founded on industrial-era thinking. You work eight hours each day so you can retire as soon as possible. Work is mundane, takes up time and is hard. 

Today, the most successful people love what they do, in both work and life. In fact, they continue to work, even though they stopped having to a long time ago. 

Don’t have a goal to limit or contain the amount of work you do. Find a vocation that you find (on balance) fulfilling. Every day my goal is to sleep peacefully, work purposely and live passionately. 

7. Work hard — but not for the reasons they tell you 

Working ‘hard’ on its own is likely a mistake — you get diminishing marginal returns for your effort. But in the long term, the additional knowledge you build from spending more time honing your craft compounds. 

You rarely meet a successful person in any endeavour who got to where they are without working hard. But it’s the repeated act of hard work itself that leads to their success, as opposed to the hours spent.

An insignificant amount of ‘additional effort’ each day compounds to a significant difference in outcome over the course of your career. 

8. Develop lateral, not linear, skills 

Prior to the advent of computing power, learning more and more about less was a pretty good strategy (assuming the ‘less’ had some value). This is why professions have been so profitable historically. A specialist doctor still gets paid more than a generalist doctor. 

Now, we’re seeing a paradigm shift away from linear skillsets, which are typically predicated on the storage of knowledge.

Take John, for example. He knows the tax code back-to-front. Asking John a tax question is worth $1,000 an hour. John’s comparable advantage is storage and search of information.

Today, Google can do storage and search better than John. In five years’ time, AI will ensure that those linear skillset-based jobs don’t exist. Those that can learn less about more and more and can draw creative lines through all that knowledge to generate a unique value, will have a sustainable advantage. 

9. Don’t follow your passions 

Conventional advice is to get into an industry you are ‘passionate’ about. This misses the point and will likely destroy your passion. I was a ski-instructor for a couple of years at university — I rarely ski now. 

In fact, for most of the time you spend at work, you won’t experience the product. People who work at travel companies rarely get to go on their own trips. 

It’s better to be passionate about the process: the people you’ll be working with, the problems you’ll be solving and the skills you’ll be building. These will define your experience.

Further, passions are built, not born. The passions you have as a child are likely to be different from the passions you have as an adult. So ‘following your passions’ is unlikely to be the best course.

10. Retire throughout your career 

The industrial-era goal was to retire as young as possible, as soon as there was no economic necessity to work. My father retired at 50. But failed to enjoy his career. The happiest people I know never want to retire — because they get so much fulfilment from what they do. 

Instead, take your retirement between roles.

No-one will notice if you take a couple of months between roles to experience all that life has to offer — even if this is within the same organisation. (Hint: if they aren’t supportive, tell them you are resigning and happy to reapply for your role in two months.)

11. Find roles that are fun — not ones that are sensible 

By fun, I mean creating something great, overcoming a tough challenge, raising a family, working with great people to solve a challenge. Having a career with this type of fun will fulfil you in unexpected ways. 

I decided to start a law firm, without a law degree. Then start a tech company, without knowing how to code. Crazy in hindsight. But ‘fun’ in retrospect. 

Your life at work makes up much of your life’s work. Make it count.

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