22 Points On How to Have a Successful Career
Much to my surprise, almost every week someone reaches out to me to seek career advice. I suspect my only qualification for this request is that, since starting my 'career' at age 12, I have made many mistakes.
Across my ‘career’, I have been: 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 labourer &, for most of the last decade, a CEO.
Beyond selecting your life partner the choices you make about your career may be the most impactful decisions you make in life. Sadly, we aren’t taught much about what’s important — which leads us to often make bad calls.
Indeed, much of the societal pressure and advice we receive drives us to make terrible career decisions.
I have done better than I had expected, largely because I was fortunate to learn some of these principles. It's hard to distil 26 years of lessons into one Latte, so I put this together to share some of what I have learned with those who asked for my help.
People seemed to like it and asked if they could share it, or suggested I should publish it. In the hope these insights might help you, here they are.
I just wish I had learnt them a little earlier:
1. The core principles: The three legs of the stool
You should hope to have a career that ‘supports your life goals’, ‘gives you energy’, and ‘plays to your strengths’. In that order. Miss one of these ‘legs’ and the stool falls over.
Want to know why so many talented people have mid-life crises?
They centre their life on their (mainly economic) career goals. As a result, they wake up at 45 to find themselves in jobs they don't love, in poor relationships with those that matter, unhealthy, and fundamentally unhappy.
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
99% of ‘career advice’ is terrible.
While it is well-intentioned, is it is typically founded on personal biases. The advice I received from my dad was based around what worked for him, his interests, his life-orientation, and skills.
Weigh any advice by a simple fact: people typically have greater confidence in what someone else should do, than what they should do.
Be very sceptical of anyone who tells you what you should do - including yourself.
The second problem is that ‘what should you do’ is too complex a question. When the mind finds something overwhelmingly complex it defaults to simplistic answers such as ‘I studied law — so I should be a lawyer’ or ‘bankers make great money...so I should be a banker’.
The amount of talent and time that has been lost because of this simple failure is a (first-world) tragedy.
Want to know the secret?
Change the question. Focus on understanding what gives you energy, and what takes your energy. Work out how to do more of what gives you energy and do less of what doesn’t and you will end up in a pretty good place.
3. Play your cards, and improve your hand over time
Everyone is dealt a certain set of cards. The good news is that you can, with hard work and opportunity, swap the cards and improve your hand. But ultimately you need to play the cards in your hand each round as best you can.
To optimise your outcome work out what is your 'ace', your 'superpower', your 'wildcard' and double down there. Everyone has one - you just may not see it yet.
4. The three things that ultimately matter:
There are really only three things that really matter in life. These are the ‘platforms’ that your happiness and success will be founded on.
- Who you are with
- Where you live
- What you do
They are in that order.
People consistently make two mistakes.
- They mix the order up (typically choosing ‘what’ over ‘who’ and ‘where’)
- They change more than one variable at once and enter ‘future shock’.
Doubt me? Look into research on what people regret when they are dying (here).
5. ‘Who’ matters more than ‘What’ in work too
Many people join companies because they 'love' the product, the market, the industry, the salary, the perks. Ultimately, none of those things matter.
I would prefer to work with brilliant, inspiring people, in the funeral home industry (I should know. I once worked in the funeral home industry) than average people in an elite fashion house (I worked there too).
It is ‘who’ that defines life’s journey. It’s ‘who’ that teaches you, and invests in you. It is ‘who’ that inspires you to be your best version.
You become the product of the 10 people you spend the most amount of time with. It is likely that 8 of these people will be from work. Choose carefully.
Never work with B grade people or people who don’t share your values.
6. 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 with B Grade bosses.
What’s a good boss? Really just two things:
- You can learn from them
- They genuinely care about your success.
When I look back at my career I wasted time working for people who didn’t have those two attributes in spades.
7. 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 less on personal growth. In the short term, this works 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 incremental at first (staying at a company you don't like to get that next promotion on your CV). But it ultimately leads you to fall into the ‘income trap’ — being trapped in a career you don't like because changing would be too disruptive to your lifestyle.
It’s easy to increase your lifestyle, it’s hard to decrease it.
Some of the best career decisions I have made involved taking pay cuts. Make tough calls while you are still young, it will get harder each year of your career.
My mantra: Hard decisions: easy life. Easy decisions: hard life.
8. Work/Life Balance is a fool’s gold. Work/Life integration is a better goal.
Much of what we have been taught to believe about careers is founded on industrial-era thinking.
As we moved from the bucolic fields of the agricultural revolution to the horrible factories of the industrial revolution we began to see work in a different light.
As a farmer or hunter/gatherer, your work was a relatively pleasant part of life, you were outdoors and often surrounded by family and friends. As a factory worker, your work was a terrible burden. Mundane, dangerous, inhuman. Naturally, we began to see work as ‘selling our time’ to buy ‘our life’.
What you find in the most successful people you meet is that they love what they do both in work and in life. Work is still hard. But they grow to love the process of building something with great people. And love spending time with those they love. Magic.
Most multi-millionaires continue to work, even though they stopped having to a long time ago.
Hence, having the goal of trying to limit or contain work is dooming you to make poor choices about your career.
Interestingly, people who work 9–5 watch a lot more television and experience a lot less ‘life’ than those who take a more integrated view of their careers.
It’s vastly better to spend the same energy to find a vocation that you find (on balance) as fulfilling. As with anything important, this search may take time, and come with big sacrifices. But the journey alone will be worth it.
Every day it is my goal to sleep peacefully, work purposefully, and live passionately. I don’t always get there on the sleep – but I am working on it.
9. Work hard — but not for the reasons they tell you
Working hard limits your freedom in the short term. Creates your freedom in the long term.
Yet '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.
This is why you rarely meet a successful person in any endeavour who got there without working hard. It wasn’t the hours they put in that made them successful, (if that was the case success would be a linear progression), it was that they got better as a result of working hard.
The economic system is at it's core a sorting mechanism. It's goal is to allocate the best talent to the most important opportunities. You may not know it, but you are moving up and down in that sorting machine every day. An insignificant amount of additional effort each day compounds to a significant difference in outcome over the course of a career.
10. Find your superpower…and double down
For almost any skill on earth, the top 1% of people are wealthy and successful. It almost doesn’t matter what it is. But the scarcer and more in demand the skill set the better. Search out your superpower, and double down.
11. Understand ‘Power Laws’
90% of the prize pool in any sport goes to the top 5% of athletes. The richest 1% own more wealth than the bottom 90%. Like it or not, these are ‘Power Laws’ playing out.
What’s the lesson here?
Being 1% better doesn’t deliver a 1% better outcome. It delivers a 20% better outcome (in some areas - like building a technology company this can be a 100X difference).
Deliver 1% more value every day will get you a 3800% improvement in a year.
12. Success is a function of your ability to create value, capture value and scale value
This again is a three-legged stool. A talented musician who busks may create a lot of value for people — but can’t capture much of that value and can’t scale any value. If that same musician playing that same song can sell millions of CDs she can create/capture/and scale value.
You can only sell an hour of time once. A better strategy is to find something that people value, where they will share a reasonable amount of the value with you and find a way you can scale that value.
13. Position yourself into ‘positive growth cycles’
I learnt this many years ago from Bill Gates. He recognised that a) computers were going to be a big thing b) personal computers were going to grow more rapidly than mainframes c) software was going to make up an increasing proportion of the value of a computer. The compounding effect of these trends made him the youngest billionaire in history.
What Gates figured out was that if he worked hard, and executed well, the tailwinds of history would take care of the rest.
14. Work for high-growth companies
Companies with high growth provide more opportunities than they can fulfil every year. This provides the opportunity for ‘all ships to rise with the tide’. Conversely, succeeding in companies in shrinking sectors is like running up the down escalator.
15. Margins maketh the man (or woman)
Profit Margins allow for all sorts of largess. Great people, lots of development, nice offices, innovation, good pay, growth. The margin of the company you work for is likely to define your experience.
It’s no surprise that working in businesses with +70% GM (software, finance, pharma, consulting) are often the best places to be - while retail has always been tough.
16. Develop lateral, not linear skillsets
Prior to the advent of computing power, learning more and more about less and 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.
However, there is a paradigm shift that is playing out. Trying to defy or deny it is like trying to prevent the sun coming up tomorrow.
These ‘linear’ skillsets are normally predicated on storage of knowledge. E.g. John knows the tax code back-to-front. So asking John a tax question is worth $1000 an hour. John's comparable advantage is storage and search of information.
Google can do storage and search better than John. So over time, John is going to become less valuable.
Today there are probably 20,000 Radiologists around the world making hundreds of thousands of dollars. In five year’s time, A.I will ensure that most of those jobs don’t exist.
Conversely, those that learn ‘less and less about more and more’ and can draw creative lines through that knowledge to generate a unique value will have a sustainable advantage.
Focusing your education on information storage, in a narrow domain, will lead to diminishing returns. Processing or 'applying' cross-functional knowledge in creative ways still has a long way to run.
17. 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 while at Uni - I rarely ski-now.
Most of your time 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 will be working with, the problems you will be solving, the skills you will be building. As these define your experience.
Likewise, ‘sexy’ industries (advertising, fashion, travel) attract a lot of people. When Supply is greater than Demand you get Low prices for skills — so although your job isn’t more interesting, you get paid less.
If you can find an organisation where you are 'holding a candle to challenge the might of the night'. Doing something that advances humanity in some way. You are more likely to be engaged - as this is our purpose on earth.
But the key here seems to be to work out what gives you energy: Is it working with a particular type of people? Is it solving a particular type of problem?, Is it helping people?. Find a role that you can do as much of that as possible, in a business that has ‘positive tailwinds’ and you will be on your way.
18. Passions are built — not born
People typically have a ‘fixed mindset’ when it comes to their beliefs about their passions.
It’s strange because I would be surprised if anyone came out of the womb passionate about stamp collecting. They learnt it. Their passion was built, not born.
They did something and found there was some sort of reward to the activity (praise from their grandfather, success in a competition, luck at finding a rare stamp). The big dopamine hit from that reward did the rest, carving a deep neural pathway, and suddenly they had a 'passion'. They spend their time searching for that next ‘hit’.
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.
I didn't wake up passionate about transforming the legal industry, I can assure you. I built my passion.
19. Don’t sell today, to buy tomorrow
Tomorrow may not exist and is almost guaranteed to be inferior. Selling your time today (doing something you dislike), in the hope that you can buy a better tomorrow is a fool’s strategy.
20. Retire late, not young
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 most happy people I know never want to retire — because they get so much fulfilment from what they do. What a wonderful way to live life.
I learnt this one late. I am far happier having known it.
21. Take your retirement between roles
A month in your twenties is worth more than a month in your fifties.
No-one will notice if you take a couple of months of 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).
Across my career I have: been a charter boat skipper in Greece, hitchhiked across ‘the Stan’s’, ridden a motorbike across India, climbed the highest mountain in South America.
I don’t regret a moment of it.
22. Orient around second-order fun
There are two types of fun. First-order (e.g. amusement park rides, video games, jokes). Largely you will never remember this type of fun — because it is the sugar hit of life. You certainly won't speak about it on your death bed.
Then there is second-order fun. This is creating something great, overcoming a tough challenge, raising a family, working with great people to solve a challenge. Try to have a career with as much second-order fun in it - it will fulfil you in unexpected ways.
Run to the fire. Find roles that seem ‘fun’ - not the ones that seem 'sensible'.
I decided to start a law firm, without a law degree. Then start a tech company, without knowing how to code. Crazy in hindsight. Tough. But 'fun' in retrospect.
Finally, Be the superhero in your life adventure
When you look forward life seems like a complex, random, high risk, maze. It’s only with retrospect that you will be able to join the dots, and realise it is all going to be OK.
Many moments in your career will seem decidedly un-fun. In these moments remind yourself of what a privilege it is to be able to make career choices. Most people in human history didn't have that opportunity.
The most interesting and fulfilled people I know see it all as a grand adventure. An adventure where they get to be the superhero in their life's narrative. Be that person.
Your life's work is much of your life's work. Make it count.