From youth we are barraged with the question “what do you want to do when you are older”. We are expected to know with prescient foresight where we will end up and how we will get there. And this continues into university. It results in students choosing careers by what first comes to mind – availability bias at its finest. The consequence is often thoughtlessly mimicking the paths of others.

This article is my personal guide to career design.

I’ll start by reframing career design. Then I’ll provide four heuristics that help me decide what to focus on.

Step 1: Reframing career design

First up, let’s reframe the most insidious yet widespread myth of career design: you need to know what you want to do.

This myth is perpetuated by internships, grad roles, LinkedIn, social conformity, etc, etc.

But searching for career certainty is career limiting.

Why? Because searching for certainty (1) closes you off to other opportunities, and (2) means that you defer your life’s trajectory to a decision made by your 20-year old self.

Searching for certainty pigeonholes your future options. Don’t be a pigeon.

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James Gorman, CEO of Morgan Stanley, puts it best:

Life is a journey. If you rush the journey,
a) you’re not going to have as much fun, and
b) you may end up in a destination that really wasn’t intended

So if career certainty is not the answer, how do you know what to focus on?‍

Step 2: How to know what to focus on

I present four heuristics, in decreasing order of importance, to help you decide what to focus on.

A: The ‘interest’ heuristic

You should follow an interest compatible with your skills.

This heuristic has two parts.

First, it is about finding your interests. Not necessarily something you love. But some interest. Preferably an interest relevant to the career world.

Second, it is about finding your skills. It’s important that the interest you follow is aligned with your skills. If your interest is aligned to your skills, you’ll be good at what you pursue. If you’re good at what you pursue you will (a) be rewarded monetarily, and (b) enjoy it. We enjoy what we’re good at.

Ray Dalio puts it best:

“The happiest people discover their own nature and match their life to it.”

Read that quote again. Seriously!

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B: The ‘learning’ heuristic

You should select tasks where you can learn the most.

Constant learning pays off in the long run. It’s the way the world works.

To get what you want, you need to deserve what you want. And the trick to be deserving is to become more talented.

Personally, I’ve taken this learning heuristic to an extreme. I was tutoring for $150/hr. But I recently stopped tutoring to start interning for free.

Working 10hrs per day means I am giving up $1500 daily. But for me learning comes first because learning heightens my ability to earn in the future. It’s simple delayed gratification.

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C: The ‘opportunities’ heuristic

You should select jobs based on the opportunities they create.

Learning is important. But equally important is (1) knowing the right people, and (2) being in the right place at the right time.

Here are three sub-rules you can follow:

(1) Choose the Option that Creates More Options

When you have the choice of two options, often it’s wise to choose the option that creates more options. This is particularly true during youth. Optimise for optionality, skills and relationships, not money.

This might mean starting a career in investment banking or management consulting even if you don’t want to spend your life there.

(2) Seize Anything that Looks Like an Opportunity (sometimes)

1. Seize any opportunity, or anything that looks like an opportunity. They are much rarer than you think.
2. Many people do not realise they are getting a lucky break in life when they get it.

If a big banker (or a CEO or a consulting partner or a big thinker) suggests an appointment, cancel anything you have planned. You may not see such a window open up again. – Nassim Nicholas Taleb

The flip side is to be extremely selective. It’s either “hell yes” or “no”.

The way I mediate these two points of view is as follows. Early in your career, say yes to anything that looks like an opportunity. Later in your career, be extremely selective.

(3) Don’t Worry About Being a Small Fish in a Big Pond

Being a big fish in a small pond sucks. You hit the walls quickly. There is no room to grow and nobody will care.

But being a small fish in a big pond is where opportunities lie. Choose the fastest growing companies to join, the hardest internships to attain, and the biggest markets to start a new company.

D: The ‘risk’ heuristic

Select riskier jobs when you are younger.

This heuristic has two components: (1) riskier jobs, and (2) when you are younger.

(1) Why riskier jobs?

There is a positive correlation between risk and reward.

‘Standard careers’ – think consulting, investment banking, accounting, etc. – have capped downside (i.e. low risk). But this means that they also have capped upside.

However, ‘non-standard careers’ – think startups – have unlimited upside. This means that riskier jobs can yield much higher rewards. However, the downside is capped at bankruptcy, which brings me to my second point.

(2) Why when you are younger?

Downside is always capped at bankruptcy.

When you are 20, bankruptcy might cost you between $1,000 and $100,000.

When you are say 40, bankruptcy might mean losing between $1,000,000 and $10,000,000.

It takes much longer to recover from a $1M drawdown than a $1,000 drawdown. When you’re 20, without kids and living at home, you can recover from downside more quickly, allowing you to take more risks.

Finally, luck favours the one who tries. Taking risks when you’re younger gives you a better chance of being on the receiving end of luck. If you’ve got a 25% chance of succeeding, it takes 4 tries on average to succeed.

You need to be in the arena to have a chance.