How to Plan a Career Around Luck

Kahneman’s implication is that the difference between moderate and great success is mostly luck, not skill. Chance plays a much greater role in our careers than we might wish or even realise, says Thompson in HBR. Most of us can live with the upside of this observation: we tend to claim credit for good luck anyway. But the downside — the thought of our careers as the playthings of fate — is almost unbearable. Fortunately, we can make decisions that help minimise the influence of bad luck on our lives.

Nassim Nicholas Taleb argues that £1 million earned as a dentist is not the same as £1 million earned as a rockstar because success as an artist depends much more on chance. If you imagine a game of “career roulette,” you end up a starving artist 99 times for every time you end up a rockstar. If you want to minimise the chance of bad luck, he says, be a dentist. There are no “starving dentists.”

If minimising the chance of an unacceptable outcome is our goal, what should we look for, when career decisions loom? Here are three answers.

The role of chance in determining performance

The first question to answer is how much of the success in a given field, or for a given project, is due to chance. Domains with a lot of uncertainty – where cause and effect are not well understood, or the context is changing constantly, or factors over which you have no visibility or control play a large role in determining performance – have the highest likelihood of skilled people failing. Evidence of the role of chance often comes in the form of high variance of performance – a right-skewed distribution of project outcomes. We see high variance in investment performance, new product launches, startups, creative industries, and academia, all areas where luck plays an outsized role.

The number of tries you have before poor performance is attributed to skill

Extreme uncertainty is only a problem if the organisation holds you responsible for failure that has more to do with chance than with your skill. Well-run organisations will deal with high-variance projects by relying on process metrics and by judging you on diversified outcomes. Process metrics are easiest when the causal mechanism linking behavior and performance is well understood: driving down cycle time in software experiments allows for more experiments, which produces better results. Diversification is either concurrent (making a portfolio of many investments that are held over the same time horizon) or serial (making a series of investments that average out to a portfolio).

The startup world offers an example of serial diversification: everyone recognises that, even entrepreneurs who “do everything right,” will fail more likely than not. But entrepreneurs can diversify over time by being involved in different ventures – dramatically increasing the chance that skill will pay off over time. While luck is the biggest factor in “home-run” successes, the ability to have investors say “call me when you’re starting your next company” can be achieved mostly through skill.

The degree to which early success causes subsequent success

If early success actually causes later success, the cream doesn’t always rise to the top. When success breeds success and initial success is largely random, the most successful people are those whose early luck compounded – skill doesn’t necessarily tell over time, because diversification is impossible. Sociologist Robert Merton first recognised this phenomenon in academic success and dubbed it “the Matthew Effect,” quoting a Bible passage in which the rich get richer and the poor get poorer.

Mitigating the risks of uncertainty in your career

Risk for our purposes is the chance of an outcome you can’t afford – so risk is entirely in the eye of the beholder. Often, skill can ensure that we meet the minimum economic or psychological thresholds we want from our work. But we can use an understanding of luck to pick strategies that minimise unnecessary career risk. Based on what we know about luck, here are some ways to avoid its downsides:

Avoid rigged games – Think hard about accepting a project that is highly uncertain if your performance will be compared to low-uncertainty projects.

Know what you care about – The more important relative performance is, the more you should avoid luck-dominated options, where the difference between good and great more likely results from luck than skill. Conversely, the more you care about “impact” – that the world look different as a result of your work – the more you should consider high-uncertainty choices. If you care most about certainty and social approbation, become a doctor; if you care about expected impact, start a healthcare company.

Reduce risk by smart timing – Pay attention to the order of decisions. Often reversing the order of two decisions can dramatically change their total risk. For example, starting a company as your first job out of college has very little downside – the worst case, you get interesting, valuable experiences that differentiates you among a field of bland candidates. Starting the same company after three years in your first job entails greater financial and career opportunity costs. (It often is still a good idea, but the potential downside is greater.)

Create portfolios – When operating in high-uncertainty environments, look for opportunities to diversify. As a product manager, you can run quick experiments to remove uncertainty from potential projects; as a middle manager, you can sponsor more than one project to increase the probability and magnitude of success on risky projects.

Reframe the risks you’re taking – Poker players think in terms of expectation – whether a given decision, on average, would make or lose money – as a way of avoiding decision regret and outcome bias. Often the most rewarding professional experiences have the most uncertainty. Instead of concentrating on the results of a decision, think about its expected value – both in financial and psychological terms.

Focus on what you can control: Some aspects of our lives are either highly predictable or naturally diversified. Relationships tend to be both: putting effort into friendships almost always strengthens them, and we have both many friends and many opportunities to strengthen each friendship. Invest in relationships, and they’ll pay a highly reliable dividend.