One thing I’m continually surprised by is how little time people spend at the start of their careers choosing their direction, in proportion to the amount of time they spend pursuing said direction.

I’m going to broach this subject by looking through magnifying glasses of different powers. The first magnifying glass will zoom in to understand why it is psychologically and practically so difficult for an individual to meander first and master later. The second magnifying glass will zoom out to explore why our economic and cultural systems have elevated exploration as a privilege, rather than a right.

magnifying me

Within the space of five years, I’ve built, scaled and experienced big tech, challenger brands, tiny startups, and global communities. I’ve been part of a 20-person VC-backed company, a 15,000-person public company (Mum, if you’re reading, no - I’m not going back to LinkedIn just yet 😆), a 2-person founding team, a 50-person challenger university and a 5-person bootstrapped startup. I’ve worked across four different countries, 1 remote job, 2 hybrid jobs, 1 meant-to-be-in-person-but-COVIDified-job, and 1 fully in-office job. I’ve been a data analyst, a generalist, a consultant, a Head of Partnerships/Growth/Special Projects, and a founder. In short: I’ve been exposed to a lot of different working environments.

As I was building out this first chapter of my career, it felt like absolute chaos. Indeed, “building” is far too intentional and grand a verb to describe it. But looking back, it’s easy to see that I treated the first five years of my career as a series of experiments. What both my past and present self can agree on is that I have spent half a decade exploring a range of potential directions. When I consider the amount of time I have left in my career–probably between forty to fifty years–five years doesn’t seem like a long time at all to commit to such an important endeavour: choosing my direction.

on choosing versus pursuing

Let’s try and make sense of this by considering one of life’s other most important decisions: choosing who we’re going to spend our life with. The vast majority of people in the western world choose to date at least a handful of people before they settle down with their life partner. Rationally, this makes sense. Most people aren’t keen to make such a critical decision on the basis of just one or two relationships (forgive the rational tone, would you believe I’m actually a hopeless romantic?) I think that’s why, over the past few years, a number of my friends who had been in long-term relationships since their teen years started confiding in me that they weren’t sure they could settle down with their current partners. Even if you love someone deeply, it can be difficult for your younger self to stare down the long, shadowy corridor of your future and feel unbridled confidence in your decision. It is very human to wonder if there might be someone out there who is better suited to you. I’m not saying that there’s a right or wrong here. Love, as we know it, is highly illogical and complex. But experiment with me: what might happen if we were to approach our careers in a similar way?

climb a bunch of hills

A few years ago, I was wandering around London with an engineer friend, who–for some relevant reason my memory simply refuses to cough up–started explaining hill climbing algorithms to me. Imagine a landscape with hills of varying heights, she said. You’re dropped randomly somewhere on the landscape and your job is to find the highest point. What’s your first move?

Umm, I replied hesitantly.

To any behavioural economists reading this: yes, yes, I know you know the answer. To everyone else: don’t worry, they’re just getting excited because humans are weird and these algorithms tend to reflect that weirdness.

Now, before pushing you straight into a pool of human-algorithmic weirdness, I want to make something clear. I use the term “highest point” throughout this essay, not as a value judgement about any particular path or strategy, but more as a synonym for the rather soulful, quasi-spiritual, potentially non-existent concept of one’s “calling”. If this doesn’t resonate with you, please feel free to substitute whatever does–pursuit, purpose, praxis–take your pick.

Put simply, there are three types of hill-climbing algorithms. The simplest one is making your first step one that takes you higher. This is how most young people build their careers. They find themselves plopped in an often random part of the landscape with no clue how they got there–because our initial coordinates are largely decided by factors outside of our control: who our parents are, where we went to school, what country we were born in, what language we speak etc–they spot the hill closest to them, and they start ascending as if their life depends on it. The pressures of the real world, coupled with the harshness of the current economy–make the first hill you see the least uncertain, and therefore the least anxiety-inducing. I mean, of course we climb it.

There are two problems with this approach. The first is that these folks often fall victim to sunk cost fallacy. It’s much easier to stay at the same company you’ve been at for 7 years, because that promotion your manager has promised you for the last 627 days is finally “on the agenda for next week”! Even though we rationally know the promotion isn’t going to materialise, we can’t bear to waste the effort we’ve already invested. The second problem is that these people stay the course, sometimes in search of stability, but often just out of pure habit. This is a phenomenon known as “status quo bias”, a cognitive phenomenon that describes how people tend to prefer the familiar over the unfamiliar, even if the unfamiliar option may be the better one.

The slightly more complex version of the algorithm is when things get a little spicy. In this version, you do a lot of random wandering. The point? To increase your odds of finding a higher hill before you start your climb. This means that when you get to the higher hill, you can be much more intentional and confident about your climb. You tend to do a lot less second-guessing as well, because you have higher conviction you’re already at a pretty high point in the landscape.

The best algorithm means dropping yourself into random parts of the landscape multiple times and ascending a few steps whenever the terrain seems promising (I use the word “best” loosely because while in algorithmic terms this may be the best option, I’m not arguing it’s the best way to build a career). When you’ve done this a few times, you can circle back and decide which hill was highest, before going full-throttle on your climb. The problem with this approach, of course, is that others (including the market) will often perceive you as a commitment-phobe (hark, the Gen Z haters siiiingg). The conclusion I’ve drawn is that as long as you develop a compelling narrative around your career strategy and why your decisions have taken you up a number of hills, you can persuade hiring managers that there was method to your madness (at least long enough for them to hire you and for you to prove your worth).

the myth of the best strategy

You probably came here expecting me to share some hot take about the best strategy for building your career. If you pushed me to give you an answer, I would say: embody the third algorithm to the extent that you are able. Logically, it makes most sense to meander first, and then climb. This is because you simply don’t have enough data and insight at the start of your career to make an informed decision about which hill you might have most success and enjoyment ascending. Only when your career experiments are exposed to the oxygen of real environments and patterns, can new compounds be formed.

Indeed, in Clayton Christensen’s How Will You Measure Your Life, he writes about how in business you can set out with all the deliberate intention in the world, but winning strategies are most often driven by unexpected lightbulb moments that emerge as cracks in your initial strategy when it collides with reality. This is what he calls emergent strategy.

Front-loading exploration at the start of your career–whether it’s deliberate or not–enables you to create space for emergence. Once you have done sufficient exploration, your emergent strategy will lend you a spade to dig with, and you can begin to excavate until you hit upon gold.

This is the simple answer. The shades-of-grey answer is: there is no “best” strategy. The algorithm that you embody, whether intentionally or inadvertently, is dependent upon your goals. Above, we assumed that people are optimising for the greatest success or enjoyment in their career. But–however counterintuitive it may seem–many people are not. Why? Because to do so is an inherent privilege.

the unspoken privilege of agency

I’m not the first person to use this analogy to describe careers, nor will I be the last. What I have found other writers neglect to highlight, however, are the characteristics displayed by people who happen to embody the third algorithm.

In my experience (small sample size in the grand scheme of 8.2 billion people, but go with me), a combination of traits often found in the most ambitious people enable us to go in search of the highest point in the landscape. These are:

• a higher-than-average risk tolerance

• a chip on one’s shoulder (often derived from being part of a historically marginalised group)

• a deep-seated belief (or, in fact disguised insecurity) in oneself

• a high level of agency

• a certain flavour of inherited privilege

Whether by smart intention or by happy accident (read: definitely by happy accident), I have so far embodied the third algorithm. My inexpert psychoanalysis? I have a mid-to-high risk tolerance (partly a vengeful crusade against my younger self for spending the first 20 years of my life taking zero risks, and partly informed by a familial safety net); an immigrant-infused chip on my shoulder; a profound desire to fulfil my potential; and a high level of agency that has been sharpened by repeatedly choosing to do the hard thing.

While there may be a theoretically optimal strategy, it’s clear that the ability to pursue this strategy is tightly braided with privilege and the nuances of personal circumstance. And so the answer to my earlier question has become apparent: most people don’t spend more time at the start of their career choosing their direction because they simply don’t have the privilege to do so. This results in the vast majority of the population embodying the first algorithmic strategy: pursuing random career avenues that serve neither themselves nor the collective.

To continue enabling only the privileged few to pursue the optimal strategy, we undermine our collective ability to solve our greatest challenges. Why? Because the “1 in 60” rule in aviation also applies to careers. Being just 1° off course over 60 nautical miles will put you 1 nautical mile away from your intended track. In laywoman’s terms: small deviations from your intended direction can accumulate over time and leave you far from where you intended to be.

So, my question has evolved.

from individual exploration to collective emergence

Let’s assume our collective objective is to mobilise as many humans as possible around challenges they are uniquely energised and well-positioned to tackle, so we can collaboratively progress our society (and have fun while doing it). We’ve established that the optimal way for people to find the right hills is to give them more time to randomly explore, before choosing the hill they wish to ascend. That means we need to find creative ways to carve out pockets for emergence within practical constraints, by dramatically reducing the risk an individual has to take on in front-loading exploration.

I’m inspired by both Clayton Christensen’s description of emergent strategy (as referenced above), as well as adrienne maree brown’s definition of emergence; it “emphasizes critical connections, authentic relationships, listening with the body and the mind…[it] is beyond what the sum of its parts could even imagine.”

In our individualistic culture, what we often forget is what Octavia Butler articulates so well: “civilization is to groups what intelligence is to individuals. it is a means of combining the intelligence of many to achieve ongoing group adaptation,” (Parable of the Talents, 1998). In this way, creating pockets for emergence serves not only the individual embarking upon the exploration, but also collective civilisation. Somehow, we need to find ways to offset the status quo bias and loss aversion that govern people’s behaviour, by making the unfamiliar, the emergent, seem exceptionally more attractive and secure.

I believe achieving this objective is primarily the remit of the organisation and the state, versus that of the individual. Over the past few years, I’ve started seeing a number of examples of this throughout the public and private sector, whether that is in the UK government’s push to cross-pollinate more knowledge between sectors through their Digital Secondments Programme, innovative concepts like U-Work borne from behemoths like Unilever, or the rise of startup secondment marketplaces. The beauty in many of these solutions lies in their aligned incentives: giving the individual more flexibility to explore different hills, while unlocking the power of diversity and interdisciplinary knowledge-sharing for the benefit of the organisation.

The beauty of thinking through writing is that you often surprise yourself with your revelations. In this instance, what began as an attempt to understand the individual has evolved into a clear collective imperative. The real challenge lies not only in convincing individuals to explore more, but in redesigning our systems to make exploration less of a privilege and more of a right.

Thanks for the edits and inspo:

• Meg, my friend who patiently explained hill-climbing algorithms to me

• Climbing the wrong hill, by Chris Dixon. Discovering this after I drafted this essay illustrates the sheer wonderment of the internet

• How will you measure your life, by Clayton Christensen