Welcome readers old and new. This is one of Thomas Hollands’ notes in his search for ideas which are surprisingly general, or generally surprising. You can find all past issues here.

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Algorithms for a successful career: hill climbing or valley crossing?

Here’s something I wish I’d learned a few years ago:

There are two ways to succeed in your career: you can climb hills, or cross valleys. Both of them work. But if you hill-climb unthinkingly you might end up miserable. And if you valley-cross aimlessly you might end up unemployed. What you should do is cross into a suitable valley, then climb, climb, climb away. Let me explain.

You can think of all your potential career possibilities as an expansive landscape.

As you sweep over the terrain you can spot hills, mountains, peaks, summits; and valleys, gulleys, ravines, abysses. The higher your elevation, the more successful you are. The analogy works with whatever definition of success you like — money, respect, power, whatever.

I didn’t come up with these topographic analogies. They’re from mathematics. But they’re a useful lens to look at your career.

Different environments contain different kinds of hills, and to climb them you need different kinds of skills. Some hills are gentle and sloping — just keep trudging and you’ll get to the top. Others are sheer cliffs, requiring expertise in mountaineering, ice-climbing, and many other skills. Everyone finds it easier to climb up hills whose skills they enjoy.

At birth, you’re plonked into an environment you didn’t choose. You can climb the nearby hills, or walk along the valley floor, and see if there’s anything bigger in the valley over.

A hill climbing algorithm

Hill climbing is a well-trodden pursuit. It’s often encouraged by parents in their children. Anyone who ‘climbs’ — the real housewives of Orange County, ambitious employees ascending the rungs of the corporate ladder — takes this approach. It’s simple enough to write as an algorithm:

Work out who the people in your environment are with the most influence.
Discover what kinds of things they value. Become useful to them, and you’ll be rewarded with social capital in proportion to your usefulness.
Convert your social capital into raises, promotions, and claim more responsibility for yourself.
Congratulations, you have gone up a rung! To keep climbing, return to step 1.

Hill climbing is often a slog, but it works. If you start hill-climbing, you can be sure you’ll end up at higher ground from where you started. It might be slow and monotonous, but you know if you join a big company and keep plodding along, you’ll eventually get promoted.

A valley crossing algorithm

Valley crossing is a relatively rarely recommended course of action. It’s a risk: you can’t see into valleys you haven’t yet visited. You can’t know if there are opportunities in an industry you’ve never worked in. Perhaps the valley down the road has cliffs too sheer to climb. Or maybe it’s a flood plain, with no hills for miles. Unless you see for yourself, you can’t know for sure. If you get stuck in a valley without climbable hills for too long, you’re in trouble (read: unemployed).

You can state an algorithm for valley crossing too. Its easy to say, and harder to do:

Identify the kinds of hills you’re suited to climbing
Go from valley to valley, looking for hills you can climb easily
Climb those hills (see the hill-climbing algorithm, above)

If you’re in a valley you’re happy with, to become successful you still have to climb the surrounding hills. But in the right environment, this is no slog. If your skills are suited to the hills you’re climbing, climbing doesn’t feel like work at all. You can float — almost effortlessly — to the top.

Valley crossers explore, hill climbers exploit

Hill-climbing is an exploitative strategy: you’re trying to get to the top of your local environment, to a vantage point where you might be able to see above the clouds.

Valley-crossing is an explorative strategy: you’re trying to find a new environment, one with hills that you find easier to climb.

Hill-climbing is a settling strategy: you make the most of the situation you find yourself in.

Valley-crossing is a reaching strategy: you go and find a new situation you’d like to make the most of.

Hill climbing is a low risk strategy: there’s always a slope that you can ascend. Valley crossing is an uncertain strategy: along the valley floor, it’s not obvious which way to go.

Hill-climbers treat their environment as static, and optimise their way to the highest position they can get to.

Valley-crossers treat their environment as dynamic, and wend their way to the most hospitable valleys they can find.

Hill-climbers find people who they’d like to be useful to. Valley-crossers find things they’d like to become useful at, and eventually people find them.

If you only cross valleys you end up a dilettante — you regret not committing to anything. If you climb one solitary hill, you end up a bore — you regret not trying anything new.

Thomas Hollands @tdoggyholhol

Much of “success” boils down to: 1. Find things you want to do. 2. Just keep doing the things you want to keep doing Eventually you’ll get good enough at those things to be useful to someone

Do what you’re suited to

One of my good friends, H, is a natural hill-climber. H works for an oil and gas company that you’ve definitely heard of. He’s incredibly hard working. In every environment he found himself in, he rose to the top. He excelled in school. Got one of the highest grades at university. And was promoted early at work. He’s happily plodding up his hill.

H is conventionally successful. But he never chose any of those successes. H didn’t choose his school, nor what he studied. He selected the degree that would make him appear the most intelligent to others. And his career? He’s only done one interview in his life. He applied where everyone else was applying, and seized the first opportunity he was given. Hill-climbing works well for him. But he doesn’t know whether anything else would work better.

I’m a natural valley-crosser. I’ve tried dozens of jobs over the past half-decade; I’ve explored many unprofitable valleys. I’m hardly conscientious. I’m restless. As soon as I realise I don’t want to work somewhere, I do the bare minimum to get by. I’ve had mixed successes. I did adequately in school, but failed to get into the universities expected of me (and by extension, that I expected of myself). I did well at university, but not because I worked hard. I just loved solving physics puzzles — and deliberately sought out ones that made my brain ache. And in my career? I’ve probably done a hundred interviews already. And failed almost all of them.

I used to joke that H was the best coper I’d ever met. We lived together in our second year of university, and a bright light from the hallway used to illuminate our neighbouring bedrooms at night. After my first sleepless night, I bought a thick piece of card, and fashioned a window cover to block out the light. I offered to do the same for H, but he just got used to being bathed in light at night instead.

I tried out hill-climbing for a while. I worked fairly hard at my university exams in my first couple of years. I got onto the internship treadmill, and pedalled my way towards a prestigious consulting job. But I couldn’t keep pushing — I couldn’t force myself to do things I thought were pointless and I didn’t enjoy.

Big Hills and Deep Valleys on the King’s Route, Madeira.

Navigating the valleys

Joining Twitter and writing online helped me get off the treadmill. Joining Twitter helped me see other valleys to explore. Writing online helped me work out which hills I’d most like to climb.

Joining Twitter lets you see the entire career landscape in one go. It’s like looking at a satellite image of earth from above, you can zoom all the way in to spot individual climbers, ascending hills in their brightly-coloured clothing. You can see valleys you’ve never spotted. You can see opportunities you didn’t know existed.

Writing prose forces you to unwind your ideas into a linear chain. Forcing your thoughts into a logical order, constrained by a grammatical superstructure, helps you work out what sorts of things you’d like to do more of — the hills that you’ll be happy to climb.

I’m glad I do both now. I wish I’d started both earlier.

Whether you choose to climb hills or cross valleys, make sure you do just that: choose. Find a skill you want to use, find a valley where that skill is valued. Then use that skill to climb that hill.

Between the cracks

#17 Cross valleys then climb hills