What you made when nobody was paying you

As a kid, I used to make films.

I'd grab my 8mm video recorder, round up my mates, come up with an idea on the spot, and see what happened. Editing the thing, laying some music over it, and finally committing it to VHS made the idea feel real. I've still got all of the tapes.

Editing was fiddly technical work – filming and cutting on 8mm tape was super awkward – adding music was harder still.

I didn't care in the slightest. I made films because I liked making films.

I wrote television scripts and film scripts. Songs. Books. Poems. Anything that would catch an idea in my head and give it somewhere sensible to live. Later came multimedia CDs and websites, and I fell in love with Desktop Publishing. I even recorded and submitted a video for my degree's dissertation which was, I'll admit, an unconventional way of going about it. It got the grade.

Looking back, I can see the same things running through all of it: creativity, expression, curiosity, a fondness for things done well, working alongside other people, the task of putting something in front of an audience, and a fascination with the whole picture rather than the small piece right in front of me.

I had no names for any of this at the time. I just liked doing it.

And then I got a job.

Jobs are interesting things. They give us money, colleagues, problems to solve, things to learn and, if we're lucky, some sense of purpose and meaning. They also give us a certain shape to work inside.

That shape can be enormously useful. A job can ask you to develop a skill you didn't know you had. It can sit you next to people who change the way you think. It can give you a discipline or a problem you'd never have found on your own. Sometimes the frame is exactly what you need.

And sometimes you look up and realise you're spending rather a lot of time inside a frame that doesn't make particularly good use of the person you've become, or the person you used to be, or even, the person that you are right now.

That isn't necessarily a problem with the job. It might just be a question of fit. Because every job is a trade.

You give the organisation your time, attention, experience, judgement and energy, and you get something back. Money, obviously – but perhaps also learning, status, friendships, flexibility, security, interesting problems, autonomy, or the chance to work with people you admire.

The trade is different for everyone. And it changes.

What looked like a brilliant deal at twenty-five can look rather different at forty. What you desperately wanted from work in one season of life can stop mattering in the next. And sometimes, the trade is not good for you at all.

There's no universal equation. The useful thing, I think, is simply knowing that you're trading, and understanding what it is.

I once worked in a startup that went through a superb period of growth. We tamed the chaos. We grew as people. We hired wonderful people, did good work, hit our targets. Eventually the company was on a fairly straight road toward an exit. By most conventional measures, things were going rather well. Everyone would tell me that.

And yet something had shifted for me.

The early days had been full of uncertainty. We were working out where we were going, solving problems that I'd never encountered before, forging our place in the market, getting stuck in to anything that needed some help, building things from nothing, making decisions on incomplete information and moving fast. I loved it.

Then, slowly, the work turned predictable. The organisation had matured. The problems were different now – more maintenance, more fine-tuning, more business as usual, more admin. The company was succeeding. And I was learning something about myself.

I'd always assumed I was motivated by success. It turned out I was motivated by a certain kind of work. Uncertainty. Making sense of things. Building. Creating. Untangling messy problems. Bringing people together. Finding a way through something that didn't yet have an obvious answer. Telling stories.

That was a useful thing to notice. Because once I understood it, I didn't have to declare the job bad, or decide I'd made some catastrophic career mistake. I just had to ask a better question.

What is the shape of me – and what kinds of environment let that shape be useful?

That question changed things. I moved sideways within the company into HR, where there was, once again, plenty of uncertainty and challenge and room to grow. The work changed. My energy changed with it.

One of the more useful things I've learned is that this can happen without anything going wrong at all.

You can have a good job. Good colleagues. A decent salary. A house. A family. A life that, from the outside, looks rather successful – and still find yourself somewhere slightly different from where you thought you were going. You can still feel that nagging voice that you're not quite becoming who you could be, or where you want to be.

Life has a way of doing this.

Decisions accumulate. Circumstances change. Other people's needs matter. Kids, mortgages and a busy life all compete. Opportunities appear, responsibilities arrive, and sometimes life simply happens to you. So you adapt. You take the next step, then another, then another – until one day you look up and realise you've travelled quite a long way from where you meant to be.

That isn't a mistake. It's just meandering with no map. And there is nothing wrong with that.

This drift isn't necessarily something to eliminate. It's something to notice and acknowledge.

I've spotted it in myself a few times – around eighteen years ago, then again about a decade later, and I'd be surprised if it doesn't happen again. Perhaps it happens to all of us. The useful part isn't preventing it. It's keeping enough self-awareness to notice when you've drifted further than you'd like.

Remember what made you curious

There's an idea I've always liked from Robert Greene: when you're trying to work out what might matter to you, look backwards.

Not because childhood holds some magical, authentic self you have to recover intact. But because before careers and mortgages and job descriptions and performance reviews and everyone else's expectations became so loud, you probably spent a good deal of time doing things purely because they interested you.

For me, that was making things. Films. Writing. Bad music. Ideas. Being on a stage. Working things out. Looking at the world and wondering how it worked.

It turns out the things I loved doing when I was young weren't random at all. They were clues.

The answer isn't to abandon your life and become the person you were at seventeen. I think it's rather more interesting than that. Look for the pattern. What did you keep returning to? What kind of problems did you enjoy solving? What made you lose track of time? What did you make when nobody was paying you to make it? What kind of activities, and people, and places, made you feel more like yourself?

Those questions don't tell you which job to take. They give you something far more useful. They give you evidence about yourself.

Greene has another good suggestion: look at the people who make you envious.

Not because you want to swap wholesale – everyone has problems, everyone has compromises, everyone is trading something. Ask instead what exactly you envy.

Is it their freedom? Their craft? Their ability to make things? Their audience? Their nerve? The way they communicate? Their confidence? The fact that they spend their Tuesday morning in a workshop making something, when you're in a meeting that is threatening to eat the morning?

Envy turns out to be surprisingly informative once you stop treating it as a comparison, or an emotion to never feel, and start treating it as a clue. You're not looking for a life swap. You're looking for the missing ingredient.

The three things I keep coming back to

Over the years I've ended up with three areas that help me make sense of all this. I think of them, a little grandly, as a kind of Trinity of Career Development.

And I've come to realise it isn't really about careers at all. It's a small map for understanding the relationship between how you naturally operate, where you add value, and what keeps you well, in both life and work.

1. Behaviour – how you show up

The first question is: how do I naturally behave? How do I make decisions? How do I communicate? What do I do when things get uncertain? How much structure do I want? How do I behave around other people, and what happens to me under pressure?

There are plenty of tools for exploring this. DISC is one I've used for years – though I'm far less interested in the label than in the conversation it starts. The useful question isn't "what type am I?" It's "what does this tell me about the way I naturally operate?"

That knowledge can be mightily insightful. It helps you see why some situations feel effortless and others take all the energy you've got. And it helps you understand other people – which is the part that really matters.

Knowing yourself isn't a licence to demand everyone else accommodate you. Quite the opposite. The better you understand your own defaults, the quicker you notice when someone else is running on a completely different set – and the easier it becomes to flex. That's where self-awareness starts being useful to other people, not just to you.

2. Strengths – where you add something distinctive

The second question is: what am I actually good at? Not what's on the job description. Not what your manager happens to value. Not what you feel you ought to be good at. Not what score you have on a skills matrix.

What are your genuine strengths?

There's an important difference between being competent at something and being energised by it. I've been perfectly competent at plenty of things I'd never want to spend all day doing, and I've spent years getting better at things simply because they were required of me.

That's useful – it makes you more capable.

But it's a different thing entirely from the work where your strengths compound: where you get better and enjoy the process and other people notice the value, all at once.

For me, that blend – making sense of messy things, finding connections, communicating ideas, creating, bringing people together – has turned up in wildly different places.

It was there when I was making scrappy films as a teenager. It was there in startups. It was there in HR. It was there in senior leadership roles. It's there in consulting, training and speaking from the stage. It's there in the podcasting and producing I do. And it was there in my early years dabbling in journalism. And it's most certainly there in the film making I still do.

The surface keeps changing, as does the company and the people. The underlying strengths have barely changed at all. That's worth knowing.

And I certainly now know when I'm in a role that is asking for none of this.

3. Wellbeing & happiness – what sustains you

The third question is the easiest to overlook: what do I need in my life to stay well and happy? Not what should make me happy. Not whether my job fulfils me. Just – what do I need?

For me, that includes writing, learning, making things, curiosity, time with people I love, being outside, noticing interesting things, and having a bit of room to follow an idea just because it interests me.

Work doesn't have to provide all of that.

Expecting one job to supply everything is asking rather a lot of a job. Some of it can live outside work, some inside, and some will change as life changes. The important part is simply knowing what those things are – because when they disappear, it becomes very hard to understand why work, or life more generally, has started to feel flat. Nothing obvious has gone wrong. You've just stopped doing some of the things that make you feel like yourself.

Put the three together and you get a map

This is where it becomes useful.

Behaviour tells you how you naturally operate. Strengths tell you where you can create value. Wellbeing tells you what you need to sustain yourself. Put them together and you get something that behaves like a map – not a career plan, not a five-year roadmap, not a document that miraculously finds you the perfect job. A map. It tells you where you are.

And it makes some of what has happened to you more obvious.

Why does this role light me up and that one drain me? Why do I love this kind of problem? Why does that environment make me feel like I'm performing a part rather than doing the work? Why am I so fascinated by what that person's doing? Why have I stopped doing the things I used to love? Why does this company drain me now, but it didn't?

Sometimes the answer isn't "I need to get better and optimise my life." Sometimes it's: "I need to make better use of the person I already am."

You will always trade something

There's a temptation in career advice to imagine that somewhere out there sits the perfect job. The perfect culture, the perfect role, the perfect blend of money, freedom, challenge, colleagues, purpose and flexibility. Perhaps it exists. I've never found it and I'm not sure I can recall meeting anyone who has.

Every choice is a trade.

Sometimes you trade autonomy for security, or money for freedom, or interesting work for experience, or flexibility for the chance to work with people you really want to work with. Sometimes you take a job because you have a mortgage and three children and that's simply the reality of the chapter you're in. There's no shame in any of it.

The point isn't to eliminate the trade. It's to make it consciously, where you can. Because knowing what you're giving up is useful information – it lets you decide whether the exchange still makes sense.

And if it doesn't, you've got something concrete to work with. Maybe you change the role. Maybe you change how you spend your time. Maybe you bring something back into your life outside work. Maybe you need a different environment altogether. Maybe you just need to recognise that this particular chapter is asking something different of you.

There are many possible answers. The first step is only ever seeing the question.

I've grown wary of anything that promises to tell people who they should become. You don't need another ideal version of yourself to chase. You probably just need to understand the one you already are a little better.

So take the tools if they help (below). Do a behavioural profile. Explore your strengths. Think honestly about what makes you happy. Look backwards at what you loved before you knew what a career was supposed to look like. Notice what makes you envious. Pay attention to the work that gives you energy, and the work that takes it. Write some of it down.

Then resist the urge to turn it into a grand life plan unless that's in your temperament. Just put it somewhere you can see it, and use it as a reference point.

When an opportunity appears, look at it. When a job starts to feel draining, look at it. When you're wondering what to do next, look at it. When life changes, update it – because the person you are at twenty-five isn't the person you are at thirty-five, and the person you are at forty-eight will have a few surprises in store for whoever you become at fifty-eight. It's the interesting bit. That's life happening.

Career development, at least as I've come to understand it, isn't about climbing. It's about paying attention – to the person you are, the work you do, and the conditions in which you seem to flourish. To the things you keep coming back to. And to the things you might have traded away without realising it.

You likely don't need to become someone else. You just need to notice when you've wandered too far from yourself, and then, when you're ready, take a step toward the things that matter.

The young Rob with the 8mm camera knew what he liked. He just didn't have the words for it yet. Most of us still have someone like him in there somewhere, waiting to be recognised – and the whole of the work, I think, is learning to see him clearly enough to let him back in where we can.

Resources

• For DISC I tend to recommend Tony Robbin's DISC profile. Whether you like the guy or not, the free survey can be pretty helpful. His unsubscribe does work too.
• For happiness and wellbeing, Martin Seligman's Authentic Happiness is great.
• For strengths, the Clifton Strengths Finder is pretty good, albeit expensive.

Alternatives to these do exist. Cultivated cannot be held responsible for the content of external links, nor their use of your email address 😄