Enough Is Enough

Examining our obsessive desire for more.

“Desire is a contract you make with yourself to be unhappy until you get what you want.” - Naval Ravikant.

We often tell ourselves we’ll feel okay when the next thing arrives, the promotion or the launch or the salary or the relationship, and then the next thing arrives and the feeling we were waiting for arrives with it... for about a week. By the time we notice what’s happening, we’ve already started chasing the next version of whatever happiness looks like.

Most people don’t really know what they’re working toward. They have a sense of more, vaguely, in the way that everyone has a sense that they should probably exercise more or read more or call their mum more often. More money, a better title, a nicer flat, a partner, a holiday somewhere people post photos from. But if you stop someone and ask what “enough” would look like, they might struggle to tell you. They’ll give you a number that’s a multiple of what they make now, or they’ll change the subject, or they’ll simply look back at you confused.

The problem is that self-reflection isn’t a skill our society seems to truly value. School doesn’t teach us how to have these conversations. And they don’t tend to come up in normal day-to-day chats with friends. Without an answer to the question of “what is enough for me?”, you’ve effectively committed to wanting more indefinitely, which is not a goal so much as a condition.

I’m not pretending I’ve got this figured out. I’m in the middle of working it out myself, and I thought it would be more useful to write about the working-it-out than to wait until I had clean answers. There are three questions I’ve been asking myself, and the rest of this piece is what each one has surfaced.

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Where is the desire coming from?

The honest answer is almost never “from me, after careful reflection.” The honest answer is something like: from my parents, who got it from theirs. Financial desires are inherited in the same way that accents are inherited. They come from somewhere, but because they’ve been with you since before you had the vocabulary to question them, they feel like preferences.

What was the relationship to money in the house you grew up in? Did your parents fight about it openly, or carefully not in front of you? Did your mum say anything about people who had more, or less? Did you feel embarrassed by something you couldn’t afford, or guilty about something you could? Did money mean freedom in your house, or security, or control, or the absence of something else that nobody talked about?

For a long time, “enough” for me meant something like “more than I’d grown up with,” which I’d never really stopped to think about. It sat underneath the decision to study engineering at eighteen, partly because I’d been told by everyone around me that I should be an engineer, and partly because I’d absorbed the assumption that engineering paid well and paying well was the relevant criterion. I’d seen my dad enjoy a successful career as an engineer, and I was interested in science and maths growing up, so it felt like a pretty simple equation.

When you trace the desire back, you usually find it came from somewhere specific, often a decision you never consciously made. You absorbed an idea about what a good life looks like at some point in childhood, the assumption locked in, and the rest of your decisions have been running on that autopilot ever since. Some of what the autopilot is doing on your behalf you’d happily endorse if you stopped and looked at it. Some of it you wouldn’t.

What does the envy do?

Most of us treat envy as a toxic emotion, something to suppress. We feel it, we get embarrassed by it, and we paper over it with a supportive comment on someone’s LinkedIn announcement. The consequence is that one of the clearest sources of information about what we want gets buried under the performance of generosity.

If you let yourself feel envy without flinching, and then ask what specifically you’re envious of, you usually get a clearer picture than the one you’d get by sitting down and trying to write a list of what you want.

When I do this on myself, the thing that comes up most clearly is experiences. Travel, food, time spent doing something memorable, particularly when it’s shared with the people I care about. I’m not jealous of people with fancy things; I’m jealous of people who get to have remarkable experiences and who have the people around them to share those experiences with. The two halves of that are inseparable for me. A great trip you took alone isn’t quite the same thing as a great trip you took with people you love.

I’m not massively impressed by ostentatious displays of wealth. Flashy cars, brands, big logos, expensive watches. None of it moves me. Large public profiles have never appealed to me as a thing to want either. Raw income for its own sake doesn’t feature on the list. When I’m honest about what I want, it has a shape, but the shape has nothing to do with status or scale.

What did they sacrifice?

When people compare their lives to other people’s, they compare on visible outcomes. The partner at the law firm, the founder who sold their company for millions, the friend with the nice flat. What gets sacrificed to produce those outcomes is rarely visible, and almost never volunteered.

You don’t see the fifteen years of weekends that got handed over for the partnership. You don’t see the relationship that ended in year three of the company, or the way the founder describes their thirties as a blur if you push them on it. You don’t see what the consultant in the nice flat had to become to afford it, and what they had to stop being on the way.

Once everything’s out in the open and the trade-offs are clear, you can ask whether you’d accept the trade. When people do the maths on what the impressive lives around them cost, most of them privately decide the trade is a bad one. Then they go on chasing the outcome anyway, because the outcome is visible and the cost isn’t, and visible things tend to win.

The other side of this question is what you yourself would refuse to put on the table. Most people are unclear about this because they’ve never had to say it out loud. Saying it tightens up a lot of decisions that would otherwise stay open.

For me, the things I’m willing to put on the table are clearer than the things I’m not. I don’t really care too much about work-life balance at this stage of my life. I never track how many hours I’m working. I often work on weekends and well into the night, and I like that I’m thinking about Rumbo most of the time, that it comes up in conversations at dinner, that the line between what I do and who I am has mostly dissolved. Some people would refuse that trade and they’d be right to for themselves. It happens to suit me for now.

What I’m not willing to trade is the time I make for my hobbies, and time with the people I care about. I’ve played sport my whole life and music is the other thing I’ve never stopped doing. Both have ended up carrying over into my work in unexpected ways. People who’ve spent years getting good at a sport or a creative pursuit tend to bring a slightly different shape of person into their working life. The years of getting beaten and starting again build a comfort with the long arc of mastery that people who’ve only ever competed in office settings don’t quite have. The version of success where I’d looked up in five years and realised my body had gone, or that I’d stopped playing music, or that I’d lost touch with friends and family because work had absorbed everything, isn’t a version of success I want. That becomes a ceiling on what I’ll chase. If a path requires giving any of that up to get to the number, the number isn’t worth getting to.

Once you’ve named what’s on the table and what isn’t, a lot of the opportunities that used to feel tempting stop feeling tempting. They ask for something you’ve already decided you won’t give, so they become easy to turn down.

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The reason Rumbo exists is that nearly all the career advice in the world starts at the wrong end. It starts with “what job should you take” or “what skills should you build” or “what industry is growing,” all of which are downstream questions. The upstream question is “what are you actually optimising for, and where did the answer come from?” Until that’s worked out, the downstream questions get answered by default, which means they get answered by whoever installed your assumptions. Rumbo’s job is to slow that down enough that the upstream question gets asked seriously, with some structure around it, before anyone goes and acts on the assumptions they inherited.

None of this is a problem you solve once. The answer drifts as you change, as your life changes, as the people around you start landing in their own versions of enough or failing to. What felt like enough at twenty-five won’t necessarily hold at thirty-two. What you can do is keep asking the question often enough that you catch the drift before it carries you somewhere you didn’t choose to go.

A friend asked me recently what number would be enough for me. I gave him a smaller answer than I would have five years ago. The ambition hasn’t gone, but it’s no longer purely financial. What I want is the freedom to keep working on this for as long as I find it interesting, and the time and means to share experiences with the people I care about. The money becomes a means to those, instead of the thing being chased for its own sake.

That’s where I’ve got to, for now. The answer will probably change again. But having one means I can notice when the wanting starts running ahead of it, instead of finding out years later that I’ve been chasing something I never agreed to chase.

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