In my time thinking and writing about career strategy, I’ve noticed there’s two big ‘buckets’ of people:
Bucket A:
- Aren’t where they want to be in terms of money, career, and status. They want to climb the ladder asap.
Bucket B:
- have achieved a lot of what they wanted to - a well-paid job, a house & car that’s paid off, toys & perks etc.
The burning question of Bucket A is “how do I get to Bucket B?”
But Bucket B?
A lot of them ask something like, “I’ve got everything I want, and I should be happy. I know this sounds like I’m just moaning, but why do I still feel empty inside?”
In other words…
A lot of Bucket B-types have achieved success, but not fulfillment.
They’ve won the outer game, but not the inner game.
But why?
They failed to recognize that the two are very different things to be chasing. The paths to fulfillment is different to that of career success.
So, today, I wanted to write about a concept that pretty much changed how I looked at my career:
I call it, optimizing your career for fulfillment. First up…
👣 Follow the path YOU want to follow
A wise man once told me,
“It’s not the thing, it’s the place it’s coming from.”
In other words, no path or job is wrong per se. It’s the underlying motivation for following the path/job that needs to be questioned.
Are you in your career because it matches your values? And because you want to do it? Or are you only in it for the money/status/power, or to please someone else?
Many of us are in careers because we randomly ended up in them.
So what do you do about it? If you recognize you’re following a path you fell into (or someone chose for you), the solution is *not* that you need to quit and start over.
Instead, figure out elements you can add to your career which more closely align to what you want.
An example: You're in finance but don't really like it for whatever reason. Try to introduce elements you like into your job. If you like teaching, start mentoring newcomers. If you're a people person, try to manage a larger team you can coach. Into tech? Explore fintech startups or introduce a new tool at work. It's about tweaking your role to fit what gives you fulfillment.
🌱 Progress, not achievement
We often fall into the trap of saying, “when I achieve X I’ll be happy.” But of course, we never are.
And that’s because fulfillment often comes from a sense of progress, not just achievement. If you don’t feel you’re growing professionally — or feel a sense of progress — in your current role, it’s hard to be fulfilled (even if you love what you’re doing).
The solution?
Invest in continuous learning instead of just binary goals.
For example, if you're a software developer, don't have your sole aim to be to get promoted to the lead developer role. Instead, learn a new programming language or upskill in a different area like project management or UI/UX design.
You can often get the biggest feeling of progress (and thus fulfillment!) by improving at something you’re really bad at or are scared of. For e.g. if you’re introverted, maybe you can prioritize getting better at public speaking.
🎯 Write a mission statement
While writing this essay, I reached out to a friend who coaches execs and other professionals. Here’s what she recommended (I loved this advice — and thanks for your permission to let me share it, Lisa!):
Take the time to write a mission statement.
Companies have mission statements. Charities have mission statements.
And you should too.
What are your core values? What’s most important to you? What are you doing this for? What are you saving for?
Knowing these things will help guide your decisions and give you a sense of purpose, which is key element of feeling fulfilled.
You can obviously do this exercise at any time, but make sure you do this at pivotal moments: Switching careers. Moving countries. Taking a new job. This may seem like a simple exercise (and it is!), but it’ll give you surprisingly more clarity than you’d expect.
🗣 How’s life outside of work?
At the end of the day, we’re social creatures.
No amount of professional success can substitute for deep, meaningful relationships.
It’s kinda like the movie “Catch Me If You Can.” Frank Abagnale’s got all the money & success he wants, but in the end, the only person he has to call at Christmas time is the cop who’s chasing him.
Do you have friends who’ve got your back? Do you spend time with family? Do you belong to a community of some sort?
Sure, the whole “kids, dog, and a white picket fence” is cliche, but only because that’s what makes a lot of people’s lives meaningful.
The takeaway: Invest in your relationships outside of work. If you’re saying ‘no’ to things that you enjoy doing (e.g. hobbies with friends and family) at the expense of making an extra dollar, it might be worth thinking about that decision twice.
🧠 A thought experiment
Think about Warren Buffett. Super rich, but also 93 years old (actually, he’s turning 94 tomorrow!).
Would you swap lives with him? All his money, but you're 94.
Probably not.
Why?
We know deep down: time’s more valuable than money.
In fact, Warren Buffett — arguably the greatest investor and allocator of money ever — would give up all his money if he could be 40 years old again.
This is an extreme thought experiment. But it contextualizes the true value of our time.
I think a big part of fulfillment is internalizing this trade off between money and time. Know when to say no, and know when to prioritize things important to you — even at the expense of the extra $.
A simple example from my work: I write this free newsletter each week. It costs a ton of $ in email costs to send. Even with the occasional sponsor, it’s not profitable. But, the replies I get are super fulfilling — so I know I should keep writing it. Similarly, in your own career, try not to abandon things you enjoy doing just because it doesn’t make a lot of financial sense — often, the real rewards are just harder to quantify.
