How to Reach Career Fulfilment

Future thinking a career is difficult. The modern dilemma finds us wanting something that:

✔ Pays us well

Has flexibility

Brings fulfilment

Involves people we like

Is something we enjoy

Makes an impact

Which can understatedly be a lot to tick off, particularly if you're just starting out in your professional journey and haven't seen what it's like to have a proper job before. As a result we have a tendency to get paralysed with career-related decisions or worse yet ignore them completely. And because we follow shitty careers advice such as "follow your passion", we also miss out on all the above entirely.

Instead, here's a definitive guide on how to reach career fulfilment, the real way.

1. Accept the Chaos Theory of Careers

Proposed by Jim Bright, the Chaos Theory of Careers subscribes to the idea that our career paths are non-linear and difficult to measure or predict.

Essentially there are too many complex factors outside of our control to presuppose a sequential career path. Careers change and evolve, sometimes in leaps and bounds in unexpected ways that make it impossible to strictly determine a career pathway based on interests, personality traits and education.

Hence, the question of “what do you want to be” is a difficult question to answer, because it is a question that is impossible to have an answer to.

2. Build Your Career Capital

If we can’t plan out our future career, why have a plan at all?

The issue of a plan ”failing” isn’t the problem. Rather, the complication arises in having a complete A to B plan and expecting it to work out to a T AND be happy with the end result.

We should centre how we think about our careers around what type of lifestyles we want to lead, what type of problems we want to solve and what type of people we want to be. And these things, as with our needs and wants can shift dramatically overtime.

But this type of introspective thinking is the metaphorical “swallowing our greens”. The hard things that no one enjoys mulling over for too long, but are important to think about and digest because they fundamentally affect how mentally healthy and fulfilled we are.

And not only are they hard to think about, most people don’t even know where to start. These are questions I’ve been dumbfounded by for a long time.

Cal Newport’s So Good They Can’t Ignore You highlights that career passion is developed through expertise and experience. Essentially, as long as you work hard and eventually become a master of your craft, you can thrive and learn to become passionate about any job you choose.

Although, while you may become a passionate master unicyclist, there’s also another piece to the equation – how much value you add to other people.

The likely reason why 43% of Americans are unhappy at their jobs is that they constantly ask themselves what they want, instead of asking “What value can I bring to my job?”.

Fulfilment in our careers occurs at the intersection of providing high expertise and high impact.

Only when we sufficiently achieve both can we realise a general sense of purpose in our work.

But how do we get there?

David Epstein’s Range dives into the significance of sampling and breadth of experience in achieving expertise and success. In it he spotlights the story of renowned tennis player, Roger Federer. Roger’s mother was a tennis coach, but was hesitant to coach him. As a young boy, Roger instead dabbled in squash, skiing, wrestling, skateboarding, basketball, badminton and tennis. Later, he credits this range of sports experience as the key to improving his hand-eye coordination and athleticism. Roger’s winding path to tennis success points to the fact that sampling can be the best route to expertise.

Likewise, the story of Vincent Van Gogh follows a man leaping from a bookshop worker, to a teacher, art dealer and preacher before finding his calling as an artist who disrupted the art world. A polymathic approach to life and a breadth of experience can often become invaluable to shaping the expertise and value you provide an organisation or cause.

When reverse-engineering this, the best way to improve your likelihood of “career success” is to build your career capital – Key strengths, experiences and knowledge you can equip to craft a career that centres how you want to live your life and maximises the value you can offer the world.

For people that don’t believe they have any strengths, then it’s about thinking about what you want to build. A good starting point is:

  • 3 industries or problem areas I’m interested in working on
  • 3 skills I want to learn
  • 3 people I want to meet or that I already know

By starting off with 3 industries of interest or problem areas, you give yourself the opportunity to explore different spaces and find what type of work brings you the most fulfilment. Whether you learn more about these industries by reading articles and news about them, conducting work experience or speaking to people working in these areas yourself - it’s a better strategy than entering them with false ideas on the reality of the industry.

Next, by crafting 3 skills, you create breadth in the work you can complete which enables you to move around these industries and discover what kind of work you most enjoy. According to Newport, having a unique set of expertise “that are both rare and valuable can be used as leverage in defining your career.”

Finally, connecting with 3 people who are more skilled and knowledgeable than you can be key in boosting your career opportunities. A survey by Performance-based Hiring revealed that 85% of all jobs are filled by networking. Therefore, connecting with people higher-up in the industry and making your skill sets known to them could be what makes or breaks your next job. And these people you want to meet don’t even have to be in the industry or problem area you’re interested in. Warren Buffet states that:

“One of the best things you can do in life is to surround yourself with people better than you are. High-grade people. You will end up behaving more like them, and they, in turn will get it back from you. It’s like a planetary system. If you hang around with people who behave worse than you, pretty soon you’ll start being pulled in that direction. Who you choose to associate with matters.” –Warren Buffett (Getting There, by Gillian Zoe Segal)

3. Expect To Do it All Over Again

One thing to keep in mind though, is that even once we’ve built our career capital – it might not be enough.

We may have still not truly connected with our work or found the right people to work with or feel as if we haven't made enough of an impact on the world.

If that’s the case then you should ask yourself how you can leverage these 3 strengths to learn more:

  • Can I use what I’ve learned in that specific industry to dive deeper into it or find neighbouring issues I’m more interested in?
  • Can I leverage my current skills to build more unique skills?
  • Can I ask the 3 people I’ve networked with to introduce me to 3 more people to learn from?

By being persistent with this cycle of experimentation you are bound to build expertise, find your comparative advantage, network and make high impact in a problem area you care about.

Having to sit in the uncertainty of not knowing how you should shape 80,000 hours of your life is difficult. In fact, it’s something I’m undergoing at the moment and really struggling through. It will be a messy process.

But what keeps me going is knowing that through this process I’ll have striven for something that creates the most value in the world. Instead of hating the 5 days of work in my 7-day week, I’ll have persisted for fulfilment. Call me mad, but “a man needs a little madness, or else he never dares cut the rope and be free.” – Nikos Kazantzakis

If you haven't already checked it out, read my last post on why common careers advice sucks in defining your career decisions.


I write about my learnings in health, tech, and lifestyle design. I’m still navigating the journey of being a 20-something.

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