016: Ambition

Doing the ambitious work

I am ambitious. A day doesn’t go by where I am not planning, assessing, evaluating, validating and executing on becoming a future version of myself that is, in some way, better than who and what I am today.

By all accounts, I’ve lived a pretty wonderful life. I did all the right things at school to position myself for a good degree at university. A slight speed-wobble in my second year of studying Actuarial Science created an opportunity to shift to Mathematical Statistics where I excelled enough to land a job at a prestigious bank. The time at the bank included winning a prestigious Innovation Award as a first year quantitative graduate and a permanent position in the first six months of a two year rotation programme. The position presented opportunities to explore new technologies that led to a position as a Junior Data Scientist playing with vehicle data. With time and foolhardy persistence, I’ve progressed to a Senior Data Scientist level. I’m still playing with vehicle data, but now in a mining context and have managed multiple projects and people with success.

Away from work, I’ve married (very happily so) my ride-or-die-one-and-only Liebsie and have been blessed with two beautiful boys (the arrival of the youngest is imminent) and two energetic cats. I’ve travelled to many parts of Southern Africa and Europe. I’ve sung in choirs on international stages. An opportunity to represent the African continent at the Cultural Olympics was scuppered by a little event called Covid. I’ve run dozens of marathons (and longer). At 33 I’m healthier than I was at 17. I’ve renovated a fixer-upper and explored how to make the perfect cup of coffee. I’ve also exercised my chops as a writer by completing post-graduate degrees, winning essay competitions, starting this blog and writing academic papers. And, I have deeply meaningful friendships.

My life has been pretty great by any “white picket fence” set of metrics. I’ve done a lot of work and felt a deep sense of satisfaction in all that I’ve achieved. And yet, there’s always this desire for “more”.

Past suffering

I look back at specific choices and think, “What if I’d done A instead of B”?

I ponder, “What if I had acted earlier on hard decisions instead of postponing?"

I beat myself up, “Yes, you’ve done this, but THAT would’ve been so much better.”

The past makes for a useful stick to beat yourself to higher and better things in the future.

As I’ve aged, this incessant striving becomes harder to maintain. When life’s frictions start wearing me down, and the few remaining hairs on my balding head indicate their rebellion against the hostile working environment by switching off their once vibrant blonde colour and defaulting to an ageing, lifeless grey I’ve learned to slow down. This in turns makes me ruminant and reflective. And through this process of looking back, I’ve started to question whether the path forward should like similar to the one that got me here.

Future suffering and the Arrival Fallacy

The greatest golfer of the current generation, Scottie Scheffler, aired his own misgivings about striving and aiming to be better before last year’s Open Championship when he said:

He swiftly obliterated the field by four shots at the final major of the year, winning his fourth major in four years. While holding the most famous trophy in golf – the Claret Jug – he also cradled the most important trophy of his life – his son, Bennett.

His clothing sponsor, Nike, then capitalised on the opportunity to drop an absolutely iconic ad.

He is a man who seemingly has it all and, yet, he also questions his life’s work.

What hope do I have to feel like I’ve “arrived” if someone who’s achieved almost everything in his sport before turning 30 feels the same emotions?

This speaks to the Arrival Fallacy – the concept that there is a place and time in the future where I’ll feel like I’ve made it. But this only leads to more rumination and epistemic suffering, because what do I mean by each of those concepts.

What do I mean by “made”?

And, more painfully, “what is ‘it’”?

What is the thing that’ll tell me that I can stop striving?

Moving beyond past and future suffering

Even when achieving, we suffer because we always blame our past selves for not being better than we actually were. If we had been better, surely we would have “made it” by now?

Our future selves stand no chance, either, because we keep moving the goalposts of what it means to “make it”.

At some point, you’ll face the following crisis: progress stops translating into meaning.

If you’re ambitious and have already done a lot of good work, but always feel like there’s a desire for “more”, this blog post is for you.

Let’s explore what popular, religious and academic texts can teach us about how to free ourselves from past suffering, prevent excessive future suffering and still keep on being true your most ambitious self.

Now:

The only arrival that we truly achieve – is in the current moment.

I finished reading Siddhartha by Hermann Hesse early in 2025. In the short, epic novel Buddhist teachings also point the titular character to this idea with the concept that most of our suffering is in the past and in the future and that we consequently neglect that which is now.

Siddhartha is a young man from a wealthy Brahmin family in ancient India. Though he is admired for his intellect and spiritual promise, he becomes disillusioned with the formal teachings of his religion. He decides to leave his comfortable life in search of deeper meaning. Throughout his journey, he goes through many different phases. First, he lives as a wandering ascetic, practicing severe self-denial only to realise that the body does not bring true enlightenment. He encounters the Buddha, but rejects his teachings believing that enlightenment can only be experienced and not taught. He then proceeds to live a sensual life by becoming a wealthy merchant, taking a lover and becoming addicted to material pleasures. Becoming aware of the futility of this life, he descends into despair and as he contemplates suicide, experiences a profound spiritual awakening by a river. Guided by the ferryman Vasudeva, Siddhartha learns to listen to the river, which becomes a symbol of unity, time, and life’s cyclical nature. Through deep observation and inner peace, Siddhartha finally attains enlightenment.

In time he teaches an old friend, Govinda, who happened to be travelling on his ferry what he has learned about relentless ambition.

Siddhartha’s story teaches us that the ambitious are right to search. Nothing good in your life will come if you do not dare to experience life for yourself - warts and all. This pursuit, however, is future-oriented and restless.

The story also teaches us that to truly find something, you need to be able to stop searching. This means that you need to add constraints to your incessant searching. I reckon that to stop searching, you need some definition of success.

A definition of success

Morgan Housel writes in his brilliant book, The Psychology of Money

Without a definition of successful searching, you will never be able to say “enough” and turn into someone who is more interested in finding instead.

I was blessed to be in a student congregation with a pastor who would often reflect on life’s big questions. He once did a series of sermons with the goal to answer the question “What is success?”. The series resonated deeply with his young congregation formed mostly of ambitious students – a group of searchers. The main takeaway that I still carry with me, 12 years later is this:

At first glance, this seems like a reduction of ambition. It seems to imply that you shouldn’t be searching, but simply be content with what you have.

I argue, though, that it transforms ambition into something more mature.

Early ambition is about proving and chasing. It uses the past as fuel to fire a future-focused and externally validated present.

Later ambition becomes something that recognises the success of the past, looks forward with hope and chooses to engage with what is present with ownership and clarity.

Note that I titled this section “a definition”, not “the definition”. We are all in different stages of life with different ambitions and levels of autonomy. Success for me, looks vastly different to success for anyone else. Having the capacity to philosophise about such lofty things is in itself a great privilege. One that I don’t take lightly.

Applying my definition of success:

From what I’ve learned, there are three things that I can do now to move from a mode of searching to one of finding:

• Choose

  
  

Self-Determination Theory (SDT) is a psychological framework that distinguishes between autonomous goals and controlled goals. Autonomous goals are chosen, internalised and aligned with your values. Controlled goals, however, are imposed by external pressures and expectations. Evidence shows that autonomous goals lead to higher wellbeing persistence and meaning, while imposed goals lead to fragility, anxiety and burnout. The key mechanism to move from a controlled goal to an autonomous goal is internalization. In effect, you need to make a choice.

But what if I’m like a glutton standing in front of a buffet, but still don’t like any of the options that I have in front of me and don’t feel compelled by any choice presented to me?Many thinkers, most notably Friedrich Nietzsche and Viktor Frankl have said that

This gives us to the key to unlocking the internalization mechanism: You don’t always get to choose your situation, but you get to choose your response to it.

By choosing, you’re saying:

I am not going to feel any different if I achieve all my lofty ambitions from what I feel now if I don’t choose the path for myself. No-one’s coming to save me and give me meaning. I must do it myself.

And that gives you unbelievable agency. Create your definition of success, make the choice and own the crap out of it.

• Compromise

There is a version of ambition that refuses compromise.

It sounds noble at first and it often feels like clarity, or even courage. A refusal to settle for anything less than the best is a belief that life, properly lived, should not require trade-offs.

But that belief runs into a structural problem, because life does not present options sequentially. It presents them simultaneously.

In Sylvia Plath’s semi-autobiographical novel, The Bell Jar, the protagonist Esther Greenwood imagines her life as a fig tree. Each fig represents a different future: a career, a family, a life of travel, intellectual recognition, intimacy, independence. Each one is desirable. Each one feels like a complete life.

The problem is not that she lacks options. The problem is that she wants all of them.

And so she waits. As she hesitates, trying to choose the perfect fig, they begin to wrinkle and fall. Eventually, they rot.

Nothing is chosen, so nothing is lived.

A similar idea appears, more bluntly, in The Witcher.

When Geralt of Rivia asks Yennefer of Vengerberg what she wants, she answers, explosively:

For a long time, I used to roll my eyes and say,

Now, though, I feel differently. I want to run 100k every week, cook healthy meals that never repeat, sleep 8 hours a night, have my DIY to-do list simultaneously completed and filled with exciting new projects, plant a veggie garden, do volunteer work, never miss church events, go on dates with my wife, raise Godly young men, publish academic papers, get a PhD, write on this blog, become a Data Science leader and, and, and…

“Everything” is an honest answer to the question of ambition, but it carries the same impossibility, because “everything” is not a goal. It is a refusal to choose between goals. By leaning into this refusal, you mask the hope that there is a path without loss. On that path, you hope that there is a configuration of life where nothing meaningful has to be given up.

I write this in bold for a reason: That path does not exist.

The more mature response is to accept that every dimension of your life cannot be optimized at the same time. By saying “yes” to something, you are automatically saying “no” to others and this is where compromise enters as structure.

By choosing a path, you exclude others and you accept the cost. Again, you get to own the choice of your response.

Again with the bold: There is no version of ambition that avoids this.

In accepting compromise, ambition becomes concrete. Without it, ambition remains an ever-expanding set of possibilities that never resolve into a tangible, messy, but undeniably real life.

You manage to make peace with the figs that are rotting under the tree. You don’t get “Everything” but you get something real.

• Community

There is an old saying, “bloom where you are planted”. While cheesy and clichéd from overuse, Nature remains a wonderful teacher.

Ambitious people can be seen as “the tallest trees in the forest”. They treat growth as something that is pursued in isolation. They believe that with enough discipline, skill and strength, they will be able to carry the full weight of life on your own. They’re the ones who, when they display weakness call themselves “a little bitch” before plunging their faces into a bucket of ice at 4am (if that’s you, no judgement, but read on for a healthier alternative).

The tallest trees, however, are also the most exposed to the elements. We often admire the tall trees for all the demands that they face. “The tallest trees catch the most wind”, we say. However, all that exposure comes with fragility.

My personal experience with trying to become the tallest tree, is that I become increasingly isolated. In doing this, I’ve looked around and overestimated my progress, I’ve defined my worth too narrowly and I’ve begun to think that all my ideas are pure gold. And that’s when the tallest tree will inevitably struck by lighting...

Enter the giant sequoia:

The giant sequoia trees that are native to the groves on the western slopes of the Sierra Nevada mountain range of California can grow close to 100 metres tall. However, these massive trees have root systems that only grow 2 to 4 metres deep. Surely a tree that large will fall over without proper support? Their secret lies in the fact that their root structures grow 20 to 40 metres wide and – critically – interweave with the other trees in the forest. Together, they share nutrients and structural support. When storms come, they anchor each other.

For the individual to grow, it needs to be a part of the system, not apart from it.

If “everything” is impossible, and if every path requires compromise, then community is one of those compromises. Despite all of the propaganda that modern advertising tells us about our snowflake-like uniqueness, we are connected social beings.

This connection is not automatic, it requires proximity, time and a certain willingness to get entangled in ways that reduce independence. And through these compromises, relationships deepen.

As Peter Dinklage said in a 2012 commencement speech:

He told graduates that the people right in front of them – their peers – matter more than chasing status, fame, or “important” outsiders. The trees in your chosen forest are the ones you get to grow with. You might not grow as tall as you could on your own, but you will gain a whole lot more...

Bringing the three C’s together:

You’ve done the work, you’ve achieved a lot. Your future self has many plans lined up, but you don’t feel like you want to pursue that path.

Choose – Stop, and decide on what is enough.

Compromise – Accept that there is no path in your life where you don’t give up something desirable.

Community – Connect with those that are on the same path.

This will unlock the ability to remain faithful to what is in front of you.

A young father’s perspective:

I’m the father of a two-year-old boy and will soon welcome another to our home. When I think of ambition now, I think of my family first.

This short clip of an interview with actor Bob Odenkirk shows this beautifully.

When asked who he is jealous of, his answer is simple. Anyone who still has little kids at home. He explains that when his children were growing up, he never questioned his purpose. He did not wake up wondering what he was meant to do or how to be meaningful.

The answer was obvious. Be a dad. Get them to school. Pick up the mess. Make them laugh. Show up.

He says,

When my first son was born, I definitely embodied the Yennefer of Vengeberg model of ambition. I wanted “Everything” and found out that the thing that would break in pursuing it, would be me. That burnout taught me a lot of what I’ve penned down here and the subsequent 18 months have brought about the same realisation as Bob.

Being a dad (and a husband!) is the greatest part of my existence. I have no qualms about giving up things that make this more difficult to live out. It means that I’m not running Comrades in 2026 (not that I won’t be writing about it in the next few weeks), it means that I won’t be drinking as much unicorn blood either and it also means that my approach to work also needed a distinct refresh (more about that soon, too).

It hit me how beautiful our life is set up now when I picked my son up from his kindergarten. As I signed him out in the class registry, I noticed that the time my wife drops him off in the morning falls in a ten minute window every morning. The same applies to when I get to pick him up in the afternoons. Driving home, we have the greatest chats. His toddler babbles reveal new understanding of everything he sees in his world and it is the highlight of my day – every day. Keeping that structure for my son(s) is my ambition now.

So, to summarise ambition: keep striving and looking for better (whatever that means for you), but when better stops being meaningful, stop searching. Define clearly what “enough” means for you and opt instead to find what you already have. Choose it purposefully and faithfully. Say no to other things that do not co-exist well with it. And finally, engage with your tribe fully. Ambition then reaches maturity.

Finally, remember to do as Scottie Scheffler did at the Open Championship: Go obliterate the opposition as your most ambitious self and finish your round with two trophies. The less important one is for winning the game and the more important one is for winning life. And never dare to confuse the importance of the two.