How To Make Difficult Life Decisions: Easy Decisions, Hard Life. Hard Decisions, Easy Life.
I sat down and made a radical decision: it was time to blow up my career.
Whenever I catch up with friends in London or Paris, many confess they feel trapped on the hamster wheel, longing to live life to the fullest.
While I’m not a life coach (Francesca’s probably the one for that!), during my financial coaching sessions some of my readers also express similar lifestyle dilemmas. Here’s how one simple exercise in 2018 changed everything for me.
My life took a dramatic turn when I applied this framework.
Here’s why this might* be exactly what you need, too.
*Not Life Advice.
KEY TAKEAWAYS
- In 2018, I had what some might call a crazy idea. I was as a Portfolio Manager at a top Wall Street investment firm — intellectually stimulated, well-paid, and riding a wave of career momentum. Walking away seemed unthinkable, the opportunity cost too high. But despite my fortunate position, I wanted something else. I craved freedom. I dreamed of spending a year (or more) cycling around the world, maybe even leaving London behind for good?
- The risks were big. Losing financial momentum, missing the intelectual stimulating environment, and stepping away from the prestige I’d worked so hard to build. But as I began to reframe my identity around real impact and adventure, my fears shifted. Even if the escape was only partially successful, I’d still gain something priceless — the chance to reconnect with my adventurous side, see the world through the eyes of a cyclist, and take back control over my life. Moments when you have health, time, energy, money, and no major responsibilities are rare; if not now, then when?
- In the end, the cost of inaction felt even bigger. We’re so good at fearing what could go wrong that we forget the heavy toll of staying the same. For me, that meant a slowing learning curve, a social impact that will never materialise, and an increasingly fragile life tethered to financial hubs and high-stakes roles. Ultimately, the risk of staying put was greater than the risk of breaking free. I needed freedom, and cycling became the ultimate embodiment of it. I never looked back.
Here is the full analysis
This post is dedicated to Leo, one of the early supporters of Bankeronwheels.com.
Easy Decisions, Hard Life. Hard Decisions, Easy Life.
How I Applied “Fear-Setting” to Redesign My Life
An emotional attachement to my firm held me back
I tried to leave for over a year, but it just didn’t work.
In 2018, I was at a crossroads. On one hand, I was going through a very difficult period in my personal life. On the other hand, my career as a Portfolio Manager had intellectual challenges, high pay, and increasing momentum. Deep down, I imagined spending a year cycling the world. The late Iohan Gueorguiev’s videos made a strong impact on me. I even considered the idea of never returning to London. But, the thought of leaving a “perfect” career felt like madness.
After 10 years, I had an emotional attachment to my firm. I tried to leave for over a year, but it just didn’t work. Only a rational framework could have made a difference. It was when I randomly stumbled on Tim Ferriss’s 3-step fear-setting framework, that I found the clarity and confidence I needed to take the leap. By late 2018 my plan was in place, and my bike and equipement ready.
a 3-step process changed my life ✍🏻
Step 1: Define Your Fears
I wrote down my worst fears — lost income momentum, missed insights from brilliant minds, and leaving behind the prestige I’d built. Then, I mapped out steps to prevent or repair each one, like staying connected with my network. Seeing these “repairs” made the risks feel manageable.
Step 2: Define Partial Success
I imagined the benefits of partial success. Even if I didn’t completely reinvent my life (in retrospect, I did), I’d reconnect with my adventurous side, see the world from a cyclist’s perspective, and regain control over my path.
Step 3: Assess the Cost of Inaction
Staying in place meant minimal social impact, and an increasingly fragile career tied to financial hubs. Ultimately, staying felt riskier than going.
This exercise led to one of my life’s biggest decisions. If you’re at a crossroads, I recommend watching Ferriss’s TED Talk to see how you might apply this approach to your own journey. After the video, I explain how I proceeded.
A 3-step framework for making tough decisions
It’s hard to detach from something that forms part of your identity. A lot of bankers end up trapped with it, especially at senior level. I thought that I needed to redefine my identity before my lack of action defined it for me.
1️⃣ how i defined my fears
The real fear: Torpedoing my career as it was gaining momentum
And missing insights from brilliant minds
- Opportunity cost of losing income growth: 💰 Just as things were seriously taking off financially as I became more senior, I worried about losing that momentum. The opportunity cost of leaving was significant, can be very disruptive if not timed well, as the biggest relative increases happen at this moment in a career. This was a real cost, mitigants appeared to me limited and repairing the damage would take a lot of time. In truth, it seemed very risky.
- Missing out on intellectual stimulation: 🤓 I thrived on being around sharp, driven people in a stimulating environment. Losing that feels like a real sacrifice, but my network would be my lifeline. Expanding it, even virtually, would keep me inspired, I thought.
- Losing the Prestige Factor 💼: It’s hard to detach from something that is part of your identity. For bankers it’s often their careers. A lot of bankers end up trapped with it, especially at senior level. I thought that I needed to redefine my identity – around real social impact and adventures – before my lack of action defined my identity for me.
PART 1: DEFINE MY FEARS, MITIGANTS AND WAYS TO REPAIR
| Define Fears | Partial Fear Mitigators | How to repair if fear materialises |
|---|---|---|
| – Income growth trajectory loss at the moment when compensation accelerates. | After my trip, I can use contracting with good tax-adjusted rates (remote if possible). | Try to go back to London, onto the same path. But outcome uncertain. |
| – Not being able to work with smart people. | Maintain my network, as firms in other leagues may lack similar talent. | Grow outside network — virtually if outside London. |
| – Not having an intellectually stimulating environment. | Recreate an intellectually stimulating environment, even virtually, with friends/people I keep in touch with. | Tough to replace, but networking bridges gaps. |
| – Missing insights from some of the brightest in the industry. | Maintain my network and map the best research, resources, and communities. | Tough to replace, but networking bridges gaps. |
| – Loss of perceived social prestige — firm and role. | Focus on redefining my identity so it’s not linked to the firm/team. | This is the wrong fear to start with; redefine identity around real social impact/adventures. |
| – Concern about continuing education/upskilling on my own without the best platform. | Collect and organize all possible resources to leverage in the future. | New platforms emerge. |
| – Closing doors if, for example, the job market shuts down in the future. | Use an emergency fund to sustain a longer bear market and revert to entrepreneurship if needed. | Tough to repair in case of bad timing; need to take different risks. |
| – Losing part of my social circle. | Recreate a social circle based on other interests I have (physics, cycling, etc.). | Be creative about building a network. |
2️⃣ What if this bold idea is a partial success?
The appeal was real, but was it enough to make the jump?
after drafting the second part, I thought it was inconclusive
- Reconnecting with My Adventurous Side 🌍: It was time to reconnect with my 20s — the bold, free spirit who was always up for the next adventure, embracing life as a traveler on a grander scale. This was somewhat lost over the decade in the City.
- Total Freedom and Seeing the World from the Saddle 🚴: The thrill of preparing for an adventure was already in itself motivating. Then the real experience of cultures and landscapes — all from the unique perspective of a cyclist. It’s a snapshot of the world that only those on two wheels can truly appreciate. It may be the only moment in my life with absolute freedom. With time, money and energy on my side.
- Maybe, Taking Back Some Control 💫: Maybe, with every mile, I’ll be reclaiming control over certain aspects of my life, clarity and confidence to steer my path in directions I may have never considered before. Stepping outside my usual circles means expanding my worldview and connecting with people who’ll open my mind in ways I never expected.
PART 2: WHAT IF ACHIEVE PARTIAL SUCCESS?
| Partial Success |
|---|
| – Reconnecting with my 20s identity — an adventure seeker in a broader sense, including being a traveler. |
| – Getting a snapshot of the world and different continents from a cyclist’s perspective. |
| – A year or more that will remain an unforgettable new experience (both physical and spiritual). |
| – Know myself better |
| – Physical benefits from cycling for a year. |
| – Fully experiencing adventure cycling. |
| – Meeting new people outside of my current ‘bubble’ — exploring new countries and ways of life. |
| – If successful, I may regain control over certain aspects of my life. |
| – Potentially leveraging this experience to pivot into something new. |
I was always seeking freedom. Cycling was the ultimate embodiment of it. But, My current situation was closer to golden handcuffs.
3️⃣ What is the cost of my inaction?
What would happen if i stay another decade in this role?
after drafting this part, I looked at the sheet and thought – it’s a no brainer.
Here is how I imagined the consequences of keeping pedalling (in front of my Bloomberg Terminal!) for another:
- 6-12 Months From Then: Health would reach a tipping point after a decade without a break performing at the highest level, and there would be a growing sense of missing out on meaningful life experiences. My technical skills would feel locally maxed out (the steepest part of the curve are the initial 5-7 years and for me it was also the most exciting time – managing portfolios and looking at various strategies during the Global Financial Crisis and the European Debt Crisis), with little space for personal growth or social impact.
- 3-5 Years From Then: The mantra ‘satisfy institutional client’ never resonated. It’s tricky when you’re working in finance and maximising your firm’s revenues is not your main life motivation. Helping real people and having an impact was something I missed. The lack of control in high-paid roles would become unsettling, as these jobs are becoming increasingly fragile. Slowly, London would feel less suited to my lifestyle that I’d want to be more balanced. And any other financial hub – Singapore, Hong Kong or even Tokyo (despite my love for Asia) – would be equally unsuitable.
- 5+ Years From Then: My main regret would definitely be the lack of social impact, as investing is profit driven. Also, optionality would reduce significantly with age. Senior roles imply reduced intellectual challenge and “golden handcuffs” make any life changing decision harder. The job is even more part of your identity. That’s why senior bankers never want to leave.
PART 3: WHAT IS THE COST OF INACTION?
| Timeframe | Potential Costs |
|---|---|
| 6-12 Months | – Physical Health after 10 years with no break – top tier roles are very demanding |
| – Mental Health: need a break after over decade at highest level. | |
| – Regret of missing out and not fully enjoy my 30s in a diverse way (like my 20s when I travelled extensively) | |
| – Now wrong side of asymmetry – After 10 yrs, my technical skills reaching local plateau | |
| – No real sense of social impact with my role (“make institutional client happy/perform”) | |
| 3-5 Years | – No social impact through current role. |
| – Potential Mental Impact: due to lack of control (I want at least an illusion of) | |
| – Loss of diverse identity, becoming somewhat defined by your profession | |
| – Technical skills may plateau, reducing job satisfaction. | |
| – Less Intelectually Stimulating Responsibilities – Senior roles always more commercial | |
| – Health impact of long hours – unknown but may be potentially irreversible | |
| – London doesn’t feel like the optimal place my lifestyle perspective | |
| 5+ Years | – No social impact which is a key aspiration I have |
| – Limited Mobility – strong dependencies (incl. geographical: big financial hubs: London, NYC, HK, SG) | |
| – Cash/Job Dependency – Potential long term ‘golden handcuff’ trap | |
| – Fragility – even the best can struggle with market shutdown | |
| – Health Impact – no tapper off for senior roles like in the early 2000s | |
| – Corporate insecurity – false sense of safety (artificially suppressed volatility) |
Never let a good crisis go to waste
Epilogue
What Happened After I Took the Leap
2019 turned out to be the best year in my life.
January 2019 brought a very welcome boost. The year ended up being one of the best years in my life. I cycled close to 20,000 kms across placed like New Zealand, Australia, Japan, Taiwan or Tibet. It also had a spiritual impact, that influenced my personal finances.
In 2020, as I cycled through North Africa, COVID-19 began to spread. I stopped in Morocco, and created Bankeronwheels.com to document my cycling adventures and share my insights.
My background, shaped by the work my portfolio management team did during the Global Financial Crisis and the European Debt Crisis, taught me a valuable lesson: “Never let a good crisis go to waste.” This principle became my guide during the Covid-19 ‘Crisis’, as I used that remote time to redesign my life. Financially, it was also a short and unique window of asymmetric trade opportunities in the markets that happen once in a decade.
I hope this framework can offer you clarity to make bold choices in your own life.
Looking back, COVID-19 created an unexpected opportunity to achieve something with much bigger social impact/educational mission than I had imagined. An aspect, that I was impossible in my prior life. But none of it would have happened without my cycling journey.
Why it mattered is worth another post. In the future I will share:
- My change of identity – which was the biggest benefit of my cycling adventures.
- How we live – and how we design our live now.
It took (still takes) us 👨👩👦 much longer than expected, to fully redesign an alternative lifestyle.
But, it was really worth it. I never looked back.
I hope this framework can offer you the clarity to make bold choices in your own life.
Good Luck and Keep’em* Rolling!
(* Wheels & Dividends)
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