I Left the Bank at 36: The Career I Built Wasn't Mine

Editorial note: This is a composite narrative. “Wei Ling” is a fictional character — not a real individual. Her story is AI-generated, drawn from career patterns and experiences Olivia has observed across many professionals over the years. Institutional affiliations have been fictionalised. Any resemblance to a specific person or organisation is unintentional.

Every few months I receive a message that stops me — not because of the career details, but because of a single line buried in the third paragraph that reveals the real question the person has been sitting with for years. Someone I’ll call Wei Ling sent me a message like that. She had just left a global investment bank after twelve years in capital markets, and she was building something new. She wrote: “I thought the hardest part would be the financial risk. It wasn’t. It was not knowing who I was when I stopped being useful in the way I’d been trained to be.” What follows is her story. — Olivia Bennett

There is a version of my departure from the bank that I can tell in four minutes and sounds like a TED Talk. That version has a clean arc: twelve years of deal-making, a growing hollowness, a clarifying moment, a brave leap, a meaningful mission. It is a serviceable story. It is also incomplete in the specific ways that make a story comfortable to tell rather than true.

The true version takes longer. It begins with the tombstones.

The Business Cards and the Tombstones

#

If you have worked in investment banking, you will know what a tombstone is: the Lucite display plaques commemorating completed transactions that gather on desks and windowsills over years. By the time I left, I had eleven. I also had a VP title I had reached at thirty-four, a flat in Buona Vista, a membership at a club I visited four times a year, and a business card that opened conversations in Singapore the way certain surnames open conversations in other countries.

I had gotten everything the system I had entered at twenty-four was designed to deliver. I was, by every measure I had been given, succeeding.

The hollowness began so gradually I almost missed it.

It was not burnout in the way people describe burnout — the exhaustion, the loss of function, the inability to continue. I continued. I was good at the work. I ran deal execution efficiently. I managed relationships. I answered emails at eleven at night and on Saturday mornings with something that felt, for a long time, like commitment. But somewhere around my ninth or tenth year, I started noticing that the satisfaction that used to come after a deal close — real satisfaction, the kind that stays — had shortened. The emotion was still there on closing day. Gone by the following week.

I told myself this was maturity. That deep satisfaction in work was a beginner’s feeling, and that what replaced it — professional efficacy, institutional respect, reliable competence — was the adult version of the same thing. I was not sure I believed this, but I had no framework for the alternative.

The Closing Dinner

#

The moment I cannot stop returning to happened in the third quarter of 2024. We had closed a large refinancing — a real estate developer, significant deal, the kind of mandate that generates a tombstone.

The closing dinner was at a restaurant on Marina Bay. There were eight people at the table: the client’s CFO, their treasury team, three of us from the firm. The conversation was running along the normal channels — deal mechanics, market timing, a little light social positioning. At some point the CFO made an offhand comment about the company’s expansion pipeline, a development project somewhere in Johor, and I realized, mid-sentence, that I did not know what this company actually built. Not the financial structure — that I could recite in detail. Not the debt covenants, the amortization schedule, the credit facilities. Those I knew precisely.

But what the underlying company did. What it made or built or provided to anyone. I did not know.

I had spent three months executing a transaction on behalf of a business whose real-world purpose I had never thought to examine. Not because I was incurious. Because the system I was working inside had been designed to make that question irrelevant.

I did not leave that night. I ordered dessert and gave a toast. But something shifted that I could not shift back.

The Decision I Made

#

It took me six more months to be honest with myself about what I had known at that dinner table. Not that I wanted to leave, exactly. But that the part of me that had once found the work genuinely interesting — the intellectual satisfaction of complex structuring, the craft of deal execution — had quietly finished with it, and I had been running on institutional momentum for longer than I was comfortable admitting.

I told myself a story about why this was temporary for a while. I told myself I needed a different mandate, a different geography, a different team structure. I applied to one internal rotation. I took a coffee with a headhunter at a boutique. None of it changed the density of the feeling.

What stopped me from leaving sooner was not money, though I told myself it was money. I had calculated the runway three times; the math was fine. It was this: I had been Wei Ling from the bank for twelve years. That sentence — that specific construction — was the primary way I was known to other people, and if I was honest, to myself. I had been answering the question “what do you do?” with a version of that sentence since I was twenty-four years old. I had no idea what I would say instead.

Herminia Ibarra, the organizational behavior scholar, has argued that the desire for certainty before a career change is the primary reason people stay stuck in the wrong one. In her research with professionals navigating major transitions, she found again and again that people try to plan their way into a new identity — to know who they want to become before they move — when in fact identity in these moments works the other way. You act your way in, not think your way in. You experiment before you know. The clarity comes from movement, not from stillness (HBR, December 2002).

I wish I had read that earlier. I spent almost a year trying to architect certainty before I allowed myself to move.

In January 2025, I gave six months’ notice and began planning a proper handover.

What I Lost That Nobody Warned Me About

#

The financial risk had been the story I told myself, and when the financial risk turned out to be manageable, I expected the rest to follow. It did not.

What I had not accounted for was the tribal dimension of leaving an institution like this one. You belong to a specific cohort of people who all speak the same compressed language, have survived the same particular rituals, understand the same references. That belonging is not a small thing. When you leave, you become a former member — which is not the same as a non-member. Formers occupy a specific social category that is warm on the surface and slightly awkward underneath. You are someone who chose to leave a place that others remain committed to, and that choice, however gently acknowledged, requires a small act of social renegotiation every time it surfaces.

My parents’ response was harder than the colleagues’. My father, who had worked his entire career in government and had always treated my banking career as evidence that the family had arrived somewhere important, received my news with a silence that lasted three days. He did not argue or criticize — he was too careful for that. He asked, once, whether I was certain. When I said yes, he said: “Then I trust your judgment.” I have thought about that sentence more than any other thing said to me in that year.

The identity vacuum arrived on a Monday morning in July 2025, about two weeks after I left. I woke up without a calendar. I had no meetings, no deal timeline, no eight o’clock call. The absence was physically disorienting — like standing in a room where the furniture you had always navigated around had been removed, and now you kept startling at the open space.

I had been useful in a specific, legible way for twelve years. The usefulness was gone, and what I discovered was that I had mistaken the usefulness for identity. The two are not the same thing, but they can coexist so completely for so long that the distinction becomes invisible.

What I Was Building

#

FinLit SG had been a thought before it was a plan. I had seen the gap years earlier — during the wave of reporting in 2022 and 2023 on migrant workers in Singapore losing savings to remittance scams, informal moneylenders, and fee structures designed to be opaque. Over a million migrant workers live and work in Singapore. Most send a significant portion of their wages home. Many pay remittance fees that consume eight to twelve percent of transfers annually, when alternatives exist that cost under one percent. Many carry informal debts to agents from the recruitment process that are never formally documented and almost never challenged.

My capital markets knowledge was not directly applicable. But understanding how money moves, how financial products are structured to extract value from people who don’t understand them — that I knew. The question was how to translate that into something useful at the scale of one construction worker from Bangladesh sitting in a dormitory with a limited data plan.

I started with workshops. I found an NGO partner who gave me access. I went to Sunday sessions at a community center near the Jurong dormitories and taught a two-hour financial literacy curriculum I had written in my kitchen, to rooms of twelve to fifteen people. The work was halting, slow, and more precise than any deal I had structured in a decade — every concept had to earn its place on a single slide, in English a second-language speaker could follow on four hours of sleep.

Two years later, FinLit SG has trained more than four thousand workers across three NGO partnerships and a digital curriculum that partner organizations distribute at onboarding. The impact is specific and visible in a way that deal tombstones never were: a man from Tamil Nadu who redirected his remittance to a provider that saves his family the equivalent of three months’ earnings per year. A domestic helper who recognized a lending scam and walked away. A construction crew supervisor who helped four colleagues access their legal entitlements when their agency tried to withhold wages.

I did not expect to care about causality this much. I had convinced myself that professional abstraction was a preference, an intellectual temperament. It turns out it was a constraint imposed by a particular kind of work, and I had not known that until I worked differently.

What I Would Say to Myself at Thirty-Four

#

Not “leave sooner.” That is the retrospective story, and it isn’t quite right. I needed those twelve years to build the capability that makes FinLit SG credible and effective. The structuring knowledge, the regulatory literacy, the understanding of how financial products extract value at scale — none of that came from nowhere.

What I would say instead is this: the question you keep pushing into the future — am I doing work that I would choose if I chose freely? — does not have a better moment to answer. The moment you have enough data to answer it is the moment you have already been carrying the answer for a while.

The financial risk is usually smaller than you think. The identity risk is usually larger. And the identity risk is worth taking, because the identity you are protecting by staying may not, on inspection, belong to you. It may belong to the institution that conferred it.

I was Wei Ling from the bank for twelve years. I am Wei Ling who runs FinLit SG now. The sentence is less efficient. It requires more explaining. It fits better.

Ibarra’s observation about career transitions has stayed with me long after reading it: that people who successfully reinvent themselves don’t plan their way into the new life. They act their way in, tentatively and specifically, until the new identity accumulates enough reality to replace the old one. What I see in Wei Ling’s story — and in the stories of the many professionals I work with who are navigating similar transitions — is that the distance between “the career I built” and “the career that is mine” is traversable. It is not comfortable to cross, and it does not reward hesitation. But it is traversable. — Olivia Bennett

References

#

• Ibarra, Herminia. (December 2002). “How to Stay Stuck in the Wrong Career.” Harvard Business Review. https://hbr.org/2002/12/how-to-stay-stuck-in-the-wrong-career (Accessed June 2026)
• Deloitte. (March 4, 2026). “2026 Global Human Capital Trends: Reinvention Is No Longer Episodic.” https://www.deloitte.com/us/en/insights/topics/talent/human-capital-trends.html (Accessed June 2026)
• Gallup. (April 8, 2026). “State of the Global Workplace 2026.” https://www.gallup.com/workplace/349484/state-of-the-global-workplace.aspx (Accessed June 2026)