Leadership lessons from my 50s

The Prime Minister of Singapore, Mr. Lee Hsien Loong, was enjoying a cup of coffee with Mrs. Lee, both sitting barely two metres from me. They, and their entourage, had just toured JustCo’s new co-working centre at Tokyo’s Shibuya Hikarie.

It was 27 May 2022, almost four years since I joined JustCo. In that time, we had grown the firm’s footprint from 15 centres in three cities to almost 50 centres across nine cities. Covid intervened as a blip, but it hardly slowed us down. Regardless of challenge, we just kept ploughing ahead. The Prime Minister’s visit was a milestone and a huge morale booster.

Prime Minister and Mrs. Lee at JustCo Shibuya Hikarie, Tokyo, May 2022

In that hyper growth journey, I got to experience start-up life for the first time. I had been a corporate man throughout my career and was used to working with mature teams and structures. In contrast, JustCo was relatively youthful and inexperienced. But whatever the firm lacked, it more than made up for with its global ambitions. In spades.

I was warmly welcomed by JustCo’s founders. From the start, there was leadership consensus that the firm’s next growth stage required different people, processes and systems. I reached out to my network and convinced a few seasoned professionals whom I trusted to join me. Together, we began to scaffold for expansion.

What followed were a restructured organisation, stronger ERP and HR systems, sharper performance dashboards, delegation matrixes, governance policies, and more. Coupled with new management meetings, KPIs and targets, these strategic changes focused minds and habits on the important things. A more grown-up attitude began creeping into every interaction, be it a senior leadership meeting, a project update, or a water cooler chat.

With Alex and Nick, trusted comrades who joined me at JustCo, May 2019

We transformed JustCo, and JustCo changed me into a start-up leader. The firm’s aggressive growth threw up new issues every day for my attention. Faced with scarce resources and limited teams, I became part doer, part strategist, part connector, and overall problem solver. The ubiquity was exhaustingly energising.

Adjusting to JustCo’s culture, however, was hard. Start-ups face daily pressures to prove they deserve to exist. Management decisions therefore tended to prioritise the fast and tangible. On the other hand, I agonised over the slower strategic. Abrupt changes were reasoned as agility pivots. I saw short-termism in these same changes instead. Bargaining that was prized as shrewd resembled finagling to me.

I tried to not let the dichotomies bother me. After all, the founders were industry pioneers who had built a successful business. I respected their tenacity and wanted to learn from them. They were also gracious in welcoming me into their fold and giving me space to try new ideas.

I soldiered on as best I could. The adrenaline from JustCo’s pace, plus a good pay package, masked some of the discomfort. I turned to finding meaning in growing my teams and celebrating their wins. But despite all these, my disconnect with the firm’s core culture vexed me continually. Try as I might, I could not bridge the gulf between my values and the founders’. In the end, I had to conclude that we were just very different people, and to peaceably leave it at that. We eventually parted ways in early 2023.

The JustCo stint had drained me, especially emotionally. I took a break and spent the next several months being with my family, reconnecting with friends, and returning to my faith conscientiously – all of which I had neglected. It was the healing I sorely needed as I pondered my next move.

Going solo as a leadership advisor and coach seemed an attractive next step, chiefly for the autonomy it promised. On the other hand, the downsides of independence gnawed at me. Would I be able to get business? Was I good enough? What would clients be willing to pay?

Faced with these doubts, I defaulted onto the beaten path when an opportunity surfaced to join Olea Global, a Standard Chartered backed early stage fintech. I accepted their offer to be Chief Operating Officer. The uncertainty and risks of setting up on my own were too daunting.

My momentum was strong as I dove into Olea. The fintech industry was new to me and there were lots to learn. My boss and colleagues were all likeable and, without exception, intelligent and driven. It was invigorating to be back among cosmopolitan and smart professionals.

I drew from my prior start-up experience and identified improvements for Olea’s growth. I was eager to make strategic changes. Unfortunately, life as a fintech COO was also about paperwork, operations, compliance rituals and related nitty-gritty. I did not care much for the mundane and chafed at the rigidity of the many repetitive tasks that I oversaw.

In the event, I quit Olea after two months. I told my boss candidly that the industry and work did not speak to me. It was therefore better that I left before being entrenched in the company’s operations. More importantly, the break I took after JustCo had tuned my heart towards doing my own thing. Joining Olea was a mistake that affirmed what I really longed for.

What my 50s taught me about leadership:

-       Small can be beautiful. Start-ups are uniquely vibrant. Compared to large organisations, entrepreneurial environments in smaller companies give leaders room to do much more. You will have unparalleled ability to influence and create impact.

-       Working well with others always requires some suppressing of your individuality. We make these compromises all the time. But such trade-offs can never endure if they involve differences in core values. Agreeing to disagree can only get you that far.

-       As you acquire professional and life experience, your instincts will become more acute. They are the inner voice of your true self. The older you get, the louder will that voice be. Listen to it. Heed its call.

What did your 50s teach you about leadership?

The last article in my mid-career retrospective series (the Epilogue) will drop later in 2025. Subscribe to my blog to be notified.

(This article is part of a mid-career retrospective series on my professional life. Each article in the series recounts events in one decade of my career. At the end of each piece, I summarise what those events taught me about leadership. All articles in this series are hosted on my blog.) 

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I am a Board Director and Leadership Advisor. I help CEOs and teams succeed through good leadership practices. Because good leadership matters.