Casting About (8.20.25)
Rhythms and reasons.
I was recently invited to be a guest on a podcast. Actually, to be more precise, I was recently invited to be a guest on a podcast for the first time. I add the emphasis because the invitation came as a bit of a surprise. Other than my modest Substack and sister newsletter on LinkedIn, I don’t have much of a public persona. I have done a speaker event and participated in a panel here and there, but I don’t proactively seek out or solicit such opportunities. So, to receive a reverse inquiry of this nature was unexpected, to say the least.
Initially, I thought I would simply politely decline and go back to my weekend. I’ve been having an enjoyable, but busy, summer at work. A little busier than usual, actually, because I have been protecting my weekends to focus on my family and my writing, and to make progress on a few neglected pet projects. The prospect of evaluating the opportunity, negotiating the terms of my participation, preparing my thoughts, and actually recording an inaugural podcast experience felt like a surefire way to disrupt the rhythm I had so deliberately and meticulously orchestrated.
Yet, rather than punch back a reflexive no, I decided to sit on it for a few hours. I wasn’t quite sure why at the time. The request was politely worded; the premise, appealing: a chance to talk about why I chose to leave Singapore to work in New York, and lessons I had learned along the way. But, at the risk of offending someone who might be reading this, it wasn’t quite enough to displace my jealously-guarded plans.
Still, about half a day later, I sent my reply: “Thanks for reaching out…please feel free to tell me more.”
So, what changed?
In my first posting on Substack, “On Poverty and Porosity”, I explain that I write because of the poverty of authenticity in our manicured, modern, world. Authenticity is pivotal to a concept I call “porosity”. Understanding porosity begins with the premise that we not only live in different spheres (self, home, work, community, etc.) but that we present ourselves differently in each sphere. In at least one of these spheres, we are “the best version” of ourselves. But can this “best version” travel across spheres? If we can make the borders between spheres “porous” then we should be able to bring “the best version” of ourselves from sphere to sphere. But such porosity is limited by a toxic mélange: of insecurity, ambition, jealousy, resentment, shame, guilt, trauma, and other such things. For example, we may find it difficult to be as generous with our colleagues as we are with our children, because generosity to our colleagues may come at our own expense in a way that generosity to our children does not. Understanding ourselves and increasing this porosity requires us to go “beneath the surface” of our lives – to be deeply boring, as it were.
As I considered my excuses for not doing the podcast, I challenged myself as to whether I was finding a way for the best version of myself to travel across spheres – whether my big plans to protect my weekends were in fact inhibiting my personal growth. I wasn’t actually sure. So, I decided to entertain the request while I worked this out in my own head. I won’t keep you in suspense — I did the podcast. But walking the meandering path to saying yes demanded both reflection and some brutal honesty.
Ego. The first thought that came to my mind was how to avoid saying yes just to feed my ego. I talked to Mrs. Deeply Boring and she expressed the same concern. As a prideful person, I need to be on high alert against this sort of thing. Saying yes with confidence that ego was not at the center of the decision required teasing conflicting motivations apart, a complicated task at best.
It helped that the podcast was itself new, and didn’t have a large following. But still, that’s rather easy to hide behind. You can still feel flattered even if not many people are watching. And, it occurred to me, that may actually be worse than if the converse were true (i.e. it’s more vainglorious to be overly self-inflated over what ultimately is a small thing, rather than something that is actually grand).Numbers. I’ll be honest. It did cross my head a number of times that getting on a podcast, even one with a small following, might boost my Substack and LinkedIn newsletter subscriptions. This was revealing, because I state openly that my goal is not to chase numbers. But as much as I say that, and try to mean it, prideful people are always drawn to quantifiable measures of success: grades, degrees, titles, paychecks, and eyeballs.
As with ego, it was hard to work through this one. In the end, I mentioned my writing but I omitted reference to this publication’s name. And though I did reach the point of feeling somewhat settled on this, I am grateful to have had some serendipitous confirmation, as I describe below.
Serendipity. The podcast was scheduled to be recorded on a Wednesday evening. But as I made my way from my office in Hudson Yards to the studio in Times Square, I received word that the session was off because the recording technician was not available. This posed a challenge as my schedule for the coming days was tight and it would be difficult to squeeze in an alternative time. However, I’m grateful that the session glitched, because it gave me a chance to examine my heart. I realized I would be fine if a rain date was not possible, if my calendar could not work out to allow for it. It was an important indication of my ability to let it go, to not hold on tightly to such things. (Reader, you may mentally insert a .gif of Galadriel relinquishing the One Ring to Frodo in Fellowship of the Ring here).
People. My hosts, Jolynn and Jason are, in a word, great. We first met in person at the studio that Wednesday even though the recording was called off. The delayed recording gave me the chance to get to know them better, which I was grateful for. Both of them are students at the National University of Singapore, selected to spend a year in New York as part of the NUS’ Overseas College program. Jason has a passion for entrepreneurship – the podcast was his baby, from ideation to winning sponsorship from the Singapore Global Network. Jolynn’s marketing and e-commerce savvy gave focus to the interviews and steered conversations in interesting directions.
Photo by Alan Mersom on Unsplash As we discussed alternative dates, I learned that they were both returning to Singapore for good that very weekend. So we could either record that Friday, or not at all. I wrote earlier about the difficulty in teasing apart motivations. What transpired, to my surprise and delight, was that getting to know Jolynn and Jason opened a second window through which to examine my motivations, which now had to accommodate a burgeoning desire to not disappoint my hosts, who had worked very hard to pull this all together. There is something liberating about doing something to express appreciation for the effort of others – it anchors you in a different way, and frees you from your own putative goals. I have had that experience in other contexts, but I did not expect it in this one, and it broadened my horizons and deepened my understanding of what’s possible.
Porosity. Meeting on Wednesday without the pressure of filming allowed Jason, Jolynn and me to discuss some ideas I had for the podcast. They were receptive to one idea in particular – one that was especially important to me, though I was careful not to reveal this was the case. I asked them if I could turn parts of the session around, to ask them about their own life stories, and to allow them to share some of their own experiences and successes. Initially unsure, they considered, and then agreed, and I’m glad they did. It allowed me to learn more about what was happening “beneath the surface” of their own lives, and I was grateful for that vulnerability and their accompanying authenticity.
Photo by Denise Jans on Unsplash
Authenticity. But what about my own stories? Could I share them with authenticity? The purpose of the podcast was to celebrate the 60th anniversary of Singapore’s independence from British colonial control. So while I don’t expect it to be widely viewed, in theory, anyone in Singapore might see it: friends, family, old classmates, old colleagues. How open ought I to be?
I decided to answer the questions the same way I approach my writing here on Deeply Boring/Beyond Boring: to be factual about events, to be transparent about the difficulties along the way, to not shy away from accomplishments, to be unafraid of being judged. So, I told my story with candor, about the stumbles and failures, the detours and reroutes, lest anyone think life in America is perfect. I tried to sidestep false humility, which is pride in modest dress. And I was forthright on matters I felt strongly about, including my views on racial harmony and artificial intelligence.
Accepting. Doing something new entails the uncertain. It demands that we test ourselves. In working through my motivations, I realized that this dimension — the challenge of doing something new — was a recurring source of positive energy. Some of that energy came from learning, from absorbing new information (e.g. reading articles on how to be a good podcast guest). I also derived energy from examining my viewpoints on the topics proposed — had I really thought through these issues thoroughly? It’s one thing to have views I might offer in a casual conversation or dinner discussion — but was I prepared to commit to those as a public record of my opinion on the matter? I found this process invigorating.
But primarily, I found energy in recognizing the need for, and accepting, help. Help from the wonderful Stevie Manns, who I work with. She gave me much-needed coaching and generously offered a dry run which helped settle my nerves. Help from a friend who helped me sort through my motivations, and from my parents, who I asked for advice. And, most importantly, help from Florence (a/k/a Mrs. Deeply Boring) who gave unvarnished feedback on how I sought to approach some questions. Truth may be hard to hear, but it is also unwise to ignore.
Fear. Early on, I considered not doing the podcast for shyness on account of my looks, as I am overweight and not telegenic. But I am happy about how I was able to put away such fears, recognizing what a terrible example that would set for my children. They do not know it, but they were a source of courage. I asked them if I should do the podcast; one said “Why not?” and the other offered “It might be cool.” It’s curious how we draw strength from our children. Resolving not to dwell on it, I put on one of my nicer polo shirts and got an overdue haircut, but otherwise turned up as I am.
However, the most profound lesson I learned about fear takes us full circle to where I started: ego. After a few days of wrangling with my motivations, I recognized that I was making up reasons to say no in order to avoid confronting the ego dilemma. I was afraid to do something because I didn’t trust myself. I asked myself: but how can you grow from this? I decided I didn’t want to say no simply because my motivations were complex and difficult to sort. Rather, I needed to challenge myself as a forcing mechanism to purify my motivations. Or I would never grow, whether in character, or faith.
As I worked through each of these obstacles, some in my head and some in my heart, I became increasingly relieved. I started to reframe the invitation through a new lens: it was not an opportunity to shine the spotlight on me, but an experience through which I could work with new people, on new things, in new ways, and to put human flourishing at the center of the choices I faced in doing so.
In a wonderful twist, Mrs. Deeply Boring accompanied me to the recording on Friday, which I appreciated for the encouragement, and also because she got to meet the amazing crew of students, guests and supporters who made the “Still Singaporean” podcast possible. My thanks go out to them all – I learned much more from them and the experience than they did from me.
Thank you, for the opportunity to share.
Grace and peace, J
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Thank you for sharing your story in this article and in this inspiring episode of Still Singaporean. Such a wonderful interview. I really enjoyed learning about your journey, your background, and even the connections with Bill Gates and Jeff Bezos. Your perspective on AI and your call for community and unity are uplifting and optimistic. Truly a joy to listen to!