Oct. 4, 2022

The Perils of Leadership (with Timothy Khoo)


EPISODE 58             

In this special episode of the Leadership series, I share a conversation with a fellow interior pilgrim who had tasted the heights of success in leadership but found himself tumbling into the search for authenticity and meaning when the personas that had defined him were taken from him.

My guest for this episode is a former President and CEO of a global charitable organisation who now lives with the reality of the undeniable fact that true leadership is not only exercised with skilful hands but with integrity of heart. I hope you enjoy listening to this conversation with Timothy Khoo -  existential coach, sojourner guide, and founder of Desert Odyssey.

Articles by Timothy:
Falling Into Grace
Actio Sequitur Esse – Action Follows from Essence 

Share this episode via this episode page.

CHAPTER  MARKERS
0:00:37 - Introduction
0:01:38 - Introduction to Timothy Khoo
0:05:37 - Sojourner Guide
0:10:24 - How Our Paths Crossed
0:15:20 - Why is Leadership Challenging to Exercise?
0:22:42 - Losing Myself
0:26:44 - Misaligned Character & Charisma
0:32:08 - How Different are People from One Another?
0:37:32 - Purpose & Meaning
0:38:13 - Content & Container
0:41:22 - Masks & Personas
1:00:32 - The Fraction Analogy
1:21:34 - Giving Our Souls Time to Catch Up
1:31:38 - Conclusion
Available here.

TRANSCRIPT
Available here.

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Transcript

EPISODE 58 | THE PERILS OF LEADERSHIP (WITH TIMOTHY KHOO)

I remember standing in front of the mirror. And I remember having a most surreal moment of looking in the mirror, recognizing the reflection, but literally asking myself who the expletive in the world are you? And I could not, for the life of me, answer that question because my presidency and my priesthood – the two things that define my existence – were now no longer who I was. And therefore, who is Timothy Khoo? Not a clue, not a clue.

[00:00:37] INTRODUCTION
Welcome to Becoming Me, your podcast companion and coach in your journey to a more integrated and authentic self. I am your host, Ann Yeong, and I'm here to help you grow in self-discovery and wholeness. If you long to live a more authentic and integrated life and would like to hear honest insights about the rewards and challenges of this journey, then take a deep breath, relax, and listen on to Becoming Me.

[00:01:09]
Hello again, dear listeners, now that we are a few episodes into this new series on leadership, I have a special conversation to share with you. And it is a conversation about the perils of leadership. Or more specifically, you know, what happens when we fuse our identity to the masks that we wear – the personas that we have learnt to put on in order to perform the role that we play as a leader.

[00:01:38] INTRODUCTION TO TIMOTHY KHOO
So, this special guest is Timothy Khoo, and he's the founder of Desert Odyssey; a very special and difficult to describe kind of retreat experience, for those who are in search of their true selves. He is a former president and CEO of a global charitable organization. And he has coached and mentored just so many leaders from over a hundred countries in very different vocations.

[00:02:06]
He has, you can say, rubbed shoulders with the crème de la crème, okay – people who are at the top of their vocations, people who are admired and respected. And he also works with and ministers to prisoners. So, his resume is clearly impressive and diverse, but that is not the reason why I invited him onto this podcast.

[00:02:28]
That is not the reason why I'm so excited for you, my dear listeners, to be able to listen in on this conversation that I had with Timothy. The reason why I sought him out – well, actually, that's also the same reason why I even reached out to him, I think maybe five, six years ago now – to get to know him, is because I recognized in him a fellow interior Pilgrim.

[00:02:54]
So, I'm just going to invite you to listen to these precious sharings about what life can teach those who are willing to be humbled, who are willing to encounter grace when we are at the bottom of the pit. So, without further ado, I present to you my conversation with Timothy Khoo.

[00:03:21]
Ann: Hello, Tim.

Timothy: Hi, Ann.

Ann: Welcome to Becoming Me. And thank you so much for making this time to have this chat with me.

Timothy: It's extremely special to be with you.

Ann: I don't know if you're aware, but I just started a series on leadership on the podcast. And actually, when I asked you whether you would be on the podcast, I hadn't planned on this series yet.

[00:03:49]
I mean, you've always been on my mind as one of the people to ask. Because when I think about the interior journey and the whole, you know, the journey to authenticity, I know your story and the work that you do is also very much – kind, kind of similar, right? There's an alignment there.

[00:04:09]
Timothy: Yeah. Yeah.

Ann: So, let's begin by, you know, how you – well, how you call, I guess, yourself, and what you do. You describe yourself as a sojourner guide and existential coach. Maybe you can begin there. Can you share – yeah, share with us what, you know, what's that and what do you do?

Timothy: Yeah. Yeah. Well, if I can back up a bit.

Ann: Sure.

[00:04:31]
Timothy: You know, you'd mentioned that you hadn't thought or conceived of the series on leadership, right?

Ann: Mm-hmm.

Timothy: When the invitation was issued and then somehow this segues into it. There's a part of me that goes gulp because one of the things that I've almost, I would dare say, intentionally avoided, was being, put back into – either by choice or you know, by appointment – into a place of leadership.

[00:05:04]
And again, it's for my own reasons of just feeling that – and it's not about beating myself up, but feeling that perhaps, I need to earn the right to be a leader – if ever again. Or that leadership was the thing that I exercise at one point in my life, but perhaps, not now. Then again, you know, it also goes to what is leadership.

Ann: Mm-hmm.

Timothy: Is it a position you hold, a title you have, or is it something that's perhaps a bit more nebulous?

[00:05:37] SOJOURNER GUIDE
So, the reason I brought that up was because sojourner guide was chosen – it's not a very elegant term, I don't think, at least. But it reflects the fact that I'm not a leader. I'm not here to lead you, you know, into any space of an interior journey, but here as a guide.

[00:06:02]
So, when you need me, I'm there when you don't need me – and I hope you don't, you know, for the most part – and you're on your own journey, that at certain points, I may intersect with you and accompany you on that journey, rather than be perceived as one who is leading you into that journey.

[00:06:22]
So, that's the reason for the notion of, sojourner guide. Sojourner, of course, you know, topologizes as a person on a journey.

Ann: Mm-hmm.

Timothy: And so, a guide, as opposed to a leader. "Existential coach", to be very honest with you, coaching was, became, I guess you could say, an exploration into what skillset do I have apart from working in the same charity for 25 years of my life – half of my life at that point in time – with no other skill set, conceivably, beyond that.

[00:06:59]
So, when I took the decision – and, you know, we can explore the circumstances leading up to that decision – but when I took the decision not to go back to the charity that I had been with for 25 years, at the age of 50 – not quite old enough to retire, not quite young enough to, you know, do something completely different. Or at least, in my case, so it became; what do I do that is productive and meaningful, you know, for the next – for, as I conceive of it, the last third of my life?

[00:07:37]
And so, made the foray into coaching, realizing that there was a particular brand, I guess you could say, of coaching that resonated deeply with me. And even as I made my own journey into the discovery of meaning and purpose, was helping people make sense of their journey in terms of their own discovery of meaning and purpose.

[00:08:02]
Hence, "existential". This notion of who am I and what am I here for. What am I here to do, you know, with my life?

Ann: Mm-hmm. You know, I just – when you were describing why you used the term, "sojourner guide", I was recalling actually, that's kind of the label – a similar label I use for myself when I have to try and describe what I do. I call myself an interior journey guide.

[00:08:32]
Timothy: Oh, wow.

Ann: Just, you know, wanting to be a bit more specific – interior guide, right?

Timothy: Yeah. Of course.

Ann: And the introduction to this podcast, like at a start of every podcast episode, I think I introduce myself as, you know, podcast companion and guide. Or that Becoming Me is your podcast companion and guide.

[00:08:49]
Because I, like you, I see myself as someone on the journey.

Timothy: Yeah.

Ann: And sharing my experiences of the journey. And to the extent that I have made this journey, I can be your guide, right? Like, as in, if you need me. And so, it's in that sense, there is some exercise of leadership, but it's not a static one.

[00:09:12]
It's not married to, you know, a position. But I guess, maybe both of us kind of see ourselves – it's, we're on the journey as well, and we are sharing.

Timothy: Yeah. Yeah. Yeah. And I like that, Ann. Because I think it's perhaps also, posture, right? It's – leadership tends to confer in people's minds that, you know, I'm ahead of you – not in any, you know, hubristic sense, but that, you know, I'm leading you, right?

[00:09:43]
Ann: Mm-hmm.

Timothy: As opposed to I'm accompanying you. And I think particularly in the Asian context, that's probably a very important distinction to make, because people want to be told what to do. They, you know, they want to be led. I get it and that's certainly a place for it. But the space I inhabit now – and I suspect that you as well, not suspect, but know that you as well – inhabit, is more akin to being a guide than a leader in that understood sense of the word.

Ann: Mm-hmm yeah. I guess it's a particular way of exercising influence, I suppose.

[00:10:24] HOW OUR PATHS CROSSED
Timothy: Mm-hmm, yeah.

Ann: And helping someone unlock their self-leadership, maybe, you know? –

Timothy: Absolutely.

Ann: – in a way. So, yeah, so I want to, you know, also start, and share with my listeners how our paths crossed. Because I think, it's really a very wonderful story. And I know I told this story to you before; the first time we spoke, which was now – I don't know, what three, four – maybe four years ago.

[00:10:50]
Timothy: Or more.

Ann: Or more! I can't even recall.

Timothy: Yeah.

Ann: Right, so, I was speaking with our mutual friend, Faith. And it was just a – you know, happened to be a conversation about possibilities of maybe what I could do with her and the work that she was doing.

[00:11:10]
And I think I said something along the lines of, "yeah, no, I think I'm more called to like minister to the ministers – if you know what I mean?" As in, like, I feel more called to support and pour into the people who pull the weight in serving, you know, the greater number. I don't really feel called to serve the big numbers myself. And maybe it's in a way that I spoke or whatever.

[00:11:33]
She just looked at me and she said, "you know, I know someone that you need to meet, or you should meet. You know, he speaks like you, he talks like you". She said something along lines, like, you know, very – I know you you'll probably cringe at the word, but I believe she used the word – kind of like, okay, very holy and philosophical, you know, kind of a thing. Yeah.

[00:11:54]
You know, and she asked me if I knew you – do you know Timothy Khoo? And I was like, no, I don't. But after I went home, I decided to try and Google you. And I think an old reflection of yours came up and this specific one that I read said a little bit about your story – which I will ask you to maybe just share, you know, a little bit about, so we understand the context. But I think what made me feel like I really should, or I really needed to reach out to you and connect –

[00:12:25]
– I felt like it was like a Holy Spirit prompt was because o, our mutual – our other mutual friend, Friar John. Right?

Timothy: Yeah.

Ann: And you named him by name, and you said he was a spiritual director, and he was a former spiritual director of mine and a good friend. And what caught me was that the context of what you shared in that piece of writing was a fall from grace – which turned out to be, as Friar John said, was more a falling into grace.

[00:12:56]
Timothy: Mm, yes, exactly. Yeah.

Ann: And that drew me because when we talk about leadership, usually, actually it isn't even just in secular context – I would say even very much so, even in the religious context that we are in. I mean, I'm Catholic, you're Christian as well – Anglican. You're an ordained minister as well, in your tradition.

[00:13:19]
And we often think of leadership as, you know, having to be whiter than white. I don't know. You know, kind of like morally upright; you shouldn't make a false step. You have to be a role model. What happens when our inner reality actually is not aligned or equipped to the external, I guess, the performance, I think, that we feel we have to live up to?

[00:13:41]
Timothy: Yeah. Yeah.

Ann: I had my own version of failure and, you know, and fall. And it was – it took me so long to reconcile with it. But it was what began – well, it started me in earnest, I think, on this interior journey. And in my experience, there are so many people in leadership that have this dissonance and this struggle, but they are not – but they don't acknowledge it.

[00:14:12]
They are not aware of it. They can't bring themselves to acknowledge it yet. And so, what really caught me here was, you know, this person, you know, Timothy – who was writing about it as well. And who was sharing, a man at around at 50, which I also associate with usually kind of being at the peak of one's career – you know, kind of thing. To have this experience of your clay feet exposed, you know, being shot down and finding grace, there's no – even as I'm speaking, actually I'm trembling a little.

[00:14:56]
I feel like – I don't know why, but this often seems to be the way that God grabs our attention.

Timothy: Yeah.

Ann: And I see this kind of turn – this fall, this kind of fall into grace, as painful and humiliating as it can often be – it always is – as a call, you know? As the start of our call, I suppose like, like Saul, right?

[00:15:20] WHY IS LEADERSHIP CHALLENGING TO EXERCISE
When he – on the road to Damascus. So –

Timothy: Yeah, yeah, yeah. Our egos, you know, constantly get in the way. And I think that's significantly why leadership is so difficult to exercise. It's because you are looked up upon, there is the conference of some measure of 'you've made it'. You may not be perfect, but we'll treat you like you were because you've made it, you've attained the pinnacle of success.

[00:15:54]
You know, in my case, I was the first Asian presidency of a major global charity. You know, and then when the press gets in on that full, full page broad sheet – even here in the Straits Times, interviews, et cetera. So, you begin to believe yourself – that you actually have made it. And so, when there's any chink in your armour, any pebble in your shoe, that reminds you that you are not who you think you are and the world thinks you are, it's a lot easier.

[00:16:33]
The default is to hide it, to suppress it to, say 'I can handle it', I can deal with it. Because I cannot afford for anybody to see my vulnerabilities. And over time, you know, the encrustation of our own hubris gets thicker and thicker. And at some point in time, we know not who we are anymore.

[00:17:00]
Ann: Mm-hmm.

Timothy: And so, when our world falls apart – I remember when my world fell apart, as you know – we can delve into that a little bit deeper as we go on, Ann. But I remember when my world fell apart, I was shocked. I was shocked at my own depravity, my own duplicity. But that is, you know, taking a step back.

[00:17:25]
Totally ridiculous because I knew that that was there all along – just not wanting to admit it. Why was I so shocked that now, the edifice that I had, so studiously built up, so elegantly crafted was all crumbling? It shouldn't have surprised me, yet it did. That was how thick the encrustation of my hubris was, that I couldn't see who I really was.

[00:17:48]
And then when I was exposed for who I really was, not just the horrendous side of my duplicity, but just the honest self, the real self – I couldn't countenance it. Because I didn't recognize that person anymore – at least at that point in time.

Ann: Mm-hmm. Yeah. Right. Could you describe for us, the Timothy, that the world saw or wanted to see and that you came to believe, was you?

[00:18:20]
Timothy: Yeah. Well, I think I alluded to it early on, you know? I'd been a faithful number two at a major global organization. They were wanting to ride the wave of success and jump onto the second curve of growth. And they felt that my predecessor, who was a sterling leader, you know, had reached a certain capacity, where he couldn't grow it beyond that point.

Ann: Mm-hmm.

Timothy: And, you know, they turned to me.

Ann: Right.

Timothy: So, it was very heavy stuff that, you know?

Ann: Who did you – what I guess what I meant was, what adjectives would you use to describe that Timothy?

[00:19:01]
Timothy: Oh! Give me some. Accomplished, polished, charismatic, eloquent. Yeah. Yeah. Those sorts of adjectives, I suppose.

Ann: Mm-hmm, yeah. Yeah. I like to ask that question because I think, you know, it gives us that – it paints that mask, right? – That we wear, or that we, I guess the ideal; almost like the ideal self that we kind of want to believe that we are.

[00:19:46]
Timothy: And that was not who I was not.

Ann: Right. Exactly! I was going to say, yes, it's right – it's not who you're not. You are all these things, you still are.

Timothy: Yeah, yeah. But it was a mask. It was what I needed to do, and how I needed to function and why I was successful in what I did.

[00:20:10]
Ann: Mm-hmm.

Timothy: I think the problem was not that I was those things. The problem was that they began to define me; that I didn't, I couldn't see the more holistic picture of who I was – warts and all – amidst all these wonderful accomplishments that these took precedent and ultimately defined who I was. And I think that's perhaps where I went off the rails, so to speak.

[00:20:31]
Ann: Okay, so now with the benefit of hindsight as well, what happened? That mask, you know, that glowing sparkling Timothy that can do no wrong, I suppose, that always – okay so, now I'm kind of like adding on with my imagination, right.

[00:20:57]
You know, the one who always knows, maybe what to do, who will always succeed. I imagine you as someone who, you know, if I come to you with a problem related to this work that you do, you know, you should know – you know how to handle it, or you would give me – you would be confident and all that. So, yeah. So how did it lead you to that point of recognizing that, that wasn't real?

[00:21:28]
Timothy: Gosh, I think it was Chesterton – G. K. Chesterton, who said how much happier you would be, how much more of you there would be if the hammer of a higher God could smash your small cosmos. And I think that's it, you know? It took a sledgehammer. It wasn't something that I did on my own.

[00:21:52]
It was that moment of way beyond what I could ever conceivably imagine. I would want it on my worst enemy happen, where there was this exposure, public and unfortunately, global, right – given the position I had – and local at the same time because I was a priest at a very significant Anglican parish here, in Singapore.

[00:22:17]
And so, the sledgehammer was taken to that edifice, the encrustation. And I suddenly was reviewed for who I was; the best of me and the worst of me. Unfortunately, you know, because of the circumstances, the worst of me was in full technicolor display to the world and, yeah.

[00:22:42] LOSING MYSELF
Yeah. So, how do you get there? You get there not by choice, clearly. I don't think very many people choose to reveal the shadow side of themselves willingly. It often takes an event – seismic event, traumatic event – such as that, which happened on, in my case, August 30th, 2014 – to be that which was catalytic for the journey thereafter.

[00:23:17]
Ann: Mm-hmm. Yeah, okay. So, earlier you did say that, you know, whenever – before this event, whenever a chink maybe appeared in your armour, you kind of just press it down and, you know, think you can go on with it. Would you say that perhaps unknowingly, you have lost touch with, I guess your own humanity; the fullness of your humanity, and maybe that which is weak and vulnerable and in need and broken within you? And, you know, and until that point, I guess, at some point, this part just broke through the edifice.

[00:24:01]
Timothy: Yeah. I suppose that's – yeah. In very significant ways, that's true. Although I don't think that there was a wholesale denial of the vulnerable, broken side of me. But it was easily compensated for, by the adulation, the acclaim, the applause – the adulation. Yeah, all the wonderful "A" words, right?

[00:24:28]
And so you begin to be like, okay, so that's – yeah. I mean, I'm human. Clearly, I have faults and weaknesses, but it's not a big deal. And I think that's where the shock was; that, it's not, you know – that very scary phrase, "it's not a big deal". It is a big deal. Except that because of who you are, it seemed like it isn't a big deal when the reality of it is that it is.

[00:24:56]
And I think then – you know. So, it wasn't a wholesale denial of the broken, the fragile, the vulnerable side of me; the weak side of me. In fact, some people kind of liked the fact that I was able to preach a sermon or give a speech and pepper it with self-effacing anecdotes. But it was all very carefully crafted. So, it would show the weakness, but not too much.

[00:25:24]
Ann: Mm-hmm, yes. I can imagine how skillful you would be at that. You know, it's a craft, really. You know, and that's part of what made you so successful, I suppose – because you were good at that craft, you know? And yes. And I didn't mean to suggest, I guess, denial. I think what I – the term I used was kind of "lost"; lost touch with –

[00:25:45]
Timothy: Yeah, you're right. That's the right phrase; lost touch with.

Ann: Right, yeah. Kind of like lost touch with. It didn't – I guess, what was needed was a lot more contact and loving attention, I suppose – you know, from ourselves maybe to that part.

[00:26:00]
And what you described was, you know – kind of got neglected because even though you're not denying that it's there, you've been lulled into thinking that it's less significant or important than it actually is, right?

Timothy: Yeah. Yeah. It's an interesting – you know, that sort of reminds me of something that I read somewhere, I think? But it was just a very simple concept, and it was a part of a larger conversation – might have been even a podcast – but the point was that, as they were talking about leaders who have – as you've characterized – feet of clay, who have, in the language of the world, fallen from grace, right.

[00:26:44] MISALIGNED CHARACTER & CHARISMA
Leaders who've had that fall – moral, you know, or whatever that fall may be, you know – brought about by, was that – and this was the phrase – that their character didn't match their charisma. Or rather that the charisma was way ahead of their character. So, that then, with the charisma came, you know, the adulation, the acclaim, the applause, the admiration – and you begin to believe that's who you are.

[00:27:21]
And so, character is not neglected, but takes a side-line to the development of charisma. Because that's visible, right? Who can see my character? And frankly, I'm probably okay. But the charisma is what's out there in the public space. And so, therefore then, you know, that gets cultivated at the expense, often, of character.

[00:27:46]
Ann: Mm-hmm.

Timothy: So, how do you – in leadership, how do you – I don’t know that you can ensure – but how do you always keep your finger on the pulse or the fact that that character must keep pace with charisma in some way, in order to be fully, you know, who you are? And the word is 'integrity'; to the person of integrity that what is seen on the outside is who it is on the inside.

[00:28:12]
Ann: Mm-hmm, yeah. And I think that, 1. it's a work of grace.

Timothy: It is, it is.

Ann: I mean, personally, I don't think we can do this without some, you know, supernatural help.

Timothy: Absolutely. Absolutely.

Ann: And yes, and I think the part of the pulse, you know, that we need to have our finger on is always that, which is tender and vulnerable and scared, actually.

[00:28:36]
And which is probably why it's so hard to tend to that part, unless we really have encountered and have safe spaces maybe within ourselves and outside of ourselves, with someone. Where we can look at this reality and see it for what it is. And we're loved because we – I mean the adulation and the admiration, it's so heavy and seductive because we yearn to be loved, right?

Timothy: Yeah.

[00:29:06]
Ann: We yearn to be adored, I suppose. Even though, after a while it is shown, you know, a lot of this's actually not – it doesn't go very deep because it's resting on charisma. And a lot of these people, they don't really know us for us. But I guess the interior journey is about coming into touch ourselves first – with that part of us that needs most to be loved in its entirety –

[00:29:35]
– not for being beautiful or for being very polished or eloquent. But just because we are, right?

Timothy: Yeah, yeah. Yeah, I mean, you know, it's interesting, you mentioned that because there's a superficiality to it. And I think for me, the starkest reminder of that was post August 30th, 2014 – after I literally lost everything.

[00:30:03]
My Rolodex – I know a Rolodex is probably – it's like what? You know, someone who's a millennial or Gen Z, "what's a Rolodex?". But that, you know – your contact list.

Ann: Right, yes, yes! The contact lists.

Timothy: Yeah, my contact list evaporated, you know, as quickly as a vodka on a table. I mean, it was just evaporated, you know? And I lost contact with almost everybody, save for a few people.

[00:30:37]
And, you know, they say, when you go to prison, you really know who your friends are. Well, you know, this was a type of prison, right? A type of punishment, incarceration. And I realized that a lot of people – and not for bad reasons – but were close to me or stayed with me or were in contact with me because of the position I held.

[00:31:02]
And so, it was understandable, if you think of it that way, that I would cultivate adulation, acclaim, applause – because that's what kept people with me, right. Again, only in hindsight, you ask yourself the question: well, if I had been truly who I was and that charisma was matched with character, that I wasn't developing faster in ways that I felt would attract more people. But measured would I still have many and many friends. And it's hard to countenance that fact. And so, you just continue to go down the only road that you know. Because the momentum now is carrying you along.

[00:31:45]
Ann: Mm-hmm yeah, yeah. So, you have the unique – I mean, your life story, you know, is unique in that you have, yes, you you've been to like, in a sense, some kind of top of the world, you know – global leadership and you've rubbed shoulders with other people who are leaders. But you also do a lot of work with prisoners.

[00:32:08] SIMILARITIES & DIFFERENCES BETWEEN DIFFERENT PEOPLE
You kind of mentioned prison, right? And you actually do a lot of ministering with prisoners. On the coaching side, you also coach people who are leaders, let's say, in the corporate spaces as well, right? So, it's – you know, you look at these two kinds of like sides of your experience. It's so fascinating.

[00:32:28]
Rarely do you see it in – kind of like coming together in one person. Prison is often, you think, oh, it's like – it's pretty much as low as I can go in society, right? You're like nobody. People think that you've utterly failed. And then there are others, maybe that you know, and maybe some of them could be your clients who maybe occupying a similar space as you used to – before that fateful day – where they are, you know, they're admired and they're successful.

[00:32:56]
Maybe as their coach, you see a bit more than – you know, more than that. But there are people who are navigating that kind of space. So, I'm curious, you know, given your unique vantage point, how different are prisoners and, you know, these leaders, that people acknowledge as leaders?

[00:33:15]
Timothy: Yeah, yeah.

Ann: Or how similar – what similarities are there?

Timothy: Yeah. Yeah. William James, I think, said, "we are like islands in the sea, separate on the surface, but connected in the deep". And I think when you do deep work, you realize that our common humanity is as it is – thief or, you know, president – you know, a corporation, prisoner, or politician –

[00:33:49]
– you know, share common humanity that if you do deep work, there is really very, very little difference. The differences are, you know, the things that are more apparent; socioeconomic status, educational qualifications, you know, type of work.

[00:34:08]
But it's been wonderful to straddle because, I think there's absolute – and again, the notion of prisons, yes, populated with, perhaps a preponderance of a certain, socioeconomic – people are from a certain socioeconomic status. Nonetheless, there is an absolute honesty – why? because there's nothing to hide anymore.

[00:34:32]
And I think that's what happened to me. When all was stripped away, then you are left with a question. So, I'm standing here naked. What do I do? Pretend like I'm not? Pretend like I'm the emperor with clothes on when everybody knows otherwise. Who am I fooling? I am fooling, not just now, others, but myself.

[00:34:54]
And you go, that's not an option. And I think that's kind of the way prisoners are. They're in prison. They've got the hit shaven – which is a way to strip them of identity, right? I mean, when you go to the army, they shave your head bald because you're meant to have a similar identity to everybody else.

[00:35:13]
Well, in prison, it's the same thing. You're supposed to not have a unique identity. You are a number, you are head-shaven, you wear the same uniform – you know, white t-shirt, blue shorts. So, there's nothing to hide, metaphorically – even your head, your crown is exposed. So, there can be denial as clearly there are with some prisoners. But by and large, I find if you are able to tap into that deeper part of them, a wonderful honesty.

[00:35:49]
And I think the same thing goes for corporate executives who, if they would permit you to do deep work, the same thing happens. This beautiful space of the exploration of who I really am, as reflected in what I do, not the other way around. Not who am I, you know, or what do I do as defining who I am.

[00:36:15]
And I think that flow is – has been – oh, boy. I want to say, Ann, perhaps one of the biggest lessons that I've learned, you know – that purpose must flow from meaning, not the other way around. Not defining my meaning, vis-à-vis the purpose, the thing that I do, you know? With prisoner or politician, with someone sitting in a cell versus in a corner office, on the 50th floor. Our common humanity, mine rightly, dealt with, honestly, gives us a liberation, you know, whatever our lot in life.

[00:37:02]
But it’s just harder to get there when you're sitting in the corner office overlooking Marina Bay Sands. It's just a lot more difficult than if you are sitting in an airless cell, you know, in Changi Prison.

Ann: Mm-hmm yeah, I suppose, it's really the stripping away. I mean, if you're in the prison cell, it's helpful for you to be able to distinguish, I guess, that which is maybe more superficial and that, which is more core, right. I mean, it's already been done for you. I mean, a lot of things have been taken away from you.

Timothy: Yeah, yeah.

[00:37:32] PURPOSE AND MEANING
Ann: So, you mentioned purpose and meaning. Could you say a little bit more just because I think most people wouldn't, you know – wouldn't be familiar with the way you're making this distinction.

[00:37:51]
Timothy: Yeah. Yeah. And I think that's a good place to start and it's a distinction I'm making. By no means, presume that it'd be everybody's understanding – or should be. But the way I define it is – and you know, different people have talked about it in different ways.

[00:38:13] CONTENT & CONTAINER
I think Richard Rohr talks about content and container. I also have used the term again. It's all meant to help explain, not define, necessarily. But the difference between a eulogy and a resume. So, meaning-purpose, eulogy-resume, content-container. And the idea there is that there is purpose to our life.

[00:38:44]
We are meant to live purposeful lives. And the other quick phrase, if I may just add it in is, you know, on the column – if you think of it as columns, right? The 'meaning' column is also personhood versus the 'purpose' column – which is a mask, right? – Resume. So, it's the outward-facing self. But the issue, I think, for a lot of people – myself, most certainly – was that my outward-facing self became my meaning.

[00:39:19]
My purpose became my meaning. And you know, perhaps one of the starkest analogies – and I shall, I know your audience is a very polite audience, so I'm going to divest it of expletives. But I remember on September 1st, 2014, couple of days after, you know, my life literally, as I knew it, ended.

[00:39:45]
I was put on a year of church discipline as an Anglican priest. I was also – I stepped down from my role. And it was, at that point in time – it was all early days here – but eventually it was understood to be a year away, under discipline to kind of get my life back in order. And then, the evaluation of whether to be reinstated to those two responsibilities.

[00:40:08]
That's a separate issue for now. But on September 1st, I didn't know where this was all going to go. And I remember standing in front of the mirror, and I remember having a most surreal moment of looking in the mirror, recognizing the reflection, but literally asking myself who the expletive in the world are you?

[00:40:30]
And I could not, for the life of me, answer that question because my presidency and my priesthood – the two things that define my existence, you know – I was in a grave existential crisis because the two things that really defined me, were now no longer who I was. And therefore, who is Timothy Khoo?

[00:40:58]
Not a clue, not a clue. And the last eight years, and continuing, have been a journey in discovering, you know, Timothy Khoo.

Ann: Mm-hmm, yes. This story that you just shared brings to mind, actually, the article that I was going to bring up – first of all, that I read, I think, last year – that you wrote for the Law Gazette.

[00:41:22] MASKS AND PERSONAS
About how action follows from essence. I think, I realized we're already on this – we're on this theme ready, right? And you wrote about this experience of looking at yourself in the mirror. And you said, "I realized then, that my face had grown to fit the mask I was wearing. And now having had the mask ripped off, I was left without one, not merely a mask, but a face. The last few years have been a journey to find myself again, the person that got lost along the way".

[00:41:55]
Right, so, mask – just now you put mask also under the column of the outward-facing self, right? You said that that's with purpose. Whereas, what I call – I mean, the language that I use, often in my podcast and work – is I call it the "core identity", which isn't the outward-facing self; that personhood, the person that I am, right?

[00:42:15]
And so, actually, I was hoping that today, you could talk a little bit more about this thing; about this mask, you know? What do you mean by mask, you know? Yes, and what does it mean to have our face grow to fit that mask?

Timothy: Yeah.

Ann: So, you mentioned about how, when our meaning and our purpose kind of like, I guess – I realize both of us are using pretty big words.

[00:42:40]
I mean, I'm comfortable with it, with big words – as in, you know, I was going to say 'ontological'. And usually when I use words like this, I try to define it because I think not all my listeners are into philosophy like I am, you know? But I was going to say, you know, the way I hear you, meaning and purpose – both are important, but there is an ontological order or priority.

[00:43:05]
Okay, so by 'ontological', dear listeners, I mean, you know, like the order of being, you know – one is meant to carry more weight, which is supposed to come first, and the other rests on top of it.

Timothy: Yeah, yeah.

Ann: And I think – and what I hear you saying is that really, it's, you know, our – the things that we do, our purpose is meant to be derived from who we are.

[00:43:24]
Right, the core self, the meaning. But it happens probably often, where it gets flipped. Yeah?

Timothy: Yes. Yeah. No, I think that's a beautiful way to encapsulate it. I mean, yeah, you're right. You know, 'ontological' is not a word that's often used. But it gets the essence of, I think, what we're talking about. A couple of reference points; one is, you know, mask, personas – would be another word I would use for it.

[00:44:01]
You know, from the Greek tragedies, right? Where someone – you could tell the character, not by their costume because they wore the same thing. Women, obviously, in those days, weren't allowed, you know a public role. And so, all the characters were played by males, whether it was a female role or a male role. But the personare, you know – which you still see used for theatre productions, with this gaping hole where the mouth is projected, or the voice is projected. You can only tell what character by the mask, right – by the personare.

[00:44:38]
And so we've come to use the term persona as the mask that we wear. So, that's one reference point. The other reference point is – you talked about the article that I – and so the phrase I used; my face grew to fit the mask, is an Orwellian (George Orwell) – an Orwellian construct.

[00:44:57]
So, very quickly in his book, or not book – in his short story, Shooting an Elephant, it was political satire. So, it wasn't the political satire that connected with me. But the very simple story was, in colonial Myanmar, Burma, a colonial policeman was asked to kill an elephant. And he was asked to do it without remorse or hesitation – by his colonial masters.

[00:45:25]
And he struggled with that. He struggled with that because again, political satire because the elephant is, you know, such a huge importance, right? So, to kill an elephant by colonial, the colonists, was basically disrespecting, disregarding, you know, local sentiment, right?

[00:45:48]
What was important to them. And so, for that reason, this policeman struggled. But eventually he had to carry out his orders. And the phrase that caught my attention, apart from the political satire, quite apart from that was, it was said of this colonial policeman, he wore a mask, and his face grew to fit it.

[00:46:09]
And you know, we don't want to get into it, but you know, there have been articles about how is it that Russian soldiers are able to carry all these atrocities, you know, without seemingly any remorse? Well, when you put on a mask, and your face grows to fit it, then you become the mask.

[00:46:29]
Then the third reference point is Hannah Arendt, the political thinker, who says that people with public lives – and most of us do have some form of a public life, some more than others, you know – are judged by our personas and our performance, right? How well we do and how well we play the part.

[00:46:53]
And so her point is that personas, masks, is part of life. We have, you have probably half a dozen. I maybe have, even to this day, have half a dozen, right? I'm a father on the one hand, you know, I'm an existential coach, sojourner guide, you know, and the list goes on. And depending on the role we play, we put on a mask.

[00:47:18]
The problem is not the issue of masks or personas. The problem is that when our personas become our personhood. When our phase grows to fit the mask that we wear. So, there's no way to lay it down. That's why people struggle at the end of their career – with putting down their careers because they don't know who they are apart from the job that they've done, you know, for the last 35 years of their life.

[00:47:38]
So, how do I retire? I don't know. I don't know what it means to retire because the moment I do that, I lose a sense of my essential being, at least as they define it. So, the issue of masks is not one of, should I have a persona, or should I wear a mask or not?

[00:47:58]
It's to ensure that the mask doesn't become you – that your persona doesn't become your personhood. That your resume does not define your eulogy. That, which was meant to be a container to hold, in very necessary ways, who I am, is not mistaken for the content that resides on the inside.

[00:48:25]
And so, we spend so much time preaching the edifice and we neglect the content. Jesus himself said, you know, you guys are whited sepulchres. He said to the Pharisees, you look great on the outside, but inside you're rotting. So, we neglect the content for the sake of the container, we pursue our resumes.

[00:48:42]
We pad our resumes at the expense of our essential being, who we are, our eulogies, we wear masks. And then neglect the personhood, who carries that mask. So, yeah – so, I think those are the issues that I've had to grapple with – oh gosh, very painfully. And for these last eight years or so. But again, thrust into this space and hopefully through my own journey, being able to be of some help, shed some light for others who may be struggling with the same thing.

[00:49:20]
Ann: Mm-hmm yeah. When I was – when you mentioned about, you know, public life – well, in Hannah Arendt talking about public life, I just – my brush with, or my experience of having to live a very public life, came very early in my life, actually. It was in school. And I became known as that – you know, "Ann, the head prefect", you know both in primary school and in secondary school.

[00:49:50]
And that label followed me even after I graduated. Almost seems like whenever I'm around people from the school that I went to, that's who they saw me as. And a very good friend of mine, whom you also know, as she was my assistant head prefect, actually – I mean, long after we graduated, when she introduced me to her colleagues and everything, she introduced me as her head prefect.

[00:50:17]
Right, and the reason I'm sharing this is – it did something to me, I think. Because it was at such an impressionable age. It was, I think I was only – I was 12. The first time I was head prefect in primary school and then – so. up to, you know, 16. And being – I was a public figure in school, you know. And people knew my name, even though they didn't know me.

[00:50:45]
There were people who actually, you know – unfortunately, I don't think there was much adulation there. There were a lot of people who hated me, just by the name. You know, but there were expectations as well, from teachers, from the school principal, from other people.

[00:51:05]
I found myself – I think back then, maybe I wasn't so self-aware. Although I knew I was struggling with – not so much struggle. I knew that there were these expectations I felt like I needed to live up to. And there was a part of me that wondered why. Why do people think I'm that? Or why do the people think I'm capable of, you know, of this? That they expect me to. There was a part of me maybe that kind of knew I don't think that's me.

[00:51:36]
But there wasn't time. And I didn't know how to listen to that small voice.

Timothy: Yeah. Yeah.

Ann: You know, because in order to survive, in order to receive whatever – I guess respect or affirmation, awards, et cetera, I needed to play that role. But here's the thing. It followed me even after I left school – there's a part of me that my husband, that Henry, you know, is like, you know, "oh, the head prefect's come out" – you know. But the thing is, he says he’s someone who, I think, saw me more clearly than I saw myself for so long, right.

[00:52:17]
And he says that I'm anything but a head prefect, you know? And recently, I've had to grapple with this question; what was taken from me or what did I lose when I had to wear that mask, and wear it well? What part of my real self did I actually lose touch with? Because in some sense, I think in a very real sense, I did become that mask.

[00:52:44]
It was confusing, especially at such a young age, you know. So much so, that I carried it even into adulthood, you know? So, whether it's the good girl, the good Christian, the good Catholic – always having to be, I don't know – a role model, to succeed at everything I attempt at doing, you know?

[00:53:07]
Timothy: Wow. You know, that's such a fascinating point because I never thought of it that way, right? So, someone who is, at a very impressionable age of 12, being, you know, thrust upon with a role that is outsized to the ability of any 12-year-old to truly be able to wrap their minds around. How do you help that person ensure that while they fulfil the function, that it doesn't become, you know – well, again, to use the phrase that you've used, and we've used – so that the face doesn't fit the mask. So that, I don't know not how to be head prefect or always leading or being responsible.

[00:53:53]
Ann: Mm-hmm.

Timothy: That I can be myself in moments when I'm not having to fulfil that function. Yeah, that's – gosh. That raises a whole host of issues for the ministry of education to grapple.

Ann: Yes.

Timothy: You know, maybe what they need is the counsellor to ensure that their journey is one in which they fulfil the function without becoming the role. Yeah.

[00:54:22]
Ann: So, I think it's actually also the larger problem for society, right. Because our education system is a subset of the larger society.

Timothy: Yeah, yeah.

Ann: In a society where we often define one another by the roles we play and how well we play those roles. We are after all – you know, in Singapore – very pragmatic, right? And you know, meritocratic and all that.

[00:54:44]
So, it it's rare that we can have people mirror us for the essence, for who we are – especially if it's a young person that's still developing, still trying to figure out, you know? To be seen for who he or she is and not what he or she can accomplish –

[00:55:01]
Timothy: Yeah, yeah. Yeah.

Ann: – and you know and win for the school. And I think so whether it's a teenager or we're talking about someone who's middle aged – and so many of us continue to grapple with this. I mean, in my work as well, the people that I accompany, there are people in their fifties and sixties – and it's the same thing.

[00:55:23]
They haven't gotten in touch with, who am I, apart from the roles that I've had to play, right. I mean, whether it's career or some, let's say, stay at home moms – now the children have all grown up and they've only known and seen themselves as 'mother'.

[00:55:42]
Timothy: That's right.

Ann: Yeah. So, this mask, you know, becoming – or fusing into our identity – or decoupling; decoupling ourselves. Or I'll say like, you know, our identity from the mask. I think that's a big part of the nature of the interior journey, you know – to discover or rediscover who I am.

[00:56:04]
Maybe I never knew, you know? The way you told your story earlier is kind of like, yeah, I've forgotten who I am. I don't know who I am anymore. For me, when I first read your story or that piece, I thought, I think all along, I never knew. I never got that. I never got to the point that I knew who I was apart from the roles that I was supposed to play, you know? Isn't that something? Isn't that scary?

[00:56:27]
Timothy: It is, yeah. Oh my goodness. You're raising some really, really, critical issues and gosh. I mean, I could, yeah, gosh – you could go on for a long time. But I wonder, you know, I mean – I say this, you know, circumspectly – but I wonder whether your podcast, you know, might not have a role in helping form, you know, the thinking around how we make that journey going forward.

[00:56:57]
In a way with our kids, with ourselves, so that, we don't end up – you know, not many people thankfully will end up in the space I, you know, I ended up in – which is a decimation. But nonetheless I think many people find themselves decimated in private ways, you know? Like you said; the mother whose children now grown up and she's lost her raise on that.

[00:57:31]
The reason for being was to be a mother. And now the kids have grown up. How do I morph into a role where I continue to be a mother, but also a friend to my children, as opposed to a mother? And you see that played out in sometimes, neurotic ways of, you know, a mother who's – no disrespect intended – but not very highly educated, dealing with a son who's a CEO of a corporation, but the son is treated like a little boy that he always was.

[00:58:01]
Because my role as a mother is not one I know how to let go of. And so my son, no matter how accomplished, he may be, no matter, you know, what he's doing in life, he's always my little boy. How do you help people form that thinking so that the journey can be made in a more holistic way, in a more measured way, in a more calibrated way?

[00:58:26]
So, maybe your Becoming Me becomes, you know – has that space to speak into this issue.

Ann: Yeah. Well, I think it's actually – that's exactly what the whole podcast, or I suppose my work – and I'm realizing now – my life's work is about this journey of discovering and not just rediscovering, but really maybe discovering for the first time.

[00:58:52]
Because we didn't get to make that journey yet in our lives for so many reasons. A lot of this also touches on, I think, psychology – you know, I'm learning about how, let's say, in our families of origin, in our youngest age. Were there people who could really mirror us and attune to us for who we were?

[00:59:10]
If we didn't have that and, you know, and we all have broken versions of that because everyone's imperfect. Whether intentionally or not intentionally, we lose that ability to really begin to build that core identity – for it to be integrated, right. Which is why the interior journey now is an integration, you know – kind of like a reintegration or an integration for the first time; a healing, becoming more solid, you know?

[00:59:36]
So, all these things, the roles, whether we are, you know, say leaders as a CEO, or a parent or – you know, which is also a role of leadership. I think if they are not resting on a core that is really integrated and solid and strong, then that risk of having that flip, where then now my persona and the role that I play becomes who I am.

[01:00:03]
I think that risk becomes a lot higher, you know? Whereas our – I think our true identities, or our essence is meant to inform how we play that leadership role, right. How I am a CEO, or how I am a mother, or how I would be a head prefect. It would've been very, very different if I, you know, knew maybe who I was. And the way that I would approach things versus having only kind of like, an external – externally informed idea of what that's supposed to look like and playing to that.

[01:00:32] THE FRACTION ANALOGY
Timothy: Mm-hmm, yeah. Tolstoy – I think it was, who said that, a person – he said a man, obviously in a generic sense, is like fraction. And I'm probably mangling it, but the idea was that the numerator is who he is. The denominator is who he thinks he is – perhaps who the world thinks he is, who he wants the world to think who he is. And the larger the denominator, the bigger the fraction.

[01:01:07]
Ann: Ahh.

Timothy: So, the bigger fraction fracture. Right?

Ann: Yep, yep. The more fractured we are.

Timothy: 
You know? Exactly what you said – integrity integer, right. Whole number. So, fraction is opposite of integer. So, I think that's the mask-wearing bit. So, the numerator, the number on top is who I really am. The denominator who is who I think I am, who I want people to think I am. And that usually is a much larger number than the numerator –

[01:01:34]
Ann: Yes.

Timothy:
 – in which case then the bigger the bottom number, the bigger the fraction, the bigger the fracture.

Ann: Yes.

Timothy: Right so, we are disconnected from our essential selves.

Ann: Yes. That is so true. And actually that reminds me, you know, one of the questions I wanted to ask you was this; you know, given that we all have roles to play and every role kind of has a mask that we wear, the way I see it is, you know, coming to learn how to wear our masks lightly, you know?

[01:02:03]
And take them lightly, you know, easy to put on, easy to come off. And that the – I guess you say it now – the denominator or the numerator is the one that's the wholeness, the whole, you know – it's is the one that really carries and is present throughout so that maybe, even behind the mask – as in people are encountering more the person behind the mask, not even just the mask, you know what I mean?

Timothy: Yeah, yeah.

[01:02:26]
Ann: As in like, there's so much presence. Sometimes, I think someone who's very integrated, I think, usually has a lot of presence, right. And that presence is what we experience, even more than the role that they're playing. You experience the person, the personhood, you know? And yeah. And so, I was going to ask you, have you encountered people or leaders who have succeeded in wearing the masks lightly?

[01:02:50]
You know, so that their presence – almost to the extent that you, even though they are playing a role and, you know, wear a mask, that you – it's almost as if it's not quite there because people encounter the person behind the mask.

[01:03:04]
Timothy: Not really. Alright, that's being unfair. I, you know – I'm sure I have. But I think it's just – it's a great question. And I – gosh, no one comes to mind. I think different people have expressions of that. I read recently – and again, I think perhaps, you know, this might be helpful intervention – in a book I've been reading, was talking about second half of life.

[01:03:35]
And I think it's really the journey and the potential fractures that cause once true character to show. Right? So, there was a contrast between, Darwin – Charles Darwin, Johann Sebastian Bach. And the analogy was that Darwin, original species, in his twenties, and obviously it changed so many things. But what is little known is he struggled the rest of his life for relevance.

[01:04:11]
He just couldn't figure out how to be. Because he had a major accomplishment at 29. What's left, right? And he died, sad, despondent, and a very broken person. Johann Sebastian Bach, on the other hand, you know, probably many consider him in many ways, the father of classical music. He had four kids, one – to cut a long story short – one ended up outshining him.

[01:04:39]
Little known fact of history because we know Johann Sebastian Bach, we don't know his son. See, for the life me, can I even remember it? I read it like a week ago. But everybody started turning the son because his way of composing music – and I'm not a musician, so I can't even describe to you what that means – except that was what people started gravitating to. Instead of feeling sorry for himself, Johann Sebastian Bach reinvented himself.

[01:05:06]
He became a teacher. And he composed music to teach. And, as I understand it to this day, much of what he composed as a way to teach music, has become almost as important or as associated with Bach as the many amazing compositions in his earlier life, before his son outshone him. And I think that's part of what you are talking about. You know, how do you see the changes in your – the changes and chances of this fleeting world? And, you know, one of our liturgical prayers – amidst the changes and chances of this fleeting world, how do we steady ourselves?

[01:05:52]
How do we keep centered? How do we not allow, you know, the winds of change to change us? But to withstand if we need to. And I think part of it is the ability to pivo. The agility, to say, okay, somebody has done a better job than I have. This is fantastic. Let's, you know, let me figure out, let me work through what it is that I should be doing.

[01:06:20]
I had a very interesting conversation – very, very, quick intervention. The organization that I used to lead – between the time I left it, which was eight years ago to now – has increased its footprint of impact, and its revenue; revenue by fourfold. Impact – impact is hard to quantify. And the earlier part of – the earlier Timothy Khoo would have said, you know, get, got really upset and go –

[01:06:51]
– you know, it's probably fluke. You know, I exited at the time that they were just about to ride the crest of a wave. But the reason I know I've changed is because I rejoice, with no tinge of regret or envy. That I was not the one that brought this organization to where it is today.

[01:07:18]
And that2, for me, was probably one of the moments of grace – that the work of God in my life had brought me to a point where I can rejoice in other people's successes, as close as it was to me. I mean, I inhabited that role not eight years ago. And so, hopefully I've been able to change.

[01:07:43]
I've been able to pivot, I've been able to put the mask down because it was time to put the mask down and not constantly pine and long for it to be who I am again. It's taken a while, Ann. It's not something that has happened in a short period of time. It's taken eight years and it's still a work in progress.

[01:08:02]
Although, I think that was such a defining moment for me – to rejoice with the new CEO, you know. When he shared and I – he shared it, I think with a tinge of – should I say this? Should I not? You know, so, he was empathetic to my sentiments. But I'm glad he did. And, you know, doubly glad that I was able to receive it with joy.

[01:08:25]
Ann: Mm. I, you say it pretty easily and lightly when you tell this story, but I can feel the depth of – actually, you know, the significance of it. And I think anyone who's listening to this, who have really identified with a role, would know that feeling. Sometimes we can't help feeling that twinge, you know – of, you know, how does this reflect on me?

[01:08:53]
Or, you know, and then if I'm still very merged with that role, you know? Yeah. So then, I'm less, you know – it kind of, there's a threat of being less2, of seeing ourselves as less. So, thank you so much for – yeah.

Timothy: Yeah, yeah.

Ann: And congratulations for that progress.

Timothy: Thank you!

Ann: The mass being becoming lighter, you know. It's so funny that even though it's an old mass, it's still – there's still some weight to it, huh.

[01:09:23]
Timothy: But again, you know, it comes back to the point – so you've asked if I met anybody. Again, I'm sure I have. Would be unfair to say I haven't. I just – no one comes to mind. But the Bach story was powerful. And you know this; with every score, that music score that he wrote, he would, sign it off with the initials SDG – which is not Johann Sebastian Bach, even in its own language. But it was solely Deo Gloria.

[01:09:57]
To the glory of God alone. And I think that's perhaps, where the posture lies. That who I am, what I've become – as Brennan Manning so beautiful says in his biography; all is grace. And that, you know, I relish this moment but if someone outshines me, I think about how I might pivot to doing something that continues to – in the words of a social scientist from Harvard, Arthur Brooks, who wrote the book where he talked about Bach – is, I make the transition from fluid to crystallize intelligence.

[01:10:34]
So, there's something, there's a deposit, there's experience; good, bad, ugly, as in my case as well. But that I can mine the value and depth of those experiences and crystallize it and use it for the glory of God alone. So Deo Gloria.

Ann: You know, we've spoken about masks and persona and personhood, and as you're talking about this, you know, it's this sense of – there's the form, right?

[01:11:03]
It's like the container and the content, right? When life brings us all these, I guess, ups and downs – you know, tragedies, failures, oftentimes it's actually the down moments that have a lot of promise to help us get in touch with what's actually within the– what's really within. And when you talk about pivoting, you know, agility –

[01:11:31]
– some of these terms are pretty trendy right now. And I often hear, you know, people talk about them as things, almost like it's something that they need to perform, get it? You know, it's like, how can I then be more agile? Right? How can I do this well? But in the context of what we are talking about, existentially, I think the more deeply rooted we are in our core identity, the more solid and integrated the essence of our identity is. We'll find that it becomes easy to be agile and to pivot because that's just on the surface.

[01:12:06]
That's how, you know –that's what we do. We, you know, we play, but it's the same self that we bring into each role. And perhaps if we make the interior journey, the same self becomes – at least, the presence becomes even fuller and stronger.

Timothy: Yeah. Yeah. Fuller and stronger. And absolutely because I think, you know, again, the analogy you just alluded to – of container and content. I think that's a problem – is that we get so enamoured by the container, but in the retention of the container that has served us well, is also an enslavement or a – almost a prohibition on the fuller expression of who we are.

[01:12:55]
So, if the content is expanding as it should, then so much the container change. So, our purpose can change.

Ann: Absolutely. Yes.

Timothy: But who we are, essentially, remains the same. But if we choose to be wedded to that container that has served us well for the last 35 years, we're actually doing ourselves a grave disservice. So, beyond the wearing a mask, which, you know, doesn't confer with it, this notion of expansion – but the container and content does. Then we're actually, I think, neglecting the stewardship, responsibility that we are capable of.

[01:13:36]
Because we choose to be comfortable with the familiar versus to step into this beautiful ocean of how faith is expressed. So, it's a more expansive, a more freeing space. And perhaps if we see that, rather than say, oh, you know, rather than lament the loss of the old container, is to see the freedom that stepping out of that old container, frees us from.

[01:14:05]
Ann: And if we are really, if we're alive, we would be changing and growing. Right. I mean –

Timothy: Exactly.

Ann: – I don't have green fingers. I'm not particularly good with plants. But from what I understand, you know, if a plant is growing, you need to repot the plants; you need to change it to a larger pot.

[01:14:24]
Timothy: Exactly.

Ann: Yeah, and so, a lot to – a lot to ponder then. And that's perhaps why I think I've stopped, at some point, worrying about the container. It used to be, I think in the way that we were brought up, it's like, "what do you want to do when you grow up", right? It's like, I need to figure out what is it that I want to do, what career?

[01:14:42]
And that's the container that I – you know, it's almost like that's what's going to define me. And even just in the last 10-12 years, I realized things keep shifting in terms of the externals of what I do. But I see the continuity of the stream that's actually flowing underneath all this.

[01:15:00]
And it's actually building momentum. So, I'm actually finding greater purpose as I am clarifying my meaning. Does that make sense? Like, as in –

Timothy: Absolutely. Yeah, totally. Totally. Totally. And again, it's an iterative process. And because, you know, I do some work with university students, both here and overseas. And to say, okay guys, you know, at the age of 21, when you have your life ahead of you – to say, focus on your eulogy, it's very important.

[01:15:36]
Don't pay so much attention to your resume. It's absolutely ridiculous. Because the reality is they’re in the season of life where the resume is critically important, they're building something. But that's the point – they're building a container. And that's a necessary part of the journey.

[01:15:54]
So, let's, you know, your listeners go away with thinking Timothy is just kind of deconstructing everything. I'm not. I think it's necessary to say, that in the early stages of one's life, there is the building of a container. There is the building of a resume, there is the going out and doing purposeful things. But even in that journey, don't get wedded to the container.

[01:16:22]
Don't get wedded to your resume being defining of you. Don't get so wedded to being so purposeful that you lose a sense of who you are. Find that space. I wouldn't say of balance because balance seems like it's 50, 50 – but harmonization. So, the earlier part of our lives, the harmonization is where the resume and the container and the purpose are critically important.

[01:16:46]
I'm building something. The problem, as we've explored, you know, in this podcast, is that you come to a point where you're so wedded to these things that you don't know how to let it go when the time comes to let it go, or to change. And so, I think that's really the point – it's not one dimensional.

[01:17:11]
We are organic beings, things change. And so do the harmonization of things like resume and eulogy, container, and content, meaning and purpose – those things evolve, those things change. And being true to ourselves at each stage of that journey is really where I think that the growth and the maturity most significantly happens.

[01:17:32]
Ann: Yeah. And I think the growth happens and the evolution happens also through crisis. And I think that's why, you know, in life, we are gifted with crisis points – whether the big or small, that helps us to see maybe where there lacks harmony. Where these two things, I guess, lack harmony. And hopefully over time we learn to dance the dance, you know. And we know how to hold both.

[01:17:59]
Yeah. Yeah. So, this is actually reminding me now, of actually the work that you do. And I was hoping we could maybe round off with that – asking you a little bit about Desert Odyssey, right. So, could you tell us a little bit about what Desert Odyssey is?

[01:18:22]
Is it about this – everything that we kind of like talked about? Is it helping people, you know – kind of like learn to harmonize the resume with the eulogy and – is it?

Timothy: Yeah, no, I think, you know, even people who've been through Desert Odyssey – which in its structure is essentially a seven-day journey of exploration of discovery, of conversations.

[01:18:51]
So, again, a guide because, whilst there may be some ideas I put forward. In one session called the Discovery Session, the conversation is let's bring our experiences to bear on what we just talked about. And so, you know, they could be writing a letter to their younger.

[01:19:13]
Not being so hard on my younger self, as I would be prone to do. A letter to my future self, you know, the person I would like to become, now that I can see the things that we've talked about, right – mask wearing, et cetera. But as many people have come for Desert Odyssey, I always ask them, so, okay –

[01:19:35]
– you describe Desert Odyssey. You asked me to describe, and I can't describe it to you. You describe it. And they look at me and go, okay, I get it. I can't describe it. So, Desert Odyssey has to be experienced, not explained. But essentially, Ann, all that we talked about today, is stuff that, in a more structured way – I should say more structured way. But in a different modality we explore as well.

[01:20:04]
Yeah, yeah. Maybe I could put it this way. What kind of pilgrim or at what point of the journey would find Desert Odyssey helpful for that season in their life? Are you able to kind of just give a rough kind of sense?

Timothy: Yeah, yeah. Yeah. I've had people as young as – I think the youngest was 17. And the oldest was – oldest in their eighties.

[01:20:37]
I think it's not linear, right? At each stage in life, there are things that, we confront – crises, family of origin issues. And we don't realize how it hampers us. And so I think it's just the acknowledgement that at different points in my life, I need to take stock.

[01:21:01]
I need to find myself before I get way, way too lost. There's a wonderful story of an indigenous, Indian tribe in the Amazon who would lead tourists on, you know, on these tracks, through the Amazon. And they – these guys, you know, that tourists are decked out in their hiking boots, and you know, all the paraphernalia and these, natives are in shorts, t-shirt, and flip flops and every so often they would sit down, and they would start smoking their pipes or drinking their tea.

[01:21:34] GIVING OUR SOULS TIME TO CATCH UP
And these tourists are saying, we're not tired. How can you be tired? You know, we need to get to the destination quickly. And the re the refrain from these, you know, indigenous people are we're waiting for our souls to catch up with us. You know, Ann, there's a song by, Susan Enan, around that, you know – Bring on the Wonder.

[01:21:56]
We've pushed you down deep in our souls for too long. We've neglected you. This idea that, as Gandhi says, Mahatma Gandhi says, there's more to life than increasing its speed.

Ann: Yes.

Timothy: And I think so much of what happens now is, we just want to go faster, and we want to get there quicker.

[01:22:21]
And we run ahead of ourselves. Clearly, we run ahead of God. We run ahead of our souls. And at some point, we get lost. Where is Timothy, you know? Way back where. So, this idea of stopping to allow our souls to catch up with us, perhaps in some way, encapsulates Desert Odyssey.

Ann: I love that.

[01:22:44]
Timothy: It's the moment of standing still so that you can make the journey in now, in the interiors, you so beautifully do with the work you do, Ann. Because the interior journey cannot be doing on the run. Oh, it's hard. It's not impossible, but it's hard. And so, to allow our souls to catch up with us is to be again, integrated, right?

[01:23:07]
Ann: Yes.

Timothy: Integrated. So, as to make the onward journey.

Ann: I think we are so out of touch, often, with the pace of our souls, right. I mean, as modern people, city people. Just earlier today, I was thinking to myself, you know, when I was doing some stuff in the kitchen – if I'm really honest, there's an incredible amount of doing nothing that needs to happen in my life in order for me to do the work that I do

[01:23:34]
This kind of thing; talking about this kind of thing, creating content, or accompanying people. In order for me to be effective, it was just another realization. There is an incredible amount of doing nothing that has to happen. Does that make sense to you?

[01:23:49]
And I think it's exactly what you say. It's because my soul needs to be one with me and it needs to catch up. And sometimes that makes me feel – like the part of me that looks at how the, you know, the pace at which everything else moves around me – makes me feel like, wow, my capacity is really low.

[01:24:08]
You know? Like I can't, I can't do more.

Timothy: Yeah, yeah, yeah.

Ann: If I don't want to compromise the integrity of the work that I do – I know I'm called to do, you know. And if I let that lead me – oh my gosh. There's a lot of doing nothing. There's a lot of being, a lot of pondering, a lot of literally sitting and letting my mind dream and then things fall into place.

[01:24:31]
You know, I can actually feel the integration take place sometimes, in those moments of doing nothing.

Timothy: Yeah. No, I totally get it. And again, from a person who has not a musical bone in his body, I'll use other musical analogies since we talked about Bach. But you know – music is made with the white spaces in between the notes. Because if it was all jam packed with notes, it would be noise.

[01:25:00]
When one foot moves forward, the other footrests. So, even in the rhythm of walking, is this notion that there's an alternating reality of movement and rest – of music that is created with the white space in between. There's crescendo and decrescendo – it's all woven into the fabric of life, but we, unfortunately, human beings violate it at every turn.

[01:25:33]
We just want to turn up the volume, squeeze the notes together, run instead of walk. But the proper rhythm of life is walking. That when you walk one step, you know, you measure the steps you take, and you measure how you do it. It's in cadence with your heartbeat. So, walking is the pace of life.

[01:25:55]
And so, in a couple of weeks, I'm on the Camino Santiago with a couple of people who want to walk at the pace of life.

Ann: And let their souls catch up with them.

Timothy: And let their souls catch up with them.

Ann: Wonderful. Yeah. I love that.

Timothy: Yeah. Yeah.

Ann: I love that. So, thank you. I love that. So, that the idea of the Odyssey and, you know, the desert too – to come away.

[01:26:19]
To go away into the wilderness, maybe of our hearts or something to let our souls catch up with the rest of us, our bodies. And I think especially, our minds that are often always in overdrive.

Timothy: Yeah, that's right.

Ann: Yeah. So, where can people find out more about, Desert Odyssey if they want to join you in one of these retreats?

[01:26:40]
Timothy: Yeah. Yeah. Well, a couple of ways. One is, www.desertodyssey.com – it's actually a blog, a blog site. So, the landing page is a blog. But there are a couple of tabs. It's a very, very simple, almost simplistic website. But there's a couple of tabs.

[01:27:07]
And in, I think in one of the tabs 'about' – it's a bit of an explanation about Desert Odyssey. So, the blog is the landing page, and then there's a couple of pages. And I think there's also – there's also a kind of inquiry button that you can – but anyways, you can drop me an email, right? – timothy.khoo@desertodyssey.com. I'll be happy to respond.

[01:27:43]
Ann: Yes. I'll put those links – I'll include those links in the show notes for this episode. And would you be – are there still remaining Desert Odyssey's run this year? Will there be, other than your Camino? I know it's a different thing.

Timothy: Yeah. Yeah. Well, the plan is; I have one 27th November to 3rd December – that's local. It's probably going to be at Changi Cove, if there's enough people who sign up. But for 2023, quite exciting, actually, I have one planned in Jeju in the spring, Jeju, Korea, in the spring.

[01:28:20]
I have a potential Camino, also in the spring, late spring. And, you know, Desert Odyssey happens throughout. So again, if people drop me an email or go to the website – at the moment, I have not published anything, but – you know, as plans –

Ann: Please, you know, put me – I believe I'm on your mailing list.

[01:28:46]
I'm always hoping to see schedules, you know, when's the next Odyssey. Don't forget to make sure that I get that. Yeah. I think it's a wonderful resource. You would know, I've already recommended to quite a few people that I know – and they've all, you know, told me how helpful it is, and they've gone on to then recommend it to other people that they know, you know, their loved ones.

[01:29:07]
So, yeah. Well, I mean, you know, thank you so much, Timothy. You know, we really could go on and on about this – forever.

Timothy: We could, couldn't we?

Ann: 
Yes. It's never ending. But it's such a privilege to have this time and space, specifically on my podcast to, you know, to just have this conversation.

[01:29:30]
Thank you for having enough, you know – making enough white space in your life to have this time with me, blessing my listeners as well. I really appreciate that. I know how busy you are and how much traveling you have now that COVID, has, you know – at least restrictions have been lifted.

[01:29:46]
Timothy: Thank you, Ann. You know, it's just wonderful to have this beautiful spectrum of different expressions of that interior journey. So, what you do with the podcast clearly reaches, you know, a listenership way beyond, you know, sort of these Desert Odyssey interventions can. So, I love the complementarity of it all.

[01:30:09]
It's so wonderful to be able to see how each of us can contribute in some way to facilitating that beautiful journey. And as Mary Oliver so wonderfully asked – which I think is the space that you and I try to inhabit is – you know, when she asked, tell me what would you do with this one wild and precious life?

[01:30:32]
And I think that's it, isn't it? Helping people make the most of this one wild and precious life that we each have.

Ann: Yes. So, thank you for joining forces with me today.

Timothy: It's delight, absolute delight.

Ann: Yeah. And I hope that there will be more opportunities in future, as we explore more and more really, you know, how to help ourselves and the people that we meet, have our souls catch up with us. Yeah, I really like that. Yeah, so, thank you, Tim.

Timothy: Take care, Ann. Thank you.

[01:31:31]
So, that was my conversation with Timothy Khoo. I hope that you will check out the show notes where I have parked the links of a couple of articles that Timothy wrote. So, you can read in his own words, his first-hand account of what happened in his life, and you know, what he has been gleaning from it. I hope this episode has blessed you, and I wish you as always happy becoming.

[01:31:38] CONCLUSION
Thank you for listening to Becoming Me, where new episodes drop every first and third Wednesdays of the month. Remember, the most important thing about making this journey is to keep taking steps in the right direction. No matter how small those steps might be, and no matter where you might be in your life right now, it is always possible to begin. 

The world would be a poorer place without you becoming more fully alive. Don't forget to visit my website at becomingmepodcast.com and to subscribe to my newsletter as well as to this podcast. Until the next episode, Happy becoming!

Timothy Khoo Profile Photo

Timothy Khoo

Existential Coach & Sojourner Guide

A former President and Chief Executive Officer of a global charitable
organisation, Timothy now lives with the reality of the undeniable fact that true leadership is not only exercised with skillful hands but with integrity of heart. Living with a sense of his own flaws, he invites you to a journey of conversation and through that, the discovery of
renewed meaning, purpose, and passion.

For over a quarter of a century, Timothy has led, mentored and coached leaders from a multiplicity of vocations and positions in over a hundred countries. Residing in Singapore but with
extensive cross-cultural engagement and experience, Timothy will help you navigate the challenging yet beautiful space between using what is within you to understand what is around you.