#49: Leo: "The Most Humbling Season Of My Life"

0:00Rachel Lim: Welcome to another episode of the Who We Are podcast. Last year, Leo joined me on the podcast to talk very openly about a season of depression and finding his way through it, and also restarting at 52. I can't believe it's been a year since he did that. Time really, really flies. When we sat down again this year, we planned to actually reflect together on 2025. but as the conversation unfolded, it became clear that Leo was still very much in the middle of his journey. So I thought, you know, instead of forcing structure, we chose to stay there. This is not a story of arrival. It's a conversation about lessons, humility, starting again, becoming, being a beginner all over again while still inside the journey and work.

0:49Rachel Lim: And I hope you'll enjoy this episode with Leo. Honey, thank you for doing this with me and welcome to the very first episode of 2026. Of course. I didn't realise that I was your first guest of 2026. Yes, you are. And for full disclosure, I might or might not have Bride Leo with a good meal in exchange for doing this episode with me. But jokes aside, we really wanted to start the year by looking back together. If you listened to our episode together last year, it's been a year. You know that he also shared very openly and honestly about going through and coming out of a season of depression. And since then, I've also watched him continue to grow and find his footing in a very real and very human ways.

1:39Rachel Lim: When I first asked him to do this episode, he was actually very hesitant. And, you know, he told me like he felt like he's still very much in the journey, still walking it rather than having figured it all out. But I think that's exactly why I really wanted him here, because aren't all of us always in the journey, still learning, still becoming and still finding our way? And this conversation isn't about having answers. It's about sharing honestly from where we are now. Are you ready? Yes, of course Okay, let's do this Okay, so the first question What are you most grateful for from this past year?

2:20Yeah, so it's definitely my kids They brought me a tremendous amount of joy You know, not in a loud or dramatic way But in a very grounding way Having more time with them Being around them every day You know, we have so many precious moments that we shared together that has really been meaningful for me. It's given me a sense of fulfillment that I don't think any, you know, sort of external achievements could measure up. And I'm just grateful to have the opportunity to be the best dad that I can be, especially knowing how I was brought up. You know my dad, obviously. And my dad was very open when I was in my mid-20s or late 20s.

3:18I can't remember when he had retired. He told me, he shared with me very openly. He said that he apologized actually for not being that kind of dad or father who was close like a friend. I still remember his words, funny enough, to this day. He said his duty, he felt at that time, and like I was saying, I think same for a lot of people whose fathers were from that generation, whose parents were from that generation, where basically their duty as a parent was to provide for, in terms of putting the children through school, making sure they received their education. And that was it. yeah so obviously with with you know ollie and kira i said to myself i i was going to be a different kind of father wow um yeah so i i wanted to be the kind of father that would show up you know to be present so you know i catch myself a lot at times when the the kids would come to me and be, you know, talking to me.

4:34Excited to share with you something. Yeah, excited sharing me something or asking me a question. And, you know, I'm on my phone and I always have to catch myself, you know, to put it down straight away and to be present, right? Because, yeah, I don't know whether you happy agree with this, I'm sure. What? I want to say, I don't know whether it's an age thing, But I tell myself, you know, these are really precious moments that, you know, if you don't treasure them, you'll miss them forever. And kids grow up so quickly. And yeah, I don't want them to stop coming to me for any questions that they have or to share with me anything.

5:33So it's building that kind of relationship and bond intentionally has been definitely one of the most rewarding parts of 2025.

5:49Rachel Lim: Yeah. And I just also want to affirm you that you truly are a great dad. You are so present. You are so loving. And the kids and Leo have such a precious and special bond. And that is so beautiful to watch. And we are so grateful to have you in our family. Yeah, so let's move on to the next question. And looking back on 2025, what are one or two things you feel genuinely proud of yourself for? Wow. When I look back on 2025, one of the things I feel like really genuinely proud of myself is that I kept going on something that started very quietly and personally. Alio Olio began as something that I started at home.

6:37Now, if you all recall, it was honestly an outlet for me, a way that helped me to decompress, to de-stress after everything that had happened. And I found joy in the kitchen again. I never imagined it would grow into anything more than that and certainly not into an opportunity with Shangri-La. you know that was such a an amazing opportunity where you know i was given the chance to showcase 10 dishes that i i you know had prepared on the channel and that was something that i was really proud of for myself because the fact that i persevered it's not easy you know coming out with I guess recipes every week yeah showing up yeah there are days when I was so tired or I wasn't inspired at all you know but I told myself that you know it's important to show up like you mentioned and I kept cooking I kept sharing and I guess I kept moving on and I guess it speaks of sort of that consistency and it's something that is important I think for me.

7:51I need that sort of consistency in my life. And it's something that I guess I really respect about myself now. And of course, another big sort of, I guess, achievement for last year was Anon.

8:07Rachel Lim: Yes. That has been something, or rather that was something that's completely new to me in terms of experience. not just starting from scratch all over again, but it's basically working with my co-founders, people who have completely different working styles and ways of dealing with difficulties and challenges. So what has been the most challenging and I suppose what I'm also most proud of is learning how to really humble myself through this whole experience with starting Anon. So I've been a creative, as you know, for many years. All your life. All my life, yeah. Yes. And I think subconsciously, I carried this belief that experience should come for something.

9:03But with Anon, this is new territory to me. And I've had to learn to let go. In fact, I think most of the times, I have to lean on my co-founders, Hayden and Shirin. So it's really humbling myself to accept that, which was really challenging. Especially, you know, again, going back to what I said earlier, subconsciously thinking that all the years of experience counts for something.

9:36Rachel Lim: And being the most experienced in age also. Yes. Being the oldest in the group also didn't, you know, didn't help. I mean, you know, there were times where we would be sending messages to each other and, you know, I'll be quietly asking you, right? What does this mean? IYKYK or LFG. That's just, you know, a fun example. But of course, you know, the technical aspects as well, fabrics, how they're constructed, how pieces of clothing are constructed, and how you carry out branding properly, doing the shoots for our catalogs and products the right way as it should be done. So that wasn't easy at all.

10:30So there were moments where I questioned everything. I suppose starting over at this age is tough.

10:36Rachel Lim: And what age is this, may I ask? I knew you were going to go there. 50, I just turned 52 last year. Why don't I just say you just turned 42 10 years ago? I'm 53 this year. Hey, yeah, so I was saying that starting at this age is very tough. The learning curve is very, very steep. and I think there were times where there was regret and I questioned sort of the whole purpose of not just Anon but Alio Olio and there were times also that I really wanted to take the easy way out. You know, I think one of the things that I noticed about Leo through this entire season And it's really, I have had the privilege of witnessing his evolution, his growth, his journey.

11:34And it's really not been easy.

11:38Rachel Lim: Starting over again at this age, trying new things all over again. Starting and growing a business is really not easy. And also, especially for Leo, what's completely new is also working with co-founders, different working styles and everything. And I have really also seen him push himself to open up his world and to really try again. One of the things that I'm very proud of Leo is that I think there were so many days where, you know, there were frustrations, doubts. And there were also like so many questions. Is this the right path? Am I meant to do this? but he really decided to just open up his mind and be more receptive to what the universe and what God is also showing him about himself and teaching him in this season.

12:30Rachel Lim: And I think that's something that I'm really so proud of you because during those earlier days, I mean, Anon is still in the early stage, but during those earlier days as well, it would affect our marriage, right? There were times where we would also, you know, be frustrated, impatient. And there were many times where I also prayed for a lot of wisdom to get to Leo, to encourage him, yet also share a perspective and point of view. And maybe do you want to share what was that like? And I realized the best way to get to Leo is, besides, you know, taking us out of the house to speak, also the other best way to get to Leo is to text him.

13:13Rachel Lim: but text him while he's sleeping. I'll text him while he's sleeping like whole long messages and then the next morning when he wakes up at 5am he'll be reading it in the toilet and then he'll head straight to the gym and he'll be digesting everything. So you want to tell us what was that season like? I think firstly when I do it in the morning first thing in the morning early morning You mean read it, right? Yes, read it. Read a message. Messages. I mean, the sun isn't up yet. Everything is quiet. And there's a certain calmness that also allows me to be very relaxed, calm, and I suppose open. So I read it and a lot of the times I get agitated right away.

14:05That's your first reaction. Out goes the window, you know, in terms of being calm. So the way I do it is I read through once and I know that the first read or first glance through is going to get me agitated, going to get me worked up. Because obviously I think for me, it's just human nature. Your defenses come up or you're so quick to reason or say no, no, no, you're wrong about this and that. So then what I do is then I take it to the gym. I take my agitation also to the gym. That's where I can, you know, lift more. Yeah. But it's during that time that what gets me, the points that get me agitated sit with me.

14:59You know, as I'm agitated, I'm lifting.

15:04Rachel Lim: Maybe that's why you're in the best shape of your life. So you have asked to thank. That's a really good one. I have to give it to you. I tend to do that in the gym because I suppose that's the only time where I have a clear mind. Why, you might ask. I mean, start of the day, yes. But, you know, there's nothing much at the gym other than, you know, considering what weights you're going to lift next, the reps you're going to do. So it gives me that one hour window to either digest it or digest it and accept or, you know, digest, accept and or come up with, you know, maybe a counterpoint, you know.

16:00Because I think the best solutions come from oftentimes being able to debate about something. As uncomfortable as it may be, most of the time when I read your messages, believe it or not, eventually I get there. I read it from this acceptance that you, or rather the acceptance that I have a lot to learn from you. So I've really taught myself how to be more open, being more teachable, listening. Yeah, and just overall knowing that, what was it you said to me before also, is that if you didn't care or love me, you wouldn't even bother writing to me all those messages, right?

17:01Rachel Lim: Is there an example that you can perhaps walk us through where in the moment you felt so confronted, so uncomfortable, and how do you process that? That also allowed you to realize that, wow, I have grown. because the earlier version of Leo would not have responded this way. Wow. I know exactly which example. To provide you some context, those of you who don't know, Anon was started by Hayden, super talented. He's got a keen eye for design, color you know balance and obviously he's such a great all-round kind of guy yeah and of course Shireen you know she's she has I think out of the three of us she's probably the only one with the experience in fashion so obviously she brings that to the table, teaching us terminology for fabrics.

18:22Oftentimes, we're like, what are all these makeup on the fabric swatches we get, the composition of the fabric. So myself, being from doing interior design all my life, when we were starting out, we made a decision to have our own space. because we needed to store our stocks. And also we said, okay, not only will it be that, but it will also be where we work, we brainstorm, we design, we come together, hold community events, and more importantly, have a space where we could have our products for people to come in, spend time with us, get to know us, we get to know them and try on our clothes. So straight away, I'm like, okay, honey, this is my, you know, my specialty, my playground, right?

19:20And I took for granted that it would be me out of the three of us.

19:25Rachel Lim: To design and put together the space. Yes, yes. And yeah, we thought about this, right? Oh, you. Yeah. Me and you, you and I. You and I. I still remember that, yeah, you know, you provided your perspective on why I shouldn't just be the only one who's in charge of this. And of course, I fought tooth and nail, really fought hard with you on that one. but I guess long story short is I saw the impact that Hayden brought to the design of the space then after that obviously I said to myself put my ego aside humble yourself and think what's best for a non you mentioned both Hayden and Shireen one the best for none.

20:31So all of this I was struggling with and I had to digest it and enough to convince myself and eventually believe that yes, it is the right way to proceed.

20:53Rachel Lim: I'm going to pause here. And what got you there? because I remember very clearly also this incident, you know, and I was just praying so hard, you know, that he would slowly be open to seeing why it had to be this way. And at what point or what happened that got you to the point where you realized that, okay, I can see why? I think it's quite simple. and I'll give you an example. So back in the days when I was still working for this renowned hospitality design firm and it was a period in my career where I was a design principal and there were a few of us but the core design backbone of the firm and I was always quietly threatened in a way by a fellow design principal there was a competition where basically we we took part in the firm took part in and they assigned it to myself and this other peer colleague of mine and it was a huge huge project with a huge fee and obviously we did our work, we submitted it and eventually it went out as two options.

22:22Rachel Lim: So one was yours, one was his. Yes. And I always felt that mine was better, you know. But I told myself I didn't even need to look at what he had done. So one day, I found myself with some free time and I went to take a look at his deck. And I tell you, honey, I was like, wow. There were so many things that I told myself, man, that's so good. So creative. Why didn't I think of that? And I came to a point where I felt that actually his design is so much better. You know, why I'm saying this is because with our Anon space, Hayden and I had attempts at it. But it became very clear once I was in that, I guess, acceptance.

23:19Then I start to see, yeah, it is really, really good. And that was when I knew there was only one right choice.

23:38Rachel Lim: I feel so touched listening because I am just so proud of the man Leo has become I think this whole journey for Leo has opened up his world in so many ways and has also molded him to the man he that he's become more open, you know, and more receptive and also being able to put his ego aside when it matters. And I think that's something that we all have to learn in life. And I just want to say that I'm so proud of you, you know, in this journey. So what else, honey, are you most proud of in 2025? I'm also, wow, extremely grateful last year for you. I think we've been through a lot together. This year is actually our 10th year together.

24:44Rachel Lim: 10th year married. Yes. 10th year married. But I knew you when you were so young. Still young. Yes, you're still young.

24:59So Yeah, I mean, last year, I feel, if anything, proved probably, in my opinion, the most challenging one for us.

25:14It was that season where, you know, I had lost my career of over 20 years, starting Alio Olio, starting a non. And, you know, we had so many moments where we, or rather it was me, I was frustrated, you know, that we had a lot of disagreements and arguments. But one thing I'm really grateful is that you were so patient, very understanding and very supportive. And we just decided to choose each other through it all. I think I shared with you before as well, very openly, that not many women, I feel, or partners, will be able to stand by their husbands through that season. You know, because it's almost as if, you know, the sort of traditional notion of the guy has to be the, you know, sole breadwinner and the rock of the family.

26:27But we all know how times have changed and, you know, perspective on that has changed. You know, but like I said, you know, the way I was brought up was also very traditional. know, as I was saying, it was not easy for you at all. And for you to put aside your own struggles and to continually, you know, be there for me, be my rock, support, endless actually, endless support encouragement is something that you know I don't take for granted and it's something that I'm truly truly grateful for I told myself actually I've never shared this with you actually I told myself that you know when Ollie and Kira are much older yeah I'll share with them just how amazing and strong a mother that they have.

27:43I think it's something I truly treasure. Because honestly, I wouldn't have pulled through many, many moments, pivotal moments of last year without you. Yeah. Thank you.

28:14Okay, I need to blow my nose.

28:18Rachel Lim: Okay, let's move on to the third question, shall we? The third reflection question is, I know you spoke earlier a little bit on this, especially in the beginning on what you're proud of and also alluded quite a bit to this. But yeah, what challenged you the most last year and how did it change you? I think it's definitely how my sense of self-worth was brought back down to earth in a very real way. it forced me to confront the fact that no matter how many years of experience you have doing something, there's still so much that I really, really don't know. And that was really uncomfortable. It felt like being stripped of a layer of confidence that I had grown so used to standing on So Anon was a huge part of the humbling experience as well.

29:25Working with my co-founders, especially knowing that they are almost two decades younger than me, challenged me in ways that I didn't expect. And it was a new territory for all of us. I couldn't rely on experience alone. I had to listen more. I had to be open to being wrong I had to learn how to contribute without needing to be the one with the answers all the time or be the one to lead all the time and most definitely I also learned that I'm also not the one who's right all the time It's taught me that humility isn't about diminishing yourself. It's about staying teachable. It's about recognizing that growth doesn't stop just because you've achieved something before.

30:32I feel less attached now to needing to be the best and more open to being a student again. And in a way, I also want to sort of go, not go back, but sort of set another standard for myself.

30:50Rachel Lim: Wow. You know, we joke a lot about me starting all over again at my age. But hey, you know what? I've started to see being in your 50s doesn't mean you need to slow down. Doesn't mean you need to stop learning and growing. Yeah, I think it's that sort of framework and mindset I want to place myself in. And I have truly also seen how Leo has opened up so much in that aspect. Which is also why I always tell him, like, the man that you are growing to be makes me respect you even more. and I think it brings me so much pride and joy for Ollie and Kira also to be able to see and know one day of what Leo, their dad has gone through is going through and has emerged out of it as a much stronger man yeah, no, but thank you so much for sharing so openly, so honestly and it was so raw, so real, so vulnerable.

32:03Rachel Lim: And there are so many takeaways that we all can have just from listening to you and your journey. And, you know, as we also come to the end of the episode,

32:18Rachel Lim: I just also want to say thank you for listening. You know, this was meant to be a dual reflection episode that deservingly became a solo reflection episode for Leo because he just had so much to share and process. So if you have stayed all the way through, thank you. This conversation for me also has been a reminder that life doesn't always move in straight lines. It's not always linear. There are seasons of certainty, seasons of uncertainty, seasons of waiting and seasons of stepping forward. So wherever you find yourself right now I hope you feel a little less alone in it. So thank you for tuning in to the episode.

33:01Rachel Lim: We'll see you for the next one. Thank you.