Epilogue: Dear Trent
Field notes from Sam
Dear Trent,
I should’ve known you’d overdeliver on a simple question like, “What do you say when people ask, ‘What do you do?’” I expected five bullet points and instead I got 25,704 words—such an overachiever.
For the benefit of the other “Sams” following along, I met Trent 25 years ago. Together we’ve co-founded businesses, bought property, and navigated life’s ups and downs. Late nights, tears, stress, but also laughs, wins, and many adventures. I’m the dreamer; he’s the doer. My dreams took me overseas for a decade working in humanitarian aid and development. That work made me acutely aware of my privilege and how fortunate I am to even contemplate early retirement. I feel incredibly lucky to be having this conversation at all—talking about wealth feels uncomfortable, in a world where so many have so little.
So, I’ve been field-testing your early retirement advice and I’ve got a few reflections to share, in three parts:
What I Found Helpful
Knowing your interests and values: Obvious, yes, but not easy. I kept getting tangled up by what I truly care about vs. what I think I should care about. I realised I need a way to keep that ‘truly care’ list alive so that it shapes my daily decisions. So every day I review: 1. how I connected with family and friends, 2. my personal wellbeing across all dimensions, and 3. whether I did deeply fulfilling work (this one is last for a reason, I don’t want it to compromise the first two).
Thinking long term: Forty more years to live in early retirement? I find that thought liberating (there’s so much time to do, be and have) yet strangely urgent (I’m so much more aware that every moment counts). As the saying goes: we overestimate what we can do in a year and underestimate what we can do in ten.
Increasing my healthspan: I’d never gone to the gym before starting this early retirement business. But if I want to be riding, tramping, and travelling in my 80s, it won’t happen by chance. I find it helpful to think in decades (I must be old if I think in decades) and to have tangible goals (like being able to play on the floor with my future grandkids) to motivate present-day me.
Giving back: I won the genetic lottery by growing up in New Zealand and want to make sure I give back. I appreciated your local–national–international ‘magic wands,’ and the courage to be public about your giving. I’ve always been reluctant to talk about giving, but seeing you and others be more open has given me something to chew on. I also liked your reminder that money’s just one of many things we can give.
Investing in startups: It’s bloody fun, even if it’s likely I will lose most of the money. I love being around founders: their energy, their delusion, their stubbornness, their genius. We both know how hard it is, which makes the cheering (and commiserating) feel all the more real.
What I Want To Get Better At
My kids like to tell me, “You suck, try harder” when I can’t finish a boulder problem they’ve just scampered up. In that same spirit, here’s my list of things I want to do better:
Pursuing hospitality: This should be easy. I love spending time with people. But the organisational energy and scheduling logistics trip me up every time. Like exercise, it's getting started and building a habit that matters most. You even sent me your 8 Toasts email invite… still waiting to be used.
Strengthening social connections: I’ve got plenty of surface-level relationships, but I haven’t invested enough in the deeper ones. Moving every few years doesn’t help but, if I’m honest, that’s just an excuse. As you have pointed out, the research is clear: strong social connections are closely tied to long-term happiness and physical health. This one really matters.
Prioritising sleep: You’d think with all this extra time I’d finally be well-rested. But early retirement is surprisingly busy. I know, in theory, that sleep unlocks my ability to get more out of life. Are we sure there’s no magic REM pill that makes five hours sleep feel like eight?
Spending money: Research tells me our relationship with money is shaped early, and maybe that’s why I find it hard to spend. In my family, growing up with migrant parents, money was something you saved—not something you spent lightly. As a result I have this quiet, creeping urge to grow wealth just because I can—despite knowing it won’t make me happier. For now, I really like your idea of splurging on what really matters and being vigilant on the rest.
Final Reflections
Having money and options can change how you see yourself and how others see you: That’s part of why I prefer to keep a low profile. I sometimes worry I’ll lose touch with reality (aka be a dick head), or that people will treat me differently. But in truth, neither has to be the case—and so far, neither has been.
Retiring together: Early retirement is something I’m doing jointly with my wife, so how we spend, invest, and give is deeply collaborative. It takes time and effort, but it’s the only way to do it. I can see Kate and I systematically going through the Dear Sam advice over and over again.
Why work? Why retire? Like you, I’m not built for traditional retirement. I still want and need to apply myself to something meaningful, something that feels central to why I’m here. Not instead of being a good husband, father, son, friend, or citizen, but alongside it. There’s a part of me that’s always going to seek progress, contribution, momentum. It’s taken a few months, but I’ve pulled together some reflections on why I should (or shouldn’t) work, who I’d want to work with, when, and on what kinds of things. Having a loose framework gives my mind a bit of peace and helps me to stop second-guessing whether reading a book in the middle of the day is “productive.”
In Conclusion…
Thank you for the love you’ve put into all 25,704 words. I wonder if we’ll be reviewing them when we’re in our actual retirement homes 40 years from now? Meanwhile, I’m sure it will quietly shape the way others think about this strange, privileged chapter of life. I know it has done that for me.
So, as you’ve done time and again Trent, thank you for leading the way. This time it’s in early retirement, semi-retirement, un-retirement, full-time human-ing, or whatever strange label we give this season.
And next time we go tramping, remind me to ask for something bigger, like world peace or the meaning of life.
Here’s to the many new adventures ahead, you retired old fart,
Samwise Ng
And so concludes Season 1 of Dear Sam.
I’m going to take a break for two months before coming back with Season 2, where I interview other interesting people about their journeys. The serial entrepreneur who could stop working today and has instead chosen to go again. The author who spent a couple of years caring for her elderly parents and found herself accidentally retired. The 30-year-old who got rich from crypto. An early retiree who spent seven years trying different gigs ‘post retirement’ because she wasn’t ready to be fully retired. Etc..
Do you know anyone who has retired early? Do you know someone who can afford to retire early and has chosen not to? Please let me know by replying to this email, I’d love to talk to them.