Five years ago, I wrote a short note on my birthday about things I thought I’d learned in my first 40 years kickin’ around planet earth. It feels a bit odd to look back on the collected thoughts of a forty year old man and feel like, “Well, he still had some learning to do.” But of course when I wrote that we still had the last five years ahead of us.
Back then we had yet to experience the relief of resumed normalcy followed by the horror of watching that normalcy swallowed alive; we had yet to feel the highs and lows of the post pandemic pinball economy or the surreal backlash to the economic recovery program and vaccination initiatives that saved millions of lives; the tragically outmoded, out of touch, benign paternalism of the Biden administration, astroturfed culture wars compounded by very real European and Middle Eastern conflicts; or the slow motion political car crash of 2024 and the nervous retreat into the bushes that has defined our collective response to the events of 2025 so far.
And we had yet to witness the multiyear birthing of AGI - seemingly sparked bicameral mind-style by the invention of language models - or our current moment of stricken panic at the oncoming wave of automation and economic dislocation.
It’s been a lot. And thinking about the next five years feels a bit like glancing in the direction of G RR Martin’s moon door.
For the last two decades my main goal has simply been to make it to today - my 45th birthday. The number 44 has hung over me like a colon-shaped sword of Damocles ever since I lost my dad at that age when I was in my late teens. Regular colonoscopies since then have taught me that left to their own devices, the genes I inherited would happily do the same to me. Thank God for health insurance and the US medical industrial complex.
But today I made it to the other side of 44 and it now seems appropriate to think seriously about how I’d like to live in the years my dad never got to explore. To make the most of the opportunity to continue making a future for myself and my family here at this very, very curious time in human and machine history.
You can’t write one of these self indulgent reflections without dragging out the Gatesian proverb about overestimating what we can achieve in a single year while underestimating what we can accomplish in 10. (If true for an individual, how even more so for a society!)
But here at the five year mark on this decade how do I feel about my own development and achievements? Well, I’m alive, I’ve survived, and while I frankly haven’t done that much with those life lessons since writing them, I did manage to accomplish some other things in the last five years:
We had a daughter! We welcomed Madeline into the world in 2021 and she has grown into such an incredible, vibrant, charismatic part of our family. Watching her grow, learn, and love - her siblings, our family, her mom and I - has been magical and the center of our lives for the last half decade.
We raised some teens. I really cannot take much credit here, but I am so proud of the way our older kids have both grappled with the challenge of becoming, well, people. I don’t think there’s ever been an easy time to come of age and be a teenager, but surely the last five years have been some of the hardest. They have each navigated it with grace and style. The future is daunting but I couldn’t be more excited that they will both get to shape it in their own unique ways.
We kept improving our house. Although I have a few things to do before I’m ready to do another round of photo updates for our house fans, I’m excited to give people a look at how we’ve improved our home since we bought and remodeled it in 2020. It’s an enormous privilege to own property these days and I try to remind myself of that privilege every time something breaks or another unexpected bill appears.
I’ve helped manage some pretty significant business transformation projects. Working in communications has not gotten any easier over the last five years, and I’m proud of the change my teams and I have helped manage. I’ve gone from running comms at 2000 person companies to a 45,000 person company. I’ve learned a lot in the process and I’m proud of the value I’ve added along the way.
I’ve increased my connection with New Zealand and with my family back home. I’m lucky to have a partner who understands the challenge of living away from my family and ensuring we prioritize trips back home. In the five years since 2020, I’ve been able to get back to NZ four times, including, very meaningfully, this year for my brother’s wedding.
I’ve overhauled my health and my body (through the magic of GLPs). After years of trying to get my weight and blood pressure into healthy ranges while managing an incredibly stressful job, my doctor endorsed the idea of trying Zepbound this summer. Over the last four or so months I’ve hit my goal weight effortlessly and feel better about my health and myself now than I have at any time in the last 15 years. If you feel like you might benefit from it, I would encourage absolutely everyone to talk to their doctor about this stuff and see if it works for you. The impact it has had on me has been life changing.
I’ve written recently about where I think things are going in communications and I’ll likely have more to say about how I think the future is going when I do this year’s annual recap, but when I think about what I want the next five years to look like for me I’m mostly thinking about:
The next 250 years: In 2026, the founding vision for the US turns 250 years old and boy if it’s not the right time for us to be thinking about shoring up the framework for the next 250. I have spent my spare time lately doing some loose thinking about the necessity of a (casually and grandiosely titled) ‘United Futures Project’ to recapture the spirt of the period between the declaration of independence and the drafting of the US constitution in several work streams where it feels like we could do with a similar level of constructive, intense debate between people acting in good faith, specifically:
Institutional modernization and technology enabled participatory democracy
Global governance and international coordination
Governance frameworks for AI and biotechnology
The transition to the post-labor economy
Justice, civil liberties and privacy in an AI enabled future
Truth, trust, and information integrity.
The Post Labor Economy, specifically, will be the greatest and most immediate disruption shaping our lives and we are nowhere near prepared for the way this will overwhelm every frame of reference we have. Lately I have fallen in love with the work David Shapiro has been doing on this topic, setting out a framework for making this shift organically that leverages existing infrastructure without relying on centralized solutions (in a 1, 2, 3, 4, 5, 6 part series). If there’s one thing I’m excited about it’s popularizing discussion around Shapiro’s ideas and looking for ways to facilitate trial and adoption of these programs at the local level.
The inevitable reconstitution of social-democratic political parties. As we grapple with the effects of technology on society and the economy, I think it’s clear that today’s incumbent political parties will need to completely reinvent themselves or they will fall away (see the Federalists, Democratic-Republicans, and the Whigs). What will Labour represent when labour itself is automated and artificial? Perhaps Democrats will embrace their current identity as institutional guardians - but they will need to find a way to get people much more excited about Democracy if so. Given this period of dislocation and political de-alignment, there is no better time for all political parties to be reassessing who and what they will stand for and what they want to achieve in a future that will look dramatically different to the past.
What will the world look like if I’m fortunate enough to be writing a version of this post in five years time? Well, I hope that much of what is still true today will continue to still be true then. I hope my kids will be in a college (if that’s the path they choose) that is capable of preparing them to be human in an economy and society that will be significantly different. I hope that we’ll all continue to have economic agency and democratic agency. I hope that technology will enable us to be more human than ever - spending more time with one another, enhancing our relationships, more fully experiencing the world and our communities - and that we’ll have frameworks and institutions that enable that economically and culturally. I hope that we’ll be enjoying a period of wonder and discovery that is accessible to everyone.
That’s what I hope. Recent experience leads me to expect otherwise and previously I would have written something like “But we’ll have to make it happen.” I don’t know why, but today I feel more confident than I have in the past that the companies championing and developing AI really do have our best interests at heart. I’m genuinely encouraged by how openly they communicate about their intentions and decisions. I know people believe it’s all spin, but I do think on balance Google, OpenAI, Anthropic, and yes even Tesla, are full of people who really do care about making sure these technologies benefit society. I’m encouraged that there is real, informed, bi-partisan interest from governments around the world that is helping produce a constructive conversation between governments and AI companies. And despite my general despair about our current politics, I’m more optimistic than ever about what the longer term future will look like because of the effort and open dialog between people of good faith on both sides of the E/ACC and EA divide. I don’t think that the years between now and then will be easy, but I’m hopeful and optimistic we’ll end up in a good place.
And if I wasn’t, well, I’m not sure there’s much we can do to stop what’s coming anymore. We might as well lean into it and do what we can to make sure it benefits as many people as possible.
See you in 2030!
Love this.