Hey friends,

This is going to be a long email.

As promised, I’m sharing my results of doing the Odyssey Plan exercise that I talked about last week.

In case you missed it, it’s a life-design exercise from Stanford Business School. You’re supposed to think and write about the following prompts.

1. Write out, in detail, what your life would look like 5 years from now if you continued down your current path.
2. Write out, in detail, what your life would look like 5 years from now if you took a completely different path.
3. Write out, in detail, what your life would look like 5 years from now if money, social obligations, and what people would think, were irrelevant.

Warning - the following is pretty self-indulgent. If that’s going to make you vomit, please don’t read, or take some sort of pill beforehand. I’ll share a few reflections afterwards.

Current Path - 5 years from now

• I’m 33 years old. Married, with 2 kids.
• I’ve been doing YouTube for 10 years at this point. The podcast’s been going on for 6 years now, and we’re several hundred episodes in. The main channel has around 10 million subscribers, and I make videos about whatever I want, whenever I want. I don’t feel the pressure of an upload schedule, because my career has moved quite far away from being a “YouTuber”. The first book was a commercial success, we hit the NYT list after some cool marketing stuff, and it continues to sell. People really like it.
• I’m currently working on the second book, about happiness or purpose or something like that. Still trying to figure it out. While the first book was a “here’s a guide to being super productive and doing lots of stuff while having fun and without burning out”, the second book is “how to figure out what to do with your life, once you’ve got the basics covered”. Through research for that, I’m exploring philosophy, Buddhism, and a bunch of other interesting things to try and answer the question.
• The business is doing really well, as a lifestyle business. We’ve got a bunch of courses and digital products that continue to sell daily, without any input from me. The team runs the marketing, the ads etc. Anytime I do a video or a podcast, we plug some of the stuff, and it sells on autopilot. People love our courses and products, and the passive income they generate means that the business is very profitable and sustainable, and I can live the lifestyle of “do what I want” without having to worry about money, within reason.
• X and I are married, with 2 kids. We started a couples vlog channel when we got engaged, which has been a fun little passion project. We deliberately don’t upload consistently, and actively avoid caring about the numbers. Despite this (or maybe because of it), the channel’s grown to 1M+ subscribers and we get inundated with stuff like free hotel and resort stays, free parent/child products and other stuff like that. We’ve got a small team that manages that stuff. The way we make videos is that if we feel like vlogging on a particular day, both of us will film some footage on our phone / GoPro / whatever camera we have with us, maybe we’ll include a voiceover, and then we’ll send all that to our editor who deals with it. We’ve included our kids in some of the vlogs, but something about that feels a little off, so we avoid doing it too much, still gotta figure out how we feel about this.
• My work day is approx 4 hours long. Each day is either a writing day or a filming day. On writing days, I write for 4 hours and aim to write 2,000 words for whatever project. On filming days, I film whatever video I want, or record a podcast interview with someone cool, either in person or remotely. I spend the rest of my time hanging with the fam, reading stuff, occasionally playing video games and dabbling with streaming just for the bants.
• The team in the business has stayed small, at approx 15 people. Angus is the general manager, and we’ve had some turnover, but we’ve got a lot of people who’ve been with the business for 5+ years. They like the lifestyle, the profit-sharing, and the fact that things are pretty chill and non-metricified. We managed to get a sponsorship deal with a coworking space, so we’ve got a sick central London office that we don’t need to pay any money for.
• After the success of the first book, I get invited to do keynotes and talks at conferences all around the world. We’ve got a speaking agent who handles all that stuff. These are outrageously lucrative, and they’re a good excuse to visit different countries, sometimes with the fam, sometimes without. I mostly speak about sustainable productivity, intentional life design, finding purpose, and sometimes creator economy and entrepreneurship type stuff. These are really fun events, and I love hanging out with people afterwards, and I’d totally do this for free. On that note, “would I do this for free?” is a filter that I put all my work decisions through - I decided 5 years ago that I’d already achieved my wildest financial dreams, and chasing more money was never leading to more happiness, and so now life’s about doing what I intrinsically want to do, rather than doing what pays.

Alternative

• I’m 33 years old, married with 1 kid. We’re currently living in a van, travelling through the US. After getting married (Jul 2023), X and I decided to spend a year travelling the world, and because we loved it so much, we decided to continue for as long as it continued to be enjoyable and enriching.
• We started a couples vlog channel when we got engaged (Jan 2023), and we’ve been documenting our journey and travels ever since, with occasional sit-down nerdy videos reviewing books, podcasts, products, mental models etc. I’ve stopped uploading consistently on the main channel - I’ll occasionally make a book or tech or Q&A video on there, but the couples channel is the passion project that’s remained a passion project because we’ve been careful not to over-monetise it.