Laying The Foundations | #243

October 14th, 2023: Greetings from Taipei. I hosted a meetup this week with

Tania Wu

who has a great newsletter on embracing “Slow Life” in Hong Kong after moving to 20 countries in a couple of years with a remote company. Thanks to all friends new and old who came out. I’m planning on hosting one in Barcelona the week of November 12th when we are there for the month so let me know if you will be around.

#1 A Clarity Session In Bali

Over the last 6.5 years, I’ve been extremely independent. I do almost everything myself, even the mental strategizing about how to think about everything I’m doing. On one level this is a bit crazy but on another, it’s given me incredible freedom over my time. Without other people to work with, I can actively drop the ball on almost anything at any time. And I have, embracing time abundance to wander, contemplate, take time off, spend time with Angie and now my daughter, and start up new creative projects on a whim.

But with a cute baby in the mix, someone who I have a hard time ignoring when she’s in the same room, a lot of the things that I just sort of took care of in the open spaces of time are not getting done anymore. This means when I do sit down and work for a 3-4 hour stretch, which I’m doing about 1-2 times a week in Taiwan, I’ve been just catching up on admin stuff, not the creative work that fuels me.

While I do plan to work a little more when we leave Taiwan, this whole admin-first default is unsustainable and a risk to my desire to keep going. The whole point of this path is not to maximize any sort of traditional metric of success but to maximize aliveness and time flexibility. While I am lucky to have many things I enjoy doing, my previous approach of focusing mostly on creative work and then doing the maintenance work that is necessary as it comes up is just not cutting it anymore.

Luckily I had a thought partner to think through a new approach while I was in Bali last week. A friend of the newsletter

Georg Tanner

, who is living with his wife and two kids in Bali, offered to do a “clarity session” with me around everything I was working on. His general understanding of my work shared life priority of designing work around his family, and his ability to synthesize ideas in real-time made him a wonderful thought partner.

He used a tool, Miro, which I haven’t really explored but was perfect for something like this as it helped turn my words into a clear visual map. For example, laying out all the things I was working on, it became obvious that I was trying to do A LOT of stuff:

all my stuff mapped out

I did this in text form a few weeks back and it was helpful in terms of seeing how much was going on but something about visually doing it made it seem easier to work with. Looking at everything, I sort of laughed and was able to say, “Okay well it wouldn’t be reasonable to crush all of this, especially since I’m actively choosing to spend more time with family right now.” When I graded myself, I realized that only the writing here and my podcast were the things I was consistently able to do at a high level. This is because they are easy for me. I love writing this newsletter and no matter how little time I have, it gets done. But for the other stuff, if I want them to happen, I’m going to need another approach.

The other thought I had looking at this map was, WOW. I feel so lucky that almost all of these things are emergent from my own experiments over the last 6+ years. I literally get to work on things that I like, entirely of my own creation, and that combined support our family financially. This is fantastic.

Another thing you’ll notice is that there are two clear sides. The stuff on the left is where I love spending my time. This newsletter, my podcast, my community, and my book. Prior to publishing The Pathless Path, I spent about 80% of my time and made about 2% of my money on these activities. After publishing the book, it’s still been close to 70% of my time but now almost 40-50% of my income. I’m still adjusting to this shift and while I’ve treated the increased attention to my work as permission from the universe to double down on it, I’d be lying if I said I wasn’t still a little uncomfortable betting it all on this path. I don’t trust it’s going to be financially viable yet. While others see me as at the start of some big mission, to me it still feels very uncertain and my rational mind still wants to hedge so that we can keep living the life we want for now.

With a baby in the mix, my total time has shrunk dramatically especially being in Taiwan where I’ve been supporting Angie in taking advantage of all the things like fitness and art that are so much more familiar for her in her home country. What this means is that when I sit down to do focused work, I’ve been spending most of my time doing maintenance for StrategyU and other projects and then being a bit frustrated that I don’t have time to create.

I did a thought exercise of what I’d do if I was handed $10 Million. I quickly said:

• I’d gift StrategyU to someone to run or sell it at a discount to a consultant trying to quit their job

• I’d keep doing this newsletter, shift more attention to writing books, and the community, and would hire a researcher and business manager to help me with all of it

• I’d spend a lot more on rent and also moving services so that we could go between places a little more smoothly

While this kind of thinking makes it clear what I see as important and helps me think of ways to do some of this now, there are still many tradeoffs I need to make. From the session with Georg, I realized that a lot of what has been holding me back from shifting into a new mode has been conflicting feelings with how I think about my path.

I have a powerful sense of abundance, faith, and trust that things will work out. I have no intention of quitting anything anytime soon. It’s okay to deprioritize some of the creative projects I want to be working on in the short term.

I trust that if I keep going with my writing here in this newsletter, share my book, and continue having deep conversations on the podcast, good things will happen. Never bet against curiosity and the internet.

I am also afraid that book sales will slow, interest in my StrategyU training and courses will slow with the economy, our cost of living will rise in the US, and I may not have the time to dedicate to creating new offers.

But I have faith and evidence that I can easily react to a change in circumstances and reinvent myself and new kinds of work like I have done 50 times before.

I am afraid that if I bring people on to support me I will have to spend time “managing” people, moving away from creative work. But I’ve also realized by actually searching for people to help me, that what I see as “admin,” others actually love doing.

This is the reality of an unconventional path. There are tons of positives but uncertainty is always there for the ride. For me, it’s a feature, as I get to have a clear view of what I’m really feeling and have no choice but to face it and move forward.

Here’s the plan I developed with Georg over the coming months:

The core mission: Focus and attention on what I love doing: writing, having conversations, and acting as a node to connect others on unconventional paths. Focus on building and investing around the newsletter, podcast, and book.

The tactical next steps in the next three months:

1. Develop a clearer brand and mission around my work:

   1. Read Category Pirates suggested by Charlie Hoehn and go through reflection exercises - what “problem” does Pathless Path solve?

   2. Figure out the next steps for the Boundless newsletter. To stay on substack or move somewhere with more customization for readers?

   3. Get more marketing support help for the podcast and YouTube to continue promoting the book

2. Strengthen and revamp the Find The Others community

   1. Bring on a contractor to help improve communication around the offer and develop a sustainable plan for the next 2-3 years (in progress)

   2. Focus less on attending live events in the community & more focus on creating tools & materials that help people on unconventional paths

3. Reduce the time I spend on StrategyU to only content & teaching/coaching

   1. Define more clearly what I don’t want to do

   2. Find a contractor (in progress) to help with marketing, content & operations

   3. Explore partnerships, investigate selling the business, and other strategic options

I think one thing I realized in the session was that I needed to take a step back to take a step forward. It’s okay to focus on maintenance mode for the next few months instead of only half-committing to everything. I’ve started working with two contractors and I’m already realizing that tedious work for me can be enjoyable work for others. Despite setting an intention to spend more on the “business” this year, I’ve struggled to find the right people who are a “hell yeah.” But two people I just started working with have me feeling a lot better. and I’m excited to “spend” to do more creative work, which is really the only thing that matters for my path over the long term.

Onward and to continuing to learn, make mistakes, and figure out what comes next…

+ Georg didn’t ask me to share any of this but I’m happy to shout him out. I think he’s on to something with this and it was cool to spend time with him and see the aliveness and creative energy within his family. Here is a link to learn more.

---

#2 From Indonesian Tourism School to Selling Steel to Podcast App CEO

I sat down with my friend Jovian here in Taipei who is one of the most optimistic and curious people I’ve met. He grew up in an Indonesian family where no one had a stable job and he ended up emigrating to Taiwan at 18, staying here, and crafting a quite impressive career by hanging out on the internet, engaging with American friends online, and generally just being useful.

I think it’s a great example of the positive side of the internet. Despite spending less than 30 days in the US in his life, he’s built a life and career around US technology ideas and a network of people involved in the industry. It’s going to be a path many more people from around the world are going to take.

🎧 Listen / Watch Here

---

#3 Turning 7 Figures Into 6 Figures

I sense there will be a big market for helping retired boomers spend money, not only in ways they’re used to but also in ways that might transform their lives. I really enjoyed this “re-framing” of money management from Adam Chapman and look forward to his book about this

“I turn 7 figure investment portfolios into 6 figures every year.”

When John and Jenny came to us just over 5 years ago, they had 1.5 million in their portfolio. At our most recent meeting, they had just under $725,000—less than 50% of where they began. For most people, this would represent a colossal failure, but for us and our clients, it's a measure of success.

…

After nearly two decades working with retirees, I've learned willpower and wishful thinking aren't enough to spend the money we saved. In most cases, the money we plan to spend becomes psychologically trapped between the money behaviours we used to save our retirement nest egg and our worries about the future.

…

For John and Jenny, that meant buying their first cottage well into their 70s. Then, they bought their first boat (and learned how to drive it). Then, they added additional bedrooms because their kids enjoyed the time away from the city, which became a great way to spend more time with their grandkids. After these extra visits, they pridefully shared how smart their grandkids are—so we pushed them to fully fund education for all four of their grandkids.

Pretty cool! You can share the whole post from Adam on X and check out his work here.

+ Also check out my post on Die With Zero here.

---

Thanks For Reading!

I am focused on building a life around exploring ideas, connecting and helping people, and writing. I’ve also recently launched a community called Find The Others. There are weekly writing sessions, monthly “find the others” (literally) virtual meetups, and general supportive vibes.

• You can join Find The Others if you want to hang with us too, or if you are already a subscriber, get access here.

If you’d like to support my journey, the best ways are to:

• Buy or listen to my book, The Pathless Path (or message me if you want to bulk order at a lower price)

• Want to reach 15k+ curious humans? I’m looking for sponsors for 2023 for this newsletter or podcast. Please reach out or book a package here directly.

• Subscribe to my podcast and leave a review.

• 🤳Want To Get Started on Youtube? Friend of the newsletter Ali Abdaal (and his amazing team) have just launched their self-paced course and accelerator program on creating a thriving YouTube channel.

In addition, I recommend all of the following services (affiliate links): Collective for setting up an S-Corp in the US (recommended >$60k revenue), Riverside.fm for HD podcasting, Descript for text-based video editing, Transistor for podcast hosting, Podia or Teachable for courses, Skystra for WordPress Hosting, and Circle for running a community.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.