Before The Launch, Self-Doubt | #312

November 6th, 2025: Greetings from Taipei. Last week I launched my premium hardcover of The Pathless Path and shared an update on sales at the bottom of this post.

I dropped an unboxing video of opening up my copy on YouTube. But today I thought I’d share some reflections on some of the doubts I’ve been struggling with over the last month.

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Right now, a pallet of about 2,000 books, my specially designed hardcover of The Pathless Path, is sitting inside a single container, on a ship like this one, headed toward the US. Barring new tariffs, disaster at the high seas, getting stuck in a canal, or a global pandemic, they should be arriving in the US ready to ship out by Christmas.

In the run-up to the launch announcement last week, something I delayed for more than ten days, I wrestled with lots of self-doubt:

• Will it flop?

• Did I spend too much money on this?

• Should I have done something smaller and quicker?

• How did I spend this much?

• Am I charging too much? Not enough?

• Do people really want this?

Before this project, I’d kept all my projects simple: minimal upfront investment, bootstrap, work independently, and focus on staying profitable and cash-flow positive. With this project, I invested a large amount of money upfront, kept it mostly secret, and am announcing it as part of a major launch. I designed previous projects to quit, but with this, there is no clean off-ramp.

Despite this, as the launch announcement approached, especially after some critical feedback on the pricing, I started doing mental gymnastics, manufacturing a narrative that would give me an off-ramp, a way to say to myself, “This is fine!”

If I make back 20% of my investment, I think I could be okay with that.

I’m going to be selling this for years; any short-term outcomes don’t matter.

This is part of a larger bet and pivot; it will take time to fully develop this. It would be okay if I only sold about 20 books. I can think of it as a branding exercise.

Why are we like this? Why am I like this? I mean, seriously. Meta has burned more than $70 billion on VR bets, and I’m worried about a loss of low five figures!

Maybe these stories are right and useful, but in creating them, mostly what I was doing was resisting my own feelings.

I am nervous, afraid of looking silly, and might actually lose a bunch of money on this, and all of that is actually okay.

Deeper than this is something scarier to fully feel: I care.

I care about this book as a creative artifact and as an expression of myself and what I believe. I created it because I wanted to lean against the creative compromises that too many people make and the hyper-efficient spreadsheet logic that pervades our broader culture. Even simpler, I just wanted it to exist.

As I prepared for the launch, building out the landing page, and getting feedback, I lost track of these deeper motivations. And even though I’m not in any real financial danger and have funded the investment out of cash flow from book royalties, the idea of not at least breaking even stirred up gnarly money emotions.

It’s almost as if my subconscious dreamed up this project to test me.

You should never waste money. Never take risks.

These scripts were installed early in my life, as they are for many of us, and of course, they were useful. They helped me invest wisely, understand personal finance, and enabled me to quit my job without a plan. They also helped me easily shift into extreme frugality while not making much early on my path. But they also aren’t needed anymore. The lessons have been learned. I’ve made it to 40, never letting myself get close to financial danger. I can trust myself and trust the automatic fears a bit less.

But letting go of the scripts that shape much of our behavior early in life can be hard. It wasn’t until my thirties that I stopped seeing work as something that involved suffering. And once I let go of that, I discovered money scripts, which seem to be rooted at a deeper level in the body, the final boss of personal growth.

To let go of these money fears isn’t just being stronger or bolder or more courageous; it’s actually increasing the faith in the world that everything will be okay. For so long, a reliable mode of trusting the fear worked. But I know it’s time to see if other things can work too. This is the frontier worth exploring.

After basking in all my beautiful anxieties for a few days, I finally started writing. As soon as I started this essay, I relaxed. As I wrote, I remembered that this is the place where I can slow down and make sense of it all. I reflected on how much I love this, right now, this writing thing. And further, that a principle from the start has been that my creative work isn’t for anything. Because even when I try to do things for something else, I lose myself, drift into cynicism, and sell out my energy.

The creative work is the win.

The Pathless Path was about leaning against the pressures of the world and creating the freedom to do work that matters, no matter what.

This, I had to remind myself, is what I am trying to do with this book:

The other thing I’ve realized is that on the other side of this tangled knot of emotions is usually unfelt excitement, and as I’ve finished the creative work of this book and moved onto the prep for sharing and marketing it, I’ve been spending too much time in worry about what might go wrong and not enough in what might go right.

When I launched The Pathless Path, I literally couldn’t imagine any of what eventually happened with the book. My “best case” scenario was breaking even. This is a recurring pattern on my path; I’m almost always more focused on limiting downside than thinking about any potential good things that can happen. Again with this launch, I was falling into the same pattern.

Ultimately, in writing this, I realized that my doubt is a blessing. As my friend Lawrence Yeo writes, “If you had no doubts whatsoever about the work you’re doing, it likely means that you don’t care enough about it.”

On my previous path, I didn’t really care if we lost pitches or didn’t do our best in a client meeting, something my Senior Partners didn’t always appreciate.

Now I care, and it’s annoying as hell.

But it also means I’m moving in the right direction. I know it’s going to be a lot of fun once people get this book and start sharing their thoughts with me. And since the first couple of people have seen the book, it reminded me why I decided not to de-risk the project by printing a smaller amount, doing a long pre-sale, or raising funds first through a Kickstarter. That would have been the path of resistance.

I wanted to print a bunch, fund it up front, and put it into the world, on my terms, as a test to see what it might feel like to do something from a sense of abundance. The mantra I kept repeating throughout the project was assume success. Why? Because it’s the opposite of what I’ve always done. Scary? Sure. Potentially financially embarrassing? Also maybe.

But what is the point of this path if I can’t take risks, try bold things, and push my own capacity for growth along the way?

The first ten days of sharing this out in the world have already been exciting. I’m feeling drawn in a number of interesting directions. I’m seeing lots of possibilities for the next phase of my journey. I can also feel the genuine excitement, passion, and care I have for my work and see how it’s showing up in my life

I want to stay on this path, and I want books to be part of it.

I wanted this book to exist. And now it exists.

Isn’t that cool?

Quick Sales Update: So far, people from 20!!! Countries have purchased the book, and including gift copies, about 200 copies of the book are spoken for. This, again, has exceeded my expectations. So thank you again for supporting this!

Also a couple of people have asked about buying bulk copies either to gift or offer to their community. I’m happy to offer a small discount and we can even handle the shipping on our end. Just