Audacious Goals Scare Me | #227

June 17th, 2023: Greetings from Austin. It’s toasty here, hitting 100 most of this past week, but I haven’t found it too bad. It feels pretty similar to Taipei summers.

+ I joined Khe Hy on his newly launched “Rad Friends” podcast and talked about our relationship with work for an hour. It was a pretty personal conversation for both of us. You can check it out here.

#1 Dream Bigger?

In my jobs, managers told me I needed to “self-promote” more if I wanted to get promoted. I rarely followed this advice and instead focused on trying to do good work and getting raises and promotions by changing jobs every year and a half.

On my current path, I’ve called my approach the long, slow, stupid, fun way. It’s sort of an explicit strategy built around how much I hate trying to play the self-promotion game. Here’s how I described it almost two years ago:

Long: Focus on the meta-game of finding the work I want to keep doing indefinitely. Don’t get distracted by shiny objects.

Slow: Do things slowly. Start small and level up over time.

Stupid: Lean against obvious ways to make more money when you sense it’s not the thing that will matter over the long run.

Fun: Am I still having fun? Keep going. If not, quit, optimize, or scale back..

My podcast, newsletter, and sharing of ideas on Twitter and other places all feel like infinite games I can keep playing, and because of this, especially in the first few years, I didn’t take many extra steps to share my work. But this long-game strategy is also a good fit for me. In contrast to what a lot of other people say about creating stuff and sharing ideas on social media, I don’t feel pressure to keep doing it and don’t get drained or feel negative about how I’m spending my time.

The weird thing about the last year is that the conversation of ideas I’ve been exploring for more than five years has turned into something I can actually make money from. This is unexpected. I expected to break even or maybe even lose money on the book. I was so committed to continuing to write about these ideas that I didn’t even consider the book a potentially profitable thing.

To date. I’ve made about $110k in profit from the book and get messages almost every day from readers telling me how much they loved it. This gives me a strong incentive to play the attention game. The more people that get exposed to my ideas, the more money I can make, and the more I can continue to write about these things.

But it makes me uncomfortable. Despite all these people telling me that the book is good, I still have a default hesitancy toward doing anything too bold or out of character.

From 2018 to 2021, I operated in monk mode, staying purposefully small, explicitly rejecting anything that looked like a status or attention game and focused on exploring new ways of working and designing my life. One of the most impactful things I did during those years ended up being my attempt to adopt an anti-strategy of rejecting the popular advice to “protect your calendar” and opening up my calendar for curiosity conversations every Wednesday to anyone that wanted to talk with me. God bless Angie for listening to the nearly 400 calls with strangers I had, often repeating the same stories multiple times each Wednesday. But I kept doing them because they were incredibly generative, and the seeds of many ideas that ended up in my book were planted in those calls.

So at the beginning of 2022, I more or less maintained this same approach to life after the launch of my book. I spent no more than 2 hours on my launch, consisting of some tweets and a newsletter post, and resumed normal programming. It’s no surprise that my first month of book sales ended up being my lowest.

Two things made me get a little bolder in sharing and talking about the book. First, I was starting to receive long and thoughtful replies from people reading my book. They weren’t normal thank-you messages. They had the energy of “I NEEDED THIS BOOK SO BAD. IT IS SO GOOD,” and “I BOUGHT 10 COPIES AND FORCED MY FRIENDS TO TALK ABOUT IT.”¹

I started receiving these messages pretty early, and despite the relatively low sales, I suspected that the book had more potential than I expected. I knew I should lean into it a bit more. This is part of why I doubled down on my podcast. I had been running it since 2017, going through a few name changes from Boundless to Reimagine Work, but it felt like it needed a refresh for me to be excited about it. I renamed it The Pathless Path Podcast, started doing videos, and hired an editor. It was a way of saying to myself (and the world) that this conversation matters; let’s keep having it.

The second thing that nudged my brain out of monk mode was finding out Angie was pregnant in July. From that moment, I rode a wave of pre-dad energy to completely rebuild my Think Like A Strategy Consultant course over the summer and actually start to take the corporate opportunities I was seeing a little more seriously. This was something on my mind for a couple of years, and when I finally took everything to the next level, it gave me a little more space to lean back into the book.

In October, I arrived back in Austin, and at that point, I had sold 5,000 books or about 500 per month. But since then, I’ve sold about 22,000 more, or about 3,000 a month.

The only major thing I did was gift my book a bit more aggressively. I gifted 275 books to the EconoMe conference, 100 to the Nomad City conference, gave away 200+ books following the David Senra podcast episode, and left books around Austin:

A few of my friends have recently been pushing me to go harder.

I’m naturally not a goal person, but it’s something I’m thinking about differently after the conversation I published with podcaster Danny Miranda this week.

His goal is to sell out Madison Square Garden for a live podcast recording. When you first hear this, it sounds crazy. But he made a good point: “A lot of people choose outcomes because other people think they're amazing, but I'm choosing the outcome of Madison Square Garden because I think it's amazing.”

His own reasoning rhymes with a lot of how I think about my path:

“how do I find a goal or something so audacious that is so inherent to me based on my own life experience and trajectory that I can aim for, but not feel attached to if I don't hit it, that will still be fun if I'm in the process of achieving it.”

Which has me thinking, What is the audacious goal that’s still fun for me to pursue even if I don’t reach it?

Selling one million books? That was Danny’s prediction in January when we had lunch. It made me uncomfortable, but it did get me thinking.

Why don’t I ever generate goals like that?

I understand that other people get inspired by them, but I really don’t.

What if I pretended I cared about them?

I’m still not good with “self-promotion” and probably never will be. But this week, I created a workaround. I scheduled an “ambitious afternoon,” something I plan to do each quarter (or maybe more if it works well), where I’ll pretend I’m a bit bolder than I am.

This week I made a list of big podcasts and other people who could help me share my book. I sent out a bunch of e-mails and DMs and made some asks. My stomach felt a bit queasy, but I got through it. Maybe people will reject me or laugh at me. Oh well.

It also felt kind of good. Being a bit bolder with sharing my ideas is a reminder that I still care about this work, and I think it matters.

My struggle in this area is why I spend so much time helping and supporting others. I don’t want them to feel weird like I do. I don’t want others to feel ashamed of their work. So maybe it’s time for me to be a little braver too.

What do you think? What are some bold goals that would be fun to follow along with?

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#2 Solo Podcast Episode

Inspired by Jenny Blake, I did my first solo podcast episode in a very long time this week going through how I thought about turning down a book deal. You can check out the episode and let me know what other topics you might want me to riff on.

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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) meetups and general supportive vibes.

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1. Note: I don’t recommend forcing your friends to read my book. I personally am pretty hesitant about forcing my ideas on other people. Work is such a heavy topic. But if people are receptive to questions like, “have you struggled with your relationship with work?” then those people tend to be pretty excited that my book exists.