Speaking, Turning Off Subscriptions, Book Names | #260

March 16th, 2023: Greetings from Austin! This was a fun week as I got to hang out with many people during SXSW in Austin. I hosted an event on Monday with about 50 people, attended Steph Smith’s event on Tuesday, and was on a panel with Nick Gray, Tucker Max, Chandler Bolt, and Noah Kagan on Wednesday about publishing and books. All of this feels surreal, the fact that I’ve been able to meet and befriend so many amazing people and also get opportunities like sharing the stage with a panel of people far more successful than me. I also gave out about 200 books over the past week, leaving them around town and handing them out at events. What a week!

Pathless Path Meetup in Austin!

Speaking on a panel on Wednesday

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#1 Ultraspeaking and The Power Of Different Modes Of Communication

In the past couple of weeks, I participated in a mini-cohort of Ultraspeaking. It is ostensibly about learning how to become a better public speaker. But like so many things, it was a portal to a different way of seeing the world and for me, it’s already helped me improve how I write. Here are four reflections:

1. With writing, I can spend a lot of time thinking: I love sitting with words and thinking through what I'm trying to say. When I’m stuck sometimes I sit there for a long time and think and think and think. It usually works. So when I was forced to speak without thinking, I struggled. A lot of what I share in podcasts and other speaking things is around things I’ve spent a ton of time thinking and writing about. It sounds good but only because I’ve synthesized my ideas and put in the work. But the exercises had topics I hadn’t thought about. It was good exposure therapy and after a couple of rounds, I felt more comfortable doing it.

2. The personal is still my edge: We did this exercise where we had to tell a personal story around several random words. For example, something like “taking a walk.” My default is to talk about the personal and then quickly hide in the abstract. This became obvious in speaking. I would say something like “Walking is something all humans do,” instead of dropping into the emotional experience of going on a walk.

3. We appear far more competent than we think we are: We got to observe others go through multiple exercises and it was striking how many people would say something like “that sucked” and I would not have known without them saying anything. When we watch others speak, we can’t hear their inner critic. So don’t share the inner critic! Which gets to the next point…

4. Finish Strong, Don’t Tell The Audience “Ah that wasn’t great”: They had a great way to embrace the perception gap: finish strong. I jokingly called this the Kerri Strug principle after her miraculous broken leg landing in the ‘96 Olympics:

   

   96 was so fun

5. The details we think matter likely don’t when we go deep enough: The “accordion” exercise we did felt like powerful psycho technology the way it completely changed how I thought about getting to the essence of experiences and ideas. In the exercise, you go from 3 minutes of a speech to 2 minutes to 1 minute to 30 seconds to 15 seconds, and then back. Doing it myself and watching others, it was fascinating to see which details dropped out of the story and then when you went “back” in the other direction, what new details were added to the story. In every case, the story went from a B or C to an A. I have been thinking through some ideas on ambition for a while and I had a three-part structure of how I thought about it. But when I got down to 15 seconds, I got down to the core of it as “one of the most ambitious things in life is to live a life true to yourself.” As I moved back to the full version of this building on that core idea it was a weird feeling to notice that all the details I thought were very important in the first draft, I had easily left in the wastebasket. I’ll be using this tool again in my writing for sure

This is all to say I really loved everything I did with the team and highly recommend the course and team to anyone intrigued to do more speaking work.

Disclaimer: I did their gifted “creator cohort” and while they said it would be nice if we shouted them out, they 100% positioned the course as a gift with no expectations. I think that’s pretty cool and wish there was more of that energy in the world. So I am gladly writing and sharing a bit more about my experience.

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#2 Shifting (Back) To One-Time Gift Pricing

Last week I decided to turn off monthly subscriptions on Substack and Circle. I was spending far too much time doing stuff like synchronizing lists, manually adjusting access, processing refunds, and other administrative tasks. Given the limited time I’m devoting to work, it was a costly distraction from writing.

Moving forward, I’ll still be running the pathless path community but access will be gated by a pay-what-feels-right one-time fee. There is a suggested gift of $150 but if you want to pay less or more, that’s up to you.

As soon as I made this change, I felt great. While I cut off a $1,500 monthly recurring revenue source (though it was declining), I’m much more excited about supporting the people who decide to pay an amount that feels good for them and not feel the pressure of having to “earn” the monthly payments (whether that was true or not).

For the longest time, the writing here and in the Boundless/Pathless universe was under-monetized. I had payments open on Substack and before that on Patreon where people could support my work but it was always optional and before the community, it was less than $200 a month. From 2018 to 2021 those gifts were the only money I made from writing and the small amounts were such a vote of confidence from others to keep going. But now, I am making a decent amount of money from my book and the truth is the monthly payments from the subscriptions were not as motivating.

While writing this upcoming small book, I was writing about doing the work that feels good right now and that you know you can keep doing for a long time. For me, that’s writing and I suspect it always will be.

I’m almost at my seventh indie anniversary and it’s still surprising how often you need to reflect and pivot on this path. With so many people following me now, I get a little more nervous about people judging me but I also sense that people like this newsletter because I tend to tell you exactly what I’m thinking. And one of the things I’ve been sensing is that people opting into monthly payments don’t feel good about them either. As the monthly payment has appeared almost everywhere in the digital creator space, I sense some of the magic of supporting someone has dissipated on both sides of the transaction.

I haven’t figured out how to “do” a community well over the last year and a half from a business standpoint and one that runs on recurring payments. Despite this, it’s been inspiring to see the connections happening all over the world through the community and it seems important to keep this space alive.

I launched the community to give people a place to find others on unconventional paths and it was never something I wanted to build as a core business. With this shift, I’ll be able to shift back even more to the writing, thinking, and creating that I can commit to without any sort of incentive.

In the coming months, I should have some exciting updates about:

• A new self-paced onboarding course for the community

• A workbook companion to The Pathless Path

• My next book (title TBD)

I’ll be previewing and sharing all of these with people in the community in the coming months. You can find the link below.

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#3 Upcoming Book Names

I’m writing a short 20k-word book about how I had to look for different approaches to work after dealing with health issues, how I lost my edge on the traditional path, and how I stumbled upon what I’m calling “good work.”

I plan to release it sometime in April or May but I’m playing with some titles.

Here are some working options (full names here I couldn’t fit them in the poll):

1. Post-Hustle: My Accidental Quest For Good Work

2. Hardly Working: How I Lost My Edge & Found Good Work

3. The Search for Good Work: subtitle tbd

4. You Don’t Have To Grind: Finding Good Work & Embracing Healthy Ambition

5. Losing My Edge: The Art of Working Less & Finding Good Work

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Cool To See You Down Here 👋

Here are four things worth checking out

1. If you’d like to meet others on “pathless paths”, you can join The Pathless Path Community

2. Buy or listen to my book, The Pathless Path. If you’d like to do a bulk order you can do that here for a discount.

3. You can buy pathless path swag like a hat or shirt here

4. Subscribe to my podcast and leave a review.

Write Of Passage: Learn to write online and become an internet citizen

Affiliates: In addition, I recommend all of the following services: Ali Abdaal’s YouTube Course, 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.

Submissions: Want to share your journey with my audience? I accept drafts for submission.

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