Boundless Is Now Pathless & Other Updates

Hey all,

I sent a short note in last week’s issue but wanted to send a little more detail.

Over the past few months, I’ve been doing the inevitable maintenance work that comes with starting a bunch of stuff over a six-year period of working on my own. On an indie path, this kind of work is not fun but ultimately necessary and over time can serve as useful inflection points to inject new energy into our paths.

Over the last two weeks, I’ve moved my community and this newsletter to the pathlesspath.com domain as well as the podcast. I’ve also renamed “Find The Others” the Pathless Path community. Most of these changes took less than a couple of hours but I probably wasted far more time thinking about them over the past several months. Now that they’re done I feel excited and optimistic about the next few years and the “game” I’m playing feels more coherent. This is something I plan to write about more: the value of having a coherent meta-strategy that can give you a sense of how to spend your time on a day-to-day and week-to-week basis.

”Pathless”: Different Name, Same Themes

I never felt attached to the “boundless” name but it was a useful umbrella to explore a wide range of ideas since 2017. Nothing really changes with the renaming. I’ll continue to explore the same themes: work, unconventional paths, the creator economy, self-publishing, and travel.

The biggest benefit is that things are just a lot simpler. Here are some of the changes I’ve made with my personal ideaworld:

• From Reimagine Work to Pathless Path Podcast (May 2022)

• Boundless Newsletter => Pathless Newsletter (Oct 2023)

• Find The Others => Pathless Path community (Oct 2023)

• Pathless Path book

• think-boundless.com => pathlesspath.com and paulmillerd.me (in progress)

Overall it just feels simpler and will be a lot easier to talk about to others. In addition to renaming the newsletter, I’m going to slowly move my writing from think-boundless.com into two places:

1. personal website (tentatively paulmillerd.me but open to other suggestions) - more exploratory writing, travel reflections, and emergent topics (Note: I’d love some help on this so if anyone’s looking for a gig on moving and setting up a new site, hmu)

2. pathlesspath.com - this will be podcast summaries, writing on self-publishing, and writing related to the book themes and this newsletter

This isn’t perfect but feels good enough to move forward and at least enables me to stop thinking about all of it for another year or two.

What is happening with “Find The Others”?

I toiled for the last few months about what to do with the community I launched, “Find The Others" earlier this year. I realized that the biggest issue was that I couldn’t even articulate what I was trying to do with it and because of this I was always hesitant to even share it was a thing people could and should join. Of course, this is not a great strategy because people want to join a place where they can actually connect with other people.

So I put on my strategic business school brain, channeled my inner Simon Sinek, and asked the most important question: WHY?!?!?

Materials from Greg Isenberg’s writing on communities, a review of many other similar spaces, and thinking about Pathless Path as an idea helped me figure it out, or at least come up with a better answer than, I’m not perfectly sure. I landed on three goals that apply not only to the paid member community but this newsletter and what I’m up to more broadly:

1. Help people find others on Pathless Paths: Let my work, digital spaces, and writing serve as nodes that enable people to find others on similar journeys

2. Highlight on-ramps for life as an Internet Citizen: While the Internet is not perfect, it’s the best place to be if you want to do creative work outside the traditional institutions. Help people decide how to engage in pragmatic ways to share their work, make a living, and make some friends along the way.

3. Help people build confidence to keep going: Tactics are sexy and can help us improve our competence but confidence comes from learning to trust ourselves, and understanding why life outside the default path feels so weird.

And then I listened to this podcast with

Lenny Rachitsky

about how he is running his community alongside a newsletter. He realized early on that his main contribution was continuing to write the newsletter and creating great content. It made me realize that instead of writing and creating more stuff like mini-courses, essays, books, guides, and tools (something I actually did more of before the book), I’ve been playing community manager and admin, a role I’m not particularly good at. Company of one is great until you’re doing all the roles you suck at.

The obvious answer was: hire someone! I don’t know why it took me so long to get to this point, especially since working with a podcast producer has gone so well. I think part of it is my own resistance to anything that looks or feels like a company combined with the fact that I can figure out most things given enough time.

Luckily, I found someone the right person at the right time, someone who is actually way better at thinking about this stuff than me,

Sri Karnic

, who has been on her own self-employment journey over the last couple of years. She sent me a quick loom of thoughts on my situation and it blew me away. Watching it I realized, I was a dummy. I’ve been doing all these things I’m not good at and there are other people out there who are actually way better and enjoy these things!

Working with her has given me a lot of confidence that I can engage with the community in the flow of my work and be able to focus on writing and getting back to simply creating things that help people, something that’s endlessly motivating for me.

I’m excited to work with her and in the meantime check out her writing on trying to remain “unemployable,” which I’ve really enjoyed:

So I’m “Relaunching” With A Much Clearer Offer:

I’m excited to “relaunch” this community with some clear guardrails:

• I’m going to focus on contributing to the space from a content-first perspective: how can I create things that help people or at minimum are useful in achieving the above goals

• I’m going to lean heavily on helping to promote other people to host in-person meetups. There have been dozens of one-on-one hangs facilitated by the group and a few bigger events in London, Austin, and Taipei. We have one event coming up in Barcelona in November and another in December in NYC. I’m going to be giving $100 to any in-person event to help facilitate these and also am looking for sponsors who might want to help us go a bit bigger.

• Incentivizing long-term memberships. I’ve made the yearly and lifetime deals the “best” ones. $20/month $150/year or $299 for a lifetime

And as an early “black Friday” deal, which I’ll run all of November, you can get 15% off the annual or lifetime plans (had to manually adjust the lifetime one to $250)

As a paid subscriber to the Pathless newsletter, you get access to the Pathless Path Circle community and:

• Occasional paid content

• The Pathless Path Circle Community

• Access to tools & resources to help you on the pathless path

• Access to in-person events

• Monthly “meet the others” virtual hangouts

• Member-led writing and co-working sessions

One thing Lenny seems to have done well is organically react to opportunities in the group. As more people join, there may be more opportunities and I’ll be looking to members who might want to take a leadership role in leading events, a book club, and other things like that.

I recently surveyed members of the group and here is what people said:

I've met so many interesting people through this community and had some excellent 1-on-1s following group sessions. It's a fascinating group of individuals, all seeking more autonomy and a higher purpose in life. Think it's great how your message and vibe has united creators who would never have known about each other. - John Nicholas

It’s made my transition to a sabbatical much easier and opened up new opportunities for what might come next. -Aashay Mody

It's been nice to have conversations with some people who are in a similar journey. The calls, both group and 1-on-1, have are a helpful reminder that you're not in this alone. Jon Santiago

I love this community because I feel so natural and welcome in it! I've met so many friends who support me in my life and creative pursuits. Irena Spegar

By meeting with Paul and the group online for writing sessions and hangouts, I was able to get re-motivated to work on my own book and make meaningful progress after years of being stalled. -Jen Adams

I've gotten a lot of support from the group (and a lot from you) when navigating how to wind down my 9-5 and transition into sabbatical mode. I feel like it's just the beginning, -Saalik

Paul has the ability to shine a light on the gifts and talents people have before they believe in it themselves. This generous nudge is what most people need to build confidence in themselves to leave the traditional career path. Paul's community is like a floodlight—and an extension of his gift to help you find your way with the support of a diverse and international group of people. -Nate Kadlac

I just met up with a FTO member, Brandon and we have been walking around Lisbon and talking about the pathless life and how we navigate it. Then another member of the walking group said she also heard about your work from a friend in the US and we all connected and 'found the others.' :) -Kelly Davis

Being part of FTO community has been such a welcome addition to feel less alone on this path. I joined a year before I took the plunge and used the time to meet other likeminded people who have supported me when I eventually made the plunge. People are super friendly and willing to help on questions like defining rest or even giving direction on what next steps to take with my course. I highly recommend trying it out! -Vinamrata

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Thanks For Reading

Here are three things worth checking out

1. If you’d like to meet others on “pathless paths”, you can join The Pathless Path Community if you want to hang with us too, or if you are already a subscriber, get access here.

2. Buy or listen to my book, The Pathless Path. If you’d like to do a bulk order for gifting purposes or a book club message me and I’ll ship them to you at around $5 per copy via Amazon

3. Subscribe to my podcast and leave a review.

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.

Sponsors: I accept the occasional sponsor, please submit a request through Passionfroot

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.