Mailbag: Rituals, Strengths, Desires, What's Next | #178
April 15th, 2022: Greetings from Austin! I reached 2,000 book sales this week across all different platforms which is simply mind-blowing. Thank you so much to all of you who keep sharing your reflections on the book and buying them for friends. If you haven’t grabbed it yet, what are you waiting for?
🎧 I was on Modern Wisdom with Chris Williamson this week. Chris is an incredibly curious podcaster who’s done over 450(!!) episodes across a wide range of topics. We had a fun conversation talking about aiming at happiness instead of success, creator paths, infinite games, having “enough,” living in Austin & more. You can listen here or watch it on YT.
⁉️ Answering Questions From Readers!
#1 Charlie Becker asked: “I understand navigating our own path, but I think people need to aspire to things to contextualize their journey. People especially love rituals and rites of passage. To this end, have you heard of any ideas or suggestions you like for alternative fixed points?
This is a great question because I think it’s a struggle for many on unconventional paths. When you take a path that doesn’t fit in the narrow range of options people see as “normal,” a natural tension shows up in your life. Early on in my journey, I was surprised and shocked at this feeling. My first impulse was to make it go away but having recently run away from a structured path, I sensed that I should lean into the unknown. This is really hard, however, and the pressure to do things to make yourself legible to others can nudge people to adopt goals, labels, and pursuits that are not inherently their own (see: hustle traps).
You mention alternative “fixed points.” This is an idea from Venkatesh Rao’s Art of Gig newsletter (now sunset, but I believe his book is coming soon??). He argues that if we don’t pick alternative goals, ones that align with our own unique interests and desires, we accept default path goals. As he says about the US:
…the standard fixed point of homeownership. As in, ‘no matter what happens in the future, I’ll be a homeowner.
When your own goals overlap with the most popular goals in your country this is a great thing! Yet for people on unconventional paths (especially those with more volatile incomes) these goals can be constraining. We need alternatives. The challenge is that if we try to replicate the common fixed points with similar ones we get stuck. What is the self-employed version of a promotion? A raise? A nice title?
A helpful shift can be to move away from the “having” mode (as in I am doing this for X outcome) to “being” mode goals. Three of my own from a previous essay:
I want to continue to be able to:
Do all my work remotely
Take six months off anytime
Have kids without needing to use year-round daycare
I never will “arrive” at these goals. I’ve more or less achieved #1 and #2 but they could stop being true at some point in the future. This is pretty motivating for me and works well but these aren’t natural rites of passage or rituals. So what could be?
One answer is a long-term creative project. I’m guessing this is something that has to be at least six months long, is beyond your current capabilities, and is something you would actually enjoy doing. This is why it’s not surprising to hear about creators attempting documentaries, or short films. They usually check all these boxes.
For me, writing my book served as a rite of passage. I started the project still somewhat uncertain about my path and emerged 13 months later with renewed optimism and confidence about my future. Finishing something beyond what I knew I was capable of was an incredible feeling and perhaps might match what some of my old colleague might feel upon being named Partner at a consulting firm.
The challenge is that my rite of passage doesn’t come with any “proof” that is accepted in broader society. I deal with this by finding friends who do want to celebrate these things and find it normal to share these “wins” in group chats and in person. This means we could probably use a little more ritual in the independent / solo creator / internet weirdo world.
Some ideas for rituals:
Celebrating annual “birthdays” of people going indie (my 5-year indie birthday is May 25th!)
Making it cool to brag & celebrate reaching certain dollar amounts, sales numbers, revenue, etc… in certain products (e.g. course sales, freelance income, book sales, subscribers, podcast episodes).
Throwing away symbols from past identities or lives (for example, Michael Ashcroft told me, “when I left my job I wrote down all the reasons I didn’t like it on my business card and then burned it” 🔥
Ultimately, I see the lack of clear “proof’ of success as an opportunity of the pathless path. Learning to disconnect from the approval of others can be a useful way to reconnect with what you really want. This leads us to the next question:
#2 Nick asked several questions that sort of boiled down to “how do you know what you want?”
This is an interesting question but I’m not sure I have a great answer. This is partly because I’m not sure it can ever be answered.
In my current state, I think I “want” my current life but am not totally sure.
My doubt comes from being on my previous path and also being convinced I was doing and had everything I wanted. Through refactoring my life, I came face to face with the reality that I had overvalued certain things (nice apartments, eating out) and undervalued others (like time for creative projects and writing).
What I am sure of is that my current mix of activities, projects and relationships with people feels substantially better than on my previous path. I don’t find myself doing many things I don’t want to be doing and am quite happy and content most days.
If I were giving myself advice when I was 25, I might tell myself:
There is a state possible where you can feel deeply connected to yourself and the work you do and that it’s worth searching for.
I think this is something worth buying into for most people but necessitates an optimistic stance that many people struggle to find.
A simpler approach is likely just to test things. One thing I’ve noticed about following an unconventional path is that people tell me all the time,
“I could never do what you do!”
“I could never not have a home base!”
“I could never not have a salary!”
If you find yourself using the phrase “never” I would guess that you’ve never tested that belief. If you had, you would have said “I tried that and it wasn’t for me.”
So I’d suggest testing stuff.
Have a hunch you might like freelancing? Find a pro bono client on the side of your job. See if you like it. Have a hunch you might like long-term travel? See if you can find a month off first. Have a hunch you would be better off not drinking? Stop drinking for a month.
Test, reflect, then figure out what to do next.
The pathless path has forced me to do this and I’ve found it immensely valuable. I wish I had tested more things sooner.
And beware or when you say “I could never…”
You might be wrong.
#3 Nick also asked, “how do you know what your core strengths are? I know things like Strengths Finder exist but I cannot imagine it being truly useful in this regard.”
I think my initial reaction to this is your belief that something like strengths finder would likely not be useful. You seem pretty convinced. For me, I tend to be default skeptical as well but sense there is useful information in continuing to be open minded and curious about myself.
I took strengths finder in 2015. Here are my results
Maximizer: People who are especially talented in the Maximizer theme focus on strengths as a way to stimulate personal and group excellence. They seek to transform something strong into something superb.
Relator: People who are especially talented in the Relator theme enjoy close relationships with others. They find deep satisfaction in working hard with friends to achieve a goal.
Ideation: People who are especially talented in the Ideation theme are fascinated by ideas. They are able to find connections between seemingly disparate phenomena.
Adaptability: People who are especially talented in the Adaptability theme prefer to “go with the flow.” They tend to be “now” people who take things as they come and discover the future one day at a time.
Connectedness: People who are especially talented in the Connectedness theme have faith in the links between all things. They believe there are few coincidences and that almost every event has a reason.
Wow! These are way better than I remembered. So in terms of nailing down my strengths, I think I’d definitely recommend this test - plus I don’t think it’s that expensive.
Yet I think the hesitance you are expressing probably relates more to what to actually do with the information. In 2015 here are some suggestions from my report:
“Find a workplace in which friendships are encouraged. You will not do well in an overly formal organization. In job interviews, ask about work styles and company culture.
“Seek a career in which you will be given credit for and paid for your ideas, such as marketing, advertising, journalism, design, or new product development.”
Hmm - that’s basically what I tried to do for two years and couldn’t really find it. The option that seems obvious to me now (carve my own path, share ideas on the internet, build digital products) was not even in my imagination back then.
This points to an annoying truth - that figuring out who we are and then trying to realign our life around those things is an annoyingly slow process.
Did the test help me? It probably sharpened my awareness 0.1% more than before I took the test. But it wasn’t the information that led me towards a better path. It was my curiosity about myself that drove me to take the test in the first place.
#4 Shubhobrata asked: “How do I define the starting point of my new journey on the pathless path? (My current job requires me to stay in it for at least 5 years before I can quit- it's a contract, I don't like my job but can't quit it either at the moment because of this.”)
This is something I write about in my book and is something I wish more people were aware of - that the starting point of new paths is often impossible to pinpoint until you are looking back. And even then, its easy to trick ourselves into thinking there is a single “moment.”
Here is what I said in my book:
I had no master plan to quit my job. Even now, several years after doing so, when people ask about my journey, I’m more confused than you might expect. Choosing to leave full‑time work was not a single bold decision but a slow and steady awakening that the path I was on was not my path.
It’s tempting to tell a simpler story. People want to hear about bold acts of courage, not years of feeling lost. On my way toward leaving my job, I never had a clear picture of my next step.
On podcasts, people like to ask me, “when is the moment you knew you had to quit.” Here’s a clip of Amanda Natividad asking that:
Getting back to your specific question, I sense that you may already be on an unconventional journey, you are just distracted by your current employment status.
I worked for several years after my own unconventional journey started. I wrote on the side, created online courses, consumed a wide range of inspirational podcasts and books, and even made some meager side gig income. At the time, I would have denied being on anything except a conventional path.
The pathless path is more a mindset than a destination, label, or goal. It’s leaning into what your own desires, interests, and motivations are than what most people do and that you might discover alternatives that were not apparent to you before.
#5 Questions From Twitter
I hate screwing with the timeline (Early Edition always freaked me out a bit) but if I have to answer I might say:
You have the right impulses of prioritizing friendships and socializing but maybe drink a little less
There are amazing books. Find them ASAP
Go work in tech
Write about things that interest you
I have a recurring reminder on my calendar each morning. It looks like this:
I go into why I did this in my book, but this has been popping up on my calendar since 2014. Health is first because I was emerging from a pretty rough health crisis in my life and knew that without health, I really didn’t have much. Health is still very central to my life mostly because I have on and off issues, I’m still dealing with.
This sounds bad but it helps me focus on trying to feel good - I eat well, don’t drink, surround myself with good people, sleep a lot, and don’t overwork. I know what it’s like to feel suboptimal so I build a lot of my life around one simple reality: I might not be able to work for long stretches of time. This probably is part of why I don’t want to scale, grow, or commit to extended stretches of in-person work.
From April to June 2020 I was crushed by the side effects of tooth extraction. It was terrible and I couldn’t figure out how to bounce back. I was sleeping 12-13 hours a day and was crushed with brain fog. Luckily, through trial and error I figured out that B12 injections seemed to help me feel normal and I’ve been relying on them since.
Over the past ten years, it’s quite obvious how important my health is. But it’s also helped me to clarify other things that are important: my creative energy, my relationships, my family, and my partner.
I’m grateful for my health crisis when I was 25 to clarify this for me and it’s really helped me make decisions as an adult ever since.
In terms of work, I really feel like I have more than enough. As Derek Sivers says:
Are you helping people? Are they happy? Are you happy? Are you profitable? Isn’t that enough?
Yes, yes, yes, yes, and yes.
Most of what I want to do feels like a continuation of what I’ve been doing:
Keep learning new things
Keep improving my StrategyU offerings and leaning into corporate courses and coaching
Continue to write, most days
Do more video essays on YouTube this year
I also feel like I’m open to signals from the universe about interesting projects to pursue in the next year. I am paying attention…
Really the biggest challenge and thing that is “next” is probably starting a family. Angie and I definitely want kids and I am ready. Hopefully soon :-)
If you liked Man’s Search for Meaning or Survival in Auschwitz, you’d probably like The Forgotten Highlander. Here are a few quotes:
Hey There! Thanks for reading!
I am focused on building a life around exploring ideas, connecting and helping people, and writing. If you’d like to support my journey, the best ways are to:
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