Where the Road Bends Podcast #006: Kyle Kowalski with Steve Schlafman

I went on the Where the Road Bends podcast with Steve Schlafman on March 28, 2023.

“I spend quite a bit of time online, and Kyle is just one of those people that has really captivated my attention in the last 6 months. I’m just a real big fan of his work and everything that he’s putting into the world. I can see that it’s coming from a place deep within … What he’s doing really is a service for tens of thousands if not hundreds of thousands—and I believe, eventually, millions of people.” — Steve Schlafman

Listen: Spotify, Apple, Substack, or here:

Show notes and more below.

Where the Road Bends Podcast #006: Synthesizing Mind, Founding Sloww, Finding Purpose, Intentional Living, & More

Show Notes

0:00 — Intro

2:00 — Who is Kyle?

5:00 — What is a synthesizer?

7:30 — What was driving me in my marketing career?

9:30 — Why do so many people fall into this way of being?

11:00 — What was going on in 2015?

14:00 — What happened on Christmas Eve 2015?

18:00 — What kept you working for 2 years after the crisis?

23:30 — How did you know you were ready for entrepreneurship?

30:00 — How did you know your purpose?

40:30 — What are the 4 Sloww stages?

47:00 — Where does someone start with intentional living?

51:00 — Why is this so hard for so many?

54:30 — What is unfoldment?

59:30 — What’s your current thinking on free will?

1:05:30 — What’s the ovarian lottery?

1:09:30 — What’s next for Sloww?

1:10:30 — What does it mean to be human?

Pre-Show Q&A

Steve shared some questions prior to our podcast recording. Here’s how I answered them.

Q: Who is Kyle Kowalski?

This is a two-part answer: 1) As recently as 5 years ago, I would have said I’m a Marketing Director and rattled off my resume because my identity was primarily my LinkedIn profile. 2) Today, I’d say it depends on what level you look at. Biologically, I’m ~20k genes, 86B neurons, etc. Personally, my life roles include husband, son, brother, and dog dad. Professionally, I’m a synthesizer and solopreneur. Psychologically, I’m an INTJ, Enneagram 3 or 5, DiSC Objective Thinker, etc. Spiritually, I’m unlabelable (I should mention that spirituality to me means beyond mind, direct experience, awareness, being, etc). All of these are accurate but individually incomplete; it just depends on your perspective.

Q: You’ve written quite a bit about the idea of a lottery birth ticket. Can you tell us more about what this is? How do you think your particular birth ticket has influenced who you are today?

Lottery of Birth, 🔒Premium Synthesis, 🔒Personal Lottery Ticket

Q: You ended up spending over a decade in marketing. What was getting you out of bed in the morning during that time? What was driving you then?

My self-worth was always directly tied to my work throughout my life (school, sports, career). So, my primary motivator was never extrinsic (like money)—it was always intrinsic (doing my best so that I could feel my best; feel worthy, useful, valuable, etc). It’s not uncommon that this is driven by a fear, and I think for me it was a fear of disappointing my parents and myself (although I’m not sure where that fear originated from in my life). The upside of all this is everything that comes with being a high achiever: hard work ethic, deep focus, determination/perseverance, etc. The downside is you can be very hard on yourself, nothing is ever good enough, perfectionism, etc—not to mention untangling identity from job title.

Q: You talked about being driven by busyness, unconscious consumption, and “Keeping Up with Joneses.” Why do you think so many of us fall into this trap?

I think the American dream has evolved—or maybe devolved actually—into a dream that’s primarily focused on financial and material success. For the first 8 years of my career, I didn’t really question anything about my life or life in general. I just assumed everyone pursued lifestyle inflation, keeping up with the Joneses, and busyness as a status symbol. Now, I feel I have a better understanding of why so many fall into this trap thanks to human development theories (particularly Ego Development Theory which says the adult stage in the West is conventional stage 4—that’s what we’re currently socialized/conditioned to aim for).

Q: In 2015, you had your existential crisis. What happened?

Existential crisis

Q: On Christmas eve that year you purchased the domain for Sloww. What was the kernel of inspiration?

I emailed my dad: “Just bought the domain Sloww.co. Not sure what I want to do with it yet, but I’ve been inspired reading about downshifting, minimalism, simple living, and the slow movement.”

Q: Despite this crisis, you remained in the job for another 2 years. What kept you going? Where you working on Sloww or anything else on the side?

Those 2.5 years (2016 to mid-2018) I call my years of increasing cognitive dissonance (between what I was learning vs how I was still living). It was less about a “what kept me going” and more of a “what’s killing me inside” that grew over time and eventually reached a boiling point. During my entire 10+ year career, I was always working on side passion projects in my free time (I’m an entrepreneur who unintentionally stumbled into—and then unconsciously trapped myself in—a marketing career for a decade.). The side project I was primarily working on for the better part of my entire career was an eco-friendly lifestyle brand. Luckily, working directly in the fashion/apparel industry showed me the dark/dirty side, low profit margins, etc. It’s really a blessing that I had my final “real” job at an apparel company, otherwise there’s probably a path in an alternate universe where I’m selling graphic tees.

Q: Can you tell us about your tipping point? When did you decide that you had to leave your job?

Things got really bad by early 2018 and hit a tipping point by mid-2018. I had applied to a couple other jobs in mid-2017 and early 2018, but I withdrew from the first one (Director of Brand Marketing for American Apparel) because I figured it would be “same shit, different company,” and I got flat out rejected from the second one (Director of Luxury Watches for Garmin). There were no other jobs available that I wanted, and my current job had reached a boiling point. I couldn’t do it anymore and had no other options, so I just quit my career to pursue entrepreneurship. Sometimes you need to be backed into a corner, have the bridges burned, have no Plan B—in order to finally pursue what you already know deep down you need to pursue. Quitting your career isn’t always the clear and obvious choice.

Q: What was it like immediately after quitting your job? How did Sloww come about?

I woke up at the same time the next day and got to work! My wife still works a “normal” job to this day, so I keep the same hours so we have time together in the evenings. When I quit my career in mid-2018, I had already been working on Sloww on and off for at least a year (first post on the site was mid-2017).

Q: How did you know your purpose was to “synthesize the art of living for students of life”? How does that fit into what you’re doing now at Sloww?

I actually didn’t put my purpose into that sentence (or the similar one “synthesizing lifelong learning that catalyzes human development”) until years into the journey. It’s not something I could have told you growing up or even the day I quit my career. It’s something that unfolded and became clearer over time. I had done enough purpose-finding over 2016-17 that I had a pretty good idea of where I wanted to head directionally (even without the words to articulate it at the time).

Q: You’ve talked a lot about purpose. What does purpose mean to you? How do you suggest people find their purpose especially during a transition?

I have a Premium post on the website where I went through the first 100 links on Google if you search for keywords like “purpose,” “life purpose,” “finding purpose,” etc. There are countless views on purpose out there. What I tried to do was see if there were any patterns/themes and personally try out different models/frameworks for finding purpose. Ikigai is the one that resonated the most with me, and the one I still recommend to people to this day.

Q: Can you tell me more about Ikigai 2.0? What was Ikigai 2.0 inspired by? How is your version different?

Q: We do live in a world where money is important for basic necessities. What role does money play in Ikigai 2.0?

Money is an optional byproduct. Purpose before profit. Meaning before money.

Q: Can you talk more about the four Sloww Stages? What are they and how did you come up with them?

Q: How does someone assess where they are?

I don’t offer a formal self-assessment or test or anything like that. It really comes down to being as honest with yourself as possible (which includes being well aware of your own fears and biases). In terms of some self-assessments I’ve given myself over the years:
🔒 Behind the Scenes: My Ego Development Theory Self-Assessment
🔒 Behind the Scenes: My Self-Actualization Self-Assessment

Q: For folks just beginning their Sloww journey, how do you actually go about designing a lighter life? Can you talk more about your experiences with intentional living?

I use “intentional living” as an umbrella term that encompasses concepts like: slow living, simple living, voluntary simplicity, downshifting, decluttering, minimalism, financial independence, lifestyle design, etc. Realizing that there was this alternative/contrarian path compared to how I was living in 2015 is what started everything for me (it’s why Sloww is named “Sloww” after all). There is a big shift here from an external focus to the beginning of an internal focus. And, it starts with a lot of questioning (the watershed to the first post-conventional stage in Ego Development Theory is called “Self-Questioning”).
Start here: Sloww Stage 1: How do I design a lighter life?

Q: How has the FIRE movement influenced you?

Similar to intentional living, I had no idea of the alternative/contrarian things some people were doing with their money. FIRE blew my mind when I first discovered it in mid-2017. The most influential person for me is probably Jacob Lund Fisker of Early Retirement Extreme. I have no desire to ever retire (I’d rather do what I love until the day I die and make money as a byproduct), but I saw the principles of FIRE has a way to cut our household expenses and escape my career. FIRE gives you a new perspective on what’s possible with money.

Q: What about minimalism? Decluttering? Lifestyle design?

Minimalism: There’s a difference between “radical minimalism” and “rational minimalism.” I’m a minimalist with clothing and other “shopping” aspects of life (I’m a maximalist in other areas like information, knowledge, etc).
Decluttering: I’ve done several phases of decluttering over the years along with Marie Kondo’s method.
Lifestyle Design: Lifestyle Design 101: What is Lifestyle Design? (& 35+ Questions to Ask Yourself) & Behind the Scenes: A Look at My Personal Lifestyle Design

Q: Why do you think this is so hard for so many?

I think it’s our socialization/conditioning in Western society/culture. Ego Development Theory says the adult stage in the West is conventional stage 4—that’s what we’re socialized/conditioned to aim for (and most aren’t developing to the next stage of “Self-Questioning”).

Q: Your recently wrote, I learned that everything you learn is interconnected with everything else, and so by pulling on one thread you end up being led to another thread to another thread and to another in this giant web or network of everything interconnected and so now I feel like I’m more kind of going with the flow and letting my curiosity unfold. Talk about unfoldment and how you’re embracing this to live your life?

This came as a realization through reflection. All the dots are connected by looking back and trying to make sense of them. It’s very difficult to make sense of what’s going on when you are in the midst of it. I could have never told you my purpose in prior years. It’s something that unfolded and became clearer over time. If life is an ocean and you are a wave, it’s like flowing/surfing the wave as it is instead of trying to control the wave.

Q: I want to talk about something you’ve been exploring a lot recently: the idea of free will. Can you share with the listeners your perspective on free will? Why is this topic top of mind right now?

Free will became top of mind for me last year because of what I call a “holy shit moment” of three things simultaneously converging: 1) Conceptual (lottery of birth, free will thought experiments, etc), 2) Experiential (psychological development, subject-object relationship, enlightenment, etc), and 3) Scientific (biology of behavior, neuroscience, etc). By “converging,” I mean they were all pointing at the same thing at the same time for me. That being said, I’ve learned the hard way through countless conversations on Twitter that free will is a very touchy subject. So, now I just encourage people to investigate it for themselves. I have 20+ posts on the website to help with that process (that I’ll eventually turn into an eBook).

Q: You mention that you see lack of free will as liberating, not limiting. What does that mean to you?

Here are three quick myths about free will: 1) People think it doesn’t matter because it wouldn’t change anything about how they live their lives, but my experience is that it’s absolutely worth your time and energy and matters so much more than most people think. 2) People get stuck on a determinism vs free will dichotomy (that it’s got to be this or that), but I think that’s actually a false dichotomy. 3) People think “no free will” is a belief that you hold in your mind and act according to, but it’s not a belief (it’s a realization, understanding, and clear seeing that changes your relationship with yourself, others, and life). That last one is what makes it liberating vs limiting.

Q: If you’re embracing the idea of a lack of free will, what is next for you? How do you go about navigating life and Sloww with this mindset?

It may sound paradoxical on the surface, but none of this has led to nihilism, fatalism, feelings of predetermination, or anything like that. It’s actually the opposite. I feel like I’m watching life play out as it’s playing out. 🔒 It’s less about me living life, and more about life living me. If everything is just happening and the meaning of life is just to be alive (Alan Watts)… and if everyone’s experience is valid and no experience is bad/wrong (Eckhart Tolle)… and if everything in the universe is coherent including incoherence (David Bohm)… and if we aren’t making our hearts beat, breaths breathe, or minds think (Michael Singer)… what could there possibly be to worry about (Terence McKenna)?

Q: If you could have dinner with three of your biggest influences, alive or dead, who would you choose and why?

This is incredibly difficult to pick only three, but I’d pick people who are so psychologically developed—even enlightened—that their conversation would blow my mind (I feel like I’d be able to at least intellectually understand them even though my lived reality isn’t on their level). So, maybe Jesus, Buddha, and Ramana Maharshi.
Or, Anthony de Mello, Douglas Harding, and Joseph Campbell.
Or, a fun table with Alan Watts, UG Krishnamurti, and Jed McKenna.
Or, David Bohm, Buckminster Fuller, and Donella Meadows.
Some living people: Ken Wilber, Robert Sapolsky, Michael Levin, Iain McGilchrist, Daniel Schmachtenberger, Zak Stein, Susanne Cook-Greuter, Maria Popova, Jacob Lund Fisker.

Q: Your reading list is more than 350 books. What books would you recommend for someone facing an existential crisis or embarking on a life transition?

Read whatever you are naturally drawn to read. I think Naval Ravikant is right when he says, “Read what you love until you love to read.” My natural response was to read books about life purpose and meaning. Some I enjoyed included Man’s Search for Meaning by Viktor Frankl, Let Your Life Speak by Parker Palmer, and A New Earth by Eckhart Tolle. There are others I’m excited to read on my reading list by Clayton Christensen, James Hollis, Ken Robinson, and Stephen Cope.

Q: I ask all my guests this question: what does it mean to be human?

That’s what I’m trying to figure out: why to live, how to be human, etc. At this point, I could give you an answer like the one I gave about myself: what it means to be human depends on your perspective and what you are looking at (e.g. biology, psychology, internal, external, individual, collective, etc). I will say that things get really interesting when you go a level deeper and ask: to whom does the question ‘what does it mean to be human?’ arise? This is the direct path of self-enquiry that leads to the question ‘who am I?’

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