What if you spent 2 years figuring out how to make the next 20 awesome?

Wake-Up Call #53

Ten inches of snow in one day in April. Melted the next day. Mountain life!

Six months ago, I shared something I called my 2x20 (pronounced "two by twenty," because apparently I like confusing people).

The 2x20 is, at its core, me asking myself a big question, then trying not to run away screaming:

What can I learn, do, or build in the next two years that would let me center the next 20 around simplicity, significance, and joy?

Or, in more human speak…

What if I spent two years figuring out how to make the next twenty awesome?

It's been an experiment in intentional living. A way to shape the future instead of just letting it happen to me at a pivotal moment in my life…impending doom entrance into my third chapter…ish.

It's all about designing a life that doesn't make me want to hide under the covers and pretend I'm not home (though, if you add a good book to that equation, all bets are off!).

I went public with it here on Substack and on the Good Life Project podcast a little over a year into the project. Now, seventeen months and many experiments in, the revelations are coming fast and furious. I'm shifting from "learn/do" mode into "build" mode, which feels a lot like trying to assemble IKEA furniture with interpretive dance instructions…and a missing hex wrench.

Why am I sharing all of this?

When I first mentioned my 2x20 in September, I wondered if anyone would notice, or if it would just disappear into a sea of indifference.

Turns out, you noticed! On a scale I did not see coming.

It's been the most popular thing I've written or talked about in years. The response was fast and furious, "Tell me everything! EVERYthing! I want to do my own. Now. And, are you gonna finish those fries (sweet potato, of course)?"

It seems us Gen-Xers and late Boomers (and yes, I see you “seasoned” Millennials) are wondering what's next.

We remember dial-up internet, we miss mixtapes, we still believe Chunky Bars were health food because they had both raisins (high-fiber fruit) and nuts (healthy fats), we're tired of being semi-invisible and living with low-grade existential dread, and we want this next season of work and life to feel different. Alive. And, no, we’re not too old to make it happen.

The 2x20 speaks to this in a powerful way. It says, “hey, I see you, you’re not done, and there is a better way to craft the next big adventure.”

So, I thought it’d be helpful to check in, and share the experiments and big awakenings from the last six months. There have been many.

What follows are some of the big highlights, with a side of mild amusement.

That said, if you want the vastly-expanded, oversharing version (trust me, you do!), listen to the podcast where I go exponentially deeper, and get vulnerable on a level that makes me more than mildly uncomfortable!

Here is a link for all major podcast players.

And, if you’d rather just listen now, here ya go:

For my readers, here’s a massively digested version (that is still obscenely long).

The 2x20 Project is, at its core, an experiment in living.

It's about getting out of our heads and into the world, about trying things, seeing what resonates, and learning from what doesn't. It's about embracing curiosity and play, about giving ourselves permission to be beginners again. Even if being a beginner means looking slightly foolish. (Which, I've learned, is inevitable.) And letting go of having to succeed, or be perfect.

Because, frankly, at this age, I’m too old to have to keep pretending I know which way is up.

I've been exploring this through the lens of the Good Life Buckets:

• Vitality – physical and mental health aka trying not to fall apart.

• Connection – deep, quality relationships aka avoiding full-on hermit mode.

• Contribution – meaningful, joyful work aka what I want to be when I grow up. Again.

My major focus has been on Contribution, because that's where we spend so much of our lives (and where possibility dances more often with existential dread) is.

But first, a quick word on the other two—Vitality and Connection—because they matter. The level of your least full Good Life Bucket will always limit the capacity of the other two. So, you can’t just focus on one, and leave the others to run dry:

Vitality Bucket Update (aka, My Attempts to Not Be a Potato).

I've deepened my commitment to hiking in nature, a practice that nourishes not just my body, but my soul. But, there've been some big stumbles finding ways to build “vanishing into nature” for a few hours on a regular basis in my days. And, it feels like every time I finally find a groove, the seasons change, and I have to completely rebuild my schedule to accommodate this commitment. It's like nature is actively trying to mess with me.

It brought me back to when our daughter was an infant. Every time we finally got her into a good sleep schedule, she’d pick up some kind of bug at pre-school, we’d bring her into our bed again, then have to start over a few days later when she was better.

This time, instead of giving up, I decided to get creative, and for the first time, hiked through the winter, even in wild, snow-storms. Turns out, there’s something called snow pants, and they’re really fun.

Other experiments have included ways to add resistance training into my life, something that's become a much bigger priority as I've deepened into the research on it’s importance as we age (which, I'm excited to keep doing). And, I've explored new approaches and nervous system regulation, and stillness. Lots more detail on all in the podcast, if you’re curious. Or just want to hear me ramble about snow pants, flabby muscles, and the magic of meditation.

Connection Bucket Update (aka, Not Being a Recluse).

I’ve continued my weekly “Good Life Bucket check-ins” with my wife, a simple ritual that keeps us in sync and allows us to navigate life as a team and keep our connection strong. It’s been so important, especially as we navigate so much simultaneous change and uncertainty together, including shifts in our businesses (we work together), physical and mental health, and the state of, well, everything. And, launching an amazing daughter into the world. It’s basically like marriage therapy, but cheaper, with better coffee, and no 55-minute timer.

I’ve also been doing what I call “text roulette,” randomly reaching out to friends just to say hello, to let them know they’re on my mind. It’s amazing how powerful this simple practice has become. And how many people respond with, “Wait, are you okay?” and then, “damn, that was nice.”

My Connection Bucket was feeling pretty full heading into my 2x20, so my curiosity and experiments have been more along the lines of “tuning and optimizing,” rather than wholesale change. And, again, for more detail, check out the podcast. Or just listen to me make awkward small talk about texting.

Now, it's time for the big one…

My Contribution Bucket Experiments (aka, My Existential Crisis with Spreadsheets)

I’ve been wrestling with some big questions. Like, “What am I doing with my life?” and “Is it too late to join the circus?”

I know I am, on a DNA-deep level, a Maker. I make ideas manifest. I turn chaos into…well, slightly less chaos. But, not before I turn it into a ton more.

And, yet, in the right way, with the right focus and humans, I also do love helping people explore big, impactful endeavors, often that lead to revelation and change. I get to do both with the Good Life Project podcast. We produce media and experiences, and make a difference in people’s lives. Which is pretty cool, and I’ve been doing with a wonderful team for 13 years now.

I’ve done a fair bit of consulting, speaking, advising, coaching, and strategy work, mostly with business owners and leaders, for many years. And, I became genuinely curious about doing this in a more committed way. I began to wonder if it’d make sense to explore mode dedicated training (despite colleagues who know me well, and who’d been doing this work at the highest levels on a full-time basis for years, told me not to).

But did I listen? Of course not!

I decided to run that experiment, with the curiosity being, “would these training experiences help, and would they make it clearer whether I wanted to do more advisory/coaching work?”

Confession – I enrolled in two intensive trainings, back-to back. Both consumed months of time, energy, and resources. Both were mildly calamitous, in their own ways, and for entirely different reasons. I share tons more about them in the podcast, in case you’re also exploring new education or training as part of your next season. Or just want to hear me complain about how no one seems to get how I need to learn.

And I’ve started confronting a long-held, big fear: the fear of embracing my true identity as not just a Maker, but an artist, and all the mind-dreck I have around it.

The Artist Within (aka, My Inner Weirdo Finally Escapes)

This, perhaps, has been the most significant revelation of the past six months. I’ve realized that I’ve been avoiding pouring myself into the act of working with my hands, and making physical, visual art. Not just on the side, but in a more centered, this is serious (but also really fun), kind of way.

For years, I’ve been making excuses, telling myself that I need to achieve financial freedom first. "Once I have passive income pouring in like a rogue faucet, or I’ve built and exited enough businesses, or banked enough money, then I'll finally unleash my inner Van Gogh."

That’s just fear talking. Fear of not being good enough, fear of being judged (by myself, mostly), fear of not being able to at least contribute in a genuine way to earning a living through the purest expression of my humanity. (Deep, I know. But it’s true!)

I’ve had this visual body of work inside me for years, a whole ecosystem of words-meet-images, macro and mega-scale, and what-the-heck-is-that-even-supposed-to-be creations, but I’ve been pushing it aside, waiting for the “right” time. When I finally have the money to just not care if anyone else cares. Or would pay for it.

But there is no right time. There is only now. And also, probably later, but definitely now. This is fear talking, rather than art walking.

And so, I’ve started committing to reclaiming art-level making. I’ve started reorienting my schedule around it to make it a priority. I’m soon to clean out our garage to turn it into studio space for visual media and art.

I’m also going to start showing up and sharing the work, even if it’s messy, even if it’s imperfect, even if it looks like a toddler attacked a box of crayons. Because I know that the only way to grow is to create, to share, and to trust that my work will find its audience. Or, maybe just make me feel alive, and laugh. Either way, win-win!

As I shared on the podcast, I’ve actually started taking metal-smithing class. You can’t imagine how bad I am, and how much fun I’m having!

Plus, there’s potentially a whole new, very exciting endeavor I’m looking at bringing to life around this adventure. One that’ll invite you into on a whole different level. Think of it as “Jonathan’s Art Shenanigans,” with potential for guest appearances, collective making, and…you! But that’s a story for another time.

As above, tons more detail, especially on the deeper fears and revelations around the intersection between art, commerce, truth-telling and life, in the companion podcast. I get really vulnerable. Like, “do I need to delete this later?” level vulnerable. You’ve been warned.

Big Revelations and Gentle Reminders…

This 2x20 journey has been about so much more than just trying new things. It’s been about uncovering deeper truths, about redefining success on my own terms, and about reclaim making, especially the physical act, as a core part of my identity.

Creation is not a luxury, it’s life-blood.

It’s how I breathe, how I make sense of the world, and how I connect with my soul. I've had to confront the fear of uncertainty, the fear of not knowing what’s next. It’s been uncomfortable, yes, but it’s also been incredibly liberating. I’m learning to sit with the questions, to trust the process, and to know that the answers will reveal themselves in due time. (Or, at least, that’s what I keep telling myself.)

Life in perpetual beta.

One of the biggest revelations has been the importance of living life as a series of experiments or projects. This notion wasn’t entirely new to me. In fact, I’ve always been doing it to some extent. Even the name of one of my companies, Good Life Project, contains "Project" for a reason.

I’ve often launched new ventures or creative endeavors by saying, "I wonder if I’d enjoy this?", treating them as explorations rather than permanent commitments. That framing takes the pressure off. It makes growth feel fun and experimental instead of do-or-die. And it means if something doesn’t work, I get to say, “Well, that was a fascinating experiment,” learn what I can, and move on.

I’m also learning to be kinder to myself, to treat myself with the same compassion and understanding that I offer to others. I’m learning to embrace my imperfections, to celebrate my progress, and to trust that I’m exactly where I need to be. Even if “where I need to be” feels a bit like a roundabout in the middle of a fog bank.

I don't have to have all the answers.

I spent so much of my life trying to be the person with the answers, the expert, the wizard behind the curtain (sometimes dragged in front). And, I’ve been incredibly blessed to have checked a handful of conventional boxes of success. But on the whole, pretending to have your shit endlessly together is exhausting! And, it’s a lie.

Nobody has all the answers. The smartest, most accomplished, honest people I know will readily tell you they have way more questions than answers. We're all just figuring it out as we go. Which is why so much of my focus over the last few years has shifted to identifying better questions, developing adaptable frameworks, holding onto a beginner’s mind, living in the mystery, and trusting that the answers will come when they're meant to.

And if they don't? Well, maybe the questions are the point.

And I’m learning the power of "good enough."

I will be a forever recovering perfectionist. My standard for everything I do is obsessively and unforgivably high (except when it comes to typeohz). I used to spend hours agonizing over every detail, every word, every pixel. But I realized something profound…

Perfectionism is just a form of procrastination. It's a way of avoiding taking risks. Avoiding being seen. Avoiding letting others in. Avoiding having your humanity and vulnerability and taste exposed…and rejected.

Now, I'm trying to embrace "good enough." I'm trying to ship things, even if they're not perfect, because I know that growth is better (and so much more fun) than perfection.

Again, tons more on all of this in the podcast. And, now…

A Gentle Invitation (aka, want to work/play together?)

I’ve done a lot of advising and strategy work over the years, working with everyone from individuals and founders to leaders and teams in some of the biggest organizations in the world. But, I pulled back for a number of years to focus on other endeavors, and I’ve been feeling the call back to working with people in a more hands-on way. Especially given how powerfully the whole 2x20 concept has resonated. And, how wildly-unsupported and ignored Gen-X-ish humans, in particular, have tended to be in this season of shifting life and work aspirations.

So, if any of this resonates with you, if you’re feeling that pull to reimagine your own next season, I want to offer a gentle invitation.

What if you, too, could design your own 2x20?

What if you could craft a life that feels more aligned, more fulfilling, more you?

And, what if we could do this…together?

I’ve decided to open a handful of spots for a blend of individual and/or group 2x20 coaching. It’s all about finding guidance, support, insight, and practical tools and frameworks to craft, then build your own 2x20.

It’s about bridging the gap from saying, “I wish I could do this in my own life” to “I’m doing this, and it feels amazing, and I have people to help guide and support me along the way.”

Plus, I’ll probably share embarrassing stories and questionable life advice. What’s not to love?

I’m also working with my team to craft an immersive 2x20 retreat experience, limited to an intimate group of a few dozen people. It’ll be 3-days at a beautiful destination location in the fall. We’ve hosted some pretty epic retreats and gatherings in the past, from 450 person adult summer camps (yes, you read that right) to invite-only, deeply-intentional, high-touch international retreats with a few dozen amazing humans. This’ll be closer to the latter. Intimate, grounded, joyful, connected, and wise.

If either of these options–individual or group coaching/advising or a beautiful, intimate fall retreat–pique your interest, I’d love to hear from you.

Here’s a link to a short and sweet page with more information. (Don’t worry, this is not a big launch, no fancy landing page, videos or hard-sells. It’s a simple invitation for a very small number of inspired humans)

Learn more and sign up, if it feels right.

[Update | Saturday, May 31st]

• 2x20 Coaching with Jonathan - All 2x20 coaching sessions sold out in minutes. If you’re interested in joining the waitlist for when new spots potentially open up in the fall (no guarantees), please email sparkteam@sparketype.com.

• 2x20 3-day Palm Springs Retreat in October - Only 3 spots left! If you’re interested in securing one of the final retreat spots, check out the details and register here.

The Journey Continues.

The 2x20 adventure is not a destination, it’s a continuous unfolding, a dance between intention and intuition, planning and play. It’s about giving ourselves permission to evolve, to grow, to become more fully who we are meant to be.

My next big maker-centric experiment is now taking shape in a powerful way. Excited to share more about that over the next few months. And, as I shift more intentionally into the final 6-months of my own 2x20, and transition from primarily learning and doing into building mode. It’s going to be a fun ride. Buckle up!

Thank you for being a part of this journey with me. Your presence, your support, your own stories make all the difference. Together, let’s continue to explore, to question, to create a life that truly sets our souls on fire. And maybe, just maybe, makes us laugh, love and feel seen along the way.

With a whole lotta love & gratitude,

Jonathan

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Wake-Up Call #53 | What’s YOUR 2x20?

If you’ve read this far, something about the 2x20 is resonating.

This update was a very “top-level” overview of the last 6-months of experiments, but the awakenings run so much deeper.

So, I’d love to invite you into a much richer, more nuanced and detailed exploration. In the companion podcast, I share tons more, and get a lot more personal and vulnerable.

Listen on your favorite podcast platform here, or just click play below.

And, if you’re curious about working with me, and maybe a curated group of amazing humans, to breathe life into your own 2x20, click here to learn more.

Either way, at a minimum, noodle on the guiding question, what experiments might you run, what might you learn, do, or build in the 2 next years to help make your next 20 amazing.

And, as always, if you’re inclined, share what comes up in the comments.