Today marks dispatch #50.
This minor benchmark has me considering how much I’ve come to appreciate my cadence of writing and publishing. For an exercise that began as uncomfortable, it’s a notable pivot.1 Which got me thinking about that through-line of discomfort, what lies beyond, and how that’s shown up in my life.
→ Today’s Writing
I’m mostly okay with the faceless strangers I’ll never meet, but I’ve always been embarrassed about my real-life human connections seeing what I’ve produced. It’s a loss of control and compartmentalization that stirs up a whole mess o’ fears.
The beginnings of this newsletter were no different. I’d fret over a piece, fret over sending it out, and then mostly fret over who might read it. I even deleted a few subscribers, such as my mother-in-law… though she did find her way back on. Sorry, Linda.
Two years on however, and this regimented exposure to discomfort has reshaped once-cemented patterns. I’m now writing these fairly enthusiastically and I’m legitimately excited that Linda is—apparently, by the numbers—one of my biggest fans. Thanks, Linda.
That awareness that I should probably push through my initial discomfort is a now a well-worn path for me, but it wasn’t nearly as obvious a decade or two ago…
→ Getting Comfortable Being Uncomfortable
A friend of mine is currently in rehab. Not his first stint, but that’s usually how that thing goes.
He shared with me yesterday that a speaker had said, “The only thing you have to change is everything,” and how much that resonated, and scared him.
I echoed that this, too, was my experience. I’m 13 years sober now and have found the “Don’t do drugs” bit to be comparatively easy, relative to the whole “Change everything about your life and rewire decades of behavior” bit. Orders of magnitude.
I leaned on substances for all the classic reasons, but a prominent one was: Acceptance, love, and connection are deeply desirable, but figuring out how to get them is hard, and trying (and failing) is scary. Basically, being comfortable in your own skin. Putting work into that seemed much more critical to my long-term prospects than merely staying away from open-air drug markets and Lou Reed albums. Fix the first part, and the second part (sorta) falls into place, is what I more or less shared with my friend… Getting comfortable being uncomfortable is kinda the whole thing...
One early nudge I’m grateful for in this regard: I had this counselor 13 years back who was big on exposure therapy. She’d send me to bus stops to strike up conversations with strangers and arrange for me to meet her coworkers in an otherwise empty break room for lengthy talks. New people, new conversations, every day. Wildly uncomfortable at that stage. But… it absolutely got easier and became a foundation for new levels of comfort and capability.
→ Extreme Exposure
Maybe surprising, given the above, but I’ve said yes to a handful of public speaking gigs. Sometimes speaking to dozens. Sometimes hundreds. I never wanted to do any of them. It’s days of meaty flop sweat and undulating panic… and that’s the baseline for it going well!
But I’ve learned there’s juice worth the squeeze… resilience, skills, and a new threshold of social ease to be gained. This has to be good for me is the ringing thought when signing up for something so patently unpleasant. I’m building up a tolerance, and that opens the door for a smoother existence, personal evolution, and future opportunity.
→ Connection
In August 2015—apparently ten years ago now—I’d signed on for a timber framing workshop. I knew it would be a net positive, but man, was nine days living and working alongside a dozen strangers an intimidating proposition. I was a ball of nerves standing there sweating on a Brooklyn street corner, waiting to catch my ride to the property. Three cramped hours of treading social water with a four shiny new strangers seemed as miserable as it was daunting.
And I was right… it wasn’t a fun car ride. Not for me, anyway. Though I also know my ever-increasing social dexterity in those situations probably left the crew none-the wiser. So, baby steps.
I couldn’t have seen this coming from the street corner, but it turns out that Tom—who was piloting the car and teaching the workshop—is a pretty special human and I now count him among my most cherished friends.2 And while the workshop had its challenges, it grew more comfortable and ended up a pivotal event that produced a number of long-lasting relationships—and lit a fire under Molly’s and my own aspirations for land ownership and building projects.
→ Enthusiastic Encouragement
I sell building plans. A strange little business that Molly and I stumbled into as our land and building projects got some attention and folks would reach out for help with their own inspired builds.
An evolution that might come as a surprise to those who have known me in real life, as I’m a person who’s been occasionally abrasive and particular about who I’m willing to engage with—my customer service is EXCELLENT.
One theory I have on why I get such rave reviews is that I’m incredibly encouraging.
It tracks. My role as a champion and resource for DIY-can-do-attitude comes on the heels of creating, or saying yes to, so many experiences that were difficult yet ultimately rewarding. I know well the immense sense of accomplishment that comes from completing a seemingly impossible project that’s beyond one’s experience and skillset, and I’ve seen so much enrichment from stretching myself, building beyond my limits, and from the various little uncomfortable habits I pursue, that I’ve landed as an outsized advocate for pushing those boundaries of comfort.
“You can do this” and “Give it a shot” are frequent refrains when chatting with folks who doubt their ability to build a tree fort or a playhouse or something grander… ever a push to just create—anything—whether it’s from my plans or an entirely different project they’re mulling over.
“Start small,” I tell them. “Just start…”
…All this cajoling and persuasion is buoyed by a voluminous undercurrent of Yes, it’s going to be hard and occasionally unfun. Uncertainty is scary. But, not only can you do this thing, you’ll be better for it. You’ll end up more capable, confident, and primed to tackle the next challenge. It’s worked for me.
Discomfort → Growth
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Ironically, writing this post makes me uncomfortable. But it’s fine. I’m good. Pushing through it. Thanks for asking.
If you want to go a layer deeper on this, I spent a few years taking trips to hang with Tom while convinced that he probably didn’t like me all that much. (I’ve felt this way about a lot of relationships with quality people… a consequence of lacking identity and feeling unworthy.) Fortunately, I was also convinced that I’m a shit judge of this sort of thing and that if I pushed through my own insecurities there was likely a payoff out there. I was right, but only arrived at this conclusion after years of… wait for it… intentional discomfort.
Another great one, Jeff.
I have gratefully felt your support keep moving you are an important inspiration