Comfortably Uncomfortable: Randy Kaufman and Dustin Lowman on Growing Through Discomfort

By Randy Kaufman and Dustin Lowman

Humans are subject to an insidious push and pull between comfort and discomfort. Like any species with the evolutionary persistence to survive for millions of years, we’ve survived largely by our ability to identify and avoid threats — toothsome predators in days long past, nebulous anxieties of moneylessness and failure today.

But across this unique evolutionary arc, humans have arrived in a strange land: We’ve gotten too good at mitigating threats and eradicating discomfort. In 2024, there is a cure for nearly every ailment, a distraction from nearly every instant of boredom, a salve for nearly every blemish — a comfort to replace nearly every discomfort.

Plants may grow in stable ecological conditions, but humans aren’t so lucky. Within one’s zone of comfort lies only stagnation. With no one to challenge our points of view, no mountain to test our body’s resilience, no hardship to stretch our resourcefulness, we stop adapting, stop striving, stop growing.

Maybe it's for this reason that people like me — and like Dustin Lowman, my young marketing coordinator — embrace discomfort. At face value, discomfort reads like one more threat to neutralize.

But the more discomfort we’ve endured, and the more growth we enjoy in its wake, and the more we feel the connective line between discomfort and personal growth.

Dustin and I were discussing this on a recent call. In pursuit of a music career, Dustin faces many of the discomforts I’ve faced, and many I haven’t. What follows is a collaborative account of the discomforts that fostered our growth — and how we’ve both learned to be comfortably uncomfortable.

Randy’s Three P’s Of Discomfort: Physical, Psychological, Professional

Physical

Around the world in 180 days. After graduating college, another young female friend and I decided to travel the world. These were the days before cell phones — at best, we could telex our parents once a month. To say my parents were uncomfortable with this trip is an understatement. Indeed, the six months my friend and I spent traveling would be uncomfortable, scary, and, many times, dangerous — but in entirely constructive ways.

We visited the temples of Bangkok. We hiked 14,000 feet to the Annapurna base camp. We were chased by a rhino in the jungles of Nepal, we slept on straw mattresses in Tibet, and we took a three-week bike trip through China. We found ourselves in situations that were dangerous for anyone, let alone two 23- year-old American women. But, we embraced them, we survived, and we thrived.

Adjusting Sails. Thomas S. Monson said: "We can't direct the wind, but we can adjust the sails." This proves true in sailing and true in life. In my adult years, I’ve continued to put myself in uncomfortable physical situations. I’ve pursued numerous physical thrills, including rock-climbing, heli-skiing, and open-ocean sailing. This found me dangling off a rock face in the Gunks, navigating deep and steep ski camps in Jackson Hole, and gritting my way through overnight sailboat races.

There’s nothing like bobbing in a tiny plastic boat in the vast ocean on a dark starry night to put any problems in perspective. I’ve often thought that it's nothing short of insane to knowingly put myself in danger, and to pay exorbitant money to do so. And, yet, I’ve never regretted a single minute of these experiences.

Many would see the apparent peril in situations like these and write them off as not worth the risk. And while these situations were risky, there was none so risky that my (and my companions’) resourcefulness couldn’t handle. Embracing and managing physical risk has shown me what I’m made of — literally — and has steeled me in more mundane situations that call for endurance.

Psychological

Trifecta of suck. During a recent sailing trip, we were loving life, sailing our claret red racing boat smoothly in 20 to 25 knots on a gorgeous sunny day. I was in my happy place–the helm. Life doesn’t get better than this I thought. And then, David (my husband) popped his head up from below decks and calmly said, “Water is filling the boat. And it’s serious.”

There are few messages you want to hear less when you’re at sea than this one. Even though I “knew” it was virtually impossible to perish in Long Island Sound, close to shore on a calm sunny day with the coastguard nearby, part of me was inclined to let my fear of drowning take over and panic. And, even if we were fine, our cherished boat could have sunk.

Water filling a boat at sea — that’s actually what my fifties felt like. Having led a charmed life until then, in my fifties, my business failed, my first marriage dissolved, and I was diagnosed with cancer. It all happened seemingly at once. I found myself confronted by despair and hopelessness that I’d never before experienced.

If I learned one thing during those tortuous years, it’s that despair, hopelessness, and panic do nothing but make a bad situation worse. The grit I required to navigate my fifties (hear about my Trifecta of Suck here) prepared me to calmly take the helm while David and a sailing coach pumped out the water, stopped the leaking with old rags and zipties, called a boat tow and “but luckily” (aptly, the name of our boat), we arrived back at our slip safe. Dinner that night was joyful, as we toasted to all that we learned, ignoring what could have been a very different story.

Professional

Tough early career. Years ago, a pilates instructor told me, “There’s always an easy way to do a move, and a hard one.” True in pilates, true in life; I always do the hard one, she said.

In the ’80s, when I started my career, I chose to work in mergers and acquisitions at a big law firm. For four years, I cut my teeth on structuring deals, staying in conference rooms all night eating deli sandwiches or stale sushi, and standing up to the wolves of Wall Street who worked at Drexel Burnham. I followed this with 10 years on Wall Street myself, which was rife with its own scathing experiences, amid which I survived and thrived. Though I considered it normal, I realize in retrospect that I was living in a sea of discomfort this whole time.

New field later in life. These experiences prepared me for a slew of other professional discomforts — some of which I courted, others of which courted me: moving to Boston to work in structured derivatives (the first time I ever felt unhappy at work), moving into wealth management (a brand new field for me), and ultimately, leaving corporate America to strike out on my own.

It’s been a wonderful career not in spite of the discomfort, but because of it. The early years were tough indeed; I wouldn’t trade them for anything. They made me who I am today. With discomfort comes growth, and with growth comes the ability to to cope with professional discomfort.

Dustin: A Farewell To Control

At the time of writing, I’m 31 years old and splitting my time pretty evenly between marketing and music. I’ve pursued music before, in my early twenties, living in Nashville, TN, paying my way by waiting tables. As I described in an episode of Randy’s podcast, the experience was at first disillusioning and discouraging — but ultimately, pointed the way to this phase of my life, in which I feel substantially more purposeful and committed to my system of living.

Pursuing music has brought me face to face with what I consider to be the appetite at the core of human conduct: the craving for control. Almost everything we do is about increasing the control we can exercise over our environments: The more money we have, the more we can live in the kind of place we want to live in, amid the kind of surroundings we prefer, with the kinds of people we love, sustained by the kind of food we want to eat, keeping the kind of hours we want to keep.

The more control we have, the less we have to confront the uncertainty of life, uncertainty which, we’re cautioned, might contain survival risks. Who knows what might happen when you walk out the door, get behind the wheel, step on the subway? Who knows what evil might lurk behind which stranger’s eyes? If you watch the news, you’re fed a vision of life filled with almost nothing but threats, where the only things you can really trust are the talking heads who feed you doomsday visions and the products and services that help you fend off the imminent apocalypse.

I have this craving as much as anyone — perhaps more so because of the socioeconomic bubble in which I grew up. In my childhood and adolescence, I faced practically no threats to my survival or to the control

I could exercise over my environment — which, paradoxically, turned threats of uncertainty into boogeymen, made me incredibly sensitive to their presence (or possible presence), made me afraid that their faces would be as nightmarish as I’d always imagined.

Pursuing a music career means saying goodbye to layer after layer of control and certainty. It means embracing financial uncertainty; writing noncommercial music is not an immediately remunerative line of work, has no benefits, has no retirement plan. It means embracing physical uncertainty; I’m constantly traveling to new cities and towns to play music, places where I don’t know anyone, and don’t really know what I’m getting myself into. It means embracing emotional uncertainty; I never know how an audience is going to perceive me, or whether, when I open my heart with the songs I’ve written, they’ll open their hearts in kind.

It means embracing creative/interpersonal uncertainty. I work with all kinds of collaborators — musicians, singers, videographers, photographers, audio engineers, graphic designers, venue bookers. I can’t know upfront who’s going to understand my vision and who won’t. I can’t know whether my time and money investments in these people will pay off. I can’t know whether, when I offer constructive critique, they’ll take the critique well, or take offense.

The story we’re told is that greater control = more happiness — and by extension, that embracing uncertainty means subjecting yourself to misery (or potential misery). But as someone who ritually subjects himself to uncertainty in nearly every facet of his life, I can tell you authoritatively that the more uncertainty I confront, the happier I become.

Embracing financial uncertainty has freed me from the fear that making less money means imperiling myself.

Embracing physical uncertainty has shown me how reasonable, inviting, and hospitable the vast majority of people are, and how many people have the same desire to hear thoughtful, carefully crafted songs as I do.

Embracing emotional uncertainty has made me more emotionally resilient, better at counseling myself during difficult moments.

Embracing creative uncertainty has made me more intentional about who I invest in, who to trust with my creative vision, and how to work well in these dynamics.

The fear of uncertainty is the idea that uncertainty = threat. The embrace of uncertainty is the reality that uncertainty = opportunity — that far more often than not, people are reasonable, supportive, openhearted, and looking to help people who are motivated by a clear-eyed and righteous purpose.

Comfortable Discomfort

It’s this comfort with discomfort that binds Dustin and me. At numerous junctures in our lives, we’ve been reminded that uncertainty paves the way not to destruction, but to growth of all kinds. It may require grit to navigate, but it’s grit that makes you more resilient and wise in the long run. We would recommend a little grace too, if at all possible. For these and other stories of grit, grace, growth and gratitude, please check out our podcast, “To Grit, With Grace”: https://randykaufman.com/podcast.

We also share a deep love for music — songs that commemorate others’ moments of discomfort, and that help us work through our own. For a partial, but extensive, list of the songs that have moved me, check out my music page: https://randykaufman.com/music.

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ABOUT THE AUTHORS

Randy Kaufman, formerly a corporate tax attorney and investment banker, is now a wealth advisor who prides herself on focusing on what matters most: clients’ peace of mind, family dynamics, and getting enough, not more. Randy is a passionate student of impact investing, strategic philanthropy, and behavioral psychology (while not a psychologist, she occasionally plays one in the boardroom). She is dedicated to helping the underprivileged and is a proud member of global venture fund Acumen's advisory board. A thinker, learner, and pursuer of overarching truths, she is always eager to discuss big ideas about money, and its off-and-on associate, happiness.

Dustin Lowman writes antisensical songs: lyric-driven tunes that deconstruct the nonsense of living. He is a self-taught singer, guitarist, harmonica player, and lyricist who patterns his style on troubadour types — Bob Dylan, Leonard Cohen, Aimee Mann, Adrianne Lenker, Cass McCombs. Based in Brooklyn, Dustin performs regularly at venues in the borough, and has also appeared at the Poetry Foundation in Chicago, IL; The Bitter End in Manhattan, NY; and the Levitt Pavilion in Westport, CT. Listen to him on Spotify, and follow him on Instagram.