UW 020: Unconventional Wisdom On: Loss, Control, and Are Men Ok?
The Art of Magical Thinking and Loss
Letting Go Of Magical Thinking
Confronting Loss Head On
In the summer of 2020, the world was frozen in place. The pandemic had ground everything to a halt, yet inside me, everything was crumbling.
I found myself sitting cross-legged on a friend’s couch, Joan Didion's The Year of Magical Thinking in my lap. The afternoon light filtered through unfamiliar windows, a reminder that even this temporary refuge wasn't really mine and neither, it seemed, was the life I thought I’d been building.
I had just broken up with the woman I had been engaged to. And even though it was the right decision, letting go of those dreams —a vision of home, love, and community—felt like breaking apart a fragile world I’d spent years constructing.
I was now living in the disorienting aftermath of that decision, clinging to pieces of the past, scrolling through old photos, and refusing to block my ex on Facebook. Each small act of refusal a denial of what was already gone.
Didion’s words exposed my resistance to loss. Her subtle refusal to accept her husband’s death—keeping his shoes, resisting changing the message on their answering machine, even researching how he died as if that could change things —reflected something painfully familiar. I, too, was resisting the full weight of my loss, not yet ready to step into the emptiness it had left behind.
That summer marked the first time I confronted loss head-on. And ever since I’ve learned that loss is not a one-time lesson. It returns, over and over, demanding more honesty, more courage, and each time offering a deeper truth if we’re willing to listen.
I’ve discovered how cunningly I avoid the pain of loss.
By focusing on something new and exciting so I don’t have to miss what I’m leaving behind.
By losing myself in regret and rethinking my past choices.
And by keeping myself suspended in endless indecision, rather than accepting the consequences of my choices.
But I’ve also found something unexpected: when we finally face loss, when we let ourselves feel its full impact, we open ourselves up to appreciating what remains, and to making choices with more clarity.
This piece is about facing those losses—the ones you know are there and the ones you’ve been avoiding. My hope is that by sharing how I’ve wrestled with loss, you might find the courage to do the same. In facing it, you might discover a deeper appreciation for the life you do have and the possibilities still waiting to unfold.
You Can Take Risks And Still Avoid Loss
For a long time, I prided myself on being a risk-taker. Someone who wasn’t afraid to leap into the unknown, chase adventure, and embrace change. And on the surface, that was true. I made choices that looked daring, even reckless.
I left my hometown of Nashville and moved across the country to Portland, where I didn’t know anyone.
I walked away from a successful music career to live in a Zen monastery.
I packed up my life in Portland and moved to New York, convinced I was pursuing the relationship of my dreams.
These decisions took courage. They were leaps of faith, and they shaped me in profound ways. But recently, I’ve had to confront a hard truth: taking risks doesn’t always mean you’re facing loss. Sometimes, it’s another way to avoid it.
When you're always moving toward what's next, you never have to fully reckon with what you've lost.
The excitement of a new beginning can drown out the ache of an ending. And as long as you’re in motion, you can sidestep the grief waiting in the quiet moments.
One example stands out: my long-held dream of backpacking through Europe.
For years, I imagined myself wandering cobblestone streets in Italy, staying up late in Parisian brasseries, and standing in awe of Spanish cathedrals. The dream wasn’t just about travel; it was about freedom, discovery, and the endless possibility of new connections.
But I didn’t take that trip.
Instead of hostels in Europe, I camped under Utah’s vast, star-filled skies.
Instead of late nights in Paris, I made unlikely friends on an overnight train to Amritsar, sharing cigarettes and laughter despite the language barrier.
Instead of a driving on winding roads in the alps, I drove into Portland for the first time, the city lights shimmering on the Willamette River, filled with wonder.
These experiences were beautiful, they shaped who I am, and I wouldn’t trade them for anything.
And yet, in choosing them, I lost something. I didn’t get to be the 25-year-old wandering through Berlin with a backpack and a notebook full of possibilities. That version of my life quietly faded away while I was busy living another one.
For years, I refused to grieve that loss. I convinced myself that as long as I kept chasing the next adventure, I could still reclaim that version of my life. But time moved on, and so did I. Now, at nearly 44, the thought of strapping on a backpack and heading to Europe feels different. That window—that particular version of the dream—is closed.
Facing this truth has been painful. But in allowing myself to grieve the life I didn’t live, I’ve found something unexpected: an even deeper appreciation for the life I did choose. By mourning the loss of being a young traveler in Europe, I get to celebrate the 43-year-old who has wandered different paths, who has slept under canyon skies, who has meditated in monasteries, who has lived a life rich in experiences.
I’m learning that regret and gratitude can coexist. You can grieve the roads not taken and still cherish the ones you did. They aren’t opposites; they’re part of the same whole. This is the paradox of loss. We often think we can outrun it, that by choosing risk, we’re avoiding grief. But the truth is, loss is woven into every choice. And when we stop running, when we let ourselves feel that loss, we begin to see the full beauty of what we’ve lived.
May This Moment Last Forever
Another way I’ve avoided loss is by ruminating on the past—rehashing moments I wish had gone differently, replaying conversations I should have handled better, or imagining alternate versions of my life where I made different choices.
When regret takes hold, it’s like a loop that never ends. Instead of moving forward, I find myself stuck, trapped in a version of reality that no longer exists.
Recently I’ve struggled to see a way out of this pattern. The pull of regret was strong, and the thought of truly letting go felt impossible. Then my therapist, Mark, offered me a new perspective through a story of his own.
He told me about a time he was driving a Tibetan Buddhist teacher to an important meeting in the heart of Los Angeles. Traffic was at a standstill—red lights stretching endlessly, the minutes ticking away. Frustrated and worried about missing the meeting, Mark was on the phone trying to reschedule when he muttered, “This can’t be happening.”
The teacher, calm and smiling, looked at him and said, “Just pause. Look at all the lights ahead of us and say to yourself, ‘May this moment last forever.’”
At first, the suggestion felt absurd. Who wants a stressful, gridlocked moment to last forever? But Mark tried it.
He stopped fighting the frustration and fear and simply allowed himself to be where he was. And to his surprise, the tension eased. He accepted the situation, and in that acceptance, something shifted.
What struck me about Mark’s story is this: sometimes I simply don’t want to feel the loss in my life. I’d rather ruminate or rehash a previous conversation or choice rather than accept that I can’t go back and redo it.
When I say to myself “May this last forever” immediately I’m out of the past and into this moment. I let go of what could have or should have happened, I accept what is and start to see the beauty that is always present.
Friends Are The Most Marvelous Things
Last week, I hosted my final game night in Mexico City before heading back to the U.S. for the holidays. The air was warm with laughter, the clink of glasses, and side conversations. I paused more than once to take it all in—the faces around me, each one now familiar, each one carrying a memory of how we met, what we’ve shared, and the fleetingness of this exact constellation of people, place, and time.
In those pauses, I felt two things at once: a swelling gratitude for the joy of the moment and an ache, knowing that soon, the night would end. My apartment, once filled with noise and warmth, would return to its usual stillness. I’d wake up to empty rooms, the evidence of the evening reduced to glasses in the sink and empty pizza boxes.
Normally I would have brushed past this ache, I would rethink my decision to leave Mexico City and come back to the States, but instead, I slowed down and said, “May this moment last forever.”
Instead of trying to think my way out of the pain I tried to welcome the loss fully.
There's something beautiful about allowing deep loss to be heard and felt – after all, what is grief? If not love, persisting.
This simple practice has helped me stay grounded in what is rather than what could have been. It helps me soften into the truth that every beautiful moment holds the seeds of its own ending. The party will end. The faces will scatter. The chapter will close. And yet, even in knowing that, we can lean into the joy of now.
The Myth of Keeping All Doors Open
For much of my life, I clung to the illusion that if I just kept my options open, I wouldn’t have to feel loss. As long as I didn’t fully commit to a path, I could convince myself that all paths were still available. It felt safer that way. But what I didn’t realize is that not choosing is a choice in itself—a choice to stay stuck, a choice to freeze my life in place.
I saw this pattern clearly last year when I couldn’t decide whether to stay in Salt Lake City.
Months passed in a fog of indecision. I weighed the pros and cons, again and again, convinced that if I just thought hard enough, I could land on a choice that didn’t come with a sense of loss. I wanted a solution that allowed me to keep everything: the loving relationship I had, the Wasatch mountains in my backyard, and the crisp air after a fresh snow. But I also wanted the possibility of something new, of a different life beyond Salt Lake.
Eventually, I decided to leave. But even after making the decision, I found myself questioning it constantly. Had I made a mistake? Was I walking away from a life I’d regret losing? At first, I thought my doubt meant I’d chosen wrong. But in time, I realized the second-guessing wasn’t about the choice itself. It was about my unwillingness to face the loss that came with it.
The truth was, no matter what I chose, something was going to be lost. By leaving, I lost the rituals and relationships that made Salt Lake feel like home. But staying would have meant losing the possibility of growth, of new experiences, of a life that called to me beyond those mountains.
The truth is, I've already lost Salt Lake City. I've lost the relationships I had there, the daily rituals, the version of myself who knew how to get around downtown without a map, and knew which place to go to get the most incredible breakfast sandwich.
And here’s the hardest truth of all: even if I move back to Salt Lake it won’t be the same. That chapter - with its particular constellation of people, places, and possibilities - is over. That version of me is gone. The person who may return is different and my experience of that place would be different as well.
I'm facing a similar reality now in Mexico City. Each day brings small reminders that my time here is temporary.
I recently decided not to renew my lease for my apartment in Mexico. Part of me is worried that I’ll want to come back and will have a hard time finding a place. Another part of me is scared if I had kept this place I might not want to come back to.
But what made the decision possible was acknowledging that I was already losing this version of Mexico City—whether I stayed or left.
There's so much in the coaching and personal development world about "having it all" - as if with enough planning, enough optimization, enough hustle, we can somehow avoid having to choose, and avoid having to lose anything. But that's not how life works. You can’t have it all, and every choice you make means you are losing something that could have been.
I’m learning that to live fully is to embrace the losses that come with choosing. To feel the ache of closing one door and still trust that what’s on the other side is worth it. The more I face these losses, the more present I am to what’s actually here, and the more open I am to what’s yet to come.
You Can Choose Loss Or You Can Resist It
These past couple of years of my life have been truly humbling but as I have slowly learned to accept and face the losses in my life I notice a greater sense of ease and possibility.
By coming to terms with and grieving all the things I’ve given up, I notice that I’m more appreciative of what I have, more willing to accept what’s happened in the past, and more willing to choose what I want for the future.
I’m not saying facing loss is easy. It isn’t. Sometimes it’s gut-wrenching, sometimes it feels endless. But I do believe it’s worth it. Because in choosing to face loss, I’m also choosing to trust. Trusting in God, the universe, or whatever force guides us. Trusting that I don’t need to control or know everything to move forward.
I’m slowly letting go of my own magical thinking. That belief that if I just try hard enough, I can avoid loss. That if I keep all my options open, I can protect myself from regret. That if I make the perfect choice, I can somehow escape grief.
But here are truths I’m coming to accept:
I have left some incredible relationships. Regardless of whether or not I would choose those relationships again, there is great loss there.
I have lived this life, and not others. Even if I love the life I have chosen, there is pain in those unlived dreams.
I have let go of many possible versions of myself. Those versions of me are gone and I am sad I’ll never get to meet or live them.
And yet, in facing these losses, I find myself more whole. Each time I acknowledge what I’ve lost, I become more present to what remains. More willing to choose what I want, even when I know it comes at a cost.
My hope is that in sharing this journey, you’ll feel a little more courageous about facing the losses you’ve been avoiding. And that in doing so, you’ll discover a new way of living—not one where you avoid loss, but one where you trust yourself enough to choose it.
Because when you face loss, you’re also choosing life.
💡Coaching Tip of the Week
Accepting what we can and can’t control
One thing that my clients often bring to coaching is a feeling of anxiety or worry about some part of their life they can’t control.
They want to build a better relationship with someone but that person won’t respect their boundaries.
They want to grow their business but they can’t seem to get their prospects to return their messages.
Or maybe they want to move through a grieving process and feel more at peace with something that happened.
The challenge my clients face with situations like this is that while they care about the outcome on some level they know they can’t control it. And this loss of control sort of drives them crazy.
They perseverate on what’s going to happen and how it might feel, they lose sleep thinking about conversations they’ve had and how they could have done things differently, and they get caught in these loops of thinking and analyzing that never seem to end in satisfying conclusions
Whenever this happens I try to lead them through 3 simple questions to help them regain a sense of control:
What do you want?
What do you need to accept?
What can you do?
The reasons these three questions work so well is that they ground people into a sense of intention, helps them let go, and gets them into action.
Question 1: What do you want?
Often when we want something in life we also get an idea of how we’re going to get it.
Let’s say that you're working with the CEO of a start-up or a senior leader on your team. They might want to get the people around them to listen to and adopt an idea they have.
Some people think the best way to get others to agree with them is by building a case for how right they are. So like a lawyer, they start gathering evidence, trying to break down others’ objections, and figuring out how to push and prod people into agreeing with them.
If you’ve ever seen someone do this you know how futile it often is. The more righteous they get about their plan the more they turn people off. And the less they listen to others’ concerns the more likely other people start to ignore them.
The problem isn’t their plan it’s their approach.
That’s why I start by asking my clients this first question: What do you want?
But I don’t just take their answer at face value because a lot of times they’ll answer this question by giving me the strategy they think will get them there.
Instead, I take their answer and ask them… ok if that worked what would happen that you want?
And usually, that’s when we start to explore what they really want. As I listen to them describe the experience they want to have and the results they hope to create I do my best to help them connect to those on a deep level.
What this does is it helps them start to let go of their fixation on a certain strategy and instead begin to open to a curiosity about all the ways they might be able to create what they want.
Question 2: What do you need to accept?
Once we’ve got a clear sense of what they want I start to ask them about what they do and don’t have control over. One model I often use for this comes from the book The Seven Habits of Highly Effective People, in which Steven Covey talks about two circles: The Circle of Influence and the Circle of Concern.
Inside the Circle of Influence is everything we can influence: Your work performance, health, relationships, how you respond to challenges, your communication style, etc.
Inside the Circle of Concern is everything we worry or think about: Other people’s behavior, other people’s opinions, the economy, global events, weather, etc.
The challenge so many of us face is that our circle of concern is much bigger that our circle of influence.
We don’t like to admit it, but we don’t have control over other people’s thoughts and action, we can’t control how other people perceive us, and we often don’t have control over our own thoughts and feelings.
By asking my clients what they need to accept or what is in their circle of concern that’s outside of their circle of influence slowly they start to see that so many of the things they are fixated on aren’t things they can change directly.
This can be hard for them to accept, but often as they realize both what they can influence and what they can control the stress, and resistance they feel starts to fade.
Question 3: What can you do?
Once we’ve gotten to a place where they are clear on what they want and what they can and can’t control I then ask them, What can they do?
Part of what we see when we look at the sphere of influence is that there are actually more things inside that sphere than we first realized.
As I work with my clients and walk through the things they have control over something powerful happens, they start to see how much power they actually have to confront the problems they have.
They start to consider how a change in attitude, a willingness to listen to others, and asking for help might make getting what they want easier than they originally thought.
As they let go of the singular strategy they think they NEED to get what they want and open up to the possibility that there are many ways to influence others and create new ways forward not only do they become more creative but they become more flexible and relaxed.
These 3 questions while so simple hold an incredible power to help the people we coach really come to terms with reality and begin to understand that accepting a lack of control isn’t the end of their ability to influence others but is actually just the beginning.
🌀 Happenings
(What’s going on Tokuuuu!?!)
1. My Final Days In Mexico City
I’m now in my last week in Mexico City and the time is bittersweet. I’ve been enjoying some last good bits of food and sights. If you want to see some of the places I’ve been checking out, head on over to my Instagram.
2. Devotion Letters
I’m just a little over half way through my month of writing letters to my future wife. I’ve found this project so inspiring and a couple of people have reached out to tell me they’ve been doing their own letters.
If you’re inspired to read this project, know someone who would be inspired by it you want to share it with, or even know someone who might be my future wife (I mean what do I have to lose by putting that out there right 🤷🏻♂️) I hope you’ll check out the series and share it.
Read It → The Devotion Letters
Toku’s Treasures! 💰💰💰
(Aka cool sh*t I want to share with you)
1. A Podcast About the Plight of Men
I ran across this podcast randomly but I was glad we did. What drew me in was the discussion about the crisis that young men in America are facing.
It talks about how dangerous it is to have so many men who are broke, single, and disaffected in this country. It also addresses how men both as fathers and as mentors can start to make a difference.
Listen Here: Are Men Okay? - Apple - Spotify
2. Some Good New Music
Recently I’ve been lucky enough to be exposed to some new music and one of my favorite new artists is this group called Oh Wonder - someone described them as a Synth Pop version of Belle and Sebastian (a reference I’m sure you might not get ) I love their sensual sound and how easy they are to listen to. If you’re looking for a new group to relax to while travelling home for the holidays I recommend you check them out.
Listen Here: Oh Wonder on Spotify
3. A Great Poetry Book
Rainer Maria Rilke is one of my favorite poets and this collection of poetry is especially good. There’s something about the way he writes about nature, spirituality, and life that I find so inspiring. If you’re looking for an amazing book of poetry that will help you reconnect to the wonder of life I highly recommend it.
Read Here: From Amazon - From Powell's Books
🎉 Here's Who I'm Celebrating This Week ...
This week I’m celebrating
Ever since I moved my blog over onto Substack I’ve been finding really interesting writers I’ve been enjoying. Recently I came across this really funny blog about dating. Its wry sense of humor and wit around the challenge of modern romance made me feel a bit more relaxed and light about my own experiences of dating. If you’re looking for an interesting read that will make you chuckle and think, check it out.
Read It Here: 3 Racoons In A Trenchcoat
Inspiring Quote of the Week
"Everything I've ever let go of has claw marks on it."
―David Foster Wallace -Infinite Jest
Thank you so much for reading. Until Next time!
Love,
Toku
Unexecutive & The coachingMBA
Well written !
Cheers for The Gray Area share. I will download an episode or two now.