On Fear Of Loneliness
I recently realized deep fear of loneliness has pretty much driven my life.
Growing up, I fed the fear a mix of microwaved mac ‘n cheese + rom-coms, the fairytale love and connection so absent from the household. After years of desperately trying to fix my family to no avail, I left and fell in actual love with Latin America, the first place I truly belonged. Back in the States, I regressed to giving away all my love to romantic partners, just like I’d learned in the movies. And then I poured myself into work, travel, being the life of the party…never really receiving what I was hoping for…until 💥
I told a therapist in 2017, after my divorce, how my biggest fear had always been getting a divorce. It was the first time I’d said it out loud, I guess a bit late.
By that time, the pattern was locked in — fiercely independent, traveling the world solo, rejecting what wasn’t working, searching for something better. And self-fulfilling — attracting the same flavor of broken I learned to love as a kid, holding on tight, pushing or running away at the first sign of danger, isolating…rinse and repeat. Not so healthy!
Exploring this theme with a friend over the last couple of days, he mentioned a quote…
“And when nobody wakes you up in the morning, and when nobody waits for you at night, and when you can do whatever you want. What do you call it, freedom or loneliness?” ― Charles Bukowski
At first, they might seem to be in conflict…freedom and connection. How can one be completely free and bound by commitments with others? But that’s the small view. As I mature, I learn that the first connection to nourish is the internal one, with myself. As that blossoms, it becomes obvious how freedom and external connection are actually interdependent.
My paternal grandmother was of Scottish descent, a people who embody this mélange. Her maiden name was Anderson, passed down as my given name. The Anderson clan motto is “Stand Sure.” I’m increasingly reminding myself that this is my clan.
Anyone who knows me knows just how fiercely I care for the small slice of humans I consider my people. I found myself lighting a candle for a friend going on meditation retreat yesterday and just after, thought…“I wonder what it’d be like to offer the care I show them…to myself…to offer the care they show me…to myself…especially when I’m feeling stressed, overwhelmed (read: afraid)...”
I started feeling this love effortlessly as I kneeled to chant after lighting the candle…and again making breakfast as I realized Barkley had an ear infection — encouraging myself to pause and breathe. It’s like a switch has flipped, and all the compassion practice from the last decade is clicking, in a way that feels genuine for the very first time.
Walking back from the surf this morning, I noticed I was rushing slightly, out of aversion to the heat and humidity of the jungle, the sand sticking to my salty skin. And then almost instantly I felt myself soften…slowing down…cooling down…and soon after I found myself willingly and then easefully being with the discomfort so I could pause to take in the way the sun was falling on some dark green leaves by my feet while the morning mist rose.
Comfort was a strong lever of control for me as a child, and I’m seeing just how crippling it was after. It’s what kept me from returning to Latin America for so long. But I finally felt more of a desire for the things I love — community, surfing — than fear of the parts I don’t.



Lovely essay Andy. As soon as I saw the title of the post, I knew I had to read through it. I relate to many parts of the essay.
Loneliness is an epidemic, more so in adult divorced men, as I join the ranks.
I recently saw a movie called 'I love you, bro' which is based on the topic of how men tend to lose friends once they enter into a relationship, unlike women.
Do you wonder if if you are truly alone, if the moment you send your newsletter out, that dozens of people eagerly read it?