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On Loneliness


It’s 1:38 am.

I’m sitting in a hotel room just east of Downtown Portland.

I booked it for $15 using the Expedia Best Rate Guarantee travel hack. By the looks of the room, I wouldn’t pay that much more than that.

I went out with some friends tonight to Sinferno, a burlesque/variety show in a Portland bar. There were dozens of lonely men in the audience. I could literally feel their desperation as they longingly glared at the go-go dancers on stage.

Mesmerized by the undulating torsos and gyrating hips, they failed to notice the dozens of single women in the crowd as well. Some of them were more attractive than the girls on stage. And they were just dying for a man to approach them and make their life more interesting.

But the men didn’t approach, so both left home lonely. Disappointed, frustrated, and with a belly full of alcohol and two slices of cheese pizza.


As I walked to my car, several homeless men asked me for money. I give dollars and spare change to them a lot more than I used to. But there’s not enough cash in my pocket to give to all of them.

There’s a lot of pain in Downtown Portland. It seems like on every corner there are at least a couple of homeless people asking for spare change, smoking cigarettes, or sharing a meal that someone donated to them one way or another.

I couldn’t even imagine the depths of their loneliness. The feeling of always needing to rely on the generosity of other human beings to gather up a few dollars for a hamburger or a gyro.

With a mix of anger, sadness, and a always present state of “fight or flight,” they wander around the streets. I get into my car which has over half of my material possessions in it.

As I get in my car, I see a man sleeping on the concrete under an awning. It breaks my heart.


Earlier tonight in the bar, I shared a story of love lost with another digital nomad friend of mine. He’s gone through similar experiences and several of my other nomad friends have as well.

To the outside world, we share the pictures from the nightclubs of Colombia, the mountains of Norway, and the jungles of Mexico.

But we don’t share the stories of the women we leave behind to continue on our travels. The ones we still love who are now married. The ones who want nothing to do with us now a month after we were saying “I Love You” to each other after a week of knowing each other. The one that a piece of us wants to call right now and say, “I’m giving this all up for you. Let’s make babies together.”

We don’t share the stories of the tear filled goodbyes, failed long distance relationships, and the lonely nights sleeping on a bunkbed in a hostel room with seven teenage boys from Australia.

But that comes with the territory. Stay celibate, have tons of casual sex, or try and do something in the middle.

Right now I’m leaning more towards the celibate. But it’s hard. The situation I mean.


Being 100% on purpose requires a good deal of sacrifice.

I recently studied with David Deida in one of his five day advanced intensives. The experience was so powerful that I haven’t been able to write about it. I won’t write about it. It’s beyond words.

Something he said in that intensive stuck with me.

“A side effect of growth is loneliness.”

It’s true. The more spiritual work I do, the smaller my dating pool gets. The less I want to do things that used to appeal to me. The less I want to get black out drunk and hit on women in bars.

The more I want to keep my mind and body clean to complete my life’s purpose. The more I write things on the Internet that repel more people than they attract. The more I’m content with sitting alone in a hotel room in Portland at 2:18am.

The more I follow my desires, the more I end up on the road less traveled.


I’m very rarely actually alone. My family by blood is small, but my family by choice is huge.

I can land in any major city now and have a place to stay, friends to have meals with, and dozens of kids and pets to cuddle with. And I don’t just stay with random people. I stay with some of the brightest minds on the Internet and for either a couple of days or a week I become one of the family.

I live in a TED talk. It’s absurd how rich my life is.

But tonight I’m alone.

In this godforsaken hotel room.


In this moment there’s a piece of me that wants to fill this hole with something.

In the past I’d text, email, or call a woman I was romantically involved with. Or I’d fill the whole with alcohol, drugs, or carne asada.

But tonight I’m just sitting with it. Sitting alone in this subpar hotel room in East Portland in my underwear writing this blog post.

But that’s where you come in. You’re keeping me company tonight. And tonight that is all I need to have a good night’s rest.

So thank you for being here.

I guess life on the road is not so lonely after all when the whole world is your pen pal.

  • Yamile Yemoonyah

    I know that feeling very well. And as a female digital nomad over 35 who has to also deal with the biological clock fucking with her mind, it can be tough to stay focused sometimes. But hey, I know it’s worth it and it looks like you do as well :)

    • Mike Hrostoski

      Yeah, it’s most certainly worth it. Will I be doing this in five years? Most likely not. But I’ll be sooooooo happy I did.

  • Jupiter Jones

    Forgive me for this negative comment, but had any of those desperate men at the show approached an attractive woman in the audience, they would have been shot down immediately.

    • Mike Hrostoski

      But it would be a small win. Then they’d try again, and again, and again, and again, and again, and again.

      And one day they’d wake up and say “Whoa, I’m fearless! How did this happen? I used to be afraid of EVERYTHING.”

      At least that’s been my experience in this lifetime.

  • Tanaka


  • Sachit Gupta

    Love this post man! I think you’ll enjoy this one from Sebastian:

    • Scott Brills

      Great post–thanks for the share.

  • Betsy Fry

    Beautifully said. Although it feels lonely, you know that you are the only company you need sometimes.

  • Marcella Chamorro

    Fist bump…

  • Michael Vera

    “Most people living “normal” lives and have “normal” friends / networks.. even though on paper wouldn’t be considered “lonely” are actually the most “lonely” because most of their connections are superficial and shallow. I disagree with David Dieda on that quote and I think that’s a limiting belief. More you grow, the more you’ll be able to have deep, deep, intimate connections with real awesome people and that intimate sharing connection is worth more than 1,000 superficial acquaintances” –quote from a smart dude

    • Max Nachamkin

      Of course it’s all abut having deep connections though — you’re right!

      I think what he’s saying though is that because he’s been growing so fast, it’s harder to connect with people who aren’t on his same path (aka the vast majority of the population).

      I don’t think it’s a limiting belief — connection often happens with people who have similar values and life situations as you. It doesn’t mean that you can’t connect with others not on the same path, but that it’s less likely to develop connections (especially with a woman who doesn’t understand).

  • joshlipovetsky

    Really beautifully written blog post, Mike. Truly coming from a very deep and authentic place. Much love to you, brother.

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  • Sheri Bennefeld


    You were just part of a fabulous LOA moment. Not 5 minutes ago I was talking with my friend and host for the week about belongings. I was telling her that, “I could easily live out of suit case and I’m on a mission to shed “stuff”, lighten my load and get mobile.” Her reply, “But it’s always nice to have someplace to call home.” I find it really interesting how people equate a building and objects with home. For, so many, home is the very loneliest of places. For me, home is a place within and it appears when I’m most comfortable and with people I love and who stimulate me.

    Thanks for sending your vibes my way!

  • Therese

    Hey Mike,

    I don’t know you (yet?), but I kept seeing your name pop up on all the WDS stuff and it led me here.

    And wow, do I love this post. It really resonates with me. Reminds me of something I read by Pema Chodron (she’s my favorite) about what she calls “cool loneliness” and about the act of making friends with our loneliness and sitting with it instead of filling the space with… something:

    “It’s tough going, because it goes against the grain of an ancient neurotic pattern that we all share. When we feel lonely, when we feel hopeless, what we want to do is move to the right or the left. We don’t want to sit and feel what we feel. We don’t want to go through the detox. The experience of certain feelings can seem particularly pregnant with desire for resolution: loneliness, boredom, anxiety. Unless we can relax with these feelings, it’s very hard to stay in the middle when we experience them…”


    Hope our paths cross in Portland — I’ll make sure to say hi if I see you around :).

  • Kevin Cole

    Wow this hit deep man.

    Everything you said in here is so true.

    I left the only girl I have ever loved because our paths were clearly not going in the same direction. I have broken off friendships with friends who didn’t “get it.”

    There’s lots of fun to our lifestyle. But there’s plenty of baggage to go along with it. it’s easy to forget that we’re on the unconventional path when we only connect with people on the same journey.

    But when I head out into the “real world” and I see lots of folks wasting away their days and partying so they can forget their wasted time, I realize how deep this path is and how worthy it is.

    I have definitely been feeling that strange sense of loneliness from life off the beaten path. But I really wouldn’t have it any other way.

    Because as David Deida said “A side effect of growth is loneliness” And if I am not growing as a human being, I am dying.

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  • Mary Armstrong

    Beautiful. Thank you for writing this. I feel less alone reading it.

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