An Answer to Loneliness
Surrounded by people, but still feeling alone.
I was part of a tight-knit church youth group as a teen.
We grew up together, seeing each other every Saturday night, Sunday morning, and Wednesday night prayer meetings for over a decade.
Despite spending so much time with them, I remember one time, while sitting in the back of the church, I felt profound unseen, misunderstood, disconnected, and lonely.
I remember feeling so perplexed by how it was possible to be surrounded by people, but still feel alone.
I remember thinking:
I wish the people around me knew what I was really going through
I wish the people around me cared more
How is it that I’ve know these people for so long, but they don’t know what’s really going on for me? How come they don’t know that I’m struggling?
How come I don’t feel like I can share with them?
Looking back, I felt alone because I didn’t have anyone I could share my most personal and vulnerable thoughts. And part of it is on me — I never had the courage and initiative to share.
Some of the struggles, questions, and frustrations I had as a teen that I never felt I could voice:
“What’s the purpose of my life?”
“What’s the point of school?”
“Is college going to be the same as high school?”
“Why do I always do what I don’t want to do?”
“Why do I have such terrible self control?”
“How can I stop thinking about the girls I have a crush on?”
“How come I’m so scared to talk to the girls I like?”
“How do I get that girl to like me?”
“How come other people are so confident, but I’m not?”
“Why does it seem like everyone else is smarter than me?”
“How do I get my parents to stop yelling at me?”
I never shared those things because I was scared how people might respond.
Would they make fun of me? Would I be the only one with those questions? Would they not take it seriously and tell me to “lighten up” or laugh it off or ignore it? Would they say that it’s an “easy” solve and so I look like an idiot for not having already solved it?
So I kept my mouth shut. Kept all those thoughts to myself.
And I’m convinced that’s why I felt so alone.
Maybe that’s when I realized that loneliness wasn’t entirely about being physically isolated, but more of being relationally isolated.
There I was in church, surrounded by people I had known for years, but didn’t feel like they knew me.
My inability to fully express myself and be heard by others bred loneliness.
Alone, but not feeling lonely.
This will be news to many people.
I was in a relationship for two years.
I thought I was going to build a life with her, start a family, and til-death-do-us-part with her.
And one month ago, we broke up.
It was probably one of the most painful experiences I’ve ever gone through.
It was the last thing I had expected.
I did not see it coming.
My world was rocked.
But.
In the midst of going through the deepest sense of loss, hurt, and grief I’ve ever allowed myself to feel, surprisingly, I did not feel alone.
Even though I pretty much spent the entire following week at home, by myself, writing, journalling, and healing… I did not feel alone.
How could that be?
Every day, for about a week, I had a handful of friends checking in on me, asking me how I was feeling.
I responded with my “journal entry” of the day so I could share my process of making sense of things, feeling through the hurt, and processing what happened.
They’d read it, and then reflect back to me what I was feeling.
All the responses were empathetic, accepting, supportive, and caring.
No judgement. Letting me vent if I wanted to, asking me questions to help me reflect more deeply.
I never felt diminished. I never felt embarrassed. I never felt “less than” for going through what I went through.
No one told me to “just get over it” and “move on.”
No one poked at me when I expressed the endless slew of feelings I was feeling.
No one questioned my ‘manhood’ as a result of the situation.
No one criticized me for taking a week to do nothing but eat, sleep, and write.
And on my side, I didn’t feel scared to share the raw feelings, I wasn’t scared of how they might react, and wasn’t worried about whether I’d get made fun of.
And at the end of the day, I felt seen, supported, and cared for.
I was alone for an entire week, but didn’t feel lonely.
What happened? How was this possible?
Who were these friends? How did I come to meet these friends?
Looking Under the Hood
While working on Orenda (company I co-founded to teach teens soft skills), we developed a workshop to help students visualize all the “levels” of getting to know someone.
We had students list out all the facets of getting to know someone and then had them rank each from level 1–4 (1 = superficial, 4 = deeply personal).
Here’s a compiled spreadsheet of what 40 students came up with. Most of them are serious but some are hilariously satirical.
But I want to focus on the 3s and 4s from that list:
In my experience, when I can share the deeper parts of my life (level 3–4) with others and it is received positively and without judgement, I feel more seen.
Whether it’s sharing with my friends about what I was experiencing after the break-up, the stress I was going through as a founder, the aspirations I have for my life and career, how I arrived at some beliefs and values in my life, or about my relationship with my parents.
Whenever I share something personal (feels “risky” to share) and it’s met with kindness, curiosity, and understanding, I feel more supported and connected.
Contrast that with of the friendships I had as a teen — sharing level 1–2 things was nice and fun, but it never made be feel supported or connected in the same way.
The antidote to my loneliness was a combination of:
1) The willingness to share “risky” level 3–4 things and
2) Having people who respond well to it
“Well.. that’s nice for you Brandon, but what about me? I don’t have many people in my life that I can share personal things with. How do I find people like that?”
This is a great question!
To answer that, I’ll show you the process and tools I used to build these kinds of connections.
Tools to Make Conversations More Personal
A community or group of people is comprised of many 1–1 connections. So let’s start there.
How do you have more personal conversations 1–1 with someone?
In every conversation there are two parties, a Sharer and Listener, and of course, the roles switch back and forth during a conversation.
Getting to Personal Conversations as the Sharer
There’s two concrete things you can try as the Sharer:
It’s kind of like dipping your toes in the water to see how cold it is, and if it’s too cold, at least you just got a cold toe and not hypothermia.
Taking slight, calculated risks in conversation means that it’s less likely to “shock” the other person and reduce the likelihood of a poor response on their end.
Example:
Let’s say you have extremely intellectual friends who don’t seem to be interested in spirituality. Instead of trying to be 100% up front with them and sharing that you’ve been listening to Oprah’s SuperSoul Sunday, you can “soften” the approach to test how they’ll respond.
I’ve been listening to some interviews with Oprah lately.
That’s it! Keep it super vague and see how they respond.
If they respond positively — curiosity (inviting you to share more), enthusiasm (excitement, celebration, or affirmation), and non-judgment — then slowly reveal more!
If they respond poorly (dismissively, condescendingly, or disrespectfully), then maybe it’s a signal to not go further down that line of conversation.
Want more examples?
I made a 6-page toolkit with 10+ examples and additional commentary (my marketer friends would probably tell me to get your email in exchange for the toolkit, but hey, I’m a rebel — but for real, if you find this helpful, apply it, share it, tell me how it works for you).
Getting to Personal Conversations as the Listener
The primary tool as a Listener:
Suspending judgement in order to be curious.
In other words, when met with an idea you completely disagree with initially and/or cannot understand why anyone would believe, ask to understand instead of writing it off.
People respond much better when you become interested in them instead of judging their lifestyle/beliefs/philosophies.
Example:
The first time I met Kim was the first time I heard of meditation/mindfulness outside of a religious context. My only association with it was a Buddhist monk sitting going “ohmmmmmmm.”
The first time we met for lunch, I was surprised by how she carried herself. Kim was very embodied and would navigate the conversation based on how she felt. At the time, it made absolutely no sense to me (this was back in 2015 when I had the emotional fluency of a box of rocks).
The reflexive judgmental thought:
Wow. This lady. She is too much. She seems waaaay too woo-woo for me. This might be a long lunch…
If it wasn’t for my decision to lean into it, set aside my skepticism, and ask questions to understand her world, as well as Kim being patient with my hyper-logical thought processes and noob-mindfulness skills, I would have never discovered the awesomeness of becoming friends with her, going to her retreat, and our fun conversations about life, love, feelings, and everything in between.
Oh I might have never brought emotions back into my life if it weren’t for getting to know her better and attending her retreat.
Now, her embodied-ness makes much more sense to me, and I am an evangelist for all things Kim!
Click here if you want to see 5 more examples of people in my life who I’ve become friends with as a direct result of suspending judgement and seeking to understand instead of writing them off.
Putting it Together
If you do all you can as a Sharer, you will have some people that respond well and others who don’t.
For those who don’t respond positively, I just assume that they’re not ready to have those kinds of conversations yet.
That will happen. A lot.
If you do all you can do as a Listener, when someone shares slightly risky things about themselves and you meet it with curiosity, it will create a stronger connection and possibly be reciprocated when you share something risky yourself.
If you actively practice as a Sharer or Listener in this way with friends, family, or strangers, you will eventually meet people who are comfortable talking about a wide range of things that are deeply personal to you.
Applying the Tools
In June 2015, I felt like I only had 5 people in my life that I could have “Level 3-4” conversations with, and only one or two who lived nearby.
Out of frustration, I made it my main priority to meet people I could be fully myself with and attended conferences, events, and hosted events as much as I could.
With every person that I met, I used the same process of asking slightly risker questions, and sharing slightly more personal things. If the other person responded well, we’d go deeper.
At first, it seemed rare that I’d be able to meet this kind of person — maybe 1 in 20 people — but I kept at it. I had 1–1 conversations with hundreds of people, many of them were shorter conversations, some of them longer. But the long and deep conversations were the ones I was on the lookout for.
After 3 months, I had 2–3 new people that fit that description.
After 6 months, I had 5–6 people.
After 9 months, I had 8–9 people.
It hit a tipping point in June 2016, a year later.
It seemed like left and right I was getting introduced to people I could connect very deeply. It was night and day. I remember feeling so excited after having a whole week of nothing but great humans that I really enjoyed talking to.
Around that same time, I realized that I had met enough friends who also lived nearby, so I invited them all to meet each other on a Friday night at a boba shop called BAMBU to hang out, and it was the best kind of fun. Magical, almost.
We began to meet nearly every Friday night to hang out to talk about anything and everything (Level 1 thru Level 4). Zero judgement, zero shame, just humans talking about the beauty and ugly sides of the human experience.
And it was so refreshing.
A group of friends that I could share pretty my anything with and dive into the nooks and crannies of topics that I had only thought about, but never talked about.
An abbreviated list of things we’ve talked about as a group just to give you a glimpse.
- Dating, marriage, sexuality, pornography, monogamy/polygamy
- Most embarrassing mistakes, biggest regrets, and proudest moments
- Spiritual experiences, intellectual discussion, philosophical musings, emotional fluency, physical fitness, mental health
- Questioning societal norms, how to change them, and what drives our lives
- Soft skills, financial literacy, career best practices, reinvention, self-care
My friend Tam wrote an awesome piece about his experience of our community here.
Our community has grown to 10+ people and each person is interconnected with each other. Some even started dating. We hold friend retreats every year to spend quality time with each other, and do what we can to support each other when someone is going through something difficult.
I have some pretty badass friends. I’m very grateful to be a part of an amazing group of humans.
The result of my binge of meeting hundreds of people 1–1 to gauge what kind of conversations we could have?
A tight-knit, local community of friends I can be myself with.
And the surreal privilege/luck of being able to be alone, but still feel connected.
In Summary
It’s very possible to be surrounded by people, but feel alone.
In my experience, this is the result of not having relationships in which you feel safe to share the deepest parts of yourself.
There’s a process and tools for how to gauge if the person you are talking to might be someone you can be more ‘real’ with.
If you are diligent to leverage those tools in connecting with people, you have a much better shot at finding a group of people you jive with.
Once you have a handful of people you feel safe to share the deepest parts of your life with, it’s possible to feel supported, seen, and cared for even if you are physically alone.
Closing Comments:
- Share with me your thoughts! There’s so many layers to this. Loneliness, community, friendship, values, etc. Would love to hear how this lands on people, questions you might have, or how you may have tackled loneliness in your life.
- Do you want support to build this for yourself? Do you want some hand-holding? Happy to help, sign up here. One of my goals in life is to help people find communities for themselves like the one I feel very privileged to be a part of.
- Shout out to Tam Pham and Candace Wu for reviewing this beast of an article.
