4 min read

A lot of the time when I write these pieces, it’s almost an exercise in convincing myself of an idea. I think by publicly saying, “I believe and act this way” it helps to reinforce my inner fortitude to believe and act that way.

This is one of those times.

I’ve always been an independent guy, I’m not afraid to go places and do things on my own. But generally the actual act of traveling is the alone piece – the destination normally has the expectation of familiarity (e.g., leaving the house alone but meeting friends at destination).

I think it was just last year that I was pushed to really spend more time alone. It was a Friday night that turned into a very sleepless and anxious Saturday morning. Somewhere between the hours of 5 and 6a, I was texting my friend Janeesa and bemoaning all of the anxieties that were keeping me awake. I don’t remember the specifics, but I was at an intersection of being frustrated with my work, my romantic life, and with myself.

Janeesa made one recommendation: spend more time alone. Go on walks alone, go to breakfast alone, go to coffee shops alone, just get more comfortable with myself. 

It sounds simple, and I thought it would be simple, but it’s actually kind of a hard thing. When you’re alone, thoughts in the recesses of your mind bubble up to the forefront and can be dark and/or consuming.

I think subconsciously, I knew that. And my internal monologue tried to justify ignoring her advice with arguments like “but I have so many friends, why shouldn’t I spend that time with them? What about this project I should be doing? What about that work that needs done?” Just distractions. All of them distractions.

But here’s the thing, if you don’t spend time alone and really get comfortable and appreciate yourself, that insecurity will ALWAYS be there lurking. Your comfort with yourself is the bedrock of every interaction you have every day. If you’re upset at yourself for having made a certain mistake or decision, you may not take the leap to talk to that stranger next to you at the coffee shop. Sure, you can enjoy your lattes separately and be fine – but maybe that interaction could be a great (or at least enjoyable) one. If you’re beating yourself up internally and talking yourself down, you will project that insecurity and write the opportunity off.

I DO THIS ALL THE TIME. It’s not to say every opportunity to talk to someone should be taken, after all, I’m recommending spending time alone. I’m talking about those opportunities where the thought of “man, I should talk to that person” enters your brain – you know what I’m talking about. When you ignore that impulse, I would wager to bet it’s due to personal insecurity.

Being alone is a healing time for personal insecurity, or at least can be. But it’s not easy – in fact it is really hard. When you’re alone, you’re going to want to be alone with your phone (this is my biggest vice). That’s not being alone – that’s desperately finding distraction.

When you’re alone without your phone you’re going to start looking around a lot – looking for anything else to distract you from your thoughts. This isn’t necessarily a bad thing, there’s a lot of good observations to be made when you’re alone. You can pick pieces out of every day life that you generally don’t notice. And those observations can trigger some new thoughts and ideas.

But at some point when you’re alone, you’re going to have to answer to those insecurities and hard thoughts that are operating in the background. And sometimes, there is no answer. But fully realizing those thoughts and insecurities begins the healing process. OK, I realize I feel this. Why do I feel this? Is it right that I feel this? If it’s not right that I feel this, how do I work to change that?

If you don’t have that conversation (yes, it is with yourself) then it’s not going to go away. And sometimes, you just realize certain personality quirks that maybe you can’t change, or don’t want to. But once you realize them, and embrace them, your comfort with yourself improves.

Again, this may just be me projecting. I’d like to hear your thoughts. But if you are single on this very sacred holiday of Valentines Day, I challenge you to embrace being alone. I will be attempting to do the same.

PS: Watch this video (h/t to my sister Emily from a couple years ago).