Adventures in Awkwardness and Other Discomfortable Feats

Darren Kanthal
5 min readSep 5, 2023

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I’m not going streaking through the quad.

I can guarantee you that 100%!

Let me explain…

For many of us, the idea of doing certain things (like streaking naked through the streets of your college) is something you’re just NOT going to do. Period! Doesn’t matter how much prodding or bust-chopping your friends might do — it’s not happening.

The reason is that it goes against your values and moral makeup.

Why? It’s because you’re uncomfortable being naked in front of the world. Done and done!

On the other hand, being ‘discomfortable’ is a grey area — even though you might not do it…the more you think about it — yeah, I’ll do that! You usually know you’re experiencing discomfort when you come across things in life that make you squirm, twitch, and itch when thinking about taking action.

Discomfort is also where some of your greatest growth and trajectory come from.

It’s where you’re playing outside your comfort zone — but not SO uncomfortable that it leads to inaction.

So, what do we do with this?

How discomfortable are you willing to make yourself?

Well — the first question to explore to figure out how discomfortable you’re willing to make yourself is to ask and ponder: In what way(s) am I not meeting my own set of expectations?

This gets to the heart of where we’re falling short. It’s often where we spend plenty of brain energy and internal discussion about why we’re acting and behaving in such a way that doesn’t rise to our level of greatness.

The next question to ask and ponder is: What am I afraid of?

Don’t bullshit yourself here! All of us are afraid of something — whether that’s spiders, failing, being ridiculed, or whatever other fears may arise.

In case it’s unclear, you HAVE to be open with yourself to grow and play in the discomfort. Anything else is surface-level and insufficient. paying too much to be safe and comfortable.

Understanding Being Discomfortable

What does it mean to be discomfortable?

It means you’re not an expert nor even remotely fluent in whatever you’re about to do — for example, addressing workplace conflict with someone you really like, telling your spouse something that you’ve convinced yourself they’re going to be upset by, engaging in some physical feat that stretches your courage, going on a roller coaster, or anything else.

It means there’s a likelihood you’ll be clunky, unsure, and possibly endure a cringe-worthy experience. There’s also a real possibility that it’s not that bad at all!

Being discomfortable means trying something new in hopes of bettering yourself.

Experimenting With Discomfort

As of late, with my clients, I’ve been leaning into the idea of experimenting and figuring out what they’re willing to try (i.e., experiment) that’s different from their norm.

Very often, it’s a tweak to a “talk track” — instead of saying ‘I’m fine,’ they say ‘I’m having a productive day .’ Instead of wondering if they’re performing up to their boss’ standards — they ask! If they’re embarrassed about what they’re about to do or say — they say that! As in, ‘I feel a little embarrassed, and yet, I want to say, X.’

In these experiments, my clients are stepping into discomfort. They’re purposely and deliberately making themselves discomfortable.

From the discomfort of the experiment — they learn. They observe themselves and others in these stories. And then, they decide if they want to try the experiment again, refine or modify it, or abandon it altogether.

And here’s how it goes

Most recently, I stepped into the discomfort of giving constructive feedback to someone I was introduced to during a networking meeting. 99 out of 100 times, I would have said nothing. The goodbye from our meeting would have been the last words I’d ever speak to this person.

However, on this occasion, my coach challenged me to step into the discomfort. So I did! I gave this relative stranger constructive feedback about my interaction with him.

And guess what — it went horribly!!! He was completely unopen to the feedback, so much so that he sent me an insult-laden email after the call. I promise you I kept my feedback professional and objective. He did not.

That was my recent experiment.

The big learning — I hadn’t earned the trust of this gentleman. Next time I give constructive criticism to someone, I’ll be sure I’ve established enough trust upfront.

That’s how I’m going to modify and refine my experiment.

The Big Takeaway

As you’re working through your experiment with discomfort, remember, we’re not talking about streaking through campus here (unless, of course, that’s your thing, and hey, no judgment!), but rather embracing the growth and learning that comes from trying something new.

As the great Dr. Seuss once said, “Why fit in when you were born to stand out?” So, go ahead, sprinkle some “discomfortable” into your life — tweak that talk track, start up that conversation, take that next step into the thing that scares you.

And who knows, you might just stumble upon your very own masterpiece of growth, like me stepping into the discomfort of giving constructive criticism to someone I barely knew. What started with my best intentions and hope that someone who appeared to be closed might be open to what I had to say, ended in a rather unproductive experience and receiving an insult-laden email. Lesson learned: trust is the secret sauce.

So, here’s to experimenting, evolving, and embracing the glorious messiness of progress! And if you’re so inclined, I’d love to hear about your experiment(s) — please message or email and let me know. And if you’d like help with experimenting in your life — get in touch. I’d love to explore with you!

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Darren Kanthal

Darren is a values-driven leadership and career coach who supports mid-career leaders with transformative career action plans and candid coaching conversations.