4 Tips To Get Comfortable Getting Uncomfortable

David Horning
4 min readJan 20, 2022

Cockroaches.

My most recent Airbnb was crawling with them, which might be why the topic of discomfort is kicking around in my brain, but in a world where our expectations are increasingly getting thwarted by the unexpected, being able to adjust quickly is becoming a skill more and more companies are looking for in their employees.

Hey, leaders: your current and future employees are looking for that quality in you too.

While negotiating with the host for a refund and booking to stay at another Airbnb is a simple pivot, today’s quickly changing marketplace demands flexibility. “We’ve never done it that way” and “But we’ve always done it this way” need to be stomped on and sprayed until they’re dead.

You need to try something you’ve never done before.

You need to be bold.

You need to stand out.

You need to be unafraid to fall on your face.

You already knew that.

It’s getting in the right frame of mind to do those things that causes friction. Discomfort in the face of uncertainty is a natural part of trying something new, but in a world moving faster than it ever has, you’ve got to make the leap from unsure to action in a snap, and to do that, you need to program the proper mindset.

Before I give you the 4 tips to do that, consider this analogy:

Stepping outside of your comfort zone is like stepping into a pair of new shoes. Sure, your old shoes are basically a part of your feet — they’re so comfortable, but you’ve worn them so much, there’s holes in them and they aren’t working anymore. When you finally pick a pair that you like from (insert your favorite shoe store), you slip them on, and something doesn’t feel right. They’re not fitting to your feet like the old ones did, and they’re even rubbing against your achilles, causing some discomfort every time you take a step. You take them home, because like every other shoe you’ve ever purchased, it’s eventually going to fit comfortably, you just have to get through the friction first… and it does.

Other than thinking about shoes or cockroaches when you’re facing the discomfort of trying something new, here are 4 tips to get you into a mindset that is more likely to inspire you into action.

1. Make a list of all of the first times you’ve tried something new

Whether it was a new food, the first time you rode a roller coaster, the first time you went into the ocean, the first time you gave a public speech, your life is filled with firsts.

Put yourself into your shoes all of the times you did something for the first time and felt the relief, and even excitement, of getting through it.

2. Make a list of as many wins in your life that you can think of

These need not be huge, substantial, life changing achievements.

I’m talking about the times you’ve helped someone figure out a challenge, the times you’ve checked off even the littlest things on your to do list, or the body count of all of those roaches you left in your wake at that Airbnb.

When facing something new, we have a terrible habit of deferring to what we don’t have, when our wins far outnumber our losses.

3. Visualize the best possible outcome

You’re being lifted on your team’s shoulders and carried down the street in a parade planned by your city to appreciate the contributions made.

Your team is filled to the brim with bright, enthusiastic people going above and beyond the scope of their jobs with a sense of purpose.

You get an entire day to nap.

Whatever the vision is, start from there and work backwards by asking yourself that question “What would have to happen for that to happen?” over and over again and ending with “What can I do now?”

4. Laugh about the worst possible outcome

Seriously.

It may sound counterproductive, but if there’s something like a 4-day workweek that you’re unsure about, gather your team and brainstorm a scene where absolute chaos reigns because you made that decision.

Get as wild and out there as possible like that time Tony Hseih removed managers at Zappos. Make a video, write a script as though the national news is covering the bedlam that’s taking place at your company. Why? Confronting and exaggerating your fears head on, then laughing about the absurdity of your doomsday thinking (especially as a team) creates common ground in reality, rather than just letting those fears go unaddressed.

To get started on adapting this mindset, I’m offering a hands-on workshop Friday 2/11 at noon eastern where you’ll learn:

-Why rethinking like a comedian is important to becoming a better leader.

-3 mental pivots that open up more innovative ideas.

-How to recognize and reframe status quo thinking.

-The benefits of asking the right kinds of questions when met with external resistance.

Register today!

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David Horning

Teaching leaders to develop their sense of humor and make work more human.