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The Healthy Uncomfortable

I am quite possibly the world’s biggest fan of being comfortable.

The word, to me, conjures up an image of a big comfy couch, a roaring fireplace, and maybe a sleepy puppy to curl up with. What could be better?

So it has been a challenging, repeated lesson for me to learn that feeling uncomfortable is pretty much the only way to experience real personal growth.

I didn’t want to believe this for much of my life, and I often still rail against it now. But more and more often, I’m learning to lean into what I’ve come to call “the healthy uncomfortable.”

By this, I mean getting out of my comfort zone and doing things that seem a little impossible (or at least a tiny bit scary)—getting into the “courage zone” of the graphic here:


Buffer’s values of self-improvement, reflection, and bias toward action have helped me immensely here. In fact, feeling uncomfortable is baked right into our values:

Buffer value 3: self-improvement

It’s not the easiest habit to cultivate, but it just might be the one with the biggest payoff. Luckily, there are plenty of opportunities to practice the healthy uncomfortable. Here are 5 of them. Let’s get uncomfortable!

Uncomfortably sharing new ideas and skills

Reid Hoffman, the founder of LinkedIn, said something once that will probably live in startup infamy forevermore:

If you are not embarrassed by the first version of your product, you’ve launched too late.

This “start before you’re ready” attitude isn’t just for startups: It’s good advice for anyone trying something new.

I’m learning that feeling the healthy uncomfortable is a sign that you’re trying something (pretty much the most important step to succeeding).

When you do things like share the first portrait you’ve painted, speak a new language you’re learning to a local for the first time, or get up on stage to share a talk or personal experience, every cell of your body is going to push back against the idea.

That’s the sign you’re on the right track. If you’re not embarrassed, you’re probably too late.

Uncomfortably giving feedback

A different kind of uncomfortable lives in the idea of giving and receiving feedback.

In what I consider to be the ultimate guide to the healthy uncomfortable, the book Daring Greatly, author Brené Brown has some great advice on feedback:

“I believe that feedback thrives in cultures where the goal is not ‘getting comfortable with hard conversations’ but normalizing discomfort. If leaders expect real learning, critical thinking, and change, then discomfort should be normalized: ‘We believe growth and learning are uncomfortable so it’s going to happen here— you’re going to feel that way. We want you to know that it’s normal and it’s an expectation here. You’re not alone and we ask that you stay open and lean into it.’ This is true at all levels and in all organizations, schools, faith communities, and even families.”

So not only do we have to get comfortable with being uncomfortable, we have to stay that way.

For a long time, this idea seemed almost unbearable to me. And then I saw this image by an incredible illustrator, MariNaomi:

moment of discomfort

Talk about daring greatly! Crossing the scary chasm of the moment of discomfort looks like an impossible leap, but for the sake of what’s on the other side, don’t we have to try?

Rearranging my mind to view feedback as a kindness that we offer to a person—or to the world!—when a person or situation truly matters to us has been one of the hardest and most rewarding things I’ve ever done.

Uncomfortably leading

I’m very lucky to be surrounded by leaders at Buffer who are experts at leaning in to the uncomfortable.

In fact, their influence is absolutely the reason I’ve been able to dare even a little bit greatly. The world is changed by those who are willing to become comfortable with discomfort.

In Tribes: We Need You to Lead Us, Seth Godin writes:

“Leadership is scarce because few people are willing to go through the discomfort required to lead. This scarcity makes leadership valuable.
 It’s uncomfortable to stand up in front of strangers. It’s uncomfortable to propose an idea that might fail. It’s uncomfortable to challenge the status quo. It’s uncomfortable to resist the urge to settle. When you identify the discomfort, you’ve found the place where a leader is needed. If you’re not uncomfortable in your work as a leader, it’s almost certain you’re not reaching your potential as a leader.”

leadership discomfort

Uncomfortably building things

One way leaders can coax you into your true potential with the healthy uncomfortable is by, well, not giving you much other choice.

Maybe it’s a bit like giving the hesitating skydiver just the tiniest nudge out of the plane—guiding someone toward the decision they ultimately want to make at the moment they might be most tempted to default to fear.

Leo and Joel shared a great resource with the team not too long along around the concept of focusing on speed as a habit.

In the article, Dave Girouard, known for building Google’s enterprise apps division into a global business, shares that a certain level of discomfort means you’re moving at the right speed: “Gauging comfort on your team is a really helpful measure of whether you’re going fast enough or not. You know you’re going fast enough if there’s a low-level discomfort, people feeling stretched. But if you’re going too fast, you’ll see it on their faces, and that’s important to spot too.”

Girouard offers some insights about what this feeling looked like in practice at Google:

“While I was at Google, Larry Page was extremely good at forcing decisions so fast that people were worried the team was about to drive the car off a cliff. He’d push it as far as he could go without people crossing that line of discomfort. It was just his fundamental nature to ask, ‘Why not? Why can’t we do it faster than this?’ and then wait to see if people started screaming. He really rallied everyone around this theory that fast decisions, unless they’re fatal, are always better.”

fast decisions

Uncomfortably creating

As a writer, I’ve discovered that uncomfortable creativity is a principle I need to rediscover and re-commit to over and over again.

The more you create, the more comfortable it becomes to you—until you again get up the nerve to push yourself to that next plateau.

This is the kind of healthy uncomfortable that we’ve been recommitting to recently at Buffer. Leo defined it as the “internal struggle” over whether to hit publish.

“This is about self-discipline to go through that struggle, even if it’s felt ever so slightly, every single time. We don’t want to become churners – that churn out posts, or tweets… Every single piece of content is the only one that matters. We give it all of our attention, we want to make it excellent and we have a slight feeling of vulnerability and discomfort when we get it out… That is what creates the volatility of the piece, the opportunity for it to rise above everything else we’ve written so far.”

Chasing this feeling is incredibly counterintuitive—it’s nerve-wracking to share something personal, or weird, or different, and have no idea what kind of response you’re going to get.

I’ve learned it requires real practice and reflection to stretch to that edge. The feeling doesn’t get easier—but more often than not, it might just be worth it.

Let’s get uncomfortable! 6 questions for greater vulnerability

Can you create a habit of cultivating the healthy uncomfortable? I think you can.

Margie Warrell, author of Stop Playing Safe, offers up a few great question in a Forbes article that I’m going to use whenever I need to “re-up” on my commitment to the healthy uncomfortable.

  • Do I keep doing what’s always been done, or challenge old assumptions and try new approaches to problems?
  • Do I proactively seek new challenges or just manage those I already have?
  • Do I risk being exposed and vulnerable, or act to protect my pride and patch of power?
  • Do I ask for what I really want, or just for what I think others want to give me?
  • Do I ‘toot my horn’ to ensure others know what I’m capable of, or just hope my efforts will be noticed?
  • Do I speak my mind or bite my lip, lest I ruffle feathers or subject myself to criticism?

6 uncomfortable questions

How do you make yourself uncomfortable?

Does this idea of the healthy uncomfortable resonate with you? When is the last time you felt it? How do you stretch yourself in new and exciting directions? I’d love to hear all your thoughts in the comments!

  • Natanya

    This article really hit home for me, Courtney! I think the 6 Q’s as the end are especially lucid for sussing out what’s happening in the ‘comfort zone.’ Recently, I’ve made a conscious effort to speak when I feel vulnerable because I know that what I have to say must be worthy or I wouldn’t feel such significant emotion around it. I’ve experimented in the past with NOT speaking when I knew I had something important to say out of fear of ruffling feathers or drawing unwanted attention and criticism to myself. But the consequence of not speaking direct is that the emotion seeps out anyway and in a particularly ungraceful way. I think most people (colleagues, peers, bosses) respect when you try to be as forthright AND as respectful as possible. And perhaps, as I experienced, they will respond with such empathy and love that you may even be taken by surprise!

    • What an incredible change and challenge to yourself, Natanya! Very inspiring; and I totally agree with all your thoughtful points here.

  • Ailin Martinez

    Very powerful article. It reminds me of how creative we become when we feel vulnerable. It also makes me think of this inspiring TED talk

    • One of my all-time favorites! Thanks for adding it here, Ailin; definitely a great resource!

  • Neil McKay

    GREAT article, Courtney! My whole career in education for the last 25 years has been placing myself in uncomfortable positions before I was ready for them. From the early days of waxing high school locker room floors to managing a school district website and 12 web authors in the 1990s (while continuing my job as a custodian!) to ten years of computer, phone and network support with no training (my most valuable tool? a listening ear), to writing news releases and managing social media for the same school district, to returning to school for my long overdue BA in my 50’s, I’ve tried to find ways make myself uncomfortable, to push my boundaries. I’ve failed a lot but I’ve grown from the failures.

  • It is a great thing when you leave your comfort zone, this is where the magic happens. But as far as I see this side is not always bright. You are getting better exponentially, but what you also get is stress and in the longterm to much stress simple ruins your health. Is it the price of exceptional development?
    To be honest I think I need to learn how to handle these uncomfortable situations and how not to be stressful. Do you have any suggestions or actionable tips?:)

    • toroktomi,
      By definition, stress is the body’s reaction to change. Some stress is needed on a daily basis. Stress becomes bad when it is overwhelming. I wonder what would would happen if you tried to balance stress LEVEL and moving out of your comfort zone. Or perhaps using stress management techniques including mindful meditation for a few minutes daily. I’d be interested to know what you think.

  • Having realized about 20 years ago that my comfort zone was too small, I began to practice doing uncomfortable things and seeking new ways to stretch. From where I sit today, my comfort zone is very large, my courage zone is not as large and my terror zone is essentially nonexistent.

    I write this (quickly) to encourage you and your colleagues to keep working at this. Indeed it will serve you well.

    • Wow, so inspiring, Melissa! Would you be up for sharing any of the methods that helped you stretch? I’d love to hear!

      • Thanks for asking, Courtney. Although I warn you, this could take pages and more of your time than you’d like.

        First, I paid attention to things that made me uncomfortable and things I shied from doing. From those, I chose speaking in public and speaking in meetings. These were things that made me VERY anxious, and so I wanted to deal with this problem first.
        Then, I went out of my way to find opportunities for public speaking. One thing I noticed along the way was that few others were better at speaking than I was. This grew my confidence.
        When it came to speaking in meetings, I prepped by noting items on which I should comment. If I had time, I’d outline my pertinent points and strive to keep my comments simple and brief. I also recalled a gentleman who regularly spoke up in meetings and started with “question: …” “for information: …” or “suggestion: …” I had admired his humility and clarity.
        Then I practiced, reminding myself that since I was still living and employed, etc. this wasn’t such a bad thing to do. Eventually I was desensitized.
        Then I tackled another practice until it was barely uncomfortable. And continued until very little makes me uncomfortable.

        When it came to thinking beyond my comfort zone, I recalled that ‘classical problem solving’ involves thinking of every possible solution, then choosing among them. If I only had one or two solutions, I’d muse on the problem for a day or two. I spent time trying to develop alternative solutions, even if they were quite wacky. I also found that giving myself a calm/quiet place to contemplate the issue was helpful. These days, I spend at least 20 minutes each morning with soft, no-lyric music and (really, I confess) an adult coloring book. Next to the book is a legal pad. If I need to consider things, this is when I do it best, so I keep a list of issues to address.
        Anyway, I could coach others on this for weeks. It’s truly enjoyable for me. And again, thank you for asking.

  • Thanks Courtney for this very insightful and meaningful article. I actually thought I was the number 1 fan in the world of being comfortable. But this article has made me reconsider…

    In more ways than one :)

    • Sylvia

      Yes, I, too am a fan of the comfortable :)

    • Haha, really cool to hear that, Aaron!

  • Ah this was fantastic (and just what I needed to read this morning). I’ve pushed myself a lot in the past year, which I’m proud of. But it’s good to be reminded to keep pushing myself out of my comfort zone instead of relying on, “Well, I did something daring a couple months ago…I’m good now.”
    And this was just so fitting considering I just submitted an application to Buffer, and how terrifying it was to hit that “submit” button!

    • Sylvia

      I totally relate, Ellen~

    • All this sounds very familiar to me, Ellen! Wishing you lots of luck!

  • Liz Eckman

    I think this point is very relevant to some of the issues our country (and the world as a whole) is facing today. Mindfully engaging in situations, discussions, and behaviors that make you uncomfortable is a great way to grow and shift your perspective. Thanks for the great article Courtney!

    • Wow, great point, Liz! Thanks so much for checking this one out. :)

  • Sylvia

    So spot on, Courtney! Thank you so much for sharing!! This is so timely for me. Lately, I’ve definitely been feeling uncomfortable in so many ways, and stressing over it. But this helps put all of that in a positive framework, “it’s okay to be embarrassed and feel out of your depth, you’re meant to feel that way when you’re still growing and improving.” When I don’t feel pretty confident in something I’m presenting or the way I’m leading, it feels like I’m doing it wrong or I start to second guess myself (ex: did I not do enough research, I need to be a better communicator, maybe I’m not a good writer).

    You said, “One way leaders can coax you into your true potential with the healthy
    uncomfortable is by, well, not giving you much other choice.” And I’m so curious and eager to hear about how you’ve seen your leadership do this while maintaining goodwill and keeping it positive. In my personal experience, everyone tends to be resistant to change, including myself…so how do you get your team on-board? And how do you ask your team to try and adopt “speed as a habit” without making it a critique on efficiency?

  • Leos Stehlik

    Courtney, great reading (as usual!), thank you. I would be interested in seeing how you evolve in the direction of being permanently out of the comfort zone. We did experiment with this quite a lot about a decade ago during my days at IBM. The short term benefits seemed great. The result was people being afraid, stressed out and … disengaged as a result. The more disengaged employees, the more stressed management, the more stressed management, the stronger the push on people towards panic/danger zone.

    We did abandon the idea in the end, and returned to T.J. Watson’s idea of hiring “wild ducks”, creating best possible environment for them to thrive, and most of all, keep the wild ducks wild, never attempt to tame them.

    This is the principle upon which I build up my own company MOBILECONS Limited, and so far works well – though probably too early to tell, as we were only established 11 months ago.

    Take care

  • I think this has nothing to be uncomfortable or not, only “how to think” this issue.

  • Olivia Holt

    What a great way to start out the new year. This is exactly the push I needed to conquer my goals :). I’ve always been fairly timid but nothing feels better than jumping out of your comfort zone. You may succeed in the task or you might not, but it’s all a learning process and that’s truly what matters in the end.

    • Same here, Olivia; I struggle with confidence as well! A work in progress :)

  • Wonderful piece, Courtney! Those six questions at the end are real kickers. Especially the one about asking for what you actually want instead of what you think others want to give you. This is great motivation for ways to push myself to grow in this new year. :)

    • Awesome, so happy to hear that! Yup, I was excited to find those questions; they really brought it home for me!

  • David Meshulam

    Thank you, Courtney…my work requires me to be uncomfortable to be effective. Your excelllent 6 questions will help me to stay this way! Bravo to you!

  • Debbie Discovers

    Such a wonderful inspiring post. What would the world do without Buffer? Keep it up guys! ?

  • @courtneyseiter:disqus You are such a great writer Courtney! :) Do you want to hear something funny? I’ve been studying the Buffer values and when I got to this one “You regularly and deliberately do things that make you uncomfortable,” I thought it was a mistake. (I almost emailed saying, “I think it’s a typo.” Lol) But then I read and re-read it and the lightbulb came on. Oh, I get it now. As an entrepreneur I’ve been a risk-taker and most people look at that as crazy. This article gives me warm fuzzies to know that I’m not crazy to be in the uncomfortable zone, I’m just where I need to be. :) Thank you.

  • P.S. How is Leo such a yogi? He’s like an old wise man encapsulated in a young body. I wish I had such wisdom in my 20s…

  • I LOVED this post Courtney. My favorite part was the questions at the end because those take some real guts to actually answer truthfully and accept the answers. I’ve personally been in a ‘season of questioning/transformation’ for career goals and aspirations and reading this has been helpful! Off to share…!

  • Sheila Nico

    Great read! as I have read in the Consumer Health Digest that our mental state can really affect own lives. well yeah the comfort zone can provide you what you need, but can it give you what you want? well as they say, it is always greener on the other side. Thanks for this great article

  • Sheila Nico

    Great read! as I have read in the Consumer Health Digest that our mental
    state can really affect own lives. well yeah the comfort zone can
    provide you what you need, but can it give you what you want? well as
    they say, it is always greener on the other side. Thanks for this great

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