15 Uncomfortable Things That Will Make You More Successful
By: Meghan Keaney Anderson
Tags: Business, Careers, Leadership, Life Lessons, Startup

Nearly 2,000 Medium readers have recommended the first version of this article. So I’m bringing it back, this time with a few new uncomfortable things worth trying.

In a truly beautiful letter to his daughter Yolande, Sociologist W.E.B. Du Bois extolled the virtues of being uncomfortable.

Yolande was headed to a new school halfway around the world from the neighborhood and people she knew. It was years before women had the right to vote, and decades before the Civil Rights Movement.

Du Bois knew she would have more than a few fish-out-of-water moments. Instead of trying to shield her from them, he asked her to revel in them:

“Don’t shrink from new experiences and custom. Take the cold bath bravely. Enter into the spirit of your big bed-room. Enjoy what is and not pine for what is not. Read some good, heavy, serious books just for discipline: Take yourself in hand and master yourself. Make yourself do unpleasant things, so as to gain the upper hand of your soul. Above all remember: your father loves you and believes in you and expects you to be a wonderful woman.”

I am no W.E.B. Du Bois. I have neither his fortitude nor his stunning way with words. What I do have, however, is a small history of uncomfortable experiences that have made me stronger, and an endless sea of animated GIFs through which to illustrate those experiences.

Here are a handful of uncomfortable situations in which you should take De Bois’ advice and “Take the cold bath bravely.” You’ll be better off as a result.

Brace yourself. It’s about to get awkward.

1.Learning to take a compliment

Tell me if this sounds familiar: You work exceedingly hard. You’ve honed your skills. You know when you’ve done great work and take a quiet pride in it. And yet, the moment someone verbalizes it in the form of a compliment you can’t seem to string two words together. Instead, you revert into one of the following:

The babbling-response.

The self-deprecating response.

The total and complete blackout.

That nonsense has to stop. Here’s how to take a compliment:

Realize that someone is paying you a compliment.

Let them finish.

Seriously, let them finish.

Take a breath.

Smile and say “Thank you. That’s really good to hear.”

Move on in the conversation. Don’t over-explain. Don’t undercut yourself. Just thank them sincerely and move on with a question about how their work is going.

Why is this so hard? According to a study by Acknowledgment Works, nearly 70% of people associate embarrassment or discomfort with the process of being recognized. Sometimes, this response is caused by the dissonance we feel when someone contradicts our own self-doubt.

But that doesn’t explain why people who are genuinely proud of themselves still balk at hearing that same praise from others. For those people, it often comes down to a learned-response. In other words, you are awkward when you receive compliments because I am awkward when I receive compliments — or, if not me, then your mom; your co-workers; your icons. We’re all making each other squirm.

One way to turn that discomfort on its head is to realize that the compliment has more to do with the person giving it than with you. “When someone is complimenting you, they are sharing how your actions or behaviors impacted them,” explains Business Psychologist Mark Goulston. “They are not asking if you agree.” So don’t rob them of that moment.

2. Public Speaking

You knew this one was coming, right? Fear of public speaking is so common it has its own phobia name: Glossophobia.

Now, I don’t think I need to go into the reasons behind this particular juggernaut of discomfort. We’ve all been there. Having that many eyes and ears on you is stressful. It makes you feel as though any mistake or imperfection will be amplified a thousand times. I’m also certain you realize how compelling a good public speaker can be, and how much it can advance your ability to lead and inspire.

So all that leaves is the classic glossophobia question: How do you get over it? The answer is a mix of substantial and superficial changes.

Know the essential points. Do not attempt to memorize your speeches. Instead, memorize your key points and your pivot lines. Pivot lines are the sentences that will move you from one key point to another. They act as navigational guides for your audience and a momentary comfort zone for you. Use these pivot lines to reset, take a breath, and move to your next key point.

Do not attempt to memorize your speeches. Instead, memorize your key points and your pivot lines. Pivot lines are the sentences that will move you from one key point to another. They act as navigational guides for your audience and a momentary comfort zone for you. Use these pivot lines to reset, take a breath, and move to your next key point. Understand that everyone wants you to succeed. You are not going into battle. You are not facing a firing squad. These people you are talking to are all decent, interested folks. Many of whom also suffer from glossophobia. So know they are friendly, and talk to them like it.

You are not going into battle. You are not facing a firing squad. These people you are talking to are all decent, interested folks. Many of whom also suffer from glossophobia. So know they are friendly, and talk to them like it. Fake it. For this last point, I turn to Harvard Associate Professor Amy Cuddy. She is a brilliant researcher and a self-proclaimed introvert who noticed something fascinatingly simple about skilled public speakers: They all looked comfortable, and they all appeared to be in command — even if that appearance was all a big ruse. So she studied what happens to people’s mindset when they stood up straight, casually used the space around them, and otherwise “power-posed.” Turns out the physical act of power-posing can send biological triggers to your brain to reduce cortisol levels and increase testosterone, calming you down and empowering you simultaneously. (Here’s a blog post on science-backed tips for better public speaking if you want to learn more.)

3. Working with data

If you don’t take to math easily, then delving into data can be intimidating. But learning to use data to find opportunities and underscore your points is a game-changer in your career.

The trick to mastering data is to learn it in context. Start by getting to know the core metrics that reflect your work. Play with spreadsheets at the close of a month. Learn to recognize trends. Alter the data to see how moving one metric would influence the others. The more time you spend with the data the more natural interpreting it will become. Once you’ve done that, you can dig into the tougher stuff. Here are a couple of resources to get you started:

4. Waking up early

It’s exhausting, this modern life. While it may seem like you should squeeze as many extra minutes of sleep out of the morning as possible, the opposite is usually true. Your energy, focus and mental capacity are at their highest during the morning hours and proceed to wane throughout the rest of the day.

Take advantage of that time before breakfast when the chaos of the day has yet to set in. For most people, waking up early is a learned practice.

First, make sure you’re cognizant enough to make the decision. Putting your alarm clock right next to your pillow is bound to result in you hitting snooze from a dazed state. You can’t be expected to make smart choices while you’re still dreaming. In addition, waking up early needs to become a pleasant experience.

So if the thought of going straight from your warm bed to a shower or treadmill seems abrupt, then don’t do it. Instead, move from your bed to the cozy corner chair in your living room and read for a bit with a mug of coffee. What you do early on doesn’t matter, what matters is that you use the time in productive ways. (Read this blog post for more tips on becoming a morning person.)

5. Taking critical feedback

This one stings sometimes, but it’s important. Learning to hear criticism without turning your back to it can be one of the most fortifying achievements of your career.

Think of critical feedback as a cheat sheet. In giving you direct feedback, your manager or colleague is giving you a shortcut — your own personal konami code — to becoming better at your job.

Sometimes, even with the best intentions, taking feedback well can be a struggle. Your impulse will be to protect yourself; to get defensive, or stop listening.

So, be conscious of it. Much like accepting a compliment, take a breath when you realize critical feedback is coming your way. Listen to it all without interruption. Write down what you can. Then, ask questions to make sure you’re interpreting it right. (Read this blog post for more tips on receiving tough feedback.)

6. Giving critical feedback

The only thing worse than taking critical feedback is giving it. I’ve written about this before: Whether you’re a manager or a friend, feedback is an opportunity to help someone get better. Don’t waste it. Good coaches give feedback directly and with respect. Don’t try to soften the blow or talk around the feedback. Doing so may make you feel better but it will only serve to confuse them.

If you’re struggling to be direct, try one clear line followed by detail. For example, “John, what you’re doing isn’t working. Let’s talk through why…”

In addition, feedback is always most constructive if accompanied by recent concrete examples. Telling someone they have a bad attitude isn’t helpful — it’s far better to point to a precise moment in which that bad attitude showed up, and then explain how moments like that can become detrimental in aggregate.

Ultimately, knowing how to improve is as important as knowing what to improve. The person receiving the feedback should leave the conversation feeling empowered to change, not broken down. (Here are some more tips on how to give negative feedback without sounding like a jerk.)

7. Fighting through conflict

You know what’s more uncomfortable than fighting through a conflict with someone? Settling for an uninspired compromise, and then gossiping about that person over drinks with your coworkers. That’s WAY more comfortable than conflict. (Not to mention, way less productive.) There are two ways conflict negotiations get botched:

Either one side gives in too easily, or

both sides are too inflexible to make resolution possible.

The cleanest way through conflict is to try to discover what’s motivating the other person.

Comment trolls aside, it’s pretty rare for someone to be argumentative for no good reason. Discovering the reason will help you find a better route to solving the conflict. That’s why your best asset in settling conflict is a collection of genuine questions and a patient ear to hear the answers.

8. Exercising

I keep waiting for the study that says that exercise isn’t all its cracked up to be. It’s fair to say that study isn’t coming. Not only is exercise good for your physical health, the ties between exercise and mental capacity are becoming undeniable. (Thanks, science.)

If you like working out, skip right ahead. If you don’t, here are the only things I’ve found to work.

Find your reason. Maybe you want to lose weight. Maybe it helps you think more clearly. Maybe you have three kids, a constantly buzzing phone, and a dog all demanding your attention and exercise is your only chance to be alone. The reasons don’t matter. Just find the one that feels authentic for you and use it.

Maybe you want to lose weight. Maybe it helps you think more clearly. Maybe you have three kids, a constantly buzzing phone, and a dog all demanding your attention and exercise is your only chance to be alone. The reasons don’t matter. Just find the one that feels authentic for you and use it. Make the time. Treat exercise like you treat showering. It’s just something you do; a non-negotiable daily ritual. (Psst … here are 10 little ways to sneak in exercise at work.)

Treat exercise like you treat showering. It’s just something you do; a non-negotiable daily ritual. (Psst … here are 10 little ways to sneak in exercise at work.) Get over it. I used to hear about “runners’ highs,” a sort of delusion that sets in after you’ve done it enough that actually makes you believe jogging is fun. That may be the case for some people. It never happened for me, and wanting to like running made it easy to give up when I ultimately didn’t. Du Bois’ advice is worth hearing again here: “ Make yourself do unpleasant things, so as to gain the upper hand of your soul .”

I used to hear about “runners’ highs,” a sort of delusion that sets in after you’ve done it enough that actually makes you believe jogging is fun. That may be the case for some people. It never happened for me, and wanting to like running made it easy to give up when I ultimately didn’t. Du Bois’ advice is worth hearing again here: “ .” Find your genre. The softer alternative to the above point is to find the exercise format that you hate least. If a crowded gym makes you want to run for the hills, then work out at home or outside on your own. If you find jogging boring, join a class or sports league. Work at it — it’s worth it.

9. Unplugging

I love the internet. And smartphones? They’re like personal escape hatches that you carry with you all the time. But maybe “all the time” is not such a good idea.

According to a TIME poll of more than 5,000 people, 84% of respondents said that they could not go a single day without their cell phones, and 20% said they check them once or more every 20 minutes.

It’s not the frequency of usage that’s the problem; it’s what that level of usage does to our focus. Using our smartphones at night can make it a lot harder to sleep. When we use our smartphones nonstop it can be harder to think clearly.

So, here’s an experiment. For two weeks, set aside some screen free time blocks in your day. During that time fight the urge to open your laptop, watch TV, or glance at your phone. Sustain it for 60 minutes or more and see if you’ve gained better focus at the conclusion of the experiment. Then, go find some cat videos on YouTube to celebrate.

10. Networking and making small talk

Everyone has a small-talk formula. Some people start with the weather (nice, mild winter we’re having, eh?), while others ask how things are going with you at work.

Here’s the trick to mastering small talk: Get fascinated by it and the person wielding it.

It’s a little like being dealt a hand of cards, you can use what you have to get to bigger and more interesting plays. If someone asks you how work is, don’t say “fine” — or worse, “busy.” Tell them it’s good and follow up with, “You know, there’s one project in particular that you may find interesting.” If you’re doing the asking, take any opportunity to dive deeper. Use each question as a spring board to the next one. Eventually, you’ll hit on something substantial.

11. Admitting a mistake

You know that moment right after you realize you’ve accidentally made a mistake? That moment when the dread plummets into your stomach in one sweeping motion? Uncomfortable doesn’t even begin to describe it.

However, even that can be turned around. The most effective way to replace that sinking feeling in your gut is to assess the situation and take action. Ask yourself:

Is it immediately reversible? On a recent blog post, I had a glaring typo. This was not some extra spacing after a period, this was a blatant blemish smack in the middle of my post. And I missed it. Thankfully someone on Twitter caught it and let me know before too much time has passed.

On a recent blog post, I had a glaring typo. This was not some extra spacing after a period, this was a blatant blemish smack in the middle of my post. And I missed it. Thankfully someone on Twitter caught it and let me know before too much time has passed. Who should know? Whom does your mistake affect? Who is in the position who can help you solve it? Quickly scan the list of people that need to know about your mistake and contact them explaining what happened and what you’re doing about it.

Whom does your mistake affect? Who is in the position who can help you solve it? Quickly scan the list of people that need to know about your mistake and contact them explaining what happened and what you’re doing about it. What’s your plan? If the mistake isn’t immediately reversible, you’ll need a plan of action. A good plan is the best antidote to mistake-induced discomfort. Shift from panic to determination as soon as possible, and that discomfort will subside.

12. Getting in over your head

Of all the uncomfortable moments, getting in over your head is probably the one most worth pursuing. Sure, it’s a little scary , and there’s always the chance of failure, but nothing stretches you more or makes you more creative than having no idea what you’re doing.

So how do you put yourself in an over-your-head style situation? Raise your hand. When there’s a project no one wants, step up. When there’s a problem that has existed for years, have at it. Then break it down. Take big challenges and tackle them piece by piece. It may not always be fun, but you will almost always be better for the effort.

13. Disagreeing with your boss

There’s a reason my boss is my boss. He’s really freaking smart. He’s exceptionally good at what he does. So in the times I find myself disagreeing with him there are usually a few moments of internal back and forth before I’m ready to say so aloud. But I do so because I’ve learned that staying quiet is more damaging than polite.

It took me becoming a manager myself to realize how constructive disagreement can be. A perspective that is never tested grows shallow. Sometimes a dissenting opinion will make you reconsider. Sometimes it will make your stance stronger. Either way, the exercise of hearing different angles advances your thinking and improves your outcomes.

So spit it out. “I disagree on that point.” If that feels too direct consider framing it as a question. “What about a different approach?” Most importantly, don’t save up for a major disagreement. Practice coming at issues from different angles now. The more you present constructive counterpoints the easier it will become, and you’ll be more likely to speak up when it matters most. (For more on the value of disagreeing at work, read this post by Stowe Boyd).

14. Promoting yourself

Periodically we survey our team to get a sense for how each employee is feeling about the company and their own career development. One theme that sometimes comes back is how to get ahead without being self-promotional. Usually the comment goes something like this: “It seems like the company always recognizes the same people. I do good work, but it seems like no one notices.”

The honest response to these comments is: You’re right.

Growing companies are chaotic. They churn with activity: breakthroughs and setbacks, new projects and discoveries. Keeping up with it all isn’t practical, so managers rely on signals, and tasteful self-promotion is a valuable signal.

Self-promotion is sometimes misused to serve the ego, but there’s a way to pull it off that also also serves the company.

We are taught not to be overly self-promotional. We are encouraged to value the achievement rather than the accolades. That message is almost right. It focuses on what matters most but fails to recognize that talking about an achievement can fuel its fire. Promoting an achievement can galvanize others to bring their ideas to it and ensure future efforts learn from it. And yes, it can get you noticed.

The trick here is being judicial. Not everything you do deserves broader attention. But some things do. In those cases, talking about them doesn’t make you an attention junkie it makes you a good communicator. If the personal attention makes you uncomfortable, focus your advocacy on the work itself. Draw attention to the discovery, milestone or lessons uncovered by your effort. The company will be better for it and you will too.

15. Admitting you don’t understand something

I was a good six months into my job as a product marketer for a software company before I finally owned up to not knowing what an API was. I mean I knew what an API was. I’d Googled it, obviously. API stands “application programming interface” and constitutes a set of “subroutine definitions, protocols, and tools for building application software.” Thanks Wikipedia. (I’ll hit you up on that next fundraising round), but for all my internet research, I didn’t really understand what an API did.

Then it came time for me to explain that my company, HubSpot, was opening up more of the helpful little buggers to the public and I did not know where to begin. So, I went to my product manager and did what any ego-protecting protagonist would do, I tried to fake it.

“How would you describe this — in layman’s terms — to the average reader?” I asked.

Smooth. Always blame the reader.

“Well, developers are pretty accustomed to APIs so don’t worry about needing to educate them on it.”

Not smooth.

I folded.

“Ok, then, how would you explain it to me? I mean, will you explain it to me? I don’t get it. ”

And thus began my relationship with APIs. I still don’t understand all the details of how they work, but I’m much smarter for having gotten over myself and asked the question.

Don’t fake it until you make it. Get over yourself and ask the question.

I’ll stop there …

… but this is really just the beginning. Who knew there were so many uncomfortable things in the world? (Michael Cera. Michael Cera probably knew.)

From negotiating salary to reading “some good, heavy, serious books” as Du Bois suggests, this list could go on and on. Hopefully it will, in your responses.

Inspired to try something uncomfortable? Click the 💚 to help others find this article.