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15 Uncomfortable Things That Will Make You More Successful

15 Uncomfortable Things That Will Make You More Successful

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

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.

(And remember: Investing in your career and developing new
skills can often feel daunting — especially when you have a
day job. If you’re looking for something you can
work towards at your own pace, check out this on-demand marketing course.[3])[2]

15 Uncomfortable Things That Will Make You More Successful

Brace yourself. It’s about to get

1) Learning to Take a Compliment

Source: Reaction GIFs[4]

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

  • The babbling-response.
  • The self-deprecating response. 
  • The total and complete blackout. 

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

  1. Realize that someone is paying you a compliment.
  2. Let them finish.
  3. Seriously, let them finish. 
  4. Take a breath.
  5. Smile and say “Thank you. That’s really good to
  6. 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
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

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
[7]. “They
are not asking if you agree.”  So don’t rob them of that

2) Public Speaking

Source: Giphy[8]

You knew this one was coming, right? Fear of public speaking is so
[9] 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. 

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.

Fake it.

For this last point, I turn to Harvard Associate Professor
Amy Cuddy[10]. 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
[11] 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
[12] if
you want to learn more.)

3) Working With Data

Source: Reddit[13]

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

Source: ReactionGIFs[14]

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

Source: ReactionGIFs[16]

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[17] — 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. 

6) Giving Critical Feedback

Source: Giphy[18]

The only thing worse than taking critical feedback is giving
it. I’ve written about this
[19]: 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

 Source: ReactionGIFs[21]

You know what’s more uncomfortable than fighting through a conflict with
[22]? 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

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

Source: Giphy[23]

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
[24] 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. 

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

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.”

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

Source: Giphy[26]

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
 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
[28]. When we
use our smartphones nonstop it can be harder to think

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


Source: Giphy[30]

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. But 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

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

11) Admitting a Mistake

Source: ReactionGIFs[31]

You know that moment right after you realize you’ve
accidentally made a mistake? You know, 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 my last 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 Claire Autruong caught it[32] and
let me know via Twitter so I could edit the post before it was
too late. Claire is my favorite person of the week.
(Incidentally, she is also a full-stack freelance
[33]r —
inbound certified and nice as can be — if you’re

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.

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

12) Getting in Over Your Head

Source: ReactionGIFs[34]

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

Source: Giphy[35]

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
 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

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
 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.

14) Promoting Yourself

Source: Giphy[36]

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

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

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

Source: Giphy[37]

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[38].
(I’ll hit you up on that next fundraising round), but for all
my internet research, I didn’t really understand what an API

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

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 the comments below.

What uncomfortable moment have you conquered as a
professional? Which are you still working on that you’d add to
this list? Share with us in the comments. 

Editor’s Note: This post was originally published in
March 2016 and has been updated for freshness and