4 Things I Learned by Stepping Out of My Comfort Zone 850 Times in a Row

4 Things I Learned by Stepping Out of My Comfort Zone 850 Times in a Row

You hope to meet incredible people, but you’d rather bite your lip than make small talk with strangers. You want to build that side business you’ve been daydreaming about, but the complexities of actually starting it make the palms of your hands sweaty. Speaking up and adding value in corporate meetings could improve your reputation in the eyes of your boss, but you’re scared of saying the wrong thing. Circumstances like these – the ones that are fundamentally important in the long-term, but downright terrifying in the near-term – are incredibly common. And of course, the easiest reaction to these circumstances is avoidance. But that would be a huge mistake!

In fact, if there’s one thing I’ve learned from completing over 850 self-assigned comfort zone challenges, it’s this:

We don’t stumble accidentally into a wildly fulfilling, deeply satisfying, jaw-dropping life… we create it.  And the journey always leads us outside our comfort zone.

Before starting The Year of Fear Project, I was the least likely person on planet Earth to be interesting, adventurous, or successful (more on my story here).

Even after a decade spent studying the psychology of success and how to procrastination-proof my goals, I found tackling something outside of my comfort zone every day was the one decision that transformed every area of my life nearly overnight.

I have now gone on to speak, write, and teach students across seven continents how to get comfortable with the circumstances that make them uncomfortable.

Here’s the good news: you don’t have to invest all the hard work and hustle I did over the past several years to learn a few of the most powerful lessons from venturing outside your comfort zone.

Here’s the bad news: you can’t “unlearn” what you’re about to read…

After getting a sneak peek into just a few (of the many) life changing lessons I’ve learned, you may have no choice but to join me on this journey.

When you discover the real “secret” to getting everything you want out of life starts with one simple action – facing your fears in small ways every day – it becomes the healthiest addiction one can form.


A Comfort Zone Is The Most Dangerous Place To Live

A comfort zone is like wallpaper in most people’s lives – operating in the background, ever-present, something we never even think about.

But as much as we seemingly enjoy comfort and routine, we as human beings are often happiest when challenged and making progress. And when we commit to finding small ways to grow daily, we discover four things rather quickly:

1. Even when you are on the right track, you will still doubt yourself.

Before you practice expanding your comfort zone, you may think fear is a sign that you are on the wrong track.

I vividly remember preparing for my first cross-country move to Los Angeles from the Midwest.

Even though I dreamt about it daily, I struggled to slash it off my bucket list for four years. Every time I convinced myself to finally put my sleepy hometown in the rearview mirror, fear would overwhelm me…

  • “Am I really strong enough to do this alone?”
  • “Will I ever make friends as great as the ones I have here?”
  • “What if I’m not cool enough to hang with the hipsters in LA?”
  • “Wait… how much is rent?!?”
  • etc.

What I discovered after starting The Year of Fear Project is perfectly summed up by one of my favorite writers, Jon Acuff:  “We will never be brave enough to do what we need to do next.”

The problem wasn’t that I was losing sleep at night and sweating through my sheets at the rate of Niagara Falls. The problem was I thought I shouldn’t be.

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Even when you are on the right track, you will still be afraid and doubt yourself.

Half the battle is already won when you expect that fear will show up. It does not matter the size of the leap – little or large. From walking up to compliment a beautiful stranger, to bravely asking your boss for a raise, doubt and fear are always near when you are on the right track.  I’ll say that again…

Doubt and fear are always near, especially when you are on the right track.

And it takes practice to embrace this reality…

Instead of a stoplight, I now see doubt and fear as a spotlight – illuminating where I should go next. I realize all of the good decisions (and necessary growth decisions) that change our lives often cause us to lose a little sleep, and that’s perfectly OK.

How would your life change if you saw doubt and fear as a sign that you are on the right track? What goal or project would you bravely stick with or start up again?

2. You can love others without listening to them.

I’ll kick this off with a disclaimer:  having a few people you can lean on and trust to give it to you straight when you are being a wackadoodle is important. However, what may surprise you is that those whose advice helps you the least can sometimes be those who love you the most.

So, trust me now and believe me later:  you can love someone without listening to them every step of the way.

When you start taking risks – especially the kind of risks your loved ones don’t agree with – you become a red hot bullseye for feedback. Even when they mean well, it’s rare that they’ll just toss their hats in the air and enthusiastically shout:

“Go for it!”

“Do what makes you happy!”

“Quit that crappy sales job that is slowly suffocating your soul and go teach yoga!”


In short:  they care and want to protect you from failure.

But they may also subconsciously fear that if your life changes too much, there may not be space left for them. And that’s OK too. That’s just one of approximately a million oddball ways we humans show love.

A powerful quote that helped me release my people pleasing ways in this area came from my friend, Jesse Elder:

“The greatest gift we can give ourselves is to own our ownhappiness. The greatest freedom we can give to others is to let them have their own experience and not try to control it.”

If that’s not worthy of being tattooed on the backside of our eyelids, I don’t know what is.

And Jesse’s sentiment is also reinforced by another one of my favorite quotes…

“If you have big goals and dreams,
don’t expect others to follow you,
because you’ll represent the strength,
courage and vision they don’t have yet.”
– Peter Voogd

Bottom line: If you want to slide into the grave with less regret and make a positive impact on the world in the way only you can, I would encourage you to take calculated risks and let other people’s doubts and opinions about how you live your life be their problem, not yours.

Sometimes the greatest gift we can give others is to simply remind them of what is possible when they take a chance on themselves.

How can you take responsibility for your own happiness and allow others to have their own experience?

3. You may be called crazy before you’re considered “cool.”

When you start facing your fears, expect that people may call you “crazy” long before they call you “cool.”

These days it’s “cool” that I run two successful online businesses from my Macbook Pro. It’s admirable I’m invited to speak on stage and get interviewed on podcasts across the globe.

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But you know what wasn’t cool?

This little whacky idea I had in 2013 to do something new, different, or outside my comfort zone every day for an entire year straight. And it wasn’t just friends and family who looked at me like I had lost my mind – strangers wagged their fingers of disapproval at me too.

When I decided to do a police ride-along to collect a new experience, the dispatcher who scheduled my ride was puzzled by my idea of “fun.” Especially when it involved a bulletproof vest and waking up at 4:30 AM on a Saturday.

Kendra police ride

Result:  it was a life-changing Saturday I will never forget.

When I walked into a nursing home and asked them to nominate me their loneliest visitor because it was a good deed that had been collecting dust on my bucket list for half a decade, the staff crossed their fingers hoping I wasn’t a lunatic.

Kendra and Ella

Result:  one of the most powerful experiences of my twenties. The story has now gone on to inspire others across the globe to complete the same comfort zone challenge.

When I booked a one-way plane ticket to the Pacific Northwest to live in a city I had never been to simply because it “sounded like a great adventure,” my Grandmother didn’t sleep a wink for weeks.

Kendra travel

Result:  I had the best summer of my life.

When I had zilch speaking experience and agreed to do a 45-minute talk at Marc and Angel’s Think Better, Live Betterconference, flanked by some of the best speakers money can hire, other speakers I knew thought I was bonkers.

Think Better, Live Better conference

Result:  I worked my tail off for months, lost a lot of sleep, and walked on stage so terrified I was afraid the film crew would catch it on camera. However, when I got a standing ovation and walked off stage to see Marc and Angel smiling, I’ve never been so proud to make two great friends happy that they chose me.

Stepping outside your comfort zone doesn’t have to be a large challenge to be life-changing either.

Some of the most powerful challenges I took on were small, but significant...

  • Deciding I would go first anytime someone asked for a volunteer.
  • Wearing skirts to overcome my challenges with body confidence.
  • Simply asking for a 33% raise with confidence (I got it).

Look closely at the journey of anyone you admire. I guarantee that most of the small things that led them to being called “cool” first earned them the label of “crazy.”

And that’s great news for you and me. We now get to be cool with being called crazy, and know it is simply part of the process when we’re trying to put a positive dent in this giant spinning rock.

Nobody who changed history followed all the rules. What crazy ideas do you have that the world needs to experience?

4. You don’t have to choose between priorities and dreams. You can do both.

When you decide to start taking risks it doesn’t mean you can’t care about what other people think. Or that you get to ditch priorities like rent, kids, and student loans.

However, we often fool ourselves into thinking life has to be an either / or choice. I have to be a Mom OR I can chase my dream of opening a craft shop.

I would encourage you to make one tiny but powerful adjustment to your vocabulary:

Swap OR for AND.

I am a Mom AND I’m building my craft business on nights and weekends after my kiddos fall asleep.

I was born with a disability AND I can still travel the world.

I am a software engineer AND I am completing a world record for playing a golf course in all 50 states.

Most great ideas, inventions and businesses are built off the midnight oil in the scraps of time others discard to social media, reality TV, or mindless activities. Ever heard of Facebook? Or Snapchat?

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But, it is going to take bravery. Pushing through the doubt that is built into all great ideas. Proclaiming your dreams. Loving others without listening to them 24/7. Being cool with being called crazy before your idea blossoms. And knowing, deep down, that what you want for yourself matters as much as other priorities in your life.

The Biggest Mistake Most People Make With Their Comfort Zone

The biggest mistake I see most people make with trying to expand their comfort zone is believing it has to be “big” or reckless. After 850 comfort zone challenges, I firmly advise the opposite.

Start small.

Simply doing something outside of your ordinary routine is enough to stretch you and wake your brain up.

Consider taking a new way home from work.

Dig out a piece of clothing you bravely purchased but have not worn yet.

Walk up to the next interesting person you see and say, “Of all the creative and interesting people I’ve seen today, you’re my favorite!”

Don’t underestimate the power of tiny opportunities to stretch your comfort zone. These small actions help you meet new people and build your confidence to try bigger comfort zone challenges over time.

It Doesn’t Matter When You Start, Just That You Start

Another common misnomer is the belief that age is a factor. Age is irrelevant to when you can begin adventurously living outside your comfort zone.

If you’re older, shouldn’t you be inspired to take risks that make the most of the time you have left?

If you’re younger, don’t you want to make the next 50 years the best yet?

Again, it does not matter when you start, just that you START!

Every Day You Wake Up With An Incredible Invitation

Every morning when you wake up you are given an invitation to live a life of complete engagement and rich adventure.

Don’t turn it down!

The gifts and goals inside of you hope that today you won’t let this be another article you read and don’t take action on.

If you take one lesson away from this post I hope it’s this:

No one stumbles accidentally into a wildly fulfilling, deeply satisfying, jaw-dropping life… they create it.

Are you ready to grab today’s invitation and take it?

Here is your opportunity…

24-HOUR COMFORT ZONE CHALLENGE: In the next 24 hours, I challenge you to take one small action outside of your comfort zone. Post your idea right now in the comments section below, and I’ll come back to personally read each one (you can also ask me any questions you have).

And if you need ideas, you can grab my list of 100 Weird, Easy and Interesting Ways to Expand Your Comfort Zone.


  1. Decide one action you want to take outside of your comfort zone in the next 24-hours. If you need ideas, download this checklist.
  2. Post your intended action (personal comfort zone challenge) in the comments below. Or leave me any questions or feedback you have.
  3. I’ll come back through to read and respond.


Author Bio: Kendra Wright is a writer, speaker and location independent entrepreneur. Since creating the Year Of Fear Project in 2013, she has completed over 850 self-assigned comfort zone challenges. Kendra specializes in teaching others how to break through fear and uncertainty. Find more of her work and comfort zone challenges at

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Written by Aba Forson

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