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What I Learned About Fear From 700+ Comfort Zone Challenges

Building the one skill that can change every area of your life.



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I still have 2 spots left in my course FACING FEAR: So You Can Design (And Live) A Life You Love. It’s an online course where you go at your own pace. Want to save $100? Use the word COTTON CANDY at checkout. Details here

2013 was the hardest (and happiest year) of I’ve ever experienced.

Before I tell you why… I have to explain what the catalyst was.

It changed my life, and it may yours as well if you read this all the way through.

In the fall of 2012, I discovered that although all my dreams, goals, and ambitions were different… when I procrastinated, bailed on them, or doubted myself, I could trace the root of the cause back to one thing: FEAR.

I was afraid of failing.
I was afraid of what others would think.
I was afraid of how I’d “make money” off it.
Or, I wasn’t sure what my next steps were …and was afraid to sit in that uncertainty long enough to figure it out or learn what I needed to overcome it.

I was “drifting” through my days, addicted to checking my email and working my life away.

I was desperate to find “what my passion was” but felt the deeper I dug into it, the more confused I became.

Sound familiar?

I was still puzzled on what my passion or “purpose” was but I did know finding the answer would require:

Getting comfortable being uncomfortable.

Especially if I wanted to…

  • Do WORK that was big, innovative, and creative (awesome careers are often built by taking unconventional paths)
  • Live an interesting and adventurous LIFE that I was excited and proud to look back on


Once I discovered that FEAR was the root of everything that stopped me, I decided that I wanted to… how should I put this politely?

Punch fear in the face.

I was confident that “getting comfortable being uncomfortable” would be similar to throwing a stone onto the surface of a still pond.

The effects would ripple outward into every area of my life.

And so The Year of Fear Project was born.

Of course, it didn’t have that sexy name at the time. At first, it just looked like I had lost my mind. But don’t all genius ideas at first?

I scribbled down some simple guidelines that would be my game plan…

Do something…

  1. NEW
  2. DIFFERENT than my normal routine

Every. Single. Day.

For an entire year straight.

SPOILER ALERT: this simple decision would change the entire course of my life.

I even convinced another what I consider to be a totally sane human to join my in this project as an accountability partner.

FUN FACT OF LIFE: when you do weird interesting sh*t, 98% of the time someone is always interested in joining you.

It’s always more fun to fly your freak flag with someone else. Invite your friends.

My accountability partner lived on the west coast. And I was in Texas.

To check in we decided to text our comfort zone stretch or odd adventure every night before going to bed.

I set an alarm on my cell phone for 11PM for the next year that would punctuate my life with a powerful question:

How did you grow today?

And boy, was I about to grow.


When people ask me to the explain how the first Year Of Fear Project changed my life I can think of only one response:

I started working to live instead of living to work.

I had more magic, more late nights – early mornings, and laughter in 365 days than I had seen in the last decade of my life combined.

FUN FACT: the nights of life you remember won’t often be the ones you got enough sleep.

I also learned that…

Being brave feels a lot more like throwing up all over yourself. – Jon Acuff

Here were a few comfort challenges and adventures I tackled that year:

I started cashing in on some damn vacation days instead of working myself to death.

Here I am during a trip to New Orleans approaching street performers and snagging fun photo opps.


I started making time for all those things I always “talked about doing” but never actually did.

Such as lending my legs to a local School For The Blind, and tandem biking visually impaired kids around the city. This experience actually landed me in the local news paper. (Which was double uncomfortable because I hate being the center of attention).


I decided I wanted to make new friends who were doing awesome things.

So I started attending tons of events all by myself…on purpose. This forced me to make conversations with other people instead of staying in my bubble with people I already knew. Here I am at an art event rolling solo, and proudly reppin’ it in the photo booth.


I confronted insecurities head on.

I realized how self conscious I was with my body, and wanted to up my girl game so I bought my first skirt! Prior to this, my kneecaps barley ever saw the sunshine. I was so self conscious it was hard to even wear shorts… and I live in TEXAS PEOPLE!

I became obsessed with finding interesting opportunities in everyday life.

Like picking up this hilarious (and adorable) Canadian hitchhiking trio. I figured with that getup, they probably wouldn’t steal my car or rob me. They didn’t… but they DID serenade me with ukuleles the entire trip. #MagicMoment


I finally challenged myself to face what everybody would think…

And, the scariest one of all… at the end of 2013, after hundreds of comfort zone challenges I finally became brave enough to take my writing public after years of writing quietly in private and I launched this exact blog you’re reading right now.

High five to self, that last one definitely made me want to toss my cookies.


My project was complete. 365 comfort zone challenges in the can. More growth than I could have imagined. A full year of saying YES and exploring wherever it lead.

It was a relief to not have to scare the sh*t out of myself everyday. Yet I also knew that if I didn’t keep practicing the skill I had acquired my ability to punch fear in the face would fade over time.

For 2014, my mission became: turn adventure and comfort zone abandonment into less of a “project” and more of a “lifestyle.”

That year, I started going a bit bigger with my comfort zone challenges. I could see how my ability to be uncomfortable was compounding over time.

I prioritized my passion as much as my paycheck and went fully remote.
At the time I was working an “awesome on paper” job where I did marketing and strategy for well known entertainers in the music industry.

(Read: I earned lots of cool points at parties when people asked what I did for a living, I had paid vacation, and health insurance) #Adulting

But after the first Year of Fear, I finally realized… although I’ll always be ambitious, my life was meant to be about MORE THAN WORK.

I wanted my world to be build around ADVENTURE.

After years of being a desk jockey, my heart and soul were leading me elsewhere. Especially out of my zip code.

I craved building my work around my life and not my life around my work.

So, I took an offer to run an online business for someone else so I could go fully remote, travel the world, and work from anywhere.

Putting my notice in and honoring my urge to see the new faces in unfamiliar places is still one of the hardest things I had ever done.

I cried in my car the day I made the decision because I could no longer ignore that my dreams would never fit in anybody else’s box… and because dammit.. I had health insurance! #ThingsWeOnlyThinkAboutWhenWeAreTryingToAdult

I also wanted to throw up all over myself… (are you seeing a pattern here?) … but I was getting better and better at getting comfortable being uncomfortable.

In 2013, I had only seen the project pay off in better work-life balance, more adventure, and interesting experiences.

Now this skill had began to shape how I made decisions in every area of my life.

The job swap was just the start of the amazing comfort challenges and adventures I collected that year.

I turned my bucket list into my to do list.

One of those things was buying a one way ticket to another city I didn’t know anyone in and spending a month exploring. That year I spent a large chunk of my summer in Portland, Oregon.


I remember the day I bought a one-way ticket… all I could think was, “Who am I anymore? Doing all these crazy things!”

But I had to keep moving forward because I felt more alive than ever.

I was tapped in and turned on to my life.

Little did I know, things were just starting to take off for me and I hadn’t seen anything yet.

That year I collected a few experiences that still make me grin today:

I went white water rafting on some of the best rapids in the country.

Whitewater rafting

I rallied a few friends up and took a sunrise flight in a hot air balloon, even though my fear of heights had my kneecaps quivering the whole damn time (here’s a photo of us sneaking a bubble maker on the flight and blasting 15 of of our fellow passengers with bubbles-midflight).


I did hilarious things like participating in breaking a world record for the longest yoga chain.


I started doing consulting on the side and charged TRIPLE what I made in my “awesome on paper” job.

My ability to flip the bird on what other people thought was growing…

My baby blog had started to grow, and so had my confidence to put my gifts out into the world. Through a few comfort challenges I issued myself around my writing, I ended up getting my words onto a few mainstream sites.

Only a year earlier letting 10 people I KNEW reading my work made me want to hyperventilate. Now hundreds of thousands of people were reading them. In only a year.

That’s growth ya’ll.

But more importantly than following my heart or giving my art room to breath…

Looking back now, I feel like this was the first time in my life where I was actually proud of who I was becoming. I don’t know about other ambitious over achievers out there, but we often don’t credit ourselves for our effort and brilliance.


Here’s something surprising about this project you may not expect…

Up until 2015, I had been doing this entire project in private.

The only people who knew about it were a few close friends, and my accountability partner in the first year.

In full transparency, as 2014 wrapped up I realized had accomplished a lot of CAREER ambitions. But, my ability to maintain work-life balance and LIFE goals was starting to slip.

I felt the urge to return back to the field with another 365 challenges.

I also realized that I could use this project to inspire others into action, not just myself.

For 2015, I re-committed to another full year of fear and this time I vowed I would go PUBLIC with the project. Triple barf.

That year all my posts on social media included a curiosity inducing hashtag #YearOfFear and I was forth coming about why I was doing all these crazy, awesome, interesting (and sometimes odd) things.

In 2015, I would take the project LARGER and with more purpose and I would ask others to join me in their own self created challenges.

Some of the comfort zone challenges looked like this:

Hopping in the passenger side of a police cruiser and spending 8 hours going into the seediest parts of the city witnessing first hand the incredible danger our officers make for us every day.

Police Ridealong

Waking up at 5:30am on a Saturday morning, climbing in the back of an Austin Paramedic unit, and hitting triple digit speeds on the freeway. There’s nothing like walking into a house where someone looks at you hoping you can save their life to remind you how lucky you are that you woke up with the ultimate gift: YOUR HEALTH. Not everyone was as fortunate as you.

EMT Ridealong

I volunteered at a soup kitchen and put names to faces of the homeless people in my own community.

A particularly touching moment was when a lady ran up to me and gave me her brand new bag of socks as a “thank you” for being so bright and kind to her in the food line. I learned some of the most unselfish people in the world or the ones who have NOTHING to give, yet those with EVERYTHING to give can hang on to it so damn tight. (including myself sometimes) (photo)


I walked through the front doors of a nursing home and asked the staff to nominate me their loneliest visitor. Someone who hadn’t seen their family or a friend in awhile.

I found myself knocking on the door of a 98 year old lady named Ella. She caught me by surprise when she was the happiest f-ing 98 year old I’ve ever seen.

I asked her what the secret was to living such a joy filled life at an old age. She told me:

“Fill your life FULL of adventure. And, take lots of risks Kendra.
When you get old, you’re going to live off the memories you make when you’re young.”

In that moment, sitting in room 202 with a total stranger… I realized I had shown up to give HER a gift and she had given ME one.

Visit A Nursing Home

I never revealed to her that she was part of my #YearOfFear Project. Or that I had ONLY made it to her door because I had started putting adventure first after years of bowing down to the hustle, the grind, and other people’s priorities.

Walking down the hall after our visit, tears in my eyes…I promised myself I’d help teach other people her simple message:

Do all the things you will regret not doing.

I also took the time for small, fun things like: 

Saying YES to a last minute invite to go sailing for the first time



Challenging my bod to tackle acro yoga lessons — I didn’t even know my body could bend in some of those ways…

I also broke yet another world record by climbing into bed with 6 close friends and being a part of the worlds largest breakfast in bed party. (waffles included)

Breakfast In Bed

And the scariest thing I’ve ever done in my life….

Remember that little consulting side hustle I started in 2015? Yeah, I turned that bad boy into my full time gig.

For three weeks I couldn’t sleep after I decided to abandon the security of working for someone else, but I stuck with the fear. Because I knew…

I had to start living the life I wanted to look back on… NOW.

Taking that leap into my own business was the best (and scariest thing) I’ve EVER done. And yet…

The most rewarding part of 2015 and The Year Of Fear Project had nothing to do with ME.

This (now public project) was inspiring other people.

Total strangers were reading about my experiences and launching their own #YearOfFear projects. Around the things that matter to them.

Learning to dance.
More creativity and presence with their kids.
Getting back into the dating game after sitting on the bench.

The messages, emails and photos were pouring in.

I felt this was the beginning of honoring Ella.


My favorite thing about The Year Of Fear Project is:

It’s no longer just about me.

In 2016 I presented the project to a sold out crowd at the Think Better Live Better event.

Notice I'm wearing a lot more skirts these days :-)

Notice I’m wearing a lot more skirts these days 🙂

From the stage, I graciously asked 200 beautiful strangers to join me in The Year Of Fear Project. To make it their mission in the next 24 hours to do something new, different or outside their comfort zone.

Remember how I said people love to fly their freak flag?

Guess what.

They said yes.

And we hope you will too…[keep reading to learn how YOU can join the #YearOfFear Project]


Although getting comfortable with being uncomfortable has lead me to most of the best memories I’ve had in the last three years, there were a lot of other amazing opportunities for growth because of the project.

  • It made me the best version of myself for the other people around me: I never felt “stuck,” because I was constantly learning, growing and laughing. It made me a better friend, roommate, lover and business owner. I got out of my damn head and into enjoying my life… NOW. I realized I didn’t have to wait to be happy. I could be happy NOW. But I had to take responsibility for my own life and happiness first.
  • I discovered the power in “challenged based” approaches: the 1 year on, 1 year off pattern taught me the power in “sprinting” and “recovering.” I now take that same approach and apply it in shorter durations on my other goals. It’s help me stay sane knowing that I don’t have to always be operating at 1000 miles per hour to get to where I want to go. I always have a finish line in sight during heavy hustle zones. #WorkLifeBalanceYall
  • It cranked my creativity up an 11: consistently looking for new ways to abandon my comfort zone on a daily basis tapped my brain into more innovative thinking and strategies. This has now transferred into how I attack other challenges and goals. I don’t break out of the box, I just completely live outside of it.
  • I became more interesting, outgoing and magnetic to other people: The #YearOfFear project pushed me into the spotlight of my peer group and community. Those who live their life on their own terms are instantly seen as leader (whether they plan for it or not).

No one ever warns you that you’ll be inspire by your dreams… and also terrified by them.

That nearly all the best moments and memories you’ll ever create will often never be inside your comfort zone.

And if you simply CHANGE YOUR RELATIONSHIP with fear, it will impact every area of your life… for the rest of your life.

Today you can make simple, but powerful decision:

Run TOWARD the things that scare you, not away from them.


We’re collecting new experiences and comfort zone challenges across the globe. Do you want to join in The Year Of Fear Project?

Here’s how…

In the next 24 hours, do one thing that is:

  • NEW for you
  • DIFFERENT than your ordinary routine

Bonus points if you can bring in a friend or find a way to make a positive impact bigger than yourself.

Post your image to social media with the hashtag #YearOfFear and link back to this post to invite your friends to take the challenge with you.

When you look back at the end of your life, do you want to say…

…Wow… I sure felt safe!
… Or … wow that was an adventure!

Start living the story you want to look back on TODAY.

Begin doing all the things you’ll regret NOT doing.

Besides… the risk of breaking out of your comfort zone isn’t nearly as bad as the risk of staying in it your entire life.

Cheers to fears my friends.

Let’s tackle them together when you join the #YearOfFear Project.


TLDR: Your comfort zone is the place your dreams and aspirations go to die. If you want to live a BIG, interesting, and successful life know that fear will always be in the passenger seat. Get comfortable being uncomfortable.


Feature photo by Meegan

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