how to get out of your comfort zone as an entrepreneurIt was a cold mid-January night my Junior year at Indiana. I was sitting on my back porch with my best friend and roommate, Hank. I had spent the past year of my life trying to get one of the governing student bodies at IU to sponsor my passion project, the IU Campus Comedy Festival, to no avail. I knew if we could get funding, we could build an incredible festival with the potential to run for years, but finding someone in power that shared my vision proved difficult.

“Just do it, Timmy. You don’t need funding.”

“…But Hank…” I insisted.

“Can you do this or not?”

“Yes, but it would be better with…”

“I don’t care,” he interrupted, “just do it and they’ll come.”

Hank was forcibly evicting me from my comfort zone and I was terrified. He was shutting down the safe road and detouring me through the unknown. I didn’t know it then, but one thing I’ve learned since is that…

Your Comfort Zone is Your Idea Graveyard

Most interesting things in life happen just on the other side of your comfort zone.

– Michael Hyatt

Plain and simple, your comfort zone is where good ideas go to die. In this zone, the creative gives way to the status quo. If you’re an entrepreneur and you’re comfortable, it’s likely that you’re not pushing yourself or your business fast enough.

Outside of our comfort zone is where we start to find magic. As the saying goes, “If you want to keep getting what you’re getting, keep doing what you’re doing.” Once we break out of the comfortable, we find that rarefied air where great things can happen. One step outside of our comfort zone is were ideas have sex and we find success.

The Problem: None of This is New Information

If this is the first you’re hearing about the importance of stepping outside your comfort zone, you’ve been under a rock. This is the topic of far too many books, speeches, blog posts. I’m pretty sure that, every Spring, hundreds of commencement speakers fill out a Mad Libs about this exact topic so that a group of hungover college grads can ignore them and Snapchat their friends stupid selfies.

The real question is what are we doing about it? For most of us, we respond by retreating right back to a place of comfort, but if you know me at all, you know that I live in a place of discomfort. So if you’re looking to break out of your comfort zone, I have found the recipe that is guaranteed to do it for you.

How To Break Out of Your Comfort Zone in Three Weeks

Comedians tend to find a comfort zone and stay there and do lamer versions of themselves for the rest of their career.

– Chris Rock

Week 1 – Start Small

In my years of wavering in and out of my comfort zone, I’ve found that half the battle is breaking the monotony. In week one, we start small. For seven days, I want you to take a different route every time you get in your car. Going to work? Take a new route every day. Need to pick up milk? Pick a new store. Going to get the kids from soccer practice? Take someone else’s kids.  Edit – I’ve been informed by our lawyers that this is a felony. Please do not take anyone else’s children. Although prison would also be an interesting venture outside of your comfort zone.

The whole point of this week is to prove that you don’t have to do the same things over and over again. You can always choose to do something new. You’re training your brain to seek novelty rather than comfort, which takes us into my favorite part of the process:

Week 2 – Embrace Failure

how to break out of your comfort zone - accept yourself
Even Super Heroes need to air their dirty laundry.

We all fail daily. This week, embrace that. Don’t hide, don’t make any excuses. Think about your faults and repeat after me.

I love myself and accept myself fully.

Now insert a fault you have and repeat again.

I struggle to communicate effectively with members of my team, but I still love myself and accept myself fully.

Rinse and repeat. Do this every day in the mirror. Repeat each phrase three times. It sounds hokey and new agey, but it works. Most importantly, it leads into my favorite week…

Week 3 – Make a Complete Ass of Yourself

You know that saying “There’s nowhere to go but up from here?” We really embrace that this week. I’ve done this exercise with dozens of public speakers, comedians, and actors looking to get comfortable in their own skin and I’ve seen it work at a perfect clip, but it requires a big dose of humility.

Can you put your ego aside long enough to completely embarrass yourself?

If the answer is no, then thanks for playing, but you’re never going to truly make it out of your comfort zone. You need to lean into that discomfort if you want to succeed. One of my favorite examples of this principle in motion:

7 Guaranteed Ways to Get You Out of Your Comfort Zone For Good 

  1. Learn all the words to a shitty 90’s song. Serenade your friends.
  2. Buy 10 sweatbands. Wear them all to the gym. Grunt loudly while you curl 5 pound dumbbells.
  3. Go to a bowling alley alone. Tell the attendant you need to get a lane on the end for some privacy because you’re a semi-professional bowler who needs to get some practice in before the PBA Tournament coming up in Cleveland. Bowl a 45.
  4. Dance naked in the mirror for 15 minutes. No more, no less. Nothing you do for the rest of the day will embarrass you.
  5. Flirt with old women. I’m talking like… 80 years old… If you don’t have any old women in your life, go to MCL Cafeteria. An old woman will be provided for you.
  6. Go to a popular area for joggers and high five passer-bys. Run after people who don’t high five you back.
  7. Attempt to spend an entire day communicating exclusively with song lyrics. See how far you can get. For an added degree of difficulty, narrow it down to a genre or artist.

All of Life’s Best Opportunities Start From a Place of Sheer Terror

Everything I’m truly proud of in this life has been a terrifying prospect to me.

-Charlie Day

Remember my friend Hank who told me to forget about getting funding and just make things happen?

He was right.

After I built the comedy festival myself, funding options started coming at me from all angles. We were able to bring in the world famous Upright Citizen’s Brigade from New York and I was proud to return to Bloomington this past April for the 3rd Annual IU Campus Comedy Festival.

That’s my proudest moment. I witnessed a community come together and continue a tradition that would never have started if it wasn’t for my best friend getting fed up and forcing me out of my comfort zone.

Now I want to hear your stories. Hunckler is traveling the world to get out of his comfort zone, what are you doing right now that’s outside of your comfort zone? What do you wish you could do that’s currently outside of your comfort zone?

Drop a comment or shoot me an email to share your stories!