Putting Yourself in Uncomfortable Situations Leads to Growth

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I was first exposed to this idea while in college at Quinnipiac University in Hamden, Connecticut.

The idea: Putting Yourself In Uncomfortable Situations

uncomfortable situations 1

Here’s what happened…

A Story I’ll Never Forget

I remember I was sitting in an international business class and I was not particularly enjoying it. I was ready for the class to end so I could move on to whatever else I had planned for the day.

As the class came to a finish, the professor assigned us a video to watch before the next class. I wasn’t sure what it was about or how it was going to impact me, but I took school seriously so I made an effort to actually watch it when I got back to my dorm later that night.

I opened the Youtube link and I started watching the video. It was an interview with either a multi-millionaire or multi-billionaire international business owner that, to my recollection, was involved in some way or another in the oil industry.

I don’t remember much about the video except for one particular part where the entrepreneur spoke about an experience that they had when they were younger, maybe 15 or 16.

Their parents decided that they should go somewhere to be exposed to an uncomfortable situation in order for them to grow and become a stronger and better person.

Again, I can’t remember the exact details, but the parents sent this entrepreneur on a one way flight or bus trip out into an unknown and foreign place where he was left to fend for his own and make his way back home. To his parents, it was an essential part of him growing into someone that could face adversity.

The entrepreneur went on to explain the experience and how uncomfortable and out of place he felt during it. Not sure how to get home. Not knowing anyone. In an impoverished place.

But the biggest revelation that came out of it was that he did indeed make it home, he survived the experience, and he had a new perspective because of it.

How It Impacted Me

As a 20 some year old sitting in my

college dorm room, I too probably hadn’t been exposed too deeply to the world outside of the bubble of the Northeast of the United States that I had grown up in.

Sure, I had traveled around the Northeast to a certain extent playing travel soccer and other family vacations, but I was never put into an unknown and uncomfortable situation left to figure it all out on my own. That was a new concept to me and it honestly excited me in a way. Twenty years into my life and I was ready for adventure. Ready to experience something uncomfortable.

Thatvideo impacted me throughout my college years and it instilled a fire in me to push myself to my limits and to go to unknown, uncomfortable places, whether physical, emotional, or spiritual.

I saw the value that the entrepreneur in the video had received when forced into this situation and it inspired me to want to do the same so that I could grow as a person, learn more about the world, and understand how I could fit into it.

Over the past 10 years, I’ve continued to think about this Youtube video remembering the excerpt I just detailed in this article.

It’s been a guiding light for forcing myself to continue to grow as a person and to never feel too comfortable. When we feel over comfortable, we fall into comfortable routines where our minds aren’t being pushed to grow and advance. I don’t like that. I like feeling uncertain because I know that it will push me to become a better person, one way or another.

When’s the last time you’ve pushed yourself outside of your comfort zone?

How did it feel? How did it impact you?

Find Uncomfortable Situations!

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If you’re an entrepreneur like me, or even if you’re not and you’re working for a company, take time every year to challenge yourself and to find the uncomfortable.

Ideas to Get Uncomfortable

(1) Take a Trip

This could be in the form of a trip to somewhere exotic that you’ve never been before. Go by yourself or with your significant other and do things differently. Become engrained in the culture and meet people. See how they’re living life differently. Here’s a list of 30 places in the US you could start planning your travels to.

(2) Have the Uncomfortable Conversation

It could be in the form of having difficult conversations with the ones you love or the people that you work with.

When you sense there’s a conflict, don’t back away, dive right in and have the conversation. Conflict always leads to change and it will force you to grow in the process.

(3) Create a New Habit

It could be creating new habits that feel super uncomfortable at first. Maybe you struggle to wake up in the morning and you’re always waking up right before you need to start work. Force yourself to be uncomfortable and wake up 2 hours before work for 1 full month. See how it changes you. Read this article I wrote about morning routine for inspiration.

(4) Try New Foods

It could even be as small as forcing yourself to try new foods. Never eaten Ethiopian or Indian before? Give it a shot and embrace the flavors!

When you step outside of your comfort zone, you open an opportunity to change as a person and to gain a new perspective on different aspects of life.

If you’re someone that values personal growth, take this seriously and make an effort to embrace uncomfortableness on a daily basis.

How Do Uncomfortable Situations Apply to Being an Entrepreneur? 

As entrepreneurs, we’re constantly faced with challenges, big and small.

Starting a company from the ground up is a major challenge that thousands, possibly even millions of people embark on every year, and only a small percentage of them succeed in making it to year 2.

Does that mean that the entire year was for nothing? Absolutely not.

When we take on the mindset of an entrepreneur, we take on the burden of feeling uncomfortable and not knowing the answers to most problems that we run into.

As an entrepreneur myself, I have firsthand experience of the many challenges that can be thrown your way while growing a company, hiring people, managing the team, scaling, and so on. Every day is a new opportunity to feel uncomfortable and it forces you to change and grow FAST.

If you go into being an entrepreneur with a closed mind and a certain way of doing everything, it’s going to be a lot harder than if you enter the opportunity with an open mind willing to make mistakes and learn from them.

If you’ve already been exposed to extremely uncomfortable situations in the past and your mind and spirit has grown from it, the challenges that you’re thrown as an entrepreneur won’t feel as intense as if you hadn’t been through that adversity in the past.


There’s no set formula for how to put yourself into uncomfortable situations, but it’s a part of growth that can create real change if you embrace it and look for it.

It’s easy for us to get caught up on our “routine” and what we’re used to.

We get comfortable waking up, going to work, coming home, working out, making dinner, and going to sleep.

We get comfortable taking trips home to see family and friends.

We get comfortable going to the same restaurants, eating the same food, and drinking the same alcohol.

We get comfortable doing the same workouts and not pushing ourselves too hard.

We get comfortable traveling to the same places for vacation.

But when do we get uncomfortable?

The uncomfortable opens our eyes to new things.

The uncomfortable puts us in situations to meet new people.

The uncomfortable challenges us to grow as people.

I can’t say that I’ve perfected this either.

There’s a lot of parts of my life that I’m very comfortable in and it feels good.

However, I’m always looking for new ways to push myself out of that comfort zone so that I can continue to learn and grow.

I challenge you to do the same and to see how it impacts your life.

Thanks for reading.

If you haven’t already, join my newsletter where I share thoughts like this on a regular basis so that you can continue growing and learning each and every day as a person and entrepreneur.

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About Connor Gillivan

In the past 10 years, I’ve started 7 businesses & built two to $10M+ in annual revenue, teams of 30+ & an exit in 2019. Today, I run SEO & growth for my 4 B2B companies while teaching millions how to make SEO simple.

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