I’ve been learning how to be comfortable with uncomfortable for quite some time now. Since graduating from college in 2005 I have had one year that I would actually consider “comfortable”.

But I guess that’s the price you pay when you’re trying to accomplish your really big freakin’ dream.

Without getting into too much detail, I have felt discomfort in the last 7-8 years in each way at least one time financially (broke), emotionally (fearful), physically (unhealthy), educationally (lacking the right skills), and relationally (inability to communicate with others).

I’m confident that some of you have felt a little discomfort in at least one of those areas, yes?

While usually not fun, I believe that these periods of discomfort have been the most important experiences in my life thus far. They have been essential to my personal growth, my improved determination and motivation, and have helped me develop incredible resiliency as I push forward towards, what seems to be, an almost impossible goal.

Being comfortable with the uncomfortable, though, is a skill that most people have to learn how to do. It is not something that comes naturally to most people and a lot of us, myself included, can’t stand to be uncomfortable for even short periods of time.

During periods of discomfort we tend divert our uncomfortable feelings by engaging in activities that take us further from our goals like eating more, drinking more, watching more TV, sleeping more, doing drugs and/or participating in other abusive behaviors instead of pushing through and taking more action.

Me? I sometimes start doubt my abilities to succeed, become a little depressed, and start sleeping more…and I eat a TON of peanut butter and jelly toast (haha. I’m very serious about the toast part). I then feel like crap for a few days, become less productive, move further from my goals, and the cycle starts all over.

comfortable with the uncomfortable_sleep

Not sweet.

You may or may not know this by now, but Jake and I are trying to accomplish our big freakin’ dream by becoming adventure travel hosts on a major TV network.

Trust me when I say that it has NOT been a comfortable journey. We’ve experienced everything on the list I mentioned at the beginning of this post. We’ve lost lots of money that we didn’t have, we’ve often found ourselves emotionally drained by occasional unbelief, we’ve exhausted ourselves physically by “burning the midnight oil” on a regular basis, and we’ve had our fair share of uncomfortable discussions and arguments with each other…you could also call them yelling matches.

But being the dreamers and go-getters that we are we have to be honest with ourselves about something. We are significantly pushing the boundaries of our comfort zone at all times and we will have to deal with being uncomfortable more often than not, especially if we want to, like picture at the start of the post says, “make the magic happen.”

As we push those boundaries, we’ll encounter challenges that we’re uncomfortable facing, often times tempting us to run away and hide (or sleep more)…and towards massive amounts of peanut butter and jelly toast.

But we can’t do that!

We have to stop hiding from the uncomfortable and remember that all of this discomfort is growth. In fact, we have to be proactive and actually look for new experiences that make us uncomfortable. We need our comfortable little zone pushed, extended and expanding outwards towards our big freakin’ dream and we must realize that discomfort is inevitable…and enjoyable in the long run.

comfortable with the uncomfortable_expan

Helen Keller said it best when she said, “Security (comfort) is mostly a superstition. It does not exist in nature…avoiding danger (discomfort) is no safer in the long run than outright exposure. Life is either a daring adventure, or nothing.”

I believe that being comfortable with the uncomfortable is not only an important survival skill for life in general, but it’s a required skill for those who want to break away from the status quo and live out their big freakin’ dreams.

Life is either a daring adventure, or nothing. Be comfortable with the uncomfortable.

Here are 4 things I do to help me become more comfortable with the uncomfortable:

1. Exercise:

Not only is this important to do daily, but it’s especially important when we’re reaching outside of our comfort zone. For me, exercise sheds all negative, stressful energy that accompanies uncomfortable times. Without exercise all those negative toxins stay pent up inside you, furthering the discomfort. More importantly, exercise clears the mind so that you can face challenges head on and with more creativity, resourcefulness, and energy. Find a 20-minute activity that will get your heart pumping. It does wonders I promise.

2. Tim Ferris Comfort Challenges

In his book The Four-Hour Work Week, author Tim Ferris states “it is possible to condition yourself to discomfort and overcome it”. He trained himself for times of discomfort by putting himself in small uncomfortable situations on purpose. Put yourself in small uncomfortable situations so that you can build your up your resiliency. Ideas include eye gazing with strangers, being comfortable in silence with others (and not looking on your phone!), and asking for phone numbers of people you don’t know. Little things like this will help you start to understand and control your emotions when feeling uncomfortable so you can prepare for the really uncomfortable moments that are bound to come. If you’re really serious, then you can randomly lie down in the middle of a crowded public place for 10 seconds. Either way, find opportunities to put yourself in uncomfortable situations daily.

3. Research

Often times, I’ve found my way out of uncomfortable times by using good ol’ Google. A lot of discomfort comes from a new challenge or experience we don’t know how to handle and some research might be just the thing to get you through it successfully. Is it a financial discomfort? Physical? Emotional? Relational? You name it, there’s probably someone that’s gone through it already and they’ve provided you the answer and the relief. I use others experiences to help me all the time.

4. Patient Belief

I feel like I’ve learned quite a bit about being comfortable with the uncomfortable and nothing is more important than patient belief. It takes a lot work, but being able to navigate through discomfort really boils down to believing that these feelings and uncomfortable situations will eventually end, that you will come out of stronger than ever, and ready to take on the next challenge. How long it lasts varies. I’ve had to deal with discomfort for many, many months at time, especially financially. It was painful then, but looking back I realize that those experiences have allowed me to be more resilient in the face of new challenges. Remember, though, it’s not only patiently believing you eventually come out of it, you must do so while taking action.

What do you do to become more comfortable with the uncomfortable?


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Chad is “Ready-Fire-Aim.” That means he prefers to try first, ask questions later. He lives by the idea of “failing forward” and believes it takes 10,000 hours (or 10 years) to master whatever it is one is currently doing. Chad doesn’t want to waste the rest of his life mastering somebody else’s dream, so he’s willing to keep trying any number of his thousands of ideas until one finally works. Chad is Stampabout’s ideaman, go-getter, and the “risk” in “calculated risk.” Chad is a sales and marketing professional that has sold and marketed everything from real estate, a healthy vending franchise system, payment processing systems, and beers to local bar patrons. He owns an ecommerce consulting company, EcommerceInfluence.com, that helps his clients convert more visitors to paying customers.


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