30 Day Challenge

Key Points:

  • “A Comfort Zone Challenge is a planned action to face a fear with the primary goal of overcoming this fear or increasing your courage and confidence. This action includes a calculated risk of negative social evaluation but does not expose you to real danger or long-term negative consequences.”
  • Planned action: don’t run around like a headless chicken trying to make a challenge out of everything.
  • Primary goal: differentiate challenges from just random acts, real-life situations, and pranks.
  • Avoid real danger and long-term negative consequences: don’t mess with the wrong people and avoid places you frequent

The above key points are from http://www.comfortzonecrusher.com


Public speaking is the number one fear for most people in the US. We often think about and fear this more than death. Most people in their early adulthood don’t give much thought into their own mortality. Instead, we misalign our fears into things like rejection and embarrassment. My desire to fix this sort of misalignment was the basis for starting my comfort challenge. To step outside the safety of my comforts and to increase the range of quality experiences. It was a necessary step for me to take to increase the quality of my life.

It’s important to note that fear will always exist, but it is to our benefit to face them so that we may challenge ourselves to grow. In hindsight, doing this challenge was one of the best decisions I have ever made.

Rejection & Embarrassment

Being sure to maintain eye contact, ask for the phone numbers of at least two (the more you attempt, the less stressful it will be) attractive members of the opposite sex for three days. Girls, this means you’re in the game as well, and it doesn’t matter if you’re 50+. Remember that the real goal is not to get numbers, but to get over the fear of asking, so the outcome is unimportant.

-Tim Ferriss on getting over rejection

During my 4 years in college, I’ve made friends mostly through the following means: mutual friends, classes, or from the dorms. While this is usually the case for most people, this meant that I was missing out on potential relationships with a vast majority of interesting people that I routinely passed by.

The idea of approaching a stranger and trying to strike up conversation terrified me. I wasn’t sure what to expect from strangers. What if he/she says something mean? Then I thought, “I probably would not see him/her again, so why am I making such a big deal out of it?” I began to think logically, and I realized that I had nothing to lose, and everything to gain. This first step into getting over my fear of rejection and embarrassment would allow me to unlock greater potential for the future.

The first time I approached a stranger of the opposite sex was admittedly nerve-wracking. It’s interesting to note how simple I think the approach would have been with her male counterpart. I took on Tim Ferriss’ challenge in his book “The 4-Hour Workweek,” and approached Michelle- an attractive undergrad and aspiring healthcare professional. My anxious tendencies diffused a substantial amount after we shared a couple words. She complimented my bravery and we shared a good laugh about the difficulties of approaching strangers. She gave me her number and we went our separate ways. It was a success.

Disclaimer: I walked around campus for nearly an hour before I put on my big boy pants and approached her.

Towards the end of the challenge, I’ve learned the importance of not caring. Who cares if strangers judge or say mean things? Chances are that I will never see them again. It could also just be that they are having a bad day. We are all prone to having bad days.

This interaction happened before I started my comfort zone challenge, but it was a noteworthy event in my life. It had marked the beginning of my challenge conquest. All these social fears that I had were given healthy introspection and looked at through newly gained perspectives. After my interaction with Michelle, I grew the courage to take selfies with strangers, and my phone-book began to grow quickly with the addition of newly collected phone numbers.

People are cool, I’m pretty cool

Ask yourself, Am I the kind of person I would like to have as a friend?”

-Napoleon Hill

Strangers want to like you. This usually holds true, but there are a handful of people that might think the other way (maybe they are having bad days). Difficult people should not be given an ounce of anger, but instead pity.

I have found that smiling and laughing when talking with strangers helps them feel immensely more comfortable with you. These have to be genuine though! I’m still working on it, but I’ve seen how a genuine smile or laugh can reduce the amount of tension in social interactions. Conversations are more fluid between friends, so it is to our benefit to talk to others as if they are already our friends.

Another important thing to note is to be a person you yourself would want to be friends with. Since I’ve read the above quote by Napoleon Hill, I often ask myself if I am about to do something I would not want a friend of mine to do. It comes from honest introspection, and I have found that there are silly habits of mine that are quite easy to fix by just asking myself that one question.

Side note: No one is perfect.

Over the course of the next 3 weeks, I would approach more strangers, have lengthy (10-120 minute) and enlightening conversations with them, buy them food, fantasize about building a pirate ship/crew, and fall in love with new activities (slacklining) I would have never tried before if I had stayed within the confines of my comfort zone.


“Every great athlete, artist and aspiring being has a great team to help them flourish and succeed – personally and professionally. Even the so-called ‘solo star’ has a strong supporting cast helping them shine, thrive and take flight.”

-Rasheed Ogunlaru

How could my general mood not increase after making so many quality friends in such a short period of time? I feel a higher sense of empathy for others and have noticed increased amounts of laughter and fulfillment!

There were two times during my challenge where I had negative feelings overwhelm me. The first was brought on by my insatiable thirst for perfection. Somewhere along the line, I had forgotten again about the lessons I had learned from my first existential crisis. I fell into the trap of self-judgment and filled myself with negative ideas. “I’m a failure for x,” where x is anything I may have shortcomings in.

I can’t give enough thanks to Maple- who happened to help me take control of the self-defeating talk. She took the time to read my blog and told me in the nicest way possible way that she thought I should “chill out.” She was critical and honest, yet polite in explaining that she felt I was putting too much stress on myself. This meant to slow things down and take time to gain perspective.

I had forgotten all about the importance of “chilling out.” In order for us to grow, we must on occasion pause and give ourselves room to breath. I had been drowning in my own thoughts and self-doubt. I knew immediately during our conversation that she was right. I needed to slow down and get it right in my head that I am not and will never be perfect. Thank you Maple!

Check out Maple’s blog here!

The second time was during a walk home after a grueling night of late-night studying. Again, I began my crisis by questioning the meaning behind everything I was doing. The self-defeating talk stormed back stronger than before. I caved in to my demons and told myself that I needed to stop relying on anyone for anything. I looked at myself in the mirror and was convinced I was all I ever needed. I opened up Tim Ferriss’ new book with the intention to learn how to do things on my own when it hit me. The very fact that I opened up the book meant I was already looking to rely on someone else’s opinion for advice. That night, I read the foreward for Tim Ferriss’ new book written by Arnold Schwarzenegger.

The governator talks about his rise to success (a nebulous term at best). To summarize, he didn’t achieve his heights on his own. He rode on the shoulders of giants and looked to them for inspiration and help. It was a well timed wake-up call that almost instantaneously eradicated my self-defeating talk. I felt like I was being nudged towards the right path again. It was a warm and familiar feeling.

I rationalized that night that it would be cowardly for me to think I could do everything on my life. By doing so, it would mean that I don’t have the capacity to rely on others for help. It would mean that I have a fear of depending on others. To try and achieve everything on my own would be contradictory to all the things I’ve learned from my years on this planet and from my own comfort zone challenge! I am who I am because of all the people who have inspired and influenced me. I will accept the help of others and place trust and hope in those that I come across. I will be mindful of human error, and not judge others too harshly.


Routine, in an intelligent man, is a sign of ambition”

-W. H. Auden

The comfort challenge turned into a routine of mine. I would spend the last few hours of my nights thinking of what I should do next. Mau(a close friend who did the challenge with me) and I would share the ideas we had on Google Docs. I loved having someone to discuss potential challenges with. When challenges seemed too easy, we would ask each other for advice and keep ourselves in check.

I think one of the greatest values routines give me is the ability to budget my creative thinking. They allow me to predetermine monotonous tasks that I need to get done and spend more time and energy on the more complex tasks at hand.

In summary:

“He or she who is willing to be the most uncomfortable is not only the bravest but rises the fastest.”

– Brené Brown

I’ve learned a lot about myself over the course of these last 30 days. My biggest takeaway is that nobody is perfect, so we shouldn’t place massive expectations on others. We control the influence we let in, so we must be choosy with the things we are comfortable with. This goes for the people we interact with, the places we visit, the food we eat, etc. While flawed, we are still capable of achieving great heights through hard work and dedication. We can put intelligent systems in place to help us reach our goals.

Introspection can be used as a power tool to reassess the things that matter most. I find that I ask myself the question, “why?” for a huge number of the things I do in life. It’s interesting going deeper into that rabbit hole and figuring out why it is that you do what you do. This can be difficult at times, as a lack of sleep or difficult situations may produce mental fog and a sense of existential anxiety. We should prioritize priming our physical and emotional state so that we place ourselves in situations where we are most likely to succeed.

We should strive to make use of the tools at our disposal. As one of my favorite computer programming professors would say, “if we don’t have the tools we need, we can make them.” We are fortunate to have access to the internet, where we may find mentors who have dealt with similar situations we find ourselves in. We can effectively reduce the amount of stress and potentially save days, months, or years of time with a simple web search. Get outside your comfort zone now!

Today is the day to break free from the prison of the person you know yourself to be and step into a self you have yet to know. Will it be comfortable? No, but do it anyway.

– Debbie Ford

3 thoughts on “30 Day Challenge

  1. Pingback: 2017: The year that set the bar | AllOfPaul

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