This past Friday night I went home to cook dinner with my mom and spend some time with her as the school semester is winding down. After dinner, we were chatting and I told her that I see myself following the entrepreneurial path after graduating college. I said, "You know, somewhere along the way I gained the confidence in myself to be able to overcome any challenge I set for myself, to solve any problem I set my mind to. While I know that I could graduate and get a very well-paying job and live a comfortable life... I don't think I would be happy living a comfortable life. I've found that my happiness stems from growth, and the best way to grow is to continually challenge myself. I feel like I can accomplish some amazing things in my lifetime, and I believe entrepreneurship is the best path for me to do so - working on our world's most pressing problems." She agreed with me, but she was also curious and asked where/what I thought that "somewhere along the way" was to develop such a confidence. Well, I've been thinking on that subject and here are a few of my previous experiences that I think contributed to my bold mindset.

Keep in mind that this is not blanket advice to everyone. This is simply the things I have experienced to develop the mindset I have today.

Understand struggling is part of the learning process.

This has been something that I've learned not because of one experience, but many. Nonetheless, it's been an incredibly beneficial realization. When I learn something new, I often try to struggle as much as possible, in as many ways as possible. What I think many people don't realize is that they are learning when they struggle- but they don't feel like they're learning because they aren't yet able to see the results. A great deal of learning takes place while you're struggling; when you do something new, your brain is taking in a lot of information that may not be immediately processed. The way I see it is that I should load up my brain with as much information as possible so there's more data to learn from. Rather than not seeing results and giving up, I place trust in the learning process and know that my efforts will be rewarded.

Learn how to endure pain.

When I look back on my childhood, there were many times when I experienced pain but didn't stop what I was doing. Why did I keep going? I mean, I don't particularly enjoy being in pain, but I was having too much fun to worry about the pain.

I remember countless summer days that my friends and I would go ride on mountain biking trails for hours on end, pushing way past the point that we were tired because we were having a blast. Whenever I would crash or fall, I'd get right back on the bike and keep riding - not ready to quit. When we finally made the grueling journey back home (it stopped being fun when we got off the trails and had to bike for an additional 30 minutes to get back home), we would collapse onto my driveway and lay there because that was literally the only things our bodies would let us do.

I've also enjoyed playing soccer, and there have been many times where I have been hit with the ball in painful places, stepped on with cleats, etc. But I rarely stopped after I got injured, I kept playing because it was fun. It's not that I don't feel the pain, I just don't choose to pay attention to it. I think there's an important lesson in that - both in developing the ability to push through the pain and in finding the motivation to keep going.

I think everyone should jump off a cliff naked at least once in their lives.

So, I provide this advice mainly in a figurative sense, but one way to gain this experience is to go out and literally jump off a cliff naked - at least that's how I did it. Back in high school, there was this rock quarry that everyone loved going to and jumping off into the water during the summer. One time I went, I decided to jump off completely in the nude and I'm glad I did.

I'm not the only crazy guy to jump off a cliff naked. Shane McConkey, a world-renowned professional skier, has also been known to fly off ski jumps with his signature giant naked spread-eagle. The first time he flew off a ski jump wearing nothing more than his ski boots was immediately after attempting to do a double backflip and failing, landing on his head. However, when he hiked back up the cliff and made the jump in the nude, he landed the trick.

People waste so much time and energy worrying about such insignificant things. It can be quite empowering to not only overcome a fear but to do so in your most vulnerable state. This provides a perspective on things and helps you worry about what really matters. Be bold, stop caring so much what other people may think, and test your limits.

Establish a support network, but also occasionally interact with non-believers.

I'm incredibly fortunate to have a such a supportive community of family and friends. However, every once in a while I talk with someone and I know that they think I'm crazy or are thinking, "OK, but he doesn't really mean that." I do not blindly dismiss people that don't believe in me - if they have a good point I'll definitely consider it, but the non-believers get to go on a list of people I'll get to prove wrong. And yeah, that can be fun too.

That said, I can't express how thankful I am to have such a supportive community of friends, family, and mentors that believe in me. Having a support network is essential for when the times get tough; when you're at your weakest point, it can sometimes be a much-needed boost of confidence to hear "I don't know how you're going to do it, but I know you'll figure it out."

Learn effective communication, because you can't do it all on your own.

It's much easier to have confidence that you'll be able to accomplish your goal if you have a team, all with different backgrounds and strengths, that you can trust to work effectively. This will not happen if you cannot effectively communicate with each other. I know that I'm not an expert in a lot of areas, but to that note, I am confident in my ability to both communicate my ideas to others and understand the ideas other people attempt to communicate with me.

There are a few books that I found helpful in learning effective communication techniques which I'll list below. However, these books won't help you unless you go forth and converse with others.

  • Crucial Conversations: Tools for Talking When Stakes Are High
  • Leadership and Self-Deception: Getting Out of the Box


You'll run into problems in a completely foreign environment and be forced to come up with a solution. Better yet, travel alone. The summer after my freshman year of college I studied in Spain and spent two weeks traveling alone throughout Spain and France. After my latest trip to Europe, I remembered how beneficial it can be to just go out and explore. Half the time you don't know what you're getting yourself into, but you always make it out alive and more confident in yourself to explore new environments.