The Zen of Doing Scary Things: 7 Ways to Gain Confidence

Are you feeling a little bit trapped in your bubble of comfort? So much that you know you would just die to have a Zen of doing scary things that would inspire you to take action and grant you ways that you could gain more confidence? If this sounds at all like you, whether it is just a little or a lot, then you are absolutely not alone.

Speaking from experience, when I finished high school and went into university I was absolutely terrified to do so much as to say "hello" to another person. By the time I finished my program, I could talk to strangers no problem. Years later today, I take comfort in speaking in front of large groups of people.

What changed?

I adopted the Zen of doing scary things. I put myself in situations that I knew would terrify me, forced myself to overcome these challenges and found new ways to gain confidence. I made sales calls, I went rock climbing, I traveled and took photos of myself next to sleeping strangers at a Chess table (long story, don't ask). The point is, I did things that scared me and I continue to do so today.

Here are 7 ways that you can gain confidence through the Zen of doing scary things.

1. Get into public speaking.

The Zen of Doing Scary Things: 7 Ways to Gain Confidence

Even if you have absolutely no desire to do it professionally, get into public speaking. Sound scary? Good, that is the point. In fact, did you know that public speaking is one of the most common fears in the world? No - stop cringing at the thought of doing it. If you can get up in front of an audience of strangers and talk, then just how scary is anything else by comparison?

In fact, Toastmasters is a fantastic way to get together with a group of like-minded, supportive people who can help you get started. Even better, it exists in most countries and is relatively inexpensive to join, ranging around roughly $100 - $150 for a year's membership. You can use the online tool to find a club near you, or if you live in or around Toronto then you are welcome to come check out my Toronto Toastmasters club and I will personally welcome you.

2. Call someone you have not spoken to in a long time.

The Zen of Doing Scary Things: 7 Ways to Gain Confidence

Sometimes it really feels like talking on the phone is a lost art. Millennials such as myself rely heavily on texting and instant messaging as our primary forms of communication, so much so that when we talk on the phone there is more awkward silence than anything else.

Sounds kind of uncomfortable doesn't it? Again, that is exactly the point. If it sounded relaxing then it would not be the Zen of doing scary things. So pick up that phone and dial an old friend or a relative you have not seen or spoken to in a long time. Talk about the weather or ask how their families are doing. The point is that you are talking to someone. Not to mention that you are using this as a way to gain confidence and best of all, rekindle an old relationship.

3. Have an opinion about everything; voice it and stand by it.

The Zen of Doing Scary Things: 7 Ways to Gain Confidence
It is so bloody easy to say "I don't know" when someone asks you a question, and yet this accomplishes absolutely nothing. According to Pixar's rules of storytelling, there is a simple and extremely effective way of making a character (or yourself) more interesting.

"Give your characters opinions. Passive/malleable might seem likable to you as you write, but it's poison to the audience."

This does not apply just to storytelling. This applies to every day life! Passive and indecisive IS poison. In fact, avoid saying any of these phrases:
  • I don't know
  • You decide what to do
  • What do you want to do?
  • What should we do today?
  • I can't decide
  • etc.
Get the picture? Have an opinion and stand by that opinion, unless of course you yourself can be convinced to view things in a different light. But have opinions about as many things as you can, ranging from what clothes would look good, to where to eat dinner, to what you think about the current state of politics.

BONUS: Now go TELL other people those opinions. If you have a blog then try to write something controversial. Don't have a blog? Go to and start a new thread somewhere or reply to someone, voicing your controversial opinion about something. If people argue with you then stand by your argument. It might be scary in the meantime, but you will feel more confident after.

4. Take a job in sales.

The Zen of Doing Scary Things: 7 Ways to Gain Confidence

Remember how at the start of this article I said that when I started university I could not even say "hello" to strangers, yet by the time I finished, I could have full conversations with them? One of the very first things I did (and most powerful) that helped me gain confidence through the Zen of doing scary things was get a job in sales.

Well, technically it was not a job. It was a volunteer role in a student organization called AIESEC, but really, pretty much the same thing, except I did not get paid. I was responsible for cold calling VP's, CEO's and hiring managers in local Toronto companies, booking sales meetings and raising international internship positions. Was I scared? Absolutely not, I was completely terrified! But I also got over it... slowly, but it certainly helped.

Get a job in sales, because it will help you gain confidence like nothing else... except the other six items on this list perhaps.

5. Try eating different for a week.

The Zen of Doing Scary Things: 7 Ways to Gain Confidence

I have to be honest... this is the only item on this list that I have not personally tried, only because I love my fast food and gained my confidence doing the other items. Still, I have heard and would believe that changing your diet for as little as a week would help inspire change in your life. After all, if you can change something you hold as near and dear as your heating habits then couldn't you easily change bigger things in your life?

Mix it up! Eat bagels instead of cereal, go vegetarian, go vegan, look up new recipes on the Internet and make something you have never had before for dinner each night! Do whatever you want as long as it is different than what you have already been doing.

6. Attempt a new type of physical activity you have never tried.

The Zen of Doing Scary Things: 7 Ways to Gain Confidence

Depending on how adventurous you are, maybe this is not the scariest item on the list, but maybe it is. You tell me. Check out what fun activities are available in your area and go try some of them out. Here are a few things that you could go do either on your own, or with a group of friends:
  • Indoor rock-climbing
  • White water rafting
  • Tree-top trekking
  • Bungee Jumping
  • Skydiving
  • Pilot classes
  • Paintballing
  • Scuba diving
Is there anything scarier and more challenging than trying brand new things? As a rule, try to say "yes" more often than you say "no." Each fork in the road provides exciting new opportunities.

7. Do a partner or group activity, but do it alone.

The Zen of Doing Scary Things: 7 Ways to Gain Confidence

Okay just to be clear, I do not mean you actually have to do it alone. The activity could be done with strangers if it is something you typically need more than one person to do. For instance, maybe you want to take dance lessons or a attend a martial arts class. You might normally bring a friend, group of friends or a date to do something like this, but in this instance the challenge is to go do it alone or with the people you meet while you are there.

In fact, I will make it even easier on you. Go make an account on if you do not have one already and poke around for Meetups in your area that look like something you wish to try out! A couple of years ago, I attended a board game meetup by myself and had a blast playing games with total strangers. Whatever you choose to do, explore your Zen of doing scary things and use this 7 item list to find new ways to challenge yourself and gain confidence. After all, as Edger Allen Poe once said, "I have great faith in fools - self-confidence my friends will call it."

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