A simple process for mastering your fears


Kansas City, September 2014, several hours after a speech: I hate this, I hate this, I hate this.

I’m at a concert by myself. I don’t love going to events on my own, but I don’t know anyone in Kansas City either, so it’s either chill out in my hotel room all night, or go explore the world solo. Plus one of my favorite musicians, Lykee Li, is in town and I have a ticket to her show…

Recently, a woman I had been seeing broke the news that I was the man on the side; she had a serious boyfriend the whole time we were together with no intention of leaving him (not that it would matter; you can’t build a healthy relationship on a foundation of compromised trust). That was a fun conversation.

Being totally single still feels a bit odd to me.

Standing right next to me at the concert, waiting for Lykee Li to go on, is this stunning woman who looks to be about my age, and also appears to be alone.

I feel like I have two options, and neither one is terribly desirable:

Option 1: say, “Hi” to this woman, and see what happens. This is appealing because it opens the possibility of some sort of human connection with a cute stranger. But it also requires that I put my ego on the line because I’m opening myself to rejection and a potentially awkward experience.

Option 2: don’t say, “Hi” to the woman. This is appealing because it doesn’t put my ego at risk, but if I go this route, I know I’ll be beating myself up later on for not taking a chance.

I’ll come back to that in a second….


No one ever tells you this…

No one ever explicitly states this, so let me make it clear: your success in life is governed by your ability to leave your comfort zone and master your fear.

If you can’t leave your comfort zone, your life will never progress past where you are right now.

Most of the time when people think of leaving their comfort zone, they think of just leaping straight out. Of going all in. Of creating a do or die situation that forces them into action.

And honestly, I used to be an advocate of that approach in both word and action. But there’s a problem: long term it doesn’t work, short term it’s terrifying, and in many situations it’s gawky.

The real way to leave your comfort zone and master your fears is through reflection and calculated baby steps.

To Master Your Fears…

Start with reflection. Ask yourself:

  • “What happens if I do nothing?”
  • “What is the worst case scenario and how likely is it?”
  • “How can I reduce the chance of the worst case scenario occurring?”
  • “If the worst case scenario occurs, how can I bounce back?”

After you’ve spent a bit of time reflecting, then you have to decide: am I going to take on this fear, or am I going to learn to live within it?

Personally, I live within some of my fears. I’m terrified of sky diving, and for now, I’m fine with that. It looks fun, but I could have a full life even if I never jumped out of a plane.

But I work hard to master the fears that stand in the way of achieving my dreams. I want to be around amazing people, so I work through social anxiety. I want to build businesses that influence the world, so I work through the fear of failure. I want to see our planet first hand, so I deal with the fear of leaving the beaten path.

Lets say that you’re considering moving from New York City where you work in finance and aren’t happy, to Austin, TX so you can chase your dream of becoming a self employed artist, but you’re afraid of making a big change. The analysis would be:

What if I do nothing? Then I’ll remain unhappy as a finance person in NYC. If I want to find happiness, I’ll have to find some other source besides my work or city.

What is the worst-case scenario and how likely is it? I move to Austin, fail to make friends, burn through my savings, and need to get a job at a coffee shop or something like that to support myself. How likely is this? Well, it depends on the person, but this is fairly unlikely if you’re methodical about your work and social life.

How can I reduce the chance of the worst-case scenario? This is fairly easy. To avoid being friendless, join a rec sports league or take a class you’re interested in, and be proactive about hanging out with the people.

To avoid running out of money, start saving now, scale back your lifestyle, and get a part time job while you’re working on your business.

How could I bounce back from the worst-case scenario? Different ways for different people. Get an entry-level job. Crash with a friend or your brother while you get back on your feet. Move back in with your parents, if needed.

Then, slowly but surely, chip away at your fears

In the past, psychologists used to help people overcome their fears by hyper exposing them to the fear stimulus.

In other words, if you were afraid of snakes, they’d lock you in a room with tons of snakes, forcing you to confront your fears. This is called flooding and unsurprisingly, it doesn’t really work.

What does work is slowly chipping away at your fears with baby steps. Afraid of snakes? Start off by looking at one in a pet store. Then touch one in a pet store the next week. Then hold one that your friend owns. And so on…

If you’re thinking of moving from NYC to Austin and changing careers along the way, quitting your job and packing the van right now, would be the equivalent of flooding. It’s so damn bold and disruptive that most people – myself included – couldn’t do it. That approach will forever hold you suspended in unsatisfied desire.

A far better approach is to be slow and calculating, leaving your comfort zone a little bit each day.

Start off by working on your art business during the nights and weekends while you’re in NYC. Spend time each week studying. Save a bit more than you have been so that you’ll have a cushion when you transition careers.

Pick a date 3-6 months out in the future when you’ll leave for Austin. As the date gets closer, sell everything that you wont be bringing with you. Start looking at apartments online. Try to sell a few pieces of your art inexpensively in NYC to see if you can do it. Say goodbye to NYC.

Slowly but surely, chip away at your fears to create the reality of your dreams. The trick to mastering your fear is to gently leave your comfort zone over time. Even an inch outside of your comfort zone is infinitely better than no forward motion at all.

So, what happened in Kansas City?

In the past, I worked hard to overcome the mild-moderate social anxiety that plagues me and many other people.

I read tons of books on the topic (“How to Win Friends and Influence People” remains the best, with “The Charisma Myth” being a strong second).

Over time, I started slowly leaving my comfort zone. My first exercise with myself, several years ago, was learning to smile at and make eye contact with strangers on the street. By slowly expanding the limits of my comfort zone, I eventually got to the point where I could talk to most people in most situations.

Has the fear of rejection or humiliation in a social situation gone away? Absolutely not. In many cases, fear doesn’t vanish, instead, you learn to gain power over your fear while accepting that it’ll always be somewhat present.

I decided that I’d rather put myself out there, talk to the pretty woman and see what happens, than risk being frustrated with myself for missing a potentially cool opportunity. So I took a deep breath, smiled, and said, “Hi…”


Photo credit: “Halloween Cat” by Silversolo

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11 COMMENTS ON THIS POST To “A simple process for mastering your fears”

  1. Isaiah Collier October 14, 2014 at 6:20 pm

    Jason, I truly believe that fear most times paralyzes us and blocks any self proclaimed success story. I often tell my students that you can’t let your fear hold you hostage for life, at some point you have to simply breathe and take a step. I am one of those people that gives great advice freely, but I have a hard time following my own advice. I think you truly nailed it, when it comes to fear you have to ask yourself what is the worst case scenario and then move past it. I love to push myself out of my comfort zone usually, but sometimes I will let my fear get the better of me. I simply prefer to call it a work in steady progress. Keep up the good work, I really enjoy reading these articles.

    • Jason October 14, 2014 at 6:57 pm

      Thanks brother! Yeah, I’m with you. Far easier to tell people to face their fears and leave their comfort zone than it actually is to do it. And – and I hope I got this across – I don’t actually face all of my fears; only the ones that matter. And when I do face them, I do it pretty slowly and methodically.

      And also: you’re totally onto something: a HUGE part of managing fear is accepting it, and kind of moving forward anyways. I don’t think it ever completely goes away. At least not for me.

  2. Andrea October 15, 2014 at 2:49 pm

    I love this – thanks for providing so many useful tips and steps for conquering our fears. It’s something that I’m working and I agree, doing it methodically and at your own pace is key. Actually right now my list of fears is so long, I’m just trying to figure out which ones to tackle first!

    And sorry about the girl who was cheating – that sucks.

    • Jason October 15, 2014 at 4:56 pm

      Thanks Andrea! Yeah, I think a lot of people miss how efficient it is to move slowly and methodically as they develop themselves. I would argue that moving slowly is actually the fastest approach for these types of things.

      My list is long too. Personally, I would consider approaching that with one of two questions and moving forward:
      1) Which fear, if faced, will produce the highest leverage in my life? In other words, which one will open the most awesomness across the board if I can face it. Or,
      2) Which fear is getting in the way of my most burning desire?

      Those might help you prioritize.

  3. Andrea October 15, 2014 at 9:46 pm

    Thanks – very helpful!

  4. Danilo October 16, 2014 at 1:34 pm

    This post it’s amazing 🙂

    • Jason October 28, 2014 at 1:22 am

      Thank you!

  5. Mark Taylor October 16, 2014 at 2:34 pm

    Thanks Jason for another great article! I really like how you highlighted that how much you leave your comfort zone determines, on some level, your success in life. It reminds me of an old adage “What got you here, won’t get you there”. It’s also refreshing to hear someone say that dreams require calculated ‘baby steps’ to achieve. I’ve met people in Colorado that ‘flooded’ here; they just up and left their life to move to CO to pursue a different lifestyle or job without any planning or sense of the next day. “Chase your dreams” is what you hear most say, but here you’ve detailed a great method as to how that can play out in everyday life.

    • Jason October 16, 2014 at 4:47 pm

      Thanks Mark, I really appreciate that. Yeah, the truth for me is that most of the changes I make to my business or life are slow changes. I would argue that’s the most efficient way to do it anyways…

      Oftentimes to onlookers the change looks dramatic and fast, but that’s because they miss all the hard work, thought, and effort that went in and only see the final product.

      Some people can flood and dramatically change their lives, but it doesn’t really work. The problems, fears, whatever that they are running from will – in most cases – catch up to them.

      Finally, if you haven’t read, “What Got You Here Wont Get You There” by Goldsmith, you should check it out. Great book!

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