Scaling the Wall of Fear

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By GabeMc (Own work) [CC BY-SA 3.0 ( or GFDL (], via Wikimedia Commons

On the flight here to Dallas from Quito, we ran into heavy turbulence. And by that I mean, me white-knuckling the hand rest thinking “why oh why did I get on this plane?” while staring out the window, willing the plane to stay up type of turbulence.

Even though the experience was harrowing and extremely NOT fun, the second I walked off that aluminium tub, I promptly forgot about the whole thing.

And then once FinCon started, I barely remembered how scared I was. Even though at the time, the terror of being shaken like a rag doll while hurling through the sky at breakneck speeds was the ONLY thing I could think about.

But as I sat down to write this post, I started thinking about fear and exactly how much we tend to blow it up in our heads.

Like that time I learned how to Scuba dive.

Or that time I gave my boss my notice after working at the same company for 9 years.

Or that time I had to hit “publish” on the very first article on this site.

Every time, I hit the “Wall of Fear” (a term Pete aka Mr. Money Mustache coined during his Chautauqua presentation), I froze, like a deer-caught-in the-head-lights, and for a split second, all I could think about is running away. But every time, no matter how scared I was, I scaled that stupid fear wall, and every time I got to the other side, my fists triumphantly pumping in the air, I’ve never once regretted it.

It happened so often, I knew the drill by now. But that doesn’t mean I no longer feel the fear.

It doesn’t mean the fear isn’t real. The point isn’t to ignore the fear, but to feel it, scream in your head, and then do it anyways.

Everyone deals with fear differently, but in my case; here are the tricks I used to get over my fear:

Let Yourself Be Afraid

Don’t ignore your fear. Just because you ignore it doesn’t mean it’ll magically disappear.

Also, we don’t want fear to automatically disappear because even though it’s debilitating sometimes, fear is actually useful. Without fear, our caveman ancestors would’ve turned into mammoth chow a long time ago and we wouldn’t exist.

So as much as fear sucks, it serves a purpose.The trick is not to pretend it doesn’t exist, because that would be like trying to sleep through a rock concert. Good luck with that.

Acknowledge that your Wall of Fear is there. Then figure out how to scale it.


What’s the Worst that Could Happen?

Fear is our emotional response to a perceived threat. So, in order to scale the Wall of Fear, we need to figure out what’s the worst thing that could happen, and then figure out how to deal with it.

Take quitting my job for example. After giving my notice, my first thought was “what have I done? What if this was a huge mistake?”

My second thought was “What’s the worst that could happen?”

The first thought is instinctual but useless. The second thought actually let’s me do something about it.

So I set about writing down a list of worst things that could happen and backup plans A, B, C to combat it.

The reason why there’s plan A, B, and C, is they act like sandbags in a storm. If plan A fails, fall back to plan B, and if B fails, fall to C. That way, if shit ever hits the fan, you won’t ever be caught with your pants down because you just pull out your backup plans and go through them.

Eg. What’s the Worst that Could Happen?

The stock market crashes:

Plan A: Live within the “yield shield” of 3% (dividends + fixed income) without having to sell any assets

Plan B: Have a cash cushion that covers 3-years of living expenses (this was how long it took to recover from the last bear market

Plan C: Relocate to Thailand where you can live like a king on $20K. As we like to say “When shit hits the fan, we’re heading to Thailand.”


Our expenses go up and we have to go back to work:

Plan A: Keep coding skills up by building apps, calculators, platforms for other authors, FIRE people. Etc.

Plan B: Develop new skills like writing and public speaking. This opens you up to brand new job markets.

Plan C: Become entrepreneurs/consultants with financial consultancy, etc.


Unexpected healthcare expenses:

Plan A: If we lose our Canadian healthcare coverage due to residency requirements, buy expat insurance

Plan B: Self-insure by living in a country (like Thailand or Mexico) with high quality healthcare at low cost.

Plan C: Get a part time job with insurance coverage from abroad


Lack of friends/community in retirement:

Plan A: Stay in touch with friends back home online with Skype, FB, Twitter etc

Plan B: Build a new community of FIRE friends by attending events like FinCon and the Chautauquas.

Plan C: Volunteer and join meet-up groups to find new friends. Rent out shared accommodations on Airbnb to meet people.


Do Something USEFUL

It’s almost impossible to dwell on your thoughts if you’re concentrating on DOING something.When you’re feeling useful, you also have less reason to ruminate about everything that could go wrong.

Go out for a walk. Go for a bike ride. Go swimming or hiking. Your body AND your mind will thank you.

And if you’re an obsessive compulsive type A like me, and need to be accomplishing something AT ALL TIMES, work on putting your backup plans A, B, C mentioned above into action.

Make a list of all the things you need to do (like “look into Cigna expat insurance”, “write a book”, or “code an app” for example) and DO IT!

Surround Yourself with People Who Push You to Grow

Confucius once said:

“If you are the smartest person in the room, then you are in the wrong room.”

This is why you need people who are going to push you to grow even when you’re racked with fear. These are the people who don’t make excuses for you, don’t let you fall victim to your fear and don’t let you give up.
Let yourself by swept up by their boundless energy, their optimism, and their unrelenting ability to push past their fears.

If there aren’t people like this in your existing room, switch rooms.

Speaking at the Chautauquas and getting to know other FI bloggers and attendees was the best thing I could have possibly done to build my tribe. Now because I’ve met all these cool FI people, I now have a network of people who have pulled the FI trigger just like me that I can go to for advice and socialize with. I’m constantly texting/FB messaging Justin McCurry from to bounce ideas off of, Jeremy from to chat about travel/shrooms , and of course “GodFather” JLCollins because I need my JLCollinista fix.

And now we’ve met J. Money, Mr. Money Mustache, Alan/Katie from PopUp Business School, Jesse from YNAB, etc. Any Wall of Fear I can ever encounter has already been encountered and scaled by one of these people, and because of the Chautauqua’s and FinCon, I can go to them for advice or just a simple “What do you think of this idea?”


Dip Your Toe In the Water

Even though I wasn’t the greatest engineer, one of the best things I learned from engineering school is to test out the waters.

You wouldn’t let someone bungee jumps off a bridge without testing the rope first would you? That’s why they throw down a sandbag matching the person’s weight first.

So if you feel like quitting your job with nothing lined up feels like jumping off a cliff, throw a rock down there first to see what’s at the bottom.

Before you quit (preferable 2-5 years out), start thinking about what you want to do next. Start a side gig, start volunteering, write a blog—whatever it is that you think you’ll want to do in retirement, start doing that in spurts while working, so you feel like you have a platform to step onto when you quit.

In our case, we started writing children’s novels before we quit and started volunteering for a non-profit the year before we quit. This allowed us to have a community and a passion project to run towards when we pulled the escape hatch.

Another way to dip your toe into the retirement waters is to negotiate a sabbatical. Try a 6-month sabbatical to see if you’ll like having all that freedom and time on your hands. Do some travelling! Work on your hobbies! You have nothing to lose because if you find out you don’t like retirement, you can always go back to your job. And if you love your time off, you can hand in your notice with zero fear!

You could also use the glide path method, by stepping down into a part-time position, filling the rest of the time with your passion project, and then eventually quitting once you feel ready.


So that’s it! The Wall of Fear might look imposing and impossible to scale at first, but if you acknowledge your fear, think about what’s the worst that could happen, do USEFUL things, surround yourself with the right people, and test out the water first, you’ll scale that wall in no time!

What do you think? Have you encountered the Wall of Fear? How do you plan to scale it?

Side Note: Guess what? We’re on the ChooseFI Podcast today!

ChooseFI is one of the fastest growing FI podcasts out there and after meeting the hosts Brad and Jonathan at FinCon, I can completely see why. These guys have serious hustle and are some of the smartest people I’ve had the privilege of meeting. If you’re looking for a good podcast to check out on your commute to work, make sure to listen to ChooseFI!

Check it out:

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32 thoughts on “Scaling the Wall of Fear”

  1. Great post FIRECracker! This makes me think of a quote I read last week by Richard Branson – “Everything you ever wanted is on the other side of Fear.” And that’s pretty much what you just said. I love your methods of overcoming fear, these will be very useful for your readers too!

    I’d like to add a small piece of information. I’ve been reading a book on Buddhism. It’s very popular right now and it ruminates about the connection between some of Buddha’s philosophy and evolutionary psychology. The argument for fear goes something like this:

    You exist because your ancestors were scared, and when they got scared they looked out and didn’t get eaten. So they made it into the gene pool. But now we live in completely difference circumstances, the problem is that those very same brain circuits that helped your ancestors steer clear of the bear, are really holding you back now.

    See instead of saving you from the bear, the very same circuits are keeping you from presenting your talk, trying something new, or even just envisioning your future. So you need to learn to control your thinking to the extent that you realize this isn’t true and it isn’t going to happen. Only when you can control your thinking can you achieve your greatest potential

    One way to do this is using the suggestions you are putting in this very post! Great Post! (as usual!!!)

    1. “those very same brain circuits that helped your ancestors steer clear of the bear, are really holding you back now.”

      That’s exactly it. Buddism for the win!

  2. I am afraid of flying specially over the water. Every time I am on a plane and there is slight turbulence I freak out. So my question what did you tell yourself when you were on that plane ride ?

    1. I’m okay with regular turbulence, just not the crazy kind. But on the plus side, the plane stayed up, clearly proving that turbulence can’t easily take down a plane.

      What I told myself was just to aggressively stare out the window (helps with nausea because you’re staring at a fixed point in the distance), take an anti-anxiety med, and try to go to sleep. When the turbulence calmed down a bit, I was able to sleep.

      It also helped that I spoke to an ex-airforce pilot at Chautauqua a couple days before, who told me all the ins and outs about flying/planes so that was reassuring.

  3. Yes! The Wall of Fear post! Thank you.

    Right now, it’s hard to think of pulling the trigger, because of…well, you’re never guaranteed that you have enough. But if we bank expenses x 25+, plus a three year cash cushion, at least I can say we’re following in your footsteps. Thanks!

    1. Thank YOU for inspiring this post 🙂 Having a cash cushion definitely helps settle the nerves when you’re pulling the trigger. Knowing how cheap it is to travel instead of living in expensive metropolitan cities also helps. I’ll keep updating you on life in retirement so you can see there’s really nothing to be afraid of! Come on in, the water is just fine…

  4. Great post! I so relate to this. Relate to turbulence terror. To quitting job terror. Lack of friends/community terror. Terror that the stock market will tank. Terror I’m doing things wrong as a parent. Nothing is certain but for control freaks like me, moving forward and taking action softens anxiety. The only problem is the hamster wheel never stops! Since being in Ecuador, I’ve been thinking mucho about the wall of fear, and the need for certainty. Thanks for putting this together. I really enjoyed getting to know you and B!

    1. SO glad you came to chautauqua Ecuador! I really enjoyed our nice chat in the whirlpool/hot tub, at dinner, and our one-on-one– Chautauqua wouldn’t have been the same without you!

      Keep moving forward to keep that terror at bay! It gets easier over time, I promise 🙂

  5. My Greatest fear was buying a house to live it, not as an investment. All my RRSP money, plus $50K of TFSA and savings went into it, so lets figure $100K that was liquid, and is now tied up in one asset… scary shit… what would be the return on that if invested in a balance portfolio? 6% per year? But as luck would have it, there was no crash in Canada, and we actually got in at a good time, and only just refinanced at 2.7 % a week before the first increase in interest rates. 6 years later my head is just above water, finally.

    For us, it turned out ok, but there was no logic or financial skill involved, just blind luck. I still believe financially it might have been better to stay a renter, but rent in Victoria is just stupid now. My head hurts thinking about it, we made the decision, and now we live with it, and its ok.

  6. Hi Kristy,

    The details u mentioned, are true and valid. I think that the fear factor is always there, no matter on the type of things one does. I have encountered a lot of such issues in work in which people are unwilling to make decision in fear of subsequent consequences.

    I think that having the F-U money does go to great extent in alleviating the fear factor. This will enable me to opt for the things which I feel that it is right for me. I work because I want to and not because I have to. Your blog is definitely one which I will go when I search for inspiration.



    1. F-U money definitely helps in alleviating fear. There are a lot of things in life we can’t control, but having F-U money is definitely something we can control.

      Working because you WANT to and not because you HAVE to is the best feeling in the world! Kudos for getting there, Ben 😀

  7. Oh man, I know all about that white-knuckle turbulence fear!

    While our trip back from Japan wasn’t as bad as some of my worst experiences, it still made the kids pretty sick.

    Like most fears, turbulence might seem scary when you’re in the thick of it, but it’s really not all that bad afterall. Fear is a matter of perspective and experience.

    1. Yeah, I hate turbulence more than anything, but no way it’s going to stop me from travelling. The reward is definitely worth the risk.

      Sorry to hear that your kiddos got sick from the flight…but I’m glad the reward was worth it because it looks like they had a lot of fun in Japan!

  8. Hey Bella; happy birthday tomorrow to you, happy birthday tomorrow to you! Thanks for all the info and knowledge you pass on to us every week! Have a wonderful birthday and do something special for yourself.

    Have fun;

    1. Thanks, Robert, but my birthday isn’t for another 20 days! I may have accidentally put the wrong date on my FB page ;P Appreciate the early birthday wishes though! Awesome readers like you are why we write, so thank you for reading!

    1. Oh please. If you were there, you would’ve had those Sabertooth tigers’ heads cut off and put next to some poor schmuck’s pillow. But only because horses didn’t exist back then.

  9. I think there is a lot of great advice in this post. One of the things I am trying to do is figure out how to monetize my expertise in public speaking. I have a bunch of lessons on YouTube I have more my students. I wonder if I should create a class or how to break it down from a more academic subject to one that is palpable for a general audience. Not looking for advice per se, but I think that is a project I should do in my spare time because I love helping people with it and I am pretty good at it (25 years of training and I run our public speaking course at my university). Excellent advice Kristy!

    1. I wonder if I should create a class – Yes you should

      Break it down from a more academic subject to one that is palpable for a general audience. – Yes, just do it…

      And this advice is free by the way…

      You will know what is working once you try it, all it requires is your time, and a bit of passion. Ya you might fail, but you will definitely learn something.

      1. Spaceman gets it!

        Jason, if you have that much expertise in public speaking I definitely think there’s value in creating videos to help people. Don’t worry about it being perfect. Put it out there, then tweak it as you get feedback overtime. Once you put value out there, the streams of revenue will come to you. Don’t do it for the money. Do it because you love it.

  10. The “what’s-the-worst-that-could-happen” rule of thumb is something we always use. One of the defining moments when starting my company was realizing that if I failed miserably I could always go back to what I was doing then (W2 employee or contract position). Looking forward to FIRE, if we leave our jobs and then find out that we don’t have enough money, well we could (gasp) get another job. Fear is what makes us grow. Fear pushes us out of our boundaries and challenges us. It can make you better, faster, stronger (I’m starting to sound like Kayne) but only if you recognize it and push past it.

    Was definitely a pleasure meeting you guys at FinCon! Hope our paths cross again soon.

    1. HA! Sounding like Kayne…nobody wants that.

      Pushing past fear is definitely something that everyone struggles with, but it’s ALWAYS worth it.

      Had a great time meeting you guys at FinCon too and hope we can get together again soon!

  11. Nice post. For a moment, FIRECracker sounded like nutcracker, hearing about the turbulence! I have clocked over 100k miles in the past 2 years alone but still I find myself gripping the seat handles firmly whenever turbulence hits. Just because Fear is there doesn’t mean you are paralyzed by it. It’s the same way with investing. Fear would’ve kept people out of the equity markets for last 4 years, missing out on super gain, but now maybe a good time to take some chips off the people, as many new investors are getting onto the gravy train.

    I would’ve loved to attend the Chataqua in Ecuador but let’s hope I am able to next time. I also wish the team sets up the next one in Asia, since I spend quite a bit of time there. It would be fun to see you and Wanderer in person and know a bit more about the two “out there” Canadian couple! But you are both winners in my book, so being ‘out there’ in thinking is great thing.

    1. It’s so true. Fear also keeps people out of the markets, making them miss gains. That’s when fear becomes REALLY unhelpful.

      Would love to see you at a future Chautuaqua. If you’re in Asia, there is a cheap flight way to get to Greece from Singapore on Scoot, so if we even up having it in Greece next year, that’s could be an option 😉

  12. Great post. I agree with pretty much everything you have stated, especially having alternative plans.

    It can be tough to make the leap to leave behind a well paying stable job, even if it makes you miserable. In my mind it was almost irresponsible to do so.

    I dealt with those feelings and the fear by simply cutting back on work instead of stopping cold turkey. I started looking for part time employment opportunities, which necessitated that I think outside the box and look for work I might actually enjoy. This process can be very empowering as it provides you with a sense of taking control over your situation, even if your are not comfortable with making the leap to “retirement” right now.

    In my case it worked out well. I now work for an employer 3 days a week in a job I actually enjoy. I was fortunate enough to obtain a much higher hourly rate than I was receiving as a full time employee. I’m not nearly as stressed and have the time to do perform home projects, pursue interests, etc.

    This is the real power of reaching FI. It provides you with the opportunities to make those leaps of faith if you want to. If it’s still a bit too scary, just make smaller leaps. You are still heading in the right direction. You never know what’s out there waiting for you.

    1. Nice! Working 3 days a week at job you like sound great! I’m glad it worked out for you, RJ! And you’re right. The real power of reaching FI is the ability to choose.

  13. Great blog as usual….I think it is a common challenge for most folks…and the same thoughts go through most people’s heads…I faced similar issues when I finished grad school…hopped on a plane to the far side of the planet around 20 years ago to start my adventures .. CPO Michael

    1. Hoping on a plane to the far side of the planet is definitely an adventure! Glad you got out of your comfort zone!

  14. If you aren’t afraid it isn’t worth doing… If you want to be stronger you have to struggle, you have to go through the hard parts. It’s the truth. It works with everything. There’s a great book – “Antifragile”

    And this reminded me of the talk that Will Smith gave:

    Great to meet you guys, and I’m looking forward to seeing you again!!

    1. “everything you want is on the other side of fear”. I love it! Thanks for sharing the video and looking forward to see you guys again too!

  15. I took a deep dive into the abyss in the uncertain game called life, overcame the fear, and continue to do the transformation work out of inspiration or desperation, operating in faith by steamrolling ahead 100% @ full strength! 🙂

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