How to Defeat the 8 Fears Holding You Back From Your Dream Life

This is Chapter 3 (Part 1) of the Ultimate Simple Guide to Life series.

• Read the Introduction to The Ultimate Simple Guide to Life
• Chapter 1 | How I Used Death to Set My Life Goals
• Chapter 2 | Life’s Not That Short: Here’s Why We’re Wasteful of It
• Chapter 3 (Part 1) | How to Defeat the 8 Fears Holding You Back From Your Dream Life
• Chapter 3 (Part 2) | Boogying with the Boogeyman: How I Used Fear-Setting to Tango Through Terror

“Everything you've ever wanted is sitting on the other side of fear.” - George Addair

The problem with fear is that it sucks.

We’re supposed to be grateful that it supposedly protects us from harm, but it doesn't make us feel good or safe. 

It can be the sole reason we never try to reach our goals and are stuck living a life of regret. 

And it kind of feels like you’re being followed around by an annoying, judgemental, flailing worm monster wearing the faces of whoever's going to perturb you more at any given moment, including your own… If Fear had a LinkedIn profile, it’d be endorsed for skills like ‘Professional Dream Crusher’ and ‘Expert Party Pooper’.

More so than the “someday maybe drawer”, I do not like fear.

Unfortunately, fear is a worthy adversary.  It's not just an emotion; it’s a powerful force that shapes our decisions, influences our actions, and often holds us back from our true potential.

It’s different for everyone, can easily paralyze, gaslight, or torment you, and, worst of all, steal your last McNugget when you aren’t looking. Fear’s a b*tch.

That said, here are the key lessons that helped me muster the bravery and confidence to overcome my fears. 

1. Understanding what fear actually was, how it showed itself neurobiologically, and realizing that it was just this simplistic mechanism being triggered in my brain to “protect” me in situations where it really wasn't necessary.
2. Training myself to notice the false alarms, turn them off, and push through the inevitable discomfort.
3. Preemptively mitigate risks, avoid the worst-case scenarios, and get back to the status quo if necessary. Ultimately showing me that my fears seemed much more likely and much scarier than they actually were.

Here are the resources, in order, I used to learn those lessons and finally control my fears productively.

The Resources:

1. Taming the Mammoth: Why You Should Stop Caring What Other People Think by Tim Urban
2. The Flinch | Julien Smith
3. Fear-Setting: The Most Valuable Exercise I Do Every Month | Tim Ferriss

Here’s How I Used The Resources:

• Taming the Mammoth: Why You Should Stop Caring What Other People Think by Tim Urban taught me about the origins of fear for humans. How feeling fear is tied to our psychological needs as described in Maslow's hierarchy of needs—especially our needs for safety, belonging, love, and self-esteem.

• The Flinch by Julien Smith taught me to catalyze personal growth and development by encouraging me to seek discomfort, expand my horizons, and challenge myself in various aspects of life. Here are the summarized steps for you (as an aside, I had a blast doing all of these and they dramatically changed my life for the better):

1. Step 1: Challenge yourself by doing things that hurt, on purpose. Have a willpower practice, challenging exercise, meditation, endurance, or cold showers. Choose something that makes your brain scream with how hard it is, and try to tolerate it. The goal isn’t just to get used to it. It’s to understand that pain is something you can survive.
2. Step 2: Remember things that are easy to forget. Deepen your current relationships. Create un-birthdays or half-birthdays for your friends and stick to them. Go through old text messages to rekindle dormant friendships. It can be awkward, but that’s the point. You will make an impact by choosing to do what makes others nervous.
3. Step 3: Read more. Find thorough and in-depth analyses of subjects you find interesting, or irreverent stuff that makes you feel alive. Read things you disagree with. Build a habit of reading complex topics that feel challenging or just too difficult to understand, and then overcome your discomfort by pushing yourself to understand them.
4. Step 4: Get some scars by working with your hands. You may find that your body is much more resilient than you thought. Try to understand how things in your world work, like your car, your stereo system, or even your kitchen.
5. Step 5: Turn your phone off for a few hours each day. Having nothing to do while you’re waiting for a bus can be boring, but it’s only when you’re bored that the scary thoughts come to the surface. Switch to using a dumb phone on the weekends to prevent yourself from checking your messages.
6. Step 6: Find new friends who make you feel uncomfortable. Meet tattoo artists, homeless people, millionaires, or best-selling authors. Host dinner parties for them. Serve them bizarre food.
7. Step 7: Renegotiate your work. If you achieve X, then will your employer do Y? Ask beforehand and deliver, or if you can’t get permission, go for it anyway and ask for forgiveness. Create a new job title for yourself; then carve out the job.
8. Step 8: Start dressing as if you had a very important job or meeting, or as if you were a kid again and thought you were the coolest person on Earth. Or both 🤷♂️ . What would you do differently? How would people treat you once you did?

Step 9: Imagine that you have to leave a legacy, and everyone in the world will see the work you’ve done. Volunteer. Create something that lasts and that can exist outside of you, something that makes people wonder and gasp.

Step 10: Make something amazing, something that’s terrifying to you. Stay uncomfortable. Fight the flinch wherever you see it. Leave no stone unturned.

• Fear-Setting: The Most Valuable Exercise I Do Every Month | Tim Ferriss taught me how to methodically, logically, and preemptively mitigate risks, avoid the worst-case scenarios, and get back to the status quo if necessary. 

Ultimately helping me see my fears as exaggerated cartoon villains - sure, they look scary, and some of them should probably be wearing pants, but they're mostly just twirling their mustaches, laughing evilly for effect, and they’ll probably give you some classic monologue where they reveal their entire plan, giving you just enough information and time to thwart it. 

In short, my fears seemed much more likely and much scarier than they actually were, except for Katz from Courage the Cowardly Dog, that dude will haunt me for life. 

Anyway, as you could probably surmise from my childhood traumas and hyperactive ostrichness, I fit into the education system about as well as a penguin in a hamster wheel.

I felt like I was wasting time learning things to regurgitate them on an exam page only to forget them as soon as I walked out of the room, never to use them in my life again.

The final exam of my second year of university was the straw that broke my camel’s back (sorry Bumpy). I handed in my blue book, walked out of the room, and immediately, unlike Bumpy, felt a weightless sensation akin to what I‘d imagine Stephen Hawking felt in zero gravity– simultaneous euphoric freedom and anxious panic.

Internally, I had already decided that I was going to drop out.

On the surface though, I had already concocted a master plan—I was going to embark on what I optimistically dubbed a "gap year." That way I wouldn’t get the dropout backlash from everyone, and I would get to spend that time learning stuff I was actually interested in (unlike how to read a balance sheet, no offense to the one accountant reading this), use that knowledge to start a company (because duh, why not?), and globe-trot like a digital nomad (easy peasy, lemon squeezy, right?).

My 20-year-old dumbassery never ceases to amaze me, but, in retrospect, thank god I was naive and stupid enough to think it was possible because that’s the only reason I actually tried going after it.

My parents, understandably, were as thrilled as *that* crazy ex on the day you broke up with them...

They saw my dropping out as the equivalent of deciding to become a professional unicorn tamer. "You're making a mistake," they said. "You can't succeed without a degree," they claimed. There I was, armed with nothing but a rebellious streak and a dream, facing the world like a knight armed with a limp pool noodle.

Amidst the cocktail of disappointment, abandonment, and hurt, I knew I had to blaze my own trail. But at what cost? 

When I shared my grand plan with other friends and family, the reactions ranged from:

to... 'Are you planning to join a circus?'

A select few backed me up, saying things like, 'It’s bonkers, but hey, if anyone’s crazy enough to do it, it’s probably you.'  To those few, a big, teary-eyed thank you from the depths of my heart.

Unfortunately, belief alone is like trying to pay rent with good vibes – it doesn’t quite cut it, trust me I’ve tried.  So, I realized I needed something a tad more substantial. As it turns out, stalking people who've achieved what you aspire to achieve is a pretty solid strategy. But if you can't quite swing the stalking thing, learning from those accomplished examples who've not only conquered their dreams but also successfully coached others to do the same is the next best thing.

Enter my ‘digital mentors’ – a group of people I’ve never met but who’ve unknowingly become my life coaches. They’re the voices in my headphones, the talking heads on YouTube, and the authors of every 'How I Did It' book. They were my personal Yoda if Yoda was into podcasts, courses, and flexing on the gram.

Picture this: they've all launched their own businesses and faced their fears like champs. Their tales of triumph not only gave me hope but also some real, practical wisdom. It was like a constant reminder on Dora the Explorer of them saying, "Hey! If we can do it, you can too! 🙂" So there I was, absorbing their wisdom like a 3–year–old sponge – a digital, cartoon–loving, fear-conquering sponge.

After a couple of weeks, the gravity of my situation finally made its way through the inordinate thickness of my hard-headed skull. And trust me, mine’s enough to make a Neanderthal jealous.

I realized this journey was going to be a marathon, not a sprint, and the finish line was on another planet. It was going to take years and failure meant the worst-case scenario. 

What does that look like? Well, let me share the vanilla version of my fear-setting exercise, turned into an epic saga of doom.

Here’s a sneak peek: 

I’m on the phone with my parents, and it feels like the last call on a sinking ship. My dreams of being a digital nomad, starting a company I was passionate about, traveling the world, and sharing my success with friends and family are drifting away like that balloon I really loved but accidentally let go of.  Now those dreams are painful distant fantasies I shiver even thinking about. I'm left with no parents, no degree, no job prospects, and a mountain of debt. I’m staring at a future where I'm as employable as a chocolate teapot.

I try to get a job, but my lack of education and experience makes it impossible. Every rejection email is a reminder that I might be underqualified for life itself. Eventually, I settle for a job where 'feeling passionate and motivated for growth’ is as likely as finding my dream crush (🙋♂️@lexielimitless) waiting for me in my dream home with my dream dish (a spicy bowl of Tan Tan Ramen) and reading this guide…

Anyway, I'm trapped in a dead-end job, working long brutal hours for little pay.

Financial instability turns me into that friend who's always 'forgotten' their wallet. My social life shrinks faster than my confidence walking out of a pool on the coldest day of the year. I’m pretty sure my only remaining “friend” is Brad the barista who feels sorry for me.  I can't afford to go out, I feel like I'm constantly asking for handouts. I start to withdraw from everyone. I don’t feel like I’m worth their time or effort. I’m basically the worst possible version of Jerry from Rick & Morty.

As the years go by, my colossal blunder starts chasing me like an overzealous groupie at a Bieber cult concert. I resort to anything that could make me forget my poor life choices – from sniffing permanent markers (my nose's greatest nemesis) to watching infomercials of Scrub Daddy. Life takes a big ol’ U-turn when I get axed from my dead-end job, a departure that, to be honest, felt like getting dumped by Quasimodo – a real slap in the face with a hunchbacked glove.

So picture this: there I am, sprawled on the street, rocking my signature eau de rat piss and pigeon poop cologne, freezing, unwell, friendless, with a side of depression and an existential crisis to boot. I rack up more debt than the U.S. government. Misery? Check. Lack of fulfillment? Double check. Homelessness? Oh, you bet. Regret? So much it should've come with its own theme music.

On one particularly dire night, I start brainstorming the ultimate exit strategy. My situation seems as inescapable as a straightjacket made of familial disappointment, and I feel as useless as a waterproof teabag. I contemplate every dramatic way to bid adieu to this earthly realm, tormenting myself like Sisyphus at a sadomasochist party.

But hey, it's not over yet! Here's the plot twist: I never jump off that cliff. I just disappear into obscurity, forgotten by all who used to love me, and my once grand world-changing plans now serve as cautionary tales for parents to scare their children straight: "Study hard, kiddo, or you might end up like Uncle Adrien."

In the grand scheme of things, I pretty much took a masterclass in how to do everything wrong and leave the world in shambles – fun times :)

Now, let’s break down this fear fiesta the way I did using Tim Ferriss’s fear-setting exercise in Part 2 of this chapter on Fear: How I Learned to Dance with Wallace and Tango with Terror (coming soon).

• Next: Fear: Chapter 3 (Part 2) | Boogying with the Boogeyman: How I Used Fear-Setting to Tango Through Terror (coming soon) Connect with me and I'll let you know when it's published :)

Read Other Chapters:

• Read the Introduction to The Ultimate Simple Guide to Life
• Chapter 1 | How I Used Death to Set My Life Goals
• Chapter 2 | Life’s Not That Short: Here’s Why We’re Wasteful of It
• Chapter 3 (Part 1) | How to Defeat the 8 Fears Holding You Back From Your Dream Life
• Chapter 3 (Part 2) | Boogying with the Boogeyman: How I Used Fear-Setting to Tango Through Terror

If you liked this article, please like, comment with your thoughts, and share with anyone who might benefit. Thank you.

• Have you ever let fear stop you from doing something you regret not doing? Share your story.
• Can you share a time when confronting a fear led to an unexpected opportunity or growth?
• What's your 'Fear-Setting' process like, if you have one? Has it changed your approach to fear and decision-making?
• How have resources like this, 'Taming the Mammoth,' 'The Flinch,' or 'Fear-Setting' changed your perspective or strategies on handling fear?

Share your thoughts in the comments :)