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Today, in 10 minutes or less, you learn:

• 🧭 My Journey With Fear in Money, Business, and Life; How I’ve Used the Fear Compass Tool

• 🧠 4 Lessons on Fear in Relation to Truth, Friendship, Courage, and Margin of Safety

• 😨 Downsides of Choosing Fear

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🧭 The Fear Compass: 4 lessons on fear in decision-making

I felt deeply afraid of what I was doing.

Have you ever felt this way?

Looking back, my biggest decisions have been emotional not logical, where I’ve had to push through significant anxiety or fears. 😨

Don’t get me wrong… I love logical decision-making frameworks as much as any other productivity enthusiast:

“OK I just need to plot my options on the Eisenhower Matrix, create an Impact vs Effort Score, or…”

Yet, I’ve learned the hard way that logic alone is not enough.

In this newsletter, I’m going to deep dive into my favorite decision-making tool, The Fear Compass, and 4 lessons I’ve learned about fear in making important decisions.

But before I jump to this actionable tool, I’m going to share a bit about my journey:

My Journey With Fear in Money, Business, and Life 🗺️ 

Growing up, I was a shy and reserved kid.

I recall being in elementary school and feeling terrified of meeting new people.

This was a big reason why I gravitated towards the internet—I could thrive online while avoiding rejection in real life.

But somewhere along the way, I started challenging myself to do what I was afraid of:

• Teen’s - Performing live music, competing in debate and speech, and winning a state championship.

• Early 20’s - Moving 2x across the country from Michigan to New Hampshire for college to San Francisco for work.

• Late 20’s - Traveling the world for 1 year, starting career coaching, moving to Singapore, becoming a product leader in Southeast Asia.

• Early 30’s - Moving to Mexico City, learning Spanish, leaving my full-time job, starting consulting, teaching, and writing.

I’m grateful I did because these decisions changed my life trajectory for the better.

Many people ask why I make the decisions I do.

It wasn’t until the last couple years, that I could articulate it coherently.

The most important decisions I’ve made were not rational—they were emotional.

They were when I pushed the envelope of my comfort zone. And forced me to grow beyond my preconceived limits.

On the flip side, the unsatisfying decisions were where I did NOT do something out of fear. E.g. Not start a business (out of financial concerns), not ask for a promotion, etc.

Tony Robbins defines FEAR as an abbreviation:

False Evidence Appearing Real

While this is not a perfect definition (I’m afraid of sharks and don’t think that’s false), this applies well to the context of money and business, where many threats are imagined.

The fear of not being smart enough. Networked enough. Rich enough.

And as a result, we choose to take the safer path.

In my experience, this has frequently been the wrong path…

… which leads me to my favorite question:

Fear Compass: My favorite decision-making tool 🧰 

When faced with a difficult business decision, the question I ask myself is:

“Which option/path/choice scares you the most?”

Then do the thing.

Easier said than done, but the answer nearly always points me in the right direction.

Along the way in using this tool, I’ve learned four key lessons about fear:

Lesson #1: Fear identifies your truth 🔮 

Pema Chödrön once wrote:

Rephrased: Fear is a disguise for the real challenges you’re meant to work on.

For example, deciding to take a startup leadership role revealed my fears of being skilled in management, which forced me to go on the journey to build confidence in my management capabilities.

One corollary is that the real challenge often requires you to carve out your own path (not simply by following a paved road).

It’s easy these days to copy playbooks, best practices, etc. Information is everywhere.

This is a fine way to get started, but ultimately, the real challenge involves taking a hard journey to discovering what’s the unique thing that works for YOU.

This is your individual “truth”—which is not true for others.

For example, it’d be easy to copy content from popular creators, but I know the thing that will lead to more personal growth and defensibility in the long-run is by developing my own spiky point of view.

It’s a harder path, but worth it.

Lesson #2: Fear is your friend 👯 

My coach in San Francisco used to express the importance of redefining my relationship with fear from “fear is your enemy” to “fear is your friend.”

Before working with him, I always felt I was on a quest and fear was the menacing standing guard at the drawbridge entrance to the next kingdom.

Blocking my way.

After working with him, I adopted healthier mental visualizations.

I started imagining fear as my ally, sitting in my passenger seat and helping me navigate towards where I wanted to go on a long road-trip.

In other words, fear is your intuition giving you powerful feedback about what’s important to you.

Embracing this mindset helped me pull the trigger on taking my travel sabbatical, which led me to meet my wife and grow my career internationally.

Lesson #3: Courage = Fear + Action 🦁 

Courage is taking action when faced with fear.

And by taking action, you build confidence in your capabilities.

This starts a virtuous cycle, where as you build confidence, you get more desensitized to your initial fear— leading to more growth.

You can imagine this as a series of S-Curves:

• Each S-Curve represents your actions when faced with fear

• As you act upon your fear (with courage), your growth accelerates along the S-curve, until your capabilities and confidence grows to a point where the slope slows down

• You’re desensitized to your initial fear, and so you tackle your next set of fears, which kicks off your next S-Curve

For example, when I first moved abroad, I moved to Singapore—which felt familiar in terms of convenience and lifestyle vs the US. I could still speak English and buy many of the same products at Western grocery stores.

This gave me more confidence to move somewhere like Ho Chi Minh City or Mexico City, where there’s a bigger jump in terms of language and lifestyle differences I’ve had to adapt to.

Lesson #4: Fear offers a margin of safety 🛟 

Warren Buffett has said that “margin of safety”—or the idea of building in cushion in your investment to allow for potential mistakes and volatility— is one of the most fundamental principles of investing.

The beauty of choosing the option you’re most scared of is this typically leads you to experience more personal growth than you otherwise would have.

As a result, even if the project/business doesn’t succeed, you still pick up more capabilities and confidence—which amplifies your chances at success in the future.

For example, when I decided to work in emerging markets like Indonesia and Southeast Asia, I felt afraid of not being able to navigate the chaotic market effectively.

But I did it anyway, learned a ton, and now it’s my unique blend of Silicon Valley know-how and emerging market experience that attracted LATAM startups to my profile.

While I’m a big fan of choosing the feared path, there are real risks I’ll mention now:

Downsides of choosing fear 😨 

1. Your path is harder than you expect - You discover that you’re out of your depth. You feel like you can’t deliver results.

   1. My suggestion: Take a step back and first give yourself a pat on the back for doing what most people don’t do. Now you won’t ever have “what if?” thoughts. Then be kind to yourself, adjust your expectations, and limit your focus to taking one step at a time. Celebrate each small step forward.

2. You feel like you chose the wrong path and switch - It feels like you’ve potentially wasted your time and gone backwards.

   1. My suggestion: Focus on what you’ve learned about yourself. These are all insights you can leverage in your next path. While it may seem like a setback in a micro-lens, it’s also up to you to choose to view this as a step forward in the broader macro-lens of your life.

In Summary

If you’re feeling stuck in a decision, try tapping your intuition instead of logic.

Ask yourself, “Which option/path/choice scares you the most?”

Then take path that triggers the most fear. You won’t regret it.

🌐 Beyond your borders

🇸🇬 Ultra-rich in Asia-Pacific seeking greater balance between bonds and equities: UBS report (link)

🇺🇸 30% of US Consumers Count on Side Hustles to Pay the Bills (link)

🚢 Superyacht captain’s side hustle brings in $10,300 a month, takes 5 hours a week: This could ‘be my retirement job’ (link)

💼 Side hustles for "high" earners? (link)

🏠️ Does a mortgage that's 45% of my net monthly income make any sense? (link)

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📆 How I can help

That’s all for today!

Whenever you’re ready, here’s how I can help you:

For daily insights, follow me on Linkedin or X (@dexteryz).