How Fear Setting Led Me To Coaching

As of November 2022, I was living in Perth, Australia, with no plans to leave before the end of 2023. I had a major promotion in the works to become the fund manager for BetterLabs Ventures and the entrepreneur-in-residence for its ventures studio.

Today, in early 2023, I sit here in a funky 1960's trailer in my backyard in Southern California, coaching CEOs.

God laughs when we predict our own futures.

When my family and I unexpectedly made the decision to not get on a return flight to Perth from our vacation to see my family in December, I was left with a question: How am I going to make money?

If you know me, you know that I'm an unapologetic generalist who loves learning for the sake of teaching others. I'd been coaching entrepreneurs and CEOs for close to a decade, but it was always the side hustle of something stable.

Now, the "stable thing" was 10,000 miles away and 16 hours apart in time. Without much of a choice, I thought to myself, "I'll do coaching until I figure out my next thing."

In my gut, I knew I wanted to coach full-time, but I was afraid, and I was giving fear a seat at the table - hanging on to its every word.

Fear is a terrible advisor.

After realizing how powerful a voice my fears had, I thought to myself, what if I began seeing fear as a positive advisor, magnifying my weaknesses as a way of alerting me to potential threats to what could stand in the way of success? Or what if I saw it as a signal to advance?

You can do three things when fear comes:

1. Freeze

2. Retreat

3. Advance

Stress and fear are biologically designed to prompt us to move. According to Andrew Huberman, when a person moves toward a threat and survives, the brain activates a reward mechanism. On the other side of this high-stress environment are positive outcomes, such as increased cognitive ability and greater alertness during environmental adaptation.

Fear doesn't tell us we'll fail; it warns us of the threats to our survival, and our fear of the outcomes becomes greater than our desire to gain the reward of confronting them.

You’ve likely realized at this point in entrepreneurship that fear doesn’t go away after you make the initial leap. Scaling a company is an exercise in overcoming stages of fear.

The truth is, I'm still afraid, but I'm noticing the positive changes in my character that have come with advancing. What helped me reframe fear and find the courage to advance was an exercise I found from Tim Ferriss on fear-setting. It is a simple but profound exercise for confronting fear.

Do this exercise and see if courage shows up.

To note: this is taken directly from Tim's blog. Here are the questions.

If you are nervous about making the jump or simply putting it off out of fear of the unknown, here is your antidote. Write down your answers, and keep in mind that thinking a lot will not prove as fruitful or as prolific as simply brain vomiting on the page. Write and do not edit—aim for volume. Spend a few minutes on each answer.

1. Define your nightmare, the absolute worst that could happen if you did what you are considering. What doubt, fears, and “what-ifs” pop up as you consider the big changes you can—or need—to make? Envision them in painstaking detail. Would it be the end of your life? What would be the permanent impact, if any, on a scale of 1–10? Are these things really permanent? How likely do you think it is that they would actually happen?

   
   

2. What steps could you take to repair the damage or get things back on the upswing, even if temporarily? Chances are, it’s easier than you imagine. How could you get things back under control?

   
   

3. What are the outcomes or benefits, both temporary and permanent, of more probable scenarios? Now that you’ve defined the nightmare, what are the more probable or definite positive outcomes, whether internal (confidence, self-esteem, etc.) or external? What would the impact of these more likely outcomes be on a scale of 1–10? How likely is it that you could produce at least a moderately good outcome? Have less intelligent people done this before and pulled it off?

   
   

4. If you were fired from your job today or your company failed, what would you do to get things under financial control? Imagine this scenario and run through questions 1–3 above. If you decided to quit your job or stop running your business to test other options, how could you later get back on the same career track if you absolutely had to?

   
   

5. What are you putting off out of fear? Usually, what we most fear doing is what we most need to do. That phone call, that conversation, whatever the action might be—it is fear of unknown outcomes that prevents us from doing what we need to do. Define the worst case, accept it, and do it. I’ll repeat something you might consider tattooing on your forehead: What we fear doing most is usually what we most need to do. As I have heard said, a person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have. Resolve to do one thing every day that you fear. I got into this habit by attempting to contact celebrities and famous business people for advice.

   
   

6. What is it costing you—financially, emotionally, and physically—to postpone action? Don’t only evaluate the potential downside of action. It is equally important to measure the atrocious cost of inaction. If you don’t pursue those things that excite you, where will you be in one year, five years, and ten years? How will you feel having allowed circumstance to impose itself upon you and having allowed ten more years of your finite life to pass doing what you know will not fulfill you? If you telescope out 10 years and know with 100% certainty that it is a path of disappointment and regret, and if we define risk as “the likelihood of an irreversible negative outcome,” inaction is the greatest risk of all.

   
   

7. What are you waiting for? If you cannot answer this without resorting to the previously rejected concept of good timing, the answer is simple: You’re afraid, just like the rest of the world. Measure the cost of inaction, realize the unlikelihood and repairability of most missteps, and develop the most important habit of those who excel and enjoy doing so: action.