Starting My Company: Fear-Setting & Asymmetrical Risk

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My positioning & strategy consultancy, Three Deuce Branding, turns 23 today.

I started it from the second bedroom of my Cincinnati condo in 1997. I run it from the second bedroom of our Chicago condo today. Progress!

Back then, going solo was less common than it is today. “I can’t believe you’re doing this” was a typical response – not always in a flattering way.

Some people even said I should try it part-time first, as if that were an option. (“I can help solve your strategic challenges, but only after 6pm.”)

I was all-in from the get-go. Today, I’m sharing some background on how I chose self-employment over a steady paycheck, since this is a question I get often. Fun fact: I made this decision in about 24 hours.

My Decision Tree in June 1997

First, I considered the upsides of going solo:

  • Happiness, since I hated my new job at Horrible Fortune 200 BigCo. (A friend from that job recently texted me, “I credit [BigCo] with making me unsatisfying to yell at.” It was that kind of place.)
  • New challenges, new industries & new people.
  • Self-determination.
  • Better life balance.

Not too shabby!

Now, the downsides:

  • I probably wouldn’t earn as much as I would in an office job, at least in the first few years.
  • I could be a complete bust as a consultant, in which case I’d… find a job, I guess.

That’s the worst that could happen! Not so scary.

With this in mind, I resigned from Horrible BigCo in my eighth week on the job, and without a written business plan for my new venture.

Two principles were at play here: Fear-setting & asymmetrical risk.


I don’t think the term “fear-setting” existed in ’97, but I did a version of it. Tim Ferriss wrote the definitive post on this topic in 2017.

In short, Tim’s approach to fear-setting is:

  1. Define the worst that can happen, in detail. How could you prevent or repair such damage?
  2. Define the more probable outcomes. What are the costs of not pursuing these positives?
  3. Take action.

Fear-setting forces you to be specific. That’s its beauty. Our fears run rampant in our minds but are often rendered impotent on paper.

As shown in my example above, any fears I had, once written down, seemed pretty toothless. Try it yourself.

Asymmetrical Risk

I’ve been thinking about asymmetrical risk a lot lately. Asymmetrical risk occurs when potential outcomes are heavily stacked on one side of the decision tree.

In 1997, my options looked like this:

A. Remain at Horrible BigCo = Guaranteed misery, since BigCo was not going to change to please me.

B. Start a consultancy = Days that are more interesting and almost certainly happier.

Asymmetry! I’ll take door B, please.

Another example: There’s a pandemic. Should I wear a mask?

Mask = minor discomfort; perhaps a vague sense of “lost freedom.”

No mask = increased chances that I die and/or begin a chain of infections & death

So wear the damn mask.

Summing Up

In summary:

  • Define your fears – and what you’d do if they came to pass.
  • When decisions are small and/or easily reversed, as most decisions are, just take action.
  • When risks are asymmetrical, follow the sensible path.

Fear-setting & asymmetrical risk enrich both business and life. They’ll keep you out of most ditches. And you’ll have more interesting days to boot. 

Plus, you won’t be the guy who takes 10 minutes to figure out his drink order (tiny decision). Nobody likes that guy. 

Most Importantly: Thank You

Many thanks to my clients, my support system, my family, and my wife, Kara, without whom this 23rd anniversary would not be possible.

And many thanks to you, for showing interest in my work. It means a lot.

I’ve made some good decisions. But I’m also a very lucky man.

P.S. I’m considering writing more about the other decisions that have kept this one-man show going for 23 years. If you’re curious about those, drop me a line.

About Matthew Fenton: Matthew is a former CMO who helps brands to focus, grow and win.  Since founding his consultancy, Three Deuce Branding, in 1997, he’s helped hundreds of brands to achieve “brand clarity.”  His consulting services and speaking engagements help brands to focus on what matters through positioning, strategy and ideation.  Contact Matthew here.  He’s based in Chicago.

Copyright 2020 – Matthew Fenton. All Rights Reserved. You may reprint this article with the original, unedited text intact, including the About Matthew Fenton section.