Before we start! We’re coming up on Christmas and the best gift for me would be if you shared the newsletter with 2 other people and asked them to subscribe! If you’ve found any of my work valuable or helpful it would really help me get the word out there. Word of mouth is always the best form of marketing ❤️
Tim Ferriss might have the single greatest, what I’ll call “epiphany ratio”, of any author in the modern world.
Defined as: people who live a completely different life after reading one of his books.
When I reflect on my life, I view it as a binary. Before or after my trip to Thailand in 2017. That 7 month trip completely changed almost everything I believe about the world and the amount of gratitude for my position in it.
But, that change likely started 6-8 months before my trip with a little book called The 4-Hour Workweek.
Prior to reading the book, it had never crossed my mind that there were options in life that didn’t involve working 40 hours a week. Perhaps that was the origin of my love for challenging my own assumptions.
There are many quotable parts but one legendary line sticks out…
“A person's success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.” - Tim Ferriss, The 4-Hour Workweek
For you to understand why this is important we need to explore the concept of asymmetry. Asymmetry is the idea that the downside risks of an activity are small in comparison to the possible upside.
It’s a common idea in the investment world too, everyone looks for positive asymmetric risk.
Nobody likes uncomfortable conversations but they are justified because of their positive asymmetric risk.
There are plenty of places to have uncomfortable conversations.
At work
With friends
In your relationship
Meeting new people
The worst downside risk of an uncomfortable conversation is that you lose the person in it from your life. Usually however, the consequence is some hurt feelings or an awkward interaction.
These conversations become even more positively asymmetric when networking or meeting new people.
Why?
Because, most often, the people you are having these interactions with weren’t in your life anyways. This effectively makes your downside risk equal to 0.
Here’s how this shows up in my life:
I now have a podcast. In order for me to have guests I need to have many uncomfortable conversations through warm and cold introductions.
This means cold emails and direct messages. Things often seen as a nuisance. Uncomfortable.
The downside of this activity is that they never respond to my message.
The upside of this activity is that I am able to have an intellectual conversation with someone I admire. That person might be able to refer me to other interesting people (provided I give a good interview). Then those people could refer me to 3 other people.
The opening blurb of this newsletter is another meta-example of this concept. An uncomfortable ask from me with a largely positive upside.
Here’s how this might show up in your life:
Having a conversation with the cute girl at a house party
Downside: Awkward interaction
Upside: Wife & Kids
Talking to someone at your work conference
Downside: Awkward interaction
Upside: Better job opportunities, friendship, generate new business for your company
Sending a cold email
Downside: They don’t respond
Upside: A new job, a mentor, get invited to cool events
The best things in my life have come after uncomfortable conversations. Yours will too.