Stephen Wilson Jr. was a scientist who worked for Mars, Inc. worked. (Yes, the Candy company).
One day his boss pulled him into an office and said something that changed his life:
“Stephen, you’re about to be promoted.”
Normally a cause for celebration, but this was meant as a warning from his boss.
In a past life, Stephen was a guitarist in a small indie rock band. He also spent his evenings writing songs.
His boss knew Stephen was a damn good songwriter, and where he really belonged.
He told Stephen about the golden handcuffs:
“You’re in line for a promotion and they’re preparing you for the next level.
And you’re kind of at a crossroads.
Because if you accept (the promotion), like I did 30 years ago, your dreams of becoming a songwriter will be gone. This is going to consume every part of you.
Right now you can write songs and do this work, but in six months I’m not sure you’ll be able to do that. So I just want to give you a warning.”
That little voice in Stephen’s head, that had been there for years and years, started to get louder.
Six weeks later, with that inner voice now at a deafening volume, he gave his two-week notice, causing confusion everyone (except his boss and his wife).
He started bartending and waiting tables to make ends meet while he honed his craft and tried to land deals for country music publications…while getting rejected for not writing “bro country” songs:
He was told, “You write REAL songs. We can’t do anything with that…’
Years later, after some modest success writing songs for other musicians, he finally mustered the courage, experience and clout to record his own songs.
And last year he finally released his debut album, Dad’s sonwhich Rolling Stone named one of the best albums of 2023.
Recently Stephen brought one breathtaking cover of Ben E. King’s ‘Stand By Me’ which I’ve listened to about 10,000 times in the last month.
(Seriously, watch this video. It will give you goosebumps!).
Golden handcuffs versus awkward expansion
From 2008-2010 I also led a dual life.
I had my day job at Sixthman helping promote and produce floating music festivals. But I also spent my nights and weekends working on a little website to help nerds get fit.
My boss April and my mentor Andy (who owned the company) both knew where my heart was; they encouraged me to pursue the uncomfortable future of trying to make Nerd Fitness my career.
16 years later we are still going strong!
In Oliver Burkemans Four thousand weekshe encourages us to ask a specific question when making decisions in life:
“Where in your life or at work are you currently striving for comfort, when a little discomfort is necessary?”
Asking ourselves “what would make me happiest” will most likely lead us to the short-term, comfortable, and safe option.
Instead, we should consider which path will make us GROW as a person, or which version will make us shrink every week. We probably know the answer to the question deep down, if we have the courage to ask it.
Burkeman’s advice:
“Choose uncomfortable enlargement over comfortable reduction whenever you can.”
Yes, sometimes chasing an “awkward expansion” doesn’t result in a songwriting deal, or a successful business. I have chosen the uncomfortable path and sometimes it doesn’t work out. But that’s part of the process, and at least it removes the chance of unhealthy regret!
That brings me to today’s mission.
Let’s get comfortable with being uncomfortable
Let’s pursue uneasy expansion in 2025.
- When we do strength training, we force our muscles to feel uncomfortable by lifting heavier and heavier weights – they respond by growing and adapting.
- When we use food as a coping mechanism When we’re sad, angry, or bored, it can be uncomfortable to address our relationship with food.
- When we have awkward conversations, we can finally deepen our relationships or stand up for the things that matter to us.
Let’s ask the question in 2025:
Where in your life do you live comfortably and safely, when deep inside Do you know that the path of “awkward expansion” is what you really need to grow and help you get what you really want?
It may not be necessary to immediately quit your job, or go all in on a new goal or change…
But it may be worth asking yourself that uncomfortable question.
Life is hard, and change is harder.
Uncomfortable.
Scary.
Messy.
But if you’re willing to say NO to comfort, this might be just what you need.
-Steve
PS: We do a free 5-day workshop for people who want to build new habits that will last into 2025: it starts in a few days!