Stephen Wilson Jr. was a scientist working for Mars, Inc. (Yes, the Candy Company).
One day, his boss pulled him into an office and said something that changed his life:
“Stefan, you are about to be promoted.”
It was usually cause for celebration, but this was meant as a warning from his boss.
In a previous life, Stephen was a guitarist in a small indie rock band. He also spent his evenings writing songs.
His boss knew that Stephen was a very good songwriter and where he really belonged.
He told Stefanos about the golden handcuffs:
“You’re in line for a promotion and you’re being groomed for the next level.
And you’re kind of at a crossroads.
Because if you get [the promotion]as i got it 30 years ago, your dreams of being a songwriter will go away. This will consume every bit of you.
Right now you can write songs and do this job, but 6 months from now I’m not sure you will be able to. So I just want to give you a warning.”
That tiny voice in Stefan’s head that had been there for years and years began to grow louder.
6 weeks later, with that inner voice now at a deafening volume, he put in his 2 week notice, which confused everyone (except his boss and his wife).
He began bartending and waiting tables to make ends meet while developing his craft, trying to get published in country music… while being rejected for not writing ,Bro country songs.,:
They told him, “you write REAL songs. There is nothing we can do about it…”
Years later, after some modest success writing songs for other musicians, he finally found the courage, experience and influence to start recording his own songs.
And last year, he finally released his debut album, Daddy’s sonwhich Rolling Stone called one of the best albums of 2023.
Recently, Stephen took one out ,stunning cover of “Stand By Me” by Ben E. King,, which I’ve heard about 10,000 times in the last month.
(Seriously, please watch this video. It will crack you up!).
Golden handcuffs vs uncomfortable extension
From 2008-2010 I also lived a double life.
I had my day job at Sixthman, helping to promote and produce floating music festivals. But I also spent my nights and weekends working on a small website helping nerds get in shape.
My boss April and my mentor Andy (who owned the business) 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’re still going strong!
At Oliver Burkeman’s ,Four thousand weeks,encourages us to ask a specific question when making decisions in life:
“Where in your life or work are you currently seeking comfort when what is required is a little discomfort?”
Asking ourselves “what would make me happiest” will likely lead us to a short-term, comfortable, safe option.
Instead, we should be thinking about which path will make us GROW as a person, or which version will make us SHRINK each week. Rather, deep down, we know the answer to the question, if we have the courage to ask it.
Burkeman’s advice:
“Choose inconvenient zooming out over comfortable zooming out whenever you can.”
Yes, sometimes chasing the “awkward enlargement” doesn’t lead to a songwriting deal or a successful business. I have chosen the uncomfortable path and sometimes things don’t go well. But that’s part of the process, and at least it removes the possibility of unhealthy sadness!
Which brings me to today’s mission.
Let’s get comfortable with being uncomfortable
Let’s chase the awkward expansion in 2025.
- When we strength train, we make our muscles uncomfortable by lifting more and more weight – they respond by growing and adapting.
- If we use food as a coping mechanism when we’re sad or angry or bored, dealing with our relationship with food can be uncomfortable.
- When we have awkward conversations, we can finally deepen our relationships or stand up for the things that are important to us.
In 2025, let’s ask the question:
Where in your life do you live comfortably with comfort and safety, when? in depth do you know that the path of “uncomfortable enlargement” is what you really need to grow and help you get what you really want?
You may not need to quit your job right away or move on to a new goal or change…
But it could 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, it might be just what you need.
-Steve
PS: ,We are doing a free 5 day workshop, for people who want to build new habits that actually stick in 2025, it starts in a few days!
