Stephen Wilson Jr. was a scientist working for Mars, Inc. (Yeah, the Candy company).
One day, his boss took him into an office and told him something that changed his life:
“Stephen, you’re about to get promoted.”
Normally this would be cause for celebration, but it was more of a warning from his boss.
In a previous life, Stephen had been 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 that he really belonged.
He told Stephen about the golden handcuffs:
“You’re up for promotion and they prepare you for the next level.
And you’re kind of at a crossroads.
Because if you take [the promotion]as I took it 30 years ago, your dreams of being a songwriter will disappear. It will consume your entire being.
Right now you can write songs and do this work, but in 6 months I’m not sure you’ll be able to. 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.
6 weeks later, with that inner voice now at deafening volume, he gave his 2 weeks notice, which was confusing everyone (except his boss and his wife).
He started out as a bartender and waiter to make ends meet while honing his craft, trying to get publishing deals in country music…all while being rejected for not writing. Bro country songs:
We told him: “you write REAL songs. There’s nothing we can do with that…”
Years later, after some modest success writing songs for other musicians, he finally found the courage, experience and influence to begin 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 published a 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 vs Uncomfortable Expansion
From 2008 to 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 that helps nerds get in shape.
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!
At Oliver Burkeman Four thousand weeksit encourages us to ask a specific question when we make decisions in life:
“At what point in your life or work are you currently seeking comfort, when what you need is a little discomfort?
Asking ourselves “what would make me happiest” will most likely lead us to the short-term, comfortable and safe option.
Instead, we should think about which path will make us grow as a person, or which version will make us shrink every week. We probably know, deep down, the answer to the question, if we have the courage to ask it.
Burkeman’s advice:
“Choose an uncomfortable widening over a comfortable narrowing whenever you can.”
Yes, sometimes pursuing an “uncomfortable stretch” doesn’t result in a songwriting deal or a successful business. I chose the uncomfortable path and sometimes things don’t work out. But it’s part of the process, and at least it eliminates the risk of unhealthy regrets!
Which brings me to today’s mission.
Let’s get comfortable with being uncomfortable
Let’s continue an uncomfortable expansion in 2025.
- When we train strength, we force our muscles to become uncomfortable by lifting heavier and heavier weights – they respond by growing and adapting.
- If we use food as a coping mechanism When we’re sad, angry, or bored, addressing our relationship with food can be uncomfortable.
- When we have uncomfortable conversations, we can finally deepen our relationships or stand up for the things that are important to us.
In 2025, let’s ask ourselves the question:
Where in your life do you live comfortably, in comfort and security, when at the bottom 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 take on a new goal or change…
But maybe it’s worth asking this uncomfortable question.
Life is hard and change is harder.
Uncomfortable.
Scary.
Messy.
But if you’re ready to say NO to comfort, it might be just what you need.
-Steve
PS: We are doing a free 5 day workshop for people looking to build new habits that will truly last into 2025, it starts in a few days!
