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Stephen Wilson Jr. was a scientist working for Mars, Inc. (Yeah, the Candy company).

One day, his boss pulled him into an office and said something that changed his life:

“Stephen, you’re about to get promoted.”

Normally a cause for celebration, this was instead meant as a warning by his boss.

In a past life, Stephen had been 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:

That tiny 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 a deafening volume, he put in his 2 weeks notice, which confused everyone (except his boss and his wife).

He started bartending and waiting tables to make ends meet while honing his craft, trying to get publishing deals in country music…while getting rejected for not writing “bro country” songs:

He was told, “you write REAL songs. We can’t do nuthin’ with that…”

Years later, after some modest success writing songs for other musicians, he finally worked up the courage and experience and clout to start recording his own songs.

And last year, he finally put out his debut album, Son of Dad, which Rolling Stone called one of the best albums of 2023.

Recently, Stephen put out a jaw-dropping cover of Ben E. King’s “Stand By Me,” which I have listened to approximately 10,000 times over the past month.

(Seriously, please watch this video. It’ll give you goosebumps!).

Golden Handcuffs vs Uncomfortable Expansion

From 2008-2010, I also lived 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 helping nerds get fit.

My boss April and my mentor Andy (who owned the business) both knew where my heart was; they encouraged me to chase the uncomfortable future of trying to make Nerd Fitness into my career.

16 years later, we’re still going strong!

In Oliver Burkeman’s Four Thousand Weeks, he encourages us to ask a specific question when making decisions in life:

Asking ourselves “what would make me happiest” will most likely lead us towards the short term, comfortable, safe option.

Instead, we should be thinking which path will make us GROW as a person, or which version will cause us to SHRINK each week. We probably, deep down inside, know the answer to the question, if we have the courage to ask it.

Burkeman’s advice:

Yep, sometimes chasing "uncomfortable enlargement” doesn’t result in a songwriting deal, or a successful business. I’ve chosen the uncomfortable path and sometimes things don’t work out. But that’s part of the process, and at least it removes the potential for unhealthy regret!

Which brings me to today’s mission.

Let's get comfortable with being uncomfortable

Let’s chase uncomfortable expansion in 2025.

• When we strength train, we force our muscles to get uncomfortable by lifting heavier and heavier weight - they respond by growing and adapting.
• If we use food as a coping mechanism when we’re sad or 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 the question:

You might not need to quit your job immediately, or go all-in on 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 exactly what you need.

-Steve

PS: We’re doing a free 5-day workshop for people who are looking to build new habits that actually stick in 2025, it starts in a few days!

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Level Up Enterprises Inc. - 1831 12th Ave S. Unit 271, Nashville, TN 37203
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