Stephen Wilson Jr. is 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:

“Stephen, you are about to be promoted.”

Usually cause for celebration, it was instead meant as a warning by his master.

In a previous life, Stephen was a guitarist in a small indie rock band. He also spent his evenings writing songs.

His boss knows that Stephen is a good songwriter, and that’s where he really belongs.

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 are somewhat at a crossroads.

Because if you take (the promotion), like I took it 30 years ago, your dreams of becoming a songwriter, they will disappear. It consumes every part of you.

Right now you can write songs and do this job, but 6 months from now I’m not sure you can. So I just wanted to give you a warning.”

That little voice in Stephen’s mind, which had been there for years and years, began to grow louder.

6 weeks later, in that now deafening voice, he put in his 2 weeks notice, confusing all (except his boss and his wife).

He began bartending and waiting tables for a living while honing his craft, trying to get country music publishing deals…while being rejected for not writing The“bro country” songsThe:

He was told, “write TRUE songs. There’s nothing we can do about that…”

A few years later, after some modest success writing songs for other musicians, he finally had the courage and experience and power to start recording his own songs.

And last year, he finally released his debut album, Father’s sonwhich Rolling Stone called one of the best albums of 2023.

Recently, Stephen released a Thecreepy cover of “Stand By Me” by Ben E. KingThe which I’ve listened to about 10,000 times in the past month.

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

Golden Handcuffs vs. Uncomfortable Expansion

From 2008-2010, I also lived a dual life.

I have a day job at Sixthman, helping to promote and produce floating music festivals. But I also spend my evenings and weekends working on a small website that helps nerds get fit.

My boss April and my mentor Andy (who owns the business) both know where my heart is; 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 Burkeman’s TheFour Thousand WeeksThehe encourages us to ask a specific question when making life decisions:

“Where in your life or your work are you currently seeking comfort, when all it takes is a little discomfort?”

Asking ourselves “what will make me happy” tends to lead us to the short term, comfortable, safe option.

Instead, we should think about which path will make us grow as a person, or which version will cause us to SCREAM every week. Perhaps, deep down, we know the answer to the question, if we have the courage to ask it.

Burkeman’s advice:

“Choose uncomfortable enlargement over comfortable reduction whenever possible.”

Yes, sometimes chasing that “uncomfortable upbringing” doesn’t result in a songwriting deal, or a successful business. I choose 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 the uncomfortable expansion to 2025.

• When we do strength training, 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 are sad or angry or bored, addressing our relationship with food can be uncomfortable.
• When we have an uncomfortable conversation, we can deepen our relationships or stand up for the things that are important to us.

In 2025, let’s ask:

Where in your life are you tight-lipped living in comfort and safety, when? deep down you know that path of “uncomfortable growth” is exactly what you need to grow and help you get what you really want?

You may not need to quit your job right away, or go to a new goal or change…

But it might be worth asking yourself that uncomfortable question.

Life is hard, and change is even harder.

Uncomfortable.

It’s scary.

messy

But if you’re willing to say NO to comfort, this might be exactly what you need.

-Steve

PS: TheWe are doing a free 5-day workshopThe for people looking to build new habits that really stick in 2025, it starts in a few days!