Conquering The Fears Of My Creator Journey
Detaching from outcomes, becoming an artist and finding purpose
The purpose of this post is to pull back the curtain on the deep fears and insecurities I've battled throughout my creator journey.
I'm sharing this because I don't think I've fully embraced being a creator, an artist, an innovator… until now.
Writing this is helping me step into that identity.
This is my story of becoming a creator on the internet and discovering that business is art.
I Began Without A Plan
I wanted to live a more interesting life and create content around it on the internet.
I saw people I admired monetizing their interests and passions in a million different ways online and kept asking myself: why them and not me?
I decided I would rather die than not take a shot at it.
My goal was to go from an extremely "normal" life...
9-5 sales job
gym after work
Netflix at night
bars/breweries on the weekend
obsess over every pro sports game
to...
I didn't know
I didn't have a grand plan. That’s a big reason why I was so scared in the beginning.
I bought a bike and was ready to see where that would take me.
I started a side hustle sewing dog bandanas and was interested in sharing my business-building-journey.
But I had no roadmap to follow or clear idea of where I was headed.
What Was I Afraid Of?
None of it working.
Looking like an idiot.
People from my past making fun of me.
Being stuck working a dull corporate 9 to 5 that I hated for the rest of my life.
And a million other things.
I Was Used To Identified Outcomes
Prior to my creator journey, everything I strove for in life had an identified outcome.
grades
degrees
jobs
sales quotas
promotions
When there's a known outcome, there's a recipe to follow and a reassurance that you're making the right moves along the way.
It’s also really easy to blame anything that goes wrong on something other than yourself.
Creators don’t get this luxury.
Seth Godin's book Purple Cow helped me realize that the Industrial Era embedded this outcome-based thinking into the fabric of modern society.
Do X —> Get Y —> Be rewarded with Z
Everything is about efficiency, mass production and reduced costs.
Everything is known, uniform and predictable.
And there’s plenty of reassurance along the way.
Blame The Instructions
As much as I wanted to be a creator, my mind was used to the comfort and safety of following instructions.
Success came easy for me in corporate sales.
On the rare occasion I came up short in some area, I fell into the habit of deflecting blame to something external: the marketing department, the product department, the prospect.
I wasn’t really risking anything personal.
As I looked to break free from corporate life, the complete ownership I’d have to take if my effort failed felt foreign and intimidating.
Creating Towards An Unknown
Art is the opposite of identified outcomes.
It’s a shot in the dark.
And that meant I had to let go of outcome-based thinking.
For most of my creator journey, I thought art was paintings, music and stuff like that.
I eventually realized that art is anything that’s new, unique and unknow - so long as it connects with people and makes an impact.
If I wanted to be a creator, I had to change my mindset of what anything “should” be and accept the artistic freedom to simply create.
It helped immensely that my first business, Toasted Rye, was literally arts and crafts.
I was still bone-shakingly-terrified to make my Authentic Self vulnerable to criticism, but I summoned the confidence to create work I was proud of and ship it out into the world.
I started thinking of myself as an artist, putting in reps creating and impressing myself at what I could bring to life.

Identity Vanished, Fears Returned
Unfortunately, my fears of criticism and judgement weren’t pinned down for long.
I had gotten comfortable creating behind the veil of Toasted Rye, but I eventually shut the business down.
I decided to focus solely on creating a personal brand around my newfound love of endurance training.
I committed to the process of tweeting my ideas around fitness, mindset and how to improve your health, everyday.
This meant exposing myself to more vulnerability than I had ever felt before.
I went from saying “this is what I like” and “this is what I made” to “this is what I think”…
And that was completely terrifying.
I lost my identity as an artist and returned to outcome-based thinking, craving any reassurance that I was making progress.
In searching for an identified outcome, I saw successful creators in the fitness space, perceived myself as a fraud and felt like I was failing while looking like a fool.
You’re Supposed To Cringe At Your Past Work
It’s hard not to be consumed by the fear of judgement from others when you’re actively judging yourself.
I would look back at my social posts just days after sharing them and want to crawl out of my skin.
If I posted something true to me, I felt isolated.
If I regurgitated an opinion from a big account, I felt inauthentic.
Meanwhile, I knew friends and family were seeing it all and my mind started telling itself stories of people making fun of me.
While I was massively overestimating the judgement cast my way, I did have a few friends and family members vocalize their doubts.
I had friends screenshot my social media posts and text me them to rip on me.
I had family question my new habits and content to my face.
Their doubts magnified my own and led me to question my entire effort.
But I stuck to the process of publishing my ideas on the internet every day.
I started finding my voice and knew I would only get better with more reps.
While I still criticized myself too much, I adopted a perspective that better served me:
If I’m cringing at some things I’ve posted, it means I’m growing.
What My Favorite Authors Say About Fear
"Show me someone who claims he doesn't give a shit and I'll show you a born artist who's scared out of his wits to become that artist." - Steven Pressfield, The Artist's Journey
"They're scared because creative work is as terrifying as it is gratifying. You've put a large piece of yourself into this project. What if people don't like it?" - Ryan Holiday, Perennial Seller
"Everyone who creates feels resistance. Everyone who is seriously engaged in the deep effort of inventing and shipping original work feels the fear." - Seth Godin, The Practice
"Fear is the oldest and strongest emotion known to man, something deeply inscribed in our nervous system and subconscious." - Robert Greene, The 50th Law
Hearing some of the most prolific authors (AKA artists, creators, innovators) of all time talk about fear like this helped me accept its reality.
My Fears Made The Whole Thing Mean Something
I was afraid.
I doubted myself.
But I also trusted that creating on the internet was what I was supposed to do.
My fear forced me to strengthen my will.
A strengthened will gave my effort more meaning.
Taking action toward meaning gave me purpose.
This is the skeleton of my Creator Journey.
The Nonbelievers
I realized that what I create is not for everyone. No art is.
Some people just aren’t interested in going where I want to go. That’s OK.
I've worked hard to be patient with people who’ve resisted my change.
Because in reality, they came to know me as X.
And I didn't just decide to become Y…
I decided to become a hieroglyphic.
What I do probably looks pretty fucking weird to them!
Death Of A Salesman
Here's the identity box I put myself into in my mid-20s:
sales job
Philly sports fan
likes craft beer and goes to breweries on the weekend
I decided to break the box.
dog bandana side hustle
training for a 70.3 triathlon
documenting my journey on the internet and creating a personal brand
My desire to create and make a magnificent impact on the world is greater than my desire for sex, money or any other pleasure the world has to offer.
That's why giving up porn had such a hugely positive impact on me.
I stopped settling for short-term pleasure and gave myself a chance to transmute sexual energy into creative energy.
My supreme desire to create is also why making more money at my 9-5 never gave me any more fulfillment in life.
I like getting off and getting paid as much as the next guy...
But I was put on Earth to do something greater.
Birth Of A Business Artist
The core driver of my fitness-focused creator journey was tweeting out my ideas and insights, every day.
But as much as I was “creating”, it was still just tweets.
I wasn’t actually producing anything.
As I stayed consistent, my account grew from ~100 followers to a few thousand and I began developing digital products, pitching services and writing more long-form content.
The more I created, the less I even had time to remember all my fears of criticism and judgement that previously overwhelmed me.
As my connections increased, my online community began forming organically.
With completed projects and shipped work, I reclaimed the identity of an artist.
I returned to the creative freedom I found with Toasted Rye and started radically expanding my perception of what I could build around my love of endurance.

The Artist’s Paradox
All this talk about fear and I didn’t realize… Art REQUIRES discomfort.
Discomfort engages people and makes them curious.
Art seeks to create change.
And with change comes discomfort.
Plus, there’s a part of me that likes to ruffle some feathers!
I like to have a little fun with it every now and then. I like to talk shit on soy.
Maturing as an artist means…
detaching from my fear of judgement
realizing that I enjoy occasional judgement anyway
accepting that this is all part of the creative process
My Real Secret
Endurance sports gave me the confidence to pull it all off.
It forced me to develop patience, sit with discomfort and stay committed to the process.
The mental resiliency I developed on long rides, runs and swims translated directly to building my business.
In training sessions (and eventually races), I continually proved that I could exceed my wildest expectations of myself - if I just kept showing up and putting in reps.
I wanted to become a creator on the internet and build a career around my interests.
Today, Tribal Training is 42 athletes strong.
I get to teach, guide, help, connect and grow a community around a love of physical fitness, mental fortitude and enormous accomplishments.
Rebirth
I was scared.
I did it anyway.
It changed me.
I needed to write that down.
Do you know a creator (or aspiring creator) who would benefit from reading this?
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