Some people come out of the womb aspiring to be entrepreneurs. Not me.

My dad was a carpenter who specialized in wood floors. He was a one-man show; he hauled a 100-pound drum sander to and from every job and spent his days laying down sheets of parquet or refinishing staircases amidst a fog of polyurethane fumes.

These days, whenever he sweats it smells like fresh wood finish. That can’t be healthy. “Drop out of high school and come work with me,” he would often say to me as a teenager. “College is overrated; just get your G.E.D. and continue the family business.”

“Hell no,” I thought to myself. Self-employment horrified me not because of the working conditions, but because it sounded like I’d have to stay in one place for years, and all I wanted was to escape the rural Midwest.

  • My high school was surrounded by cornfields on three sides.
  • The house I grew up in was a tiny ranch-style home, and the bedroom I grew up in was a little under 100 square feet with no windows.
  • Offline earning potential in the rural Midwest was strangled. The Maytag factory that once employed half of town was relocated when I was a kid, tearing an economy to shreds; it was hard to dream big dreams.

Growing up low-income teaches you tenacity and resilience in ways that are sometimes difficult to describe.

Running any business — let alone my own — was a hell no. I just wanted to be free, and my dad’s life often seemed like the opposite of free.

Fast forward twenty years, and it’s safe to say I’ve flipped that hell no into a hell yes.

My five-year-old business, a quiet marketing consultancy, has had its best year ever. The numbers I’m working with these days (Both revenue and expenses) would have made teenager Nick’s stomach lurch. All in all, 2021 is the first year from which I feel I can proudly say: “I am an entrepreneur.”

And if I look back at the different career and personal steps taken to get here… there’s no way I could have predicted this outcome.

It Was 2011, And I Was Cratering

My focus as a consultant is B2B writing and marketing. But I didn’t have a career in journalism, rich parents, or years of experience.

In fact, my background is in something completely different from what I do today.

I tested well in math and the sciences as a kid. But deep down, I yearned to do something expressive, something that could let me share my authentic self:

Classical French Horn. 📯🙋🏻‍♂️

I spent my teens and early twenties obsessing over how to blow air through a brass tube. I won competitions, got to play at places like Carnegie Hall, and received an acceptance letter to Juilliard.

I leveraged this offer for a scholarship to Rice University, another top music school.

Images from the author

Once I finally accepted myself, I began to lose my drive. By the time I graduated from conservatory — which is a fancy word for “music college for nerds” — I was burnt out and ready to change careers. Easy, right?

Nope. The real world reared its ugly head, and it was a rude awakening.

Playing the French Horn isn’t what you’d call a “versatile” skill in typical job requirement vernacular.

So in 2011, I found myself experiencing the now all-too-common plight of the millennial generation:

Educated, but very unemployable.

(In fairness to millennials, most of them major in something a little less niche.)

My prospects were grim.

I was still broke, had no real work skills, and was $1,000’s upon $1,000’s of dollars in debt.

With little else to do, I packed away my French Horn and joined the working masses, opting into a seemingly never-ending conveyor belt of uninspiring jobs:

  • Barista ☕️🙋🏻‍♂️
  • Administrative assistant ☎️👨🏻‍💻
  • Retail associate 👔💁🏻‍♂️
  • Fitness instructor 🚴🏼‍♂️🙆🏻‍♂️

The day after I got my Master’s degree in music, I went to my part-time retail job and watched a decal dry on a window for seven hours.

Image from the author, c. 2011. Happy-go-lucky on the outside, f*cking screaming on the inside.

Simple as these jobs were, I wasn’t particularly good at any of them because I had spent most of my formative years in a windowless practice room.

I had no life skills.

I was so incompetent that I quit my second day of work at a part-time retail job because I couldn’t read the weekly schedule, which was sent out as an Excel spreadsheet.

(Who knew spreadsheets had tabs?)

Actually — I didn’t even quit.

What I did was even more cowardly.

Embarrassed at my inability to read an Excel file — but too shy to come out of the closet a second time as “spreadsheet-allergic” — I completely ghosted my shift.

No call, no show.

Realizing my mistake halfway through the day, I called in a panic — and was told not to worry about coming in that day.

So I stayed home and felt sorry for myself, blaring out a mournful tune on my stupid French Horn. Which is every bit as ridiculous as it sounds.

The French Horn is not meant for playing the blues.

At least, I didn’t think so…

But I wasn’t sure.

I took out my laptop and Googled “French Horn blues.”

Turns out there were some scales. I opened them up and began to play, sipping on a whiskey-spiked coffee between my bluesy dirges.

Image from the author, c. 2011.

I mangled it the first time through.

But inside of an hour, I had it mastered.

And as I sat there at the kitchen table… I realized something.

14 years of musical training hadn’t given me a ton of practical skills…but it had given me the ability to learn practical skills.

In fact, as I would come to realize later, it had given me the ability to pick up new ideas pretty quickly.

Music had given me a deep understanding of the power of repetition. (Stick a pin in that for later.) 📌

And as I became increasingly curious about online entrepreneurship in the months and years to come, my ability to “practice” business and marketing techniques suddenly became very handy.

That ability is what has helped me find my groove in the years that have followed.

Entrepreneurship dug me out of one hell of a hole.

And we’re going to talk about exactly how powerful repetition can be in just a minute.

But first, I want to tell you how it changed everything for me personally.

More importantly, I want to advise you on the mistakes I made — and what not to do when you’re getting started.

How NOT To Become an Entrepreneur

I knew I could learn new things, but I had no money. So I stayed at that retail job — they kept me on *and* taught me how to read spreadsheet tabs — for another four years.

In the interim, I started reading articles online. I would go to webinars, read certain blogs, and listen to podcasts about business and personal development.

(It seems like this is how a lot of us stumble into this world.)

The first time I purchased an information product online, I almost shat my pants. It was a $20 PDF on how to rack up credit card points.

I used that information to redeem a flight to London in 2012 and go see my sister, who I hadn’t seen in a few years. I’ve gone every year since (Minus the pandemic years). This was one of the first times purchasing information online literally changed my life.

Retail was becoming lame. But I wanted to ensure I didn’t end back up in another “annual 3% raise” situation with another company.

In reading various articles about career growth and personal entrepreneurship, I stumbled upon some negotiation tips that created a new opportunity.

I used them to pitch a business development position with a local chain of yoga studios. My negotiation efforts were probably tepid at best, but they worked; remember that this was negotiation to work with a family-owned business, not McKinsey or Goldman Sachs.

My new high-commission job was locked in. And I had created it!

And in that first year… I doubled my salary from the retail job. I socked away a lot of it in savings. My confidence grew. I kept learning and sharpening skills online.

I kept buying online courses and programs. When something works, do more of it. Websites like Coursera offer courses and programs to enhance knowledge, skills, and career prospects; explore Coursera offers and scout those discounts to begin your online learning journey.

My fascination with personal entrepreneurship took over. I had now fully abandoned the destiny college had prescribed to me, which was to spend the rest of my life wearing a tuxedo and watching a guy wave a stick while I played some dead dude’s music from 250 years ago.

My urge to scratch the entrepreneurship itch was becoming unbearable. And finally — after a night of Cabernet and one too many #AskGaryVee videos… I jumped.

Bleeding Out

People in my network were seeing the results I was getting in my day job at the yoga studio. They asked for my help… but I was bound contractually to not work with any other small business owners in the area.

(This is a tricky circumstance for a lot of you that stunts your personal entrepreneurship potential: Not being able to moonlight or have a side hustle while at your job.

Negotiate that out if you can; the soil is very fertile for employee bargaining these days.)

So I had to jump first and develop my proof of concept while I was swimming. This seemed… really not ideal, but I had a year of runway in savings.

Slowly but surely… the ground beneath me began to crumble.

As it turns out, I had huge blind spots when it came to working for myself. The biggest one was sales. Being shy and introverted — normally a strength on the internet — was devolving into an Achilles heel.

The bleed-out was fast, ruthless, and — most demoralizing of all — quiet.

No big explosions, no Housewives-style fights. Just the sound of crickets.

I knew I had a blind spot around owning a business and kept trying to buy my way out of it:

  • A signature course here.
  • A live event there.
  • A low-cost monthly membership? Don’t mind if I do.

I pulled from savings nearly every month to make ends meet. But it wasn’t enough.

My runway evaporated with incredible speed.


I was having flashbacks to my childhood, to growing up with nothing, to feeling intensely alone and isolated.

When you crawl out of shit, and then find yourself right back in it, a body sensation takes over that is difficult to describe.

I was stuck — again.

Exploring Poly(work)

This is the part of the story I don’t share very often, but I feel like career decisions like these don’t get enough visibility on the internet these days. After a year in the world of online entrepreneurship… I decided to go back to having a full-time job.

Technically, I was financially forced to. In 2017 I crawled back to an interim gig as a marketing manager to rebuild, and also to lick my wounds. But I kept my dream going, and I maintained clients on the side.

This time was different: I didn’t have a noncompete clause in my contract, which opened up a whole world of opportunity to test and iterate my offers.

I wrote more.

I worked with more clients, and expanded into different industries beyond brick-and-mortar fitness.

And eventually, an agency that was my client asked me to go full-time with them.

Over the next two years, I worked with and directly spoke to hundreds of entrepreneurs who were quite far along in their journey. The agency’s client avatars at the time were coaches and consultants making $250K-$2.5M/year in revenue.

I learned there were many, many different ways to get to these numbers — and with each approach, new levels always led to new devils.

Embracing polywork — formerly/still called side hustling/moonlighting/a portfolio career — whipped up incredible opportunities. If you have your pick, I think this is the most secure way to pursue the employee-to-entrepreneur transition.

I also felt validated: My skill set didn’t just apply to fitness business, it actually applied to lots of business owners and entrepreneurs in many different fields.

Things were going okay. I noticed that I felt the entrepreneurship itch again.

Then… another plot twist.

In 2020, A Force Majeure Appeared

Its name was COVID-19, it was a huge bitch, and like millions of other people, it made my employment wildly unstable.

The pandemic was rearing its ugly head, and most agencies were not weathering the revenue drop very well.

It was time to jump once more.

I was having flashbacks to the last time I did this and how much I fucked things up.

But I had many more advantages in my corner this time around:

  • I knew what steps to take in what order to get offers off the ground quickly and bring in cash.
  • I knew to balance prioritizing new clients while also serving existing clients. A good reputation outruns even the sexiest marketing in the long run.
  • I knew how to drum up relationships and flex my rolodex; I had been racking up brownie points for years, and it was time to cash ’em in.

But most importantly, I had memorized the feeling of repetition — and had built up its musculature over time. From that perspective… music gave me everything.

It was time to put my nose to the grindstone and be consistent in areas that would move the needle.

  • Articles.
  • Headlines.
  • Sales outreach.
  • Making new internet friends and then adding value to them.

My music school training — something I had always thought of as a career failure — was resurfacing as a fully-evolved Charizard, ready to fire-spin every obstacle in its path.

Source: Giphy

Jokes aside… the ability to be consistent became one of my most important and powerful weapons in the entrepreneurial trenches.

Things began to click.

Why I Became An Entrepreneur

Don’t get me wrong; this shit is hard. There are days when it’s really hard.

But looking back, what I wanted as a kid was freedom and autonomy to be my fullest, realest self. Entrepreneurship gives that to us in ways our younger selves would never have imagined.

And I’m a sucker for the hustle. I’d rather be climbing over obstacles Warrior Dash-style than sitting in a cubicle, having my time mercilessly managed, and watching my already-fleeting youth slip through my fingers.

I am an entrepreneur. And if you are one as well, or want to be one someday… here are some lessons learned along the way:

  • Keep learning and keep practicing. Knowledge and skill will be the thing that takes you in the direction of realizing your dreams.
  • Be careful if you’re smart. If you’re smart and/or educated, you’ll be really good at talking yourself out of stuff. Think like a bodybuilder or an engineer and follow your plan as designed.
  • Accept that you have blind spots. You’re gonna have to invest in courses, programs, and coaches. Trust me, the investment pales in comparison to how expensive blind spots can be.
  • Pressure turns rocks into diamonds. A little urgency to make things happen sooner rather than later would probably be good for you.

Final Thoughts

There’s a quote by C. Joybell C. I really enjoy (emphasis mine):

“​​We can’t be afraid of change. You may feel very secure in the pond that you are in, but if you never venture out of it, you will never know that there is such a thing as an ocean, a sea. Holding onto something that is good for you now, may be the very reason why you don’t have something better.― C. JoyBell C.

Challenge yourself to step into the unknown. Be willing to learn new things — regardless of how far along you are in your career.

When the time is right for you to make your leap, the things you’ve learned and experiences you’ve had will create the wings you need to truly take flight. ◆

Thanks for reading. 🙏🏼

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