The Entrepreneur’s First-Second Love

Everyone’s talking about “work-life balance” – but on the heels of my second divorce, I’ve got another kind on the mind: love-love balance.

No mountain high enough, bae.

Borne to long lines of entrepreneurs and historic leaders at least 7 generations deep and (selectively) mute until 11, you could say entrepreneurship was my first language. I would certainly say, it was my first love too.

I still very fondly remember my first business – even though it was nearly 30 years ago.

I handed over my last pennies like a condemned man; eager for his last meal.

For my first grade peers it was just another pop-quiz Tuesday, but for me – it was an entirely other kind of test. One that would not be graded in letters.

If you’ve started a business then you definitely know “the hunger,” and my beginnings were truly no different, except perhaps one telling detail – I was, in the most humbling of senses, hungry. Without a speck of food in the cupboards and a disabled mother to care for, the stark reality of a long-distance independent driver of a dad currently clear across the country and days from returning, made the grumbling unease in my gut all the more pressing.

With my week’s lunch money depleted by one day, I stared down at my dollar and forty cents and wondered quite what I could do. Somehow I already knew – sell what people buy.

So on my way to school, I did what any kid would do – I bought candy bars. Two, to be precise.

In 1990, that $1.25 investment left me with just fifteen cents – enough to get breakfast at my reduced-price rate, but not lunch. I didn’t usually eat breakfast (even though it was, and still is, my absolute favorite menu of food) because I was always given just enough for only lunches. But on that morning, I handed over my last pennies like a condemned man; eager for his last meal.

Biscuits never tasted so good – but it wasn’t long before reality set in, and I reeked of stress sweat.

Who Better to Sell Contraband Discreetly, But a Mute Gifted Student?

My mother’s best friend was well-enough to-do that I was in private school, and by the simple fact that I could already program in BASIC better than I could read, I was in an unspeakably tiny class of students known as the Gifted Program.

But even smart kids love candy. And more importantly, smart kids usually have smart parents – and smart parents, in that time, netted the best salaries without today’s frivolous expenses of endless cell phone upgrades.

I couldn’t be in a better market to build a side-hustle. Even so, their reality could not be further from mine, and besides – just bringing candy to school was a BIG no-no. Selling it, could get me expelled.

“Possible” consequences if I got caught aside, I was from “the wrong side of the tracks” — and it was agonizingly obvious. I didn’t have their shiny Jordan sneakers, or even any shoes by any name. Just plain old canvas hand-me-downs, with, of course, little silver jingle bells attached to the laces at each toe.

My mother couldn’t afford to lose track of me, and I was ever the adventurous kid. But that also meant you really couldn’t miss the weird girl in out-dated handmade dresses jingling down the hall – remember, this jingle was the only sound I made, as the only mute in the entire school.

Terrified? I certainly knew the definition from the dictionary by then, but the thought of selling banned materials to people who totally out-classed me, by miles — and knew it — sure taught me the true meaning of the word.

Over the last bites of my last biscuit, sweating like a Finn too-long in sauna heaven, I nevertheless seriously contemplated how I would do this thing.

Not a single solitary thing mattered but my duty to my family. Not my pride, not the threat to my school career, and not even my lacking ability for language would stop me. The only thing I cared to consider as the big hand ticked down, was how.

And I still didn’t know, when that first bell rang.

But in the first minutes of class, I got a chance to flash the goods to a classmate while holding up one finger to indicate the price – and an entrepreneur was born.

You Never Do Forget Your First

Nearly 30 years later, the candle for entrepreneurship still burns bright. The thrill of the first sale – never changes. The adrenaline from overcoming the odds and improving myself by facing ever-greater challenges head-on – still my addiction. The satisfaction and fulfillment from seeing the customer’s eyes shine with true joy for your solution – still, why I do it today.

“They say” some people are just born for it, or maybe they’re raised for it. I like to believe it’s more a chicken-and-egg conundrum: anyone can be an entrepreneur, but not everyone gets the experience to become successful.

Which brings me to my crux: so too, can anyone be married, but not everyone has the experience to make it a successful marriage. I have this theory — maybe everything good for personal relationships is good for business relationships, too.

Which is to say, maybe personal romances falter for the same primary reason business relationships do: lack of experience having them. And maybe, in both cases, more experience with more reflection is the only good answer.

So here again, even though it was 18 years ago – I still remember my first marriage, like it was yesterday.

He was the furthest from an entrepreneur anyone could be; his parents were career corporates, his parents-parents of the same cut, and he himself was going to a technical community college in hopes of landing a  — surprise, surprise — corporate job, in IT.

I could never please him, and he could never understand how I could tirelessly spend all day and night programming something other than a game. We seemed to be a good fit for both being geeks, but our reasons and lust for life were gratingly gapped.

He just wanted a life of clocking out at 5pm and besting every level of the latest game until the wee hours of pre-dawn. I wanted oh so much more. I wanted to BE more, to up-level in the real world. I wanted, like most any young entrepreneur in it for the right reasons, to change the world.

Entrepreneurship is Not Simply Something an Entrepreneur Does

This mis-alignment of principals was at the core of every argument. Apart from how he actively did me wrong by acting out for his desire to keep me — I felt hopelessly chained from my true first love of entrepreneurship, and lost my very soul. I felt unlovable, unworthy even, because I couldn’t even love myself and what I was to become, if I stayed with him.

The utter depression from that, is very, very real.

So deep, in fact, I lost my love for entrepreneurship entirely. I “gave it up” and got a J-O-B. Several, in fact. My résumé read like a serial offender’s wrap sheet, with something like a dozen times in and out of various W-4 prisons.

Little did I realize, entering my second marriage 9 years ago, entrepreneurship is not simply something an entrepreneur does.

It is every bit who an entrepreneur is – it is the entrepreneur’s way of life.

And so, the second marriage ended very much like the first, rife with depression, self-doubt, and in this case, a betrayal.

But it differed in one key point: I now knew, without a doubt, what I am.

I could finally look back on my storied life and connect the dots. At last, I saw the road ahead so very clearly – and it was because I could look back and see that every step led me to here; precisely where I belong.

Maybe it was the 4-year journey of soul-searching after being cheated on, maybe it was just the natural process of banging your head up against a familiar brick wall – either way, I’m beyond grateful to know for absolutely certain that my love is not fit for someone who can’t respect, my first love:

The Betterment of Humanity, Beginning With Myself

“Yesterday I was clever, so I wanted to change the world. Today I am wise, so I am changing myself.”


“They say” be the change you want to see in the world. I say, Be The Gift, and Redefine GDP – we have a Greater Divine Purpose, and a job is merely a convenient place to hide from our work.

My work, is everywhere that message needs to be heard: the work-place itself.

And if not for my years denying myself my truth, maybe I wouldn’t know my work so keenly. I can only be grateful for my schooling at Hard Knocks. Because not only do I have those lessons to share, I’ve also found what is arguably the first man I’ve ever truly loved.

How can I be so sure?

It’s the little things.

In 9 years of marriage, in 34 years of life, I never once made the bed except when I begrudgingly changed the sheets – if even that. This morning — like so many mornings these last few months — before I sat down to write and do my work, I noticed the bed was un-made – and fixed it. Happily. Genuinely, truly, glowing with joy, pride… and love.

For him – my entrepreneurial other half.

About Patricia Mayo

"You enable my best as I enable yours." Patricia Mayo is The Un-Editor; an award-winning marketer and 7th-generation entrepreneur who wrote the first book on managing remote teams back in 2007, and puts the dictionary in her home library's Fiction section. Mother, ubergeek, and modern renaissance woman who believes humanity can be free once information is too. Get in touch: morethansum at gmail dot com