Coming Out of the Closet as Artsy

A transformative tale

Ever have the haunting feeling that you’re living someone else’s life?

Like you’ve drifted so far from your true nature that it feels like you’ve slipped into a parallel universe? And in this alternative universe, the real you can’t stand the you in this reality? 

Just me?  

Well then, I recommend trying that out some time. And then I recommend reading this short story of how I fell off my true path. 

And how I found my way back on to it. 

Chapter 1: Slanging Software and Sanity

I was 28 years old and I was officially in my dark ages. 

I distinctly remember waking up in the night, cold-sweat, and confused as to who I was. 

Not in an ‘I don’t know my name and birthday’ type of way, but in more of a ‘my sense-of-self went walking in the woods and it can’t seem to find its way home’ sort of situation.

Without consciously giving my consent, I had become fully immersed in a sea of sales-bro douchiness and debauchery.

It must have something to do with the non-stop stress of hitting a software sales quota. Or maybe it’s the constant trying to convince people, who by default distrust you, to trust you. These pressures seem to compress all sorts of different personality types into a singular dysfunctional identity. 

Did you (or a loved one) recently start a career in software sales?

Well then, allow me to illuminate the typical character traits so that you might see the signs quicker than I did and avoid “I-don’t-know-who-the-fuck-I-am-Land”.  

First off, you’re going to want to get wildly addicted to nicotine. For me, it was those little tasty tobacco pouches called Swedish Snus. But it doesn’t matter the form or flavor you choose. The important thing to remember is to rapidly adopt whatever vices your sales colleagues bring into the office. 

It could be nicotine, it’s probably sports gambling, and it will most definitely be some form of alcoholism. 

Just make sure their toxins are your toxins, otherwise, you might find it to be a toxic work environment. 

Drink heavily Thursday, Friday, Saturday, and most Sundays. Your brain should really only be fully functional for about two-and-a-half days per week. You’ll come to relish that dull glow of refound cognition that hits around 10am Wednesday mornings right before you wash it all away again Thursday night. 

Show up to work with your glasses on Monday morning. Your eyes feel like sandpaper when you blink and you can’t get your contacts in because you haven’t gotten more than 15 minutes of REM sleep all weekend.  

Tell yourself things like “If I can just close this one big deal, it’ll make all the mind-numbing pipeline reviews and cold calls go away.” 

These are signs that you’ve entered sales-bro hell.

Want one final test?

Look in the mirror. What do you see? 

If the answer is something approximating “damn, I’m like literally just 100% pure software sales guy now… no other ingredients, sweeteners, or preservatives…sick”, then you’re probably a few months away from an identity crisis. 

Surely I used to be made up of other ingredients. How did this happen?

Chapter 2: How I Caught the Klaviyo* 

*Footnote: I told my mom I got a job at this software company named Klaviyo. She said “Oh ok - that sounds like a venereal disease.” She wasn’t wrong then and she’s not wrong now. 

One morning you wake up after 7 months of backpacking around Southeast Asia with dirty, smelly feet, and a great tan, and the next morning you wake up with a hangover and 100 unread emails from customers saying the software you sold them doesn’t work. 

Well, maybe not the next morning. Maybe more like a couple of years' worth of mornings. 

My transformation into 100%-software-sales-guy started when I innocently joined Klaviyo, a 20-person software startup out of Boston.

In the beginning, the company was so new that by default each of us early employees had our own mini-startup within the start-up. No systems or playbooks existed so we created them from scratch; like figuring out how to scrape thousands of emails to get outbound sales off the ground, or testing incentives to attract agencies to a partner program, and experimenting with different storylines for the product demo.  

But then the playbooks got built and the company scaled. And if your skills weren’t growing at the same breakneck pace as the company, you got slotted into one of the cogs in that giant wheel that you helped create. 

—

Not many people will ever have the joy or concern of working at an actual high-growth start-up. The year I started, Klaviyo was doing about $4 million in ARR (Annual Recurring Revenue). The next year we quadrupled to $16 million. Then to $50 million. Then $100M. 25x growth in 48 months.

It's nearly impossible to acquire the professional skills needed to maintain a relative stature within the power pyramid of a company like this because the pyramid is growing so goddamn fast.

So you’d be working at a $20 million company and then 2 quarters later you’d be working at a $40 million company, but you’re only 6 months older. Unless you’re a one-year-old, this simply isn’t enough time to double your cognitive development.

As Klaviyo grew at this intense rate, my relative power within the company shrank and my creative free will dissipated along with it. 

In the beginning, Klaviyo felt like a big empty canvas. All of us early employees were given a brush and encouraged to start painting. That part was fun as heck.

But a few years later, I'd painted myself into a corner, or my brush had been taken away, or maybe both.

Now that it was a maturing 300-person company, creative freedoms were narrowed as job descriptions got tighter. Bureaucracy grew, office politics were introduced, and mandatory team meetings became abundant.

Those early, exciting, chaotic days faded into orderly, efficient, (lucrative) monotony.

—

Stale as it was, I had successfully navigated my way up the sales department’s economic hierarchy. The money was great. But it was nightmarishly repetitive. 

This repetition seemed to carve a single reward circuit down the center of my brain. And as that circuit deepened, it sucked in all other motivations and qualities of my character.

Engage new lead > Close account > Get reward > Repeat. High-volume software sales and medium-volume hookups.

Transactional and heartless.

—

Now you might be thinking, “OK… soo you were in your twenties, getting paid and getting laid, what’s the issue exactly?” 

To be fair, both of those things I enjoyed thoroughly.

And that’s why it was so confusing that I felt terrible. 

To the outside world, my parents, and the Greater Boston area, I was right as rain.

But something inside me felt broken and wrong. And I couldn’t sort out the source of my discomfort.

—

My younger brother said something during that time of my life that still sticks with me. He said, with a smile, “Remember when we used to be silly together?”

As I digested his question, it flushed me with stinging sadness. His questions had forced me to realize that I’d lost an essential part of myself. 

Instead of responding to his question, I sort of laughed and pretended I didn’t really know what he meant. 

But I did know what he meant, and I knew I’d become a stranger in my own life. 

I wanted to get back to my original form. I wanted to feel that calmness that only comes with knowing you’re not betraying yourself. 

Chapter 3: The Light at the End of the Sales Funnel

Strange enough, exhausted after slanging software all day, I would get home, flop down onto the couch, and listen to Jordan Peterson lectures (Maps of Meaning and Psychology of the Bible). 

It didn’t really make any sense. I mean technically speaking I was this soulless sales-guy-kinda-womanizer-thing. Why was I listening to philosophical lectures in my free time? Huh? What?

His lectures pointed out myths from vastly different cultures that all share the same structural elements. It’s not a coincidence. It’s a reflection of mankind's deepest psychological truths. The evidence is that every culture across millennia has produced stories with similar traits. Our traits.

It sucked me in. 

Peterson then interprets these myths and stories through his professional psychological lens, simplifying the complex circuitries that make us tick. 

It was like the fuzzy, dusty inclinations I had about what drives human behavior were being rapidly crystallized into shiny beacons of hope.

—

Curious to learn what forces were driving my behaviors, I took Peterson’s Big 5 Personality Assessment. 

It was from this test that I started to understand why I felt like I was living someone else’s life, and what I needed to do to get back on track.

It turns out that I’m high in Openness. This is the personality trait most correlated with creativity. 

“Openness is a measure of interest in novelty, art, literature, abstract thinking, philosophy as well as sensitivity to aesthetic emotions and beauty” - Understandmyself.com

My initial reaction was to reject this diagnosis. I’m not artsy. This can’t be right.

I was raised to make a good living and be able to pay my own way. To not be a drag on society. 

You know who doesn’t, generally speaking, make a good living? Artists. So no, I reject your diagnosis.  

Sure, I might wear mint-green cargo joggers out to a bar while everyone else is a wearing Vineyard Vine vest and khakis. 

But that doesn’t mean I’m artsy. It just means I’m in Boston.

Don’t make me be an artist, Jordan! My Dad’s still alive and I want him to respect me!

I thought: if I admit to myself that I have a strong tendency to pursue creativity, then I’d have to quit yuppie paradise and go live out on a ledge somewhere. I’d have to eat wild wheat grass, and smell bad, and be really poor. 

So instead I just said, “Artsy?! That ain’t me, baby!” and went on stuffing Snus in my gums and giving the same mind-numbing software demo that I’d given every day, five times a day, for the last four years. 

But the laws of nature always find a way of restoring balance, don’t they? 

Chapter 4: Forceful Realignment

Peterson says that creative people are “cursed with the necessity of putting a foot out into the unknown and making sense of it… [Therefore] the worst thing a creative person can do is to not be creative because they just die.” 

I was getting ready to give my 5,000th software demo accompanied by my 5,000th Snus when my nightmarishly anti-creative work life came to a screeching halt.

I jumped on Zoom for an 8am meeting. But instead of seeing a prospective customer, all I heard was my manager’s voice.

“Patrick, this just isn’t working out.” 

I said, “If you’re firing me right now, you have to turn on your Zoom camera, c’mon man!”

He turned on his camera. Damn! Thought I had ‘em… 

So I got fired. 

The official reason was for my “complete lack of respect for sales management” - that part was certainly true, but it wasn’t the real reason. 

The reality was they couldn’t have their top sales rep moping around the office looking like he had a shotgun in his mouth all night. Especially when they were a 300-person company trying to become a 3,000-person company. I get that now. 

It was a blessing. I’d been miserable for over a year. Thank God my unconscious mind was able to set me free from the shackles of my golden handcuffs by making me skip all of those pointless internal meetings.

Still, it was an unpleasant surprise. At the time, I was the top-performing sales rep across the entire company. I guess I thought I was untouchable and I guess I was trying to find out just how long of a leash I really had. 

It turns out my leash was long enough to accommodate me coming in at 10am every day but a bit short of skipping 1-on-1s with your director and making your manager cry.

I got fired because my attitude was shit. My attitude was shit because I was miserable and bored and I was miserable and bored because I was no longer stepping out into the unknown and creating.

It was ultimately a good thing, but it tore a hole in my confidence. 

Even so, maybe this violent awakening was the only way to align my identity with my true nature. 

Chapter 5: Plotting my downfall

Although my actual death at Klaviyo was quite abrupt, I had been slowly decaying there for years. 

As the company grew from a 20-person garden snake to a 300-person boa constrictor, it slowly suffocated any sort of creative freewill I had when I joined the operation.

It’s apparent to me now that as the company grew in size and my outlets for creativity at work dissipated, my creation of chaos outside of work concentrated.

One way or another, I seek chaos. One way or another I seek to create.

If I’m not intentionally trying to create something good, I unintentionally create something bad. 

Destructive chaos is like creativity with the venom suit on. It has similar qualities; it’s unknown, and unpredictable but instead of it holding all the potential it holds absolutely none.

How many beers can you drink and still stand up straight? How brain-dead can you be at work and still be productive? Let’s see if you can take shots all night, smoke weed, and still maintain enough composure to take a girl home.

I sought unhealthy chaos in my social life as healthy chaos in my work life plummeted. And it plots coherently with the growth and size of Klaviyo. 

Here, I have the graph to prove it:

Chapter 6: Committing to Creativity

Coincidently, or perhaps not, I got fired on the first day of the pandemic. 

During this sales-bro era, my social life largely consisted of going to bars. And of course, all drinking establishments also got fired on the first day of the pandemic. 

So I lost my twisted-up work life and social life all on the same day.

I started seeking chaos in my work by creating. Attempting to build products and businesses, building little silly things at home like a bookshelf that pulls out into a desk, and writing articles under my personal brand Patty Never. 

With the rise of my creative pursuits came the slowing of chaotic socializing. I stopped getting brown-out drunk every weekend. I quit nicotine. I even sustained a healthy intimate relationship for almost 2 years. It didn’t work out. But it smashed my 2-day record. 

I’m finally getting my chaos and my order from the right places. My inverted yin-yang symbol has righted itself. 

I’m now building FeedbackFreak.com so I can be around other creative people. I want to see if the right blend of encouragement and criticism can help curious people create more frequently and more spectacularly.

It’s in the doing that my restless mind finds tread for its ever-spinning wheels. It’s the creative pursuit that returns me energy, momentum, and joy. 

Outcomes are out of my jurisdiction so my focus is on the pure act of creating. Because if I don’t create, I’ll just die.

The end.

---

I wanted to say thank you to a few people who helped me with this thing:

Miche Priest

for encouraging me to add more “personal” and take the reader to my epiphany so that it had more weight through context.

Jeremy Scharf

for numerous rounds of edits and comments. You allowed the story to come forth with your excellent organizational and story-structure skills. Your attention unstuck me many times so thank you. You’re an outstanding Feedback Freak!

kora kwok 🌊

for your honest critiques of the earlier versions of this. Those helped me find my voice and stopped me from forcing comedy in places where it wasn’t.