What We Leave Behind

It was roughly a year ago this week that I fled California in pursuit of greener economic pastures. I came to Texas an economic refugee; despite running a successful business in California for a number of years I watched my profit steadily fall beneath the relentless tide of cost of living inflation, taxes, and so on.

It’s a move I’d been wanting to make for years but timing and circumstance stayed my hand until April 2017. And it was a difficult choice too - I was leaving behind my family in California, who are a short drive away from where I lived in Los Angeles. And I really loved LA itself - it’s a great city where you could do something different every day and not see a tenth of it by the time you die.

I made the choice to leave, happily, because it’s backed by intention: I’m not going to be forced to choose between being able to financially support a family and growing my business aggressively. In California, this is a binary choice for the vast majority of people. Full stop. In Texas, it’s not - I can comfortably do both. And I will do both.

What’s surprised me during the months leading up to my choice and the year or so thereafter is the reaction I get from fellow millennials about the decision to leave. They’d understand if I was forced to move by an employer or some other circumstance, but voluntarily choosing to leave God’s chosen land in glorious California?!?! What about being far away from my family?! What about not being in the tech scene in Santa Monica or the Bay Area?! What about the great Mexican food I’m leaving behind?!?

First, let me state the following unequivocally: Mexican food in Los Angeles and San Francisco is dogshit garbage and anyone who disagrees with that should unsubscribe. San Diego does it better than anyone else in California, period. Second: Tex-Mex is vastly under-appreciated and better than most of what you can get in CA.

Now with that out of the way, let’s address the prevailing millennial mindset when it comes to life, risk, and reward.

Risk Aversion

There have been scores of articles written about the all-around worthlessness of my generation, a time-honored rite-of-passage tradition that every generation has had to endure.

The largest and most accurate criticism is that we’re fundamentally risk-averse. And you can see it in several areas of life:


  1. “Millennials aren’t just risk averse, they are the most risk averse generation since The Great Depression.” - Investopedia
  2. “More than half of people between the age of 21 and 36 have their savings parked in cash, according to a new study by the Brookings Institution, reflecting extreme risk-aversion by the so-called millennial generation.”- Wall Street Journal


  1. “Millennials Are Having Less Sex Than Other Gens, But Experts Say It’s (Probably) Fine” - Forbes
  2. “This Is Why Millennials Find Making Phone Calls So Terrifying” - Elite Daily


  1. “Millennials Are to Blame for America’s Vacation Problem” - Travel and Leisure
  2. “Millennials Are Actually Workaholics, According to Research” - Harvard Business Review

Let me lay this just so I can call out any angry Internet commenters on not reading the article later: I think most of the concerns about the millennial generation are overblown. Also, worth remembering that these trends are for populations, not individuals.

However, I concur with the above articles that the millennial mindset on the whole is vastly different when it comes to risk-taking and adventurousness than previous generations.

We’re afraid to pick up the phone and call a person we’re dating, let alone pack up our belongings and move to a new city sight unseen or demand a raise from the boss. Why?

Having graduated from college in 2008 it’s easy to understand why we’d be more cautious: our economic opportunities blew up right in front of us and in many cases delayed our ability to enter the workforce, buy homes, get credit, and start our adult lives.

That’s one explanation, but in isolation it’s insufficient. Our grandparents, The Greatest Generation, were dealt a far worse hand economically and had World War II to look forward to afterwards. I wouldn’t call them “risk averse” in the slightest.

No, what’s at the core of millennial risk aversion is unfamiliarity with hardship, status consciousness, and frankly our diminished ability or desire to form the types of interpersonal relationships we depend on to pull through under difficult circumstances.

Our grandparents are the children of yeomen farmers, assembly line workers, soldiers, and other professions that are becoming increasingly scarce or have transformed entirely. But what all of those professions had was intimate and recurring instances of hardship. Farms had famines. Factories closed. Wars were waged. Hardship was a familiar and inevitable part of their lived experiences.

We were raised in a comparatively safer, prosperous, and overall more stable world than ones previous generations have grown up in. Hardship is a much rarer and infrequent experience on average for most (but not all) families. And that’s a great thing. What many of us have lost along the way is the ability to make our own mistakes, deal with them, and live without fear of making more of them.

The oft-maligned “participation award” culture we were raised in, at least in the United States, contributes to the problem too. Learning to get back up after getting knocked down is essential to overcoming hardship and being comfortable with taking on existential risks. It’s difficult to learn that when we’re rewarded simply for showing up. How can a person ever develop grit if they don’t start before adulthood?

That prosperity I mentioned in the previous paragraph is the final pillar of our risk aversion. In the age of perpetual connectivity via smart phones and social media, keeping up with the Joneses is a game we now play on global scale. It’s an ongoing game of clipping highlight reels from our personal lives and creating a more successful projection of ourselves. Vacations, new cars, new houses, high end experiences, and speaking as a 30-something elder millennial… oh dear God, the over, over-the-top engagement photos and weddings. Was it really necessary to have two different chocolate fountains flanking either side of the ice sculptures, Tiffany?

Even if you’re not particularly materialistic or status-conscious it’s difficult to be surrounded by constant, literal “status updates” from your peer group every day and not wonder about whether or not you’re “falling behind” relative to everyone else.

Moreover, as our relationships with others increasingly move from the “real world” to the “phone world” (to borrow a term from Aziz Ansari’s Modern Romance) we’ve under-developed our ability to form meaningful, human relationships. Liking someone’s Facebook status updates and Instagram posts (or if you’re a Twitter user, being outraged at something) isn’t an effective substitute for meeting people in real-life and having actual, lived experiences. The social media arms race is about projection; projecting our success, projecting our happiness, and projecting our intellectual and moral superiority. Through continued, heavier, and more frequent use social media isolates and polarizes us. Screaming our rage through a Facebook feed on one hand and doing our best DJ Khaled impression on Instagram with the other, neither one making us whole. I have to wonder about some of my friends - when was the last time you went on a trip somewhere without posting a story about it on Snapchat or Instagram?

All of these elements, together, form a person who simultaneously yearns to project success and confidence on top of a persona that is deeply wary of existential risks necessary to achieve to success. Someone who cares more about the trappings of success than its realization. Thus, we millennials are a people dreading anything that might expose us for who we really are: cowards and underachievers who hide our inadequacies through embellished, heroic tales of our office martyrdom and perfectly captioned Instagram stories about lavish experiences we purchased on credit at 24.99% APR. Taking on true real risk is as alien an act as voting for a politician who won’t raise your taxes in California.

A significant number of my friends and acquaintances construed my voluntary move from Los Angeles, one of the world’s cultural epicenters, to Houston, TX as odd and undesirable - especially given that I had zero connections to the city. The word “retreat” was used on more than one occasion, and at one point I probably would have said the same. This is where I want to go next.

Group Conformity

Spending 40%-50% of your post-tax income on housing in cool city like New York, Los Angeles, San Francisco, Seattle, or Washington D.C. is the norm for young, millennial professionals who work in knowledge-worker type fields. It can be an extremely rewarding and fun lifestyle, especially if you’re single and childless.

Beneath the surface, many of us stomach the high cost of living in a city like LA because the perception of being from there has intrinsic social capital. It helps craft an image of ourselves as confident and urbane high-earners who are above mere mortal concerns like the cost of living. That’s hardly the truth, but it’s just one more shared delusion of grandeur we all buy into in the age of social media.

Therefore, moving from a “cool” place like Los Angeles to a… less culturally important place like Houston is interpreted as a loss of status by some. Especially leaving voluntarily. In the eyes of the most status-conscious it means you gave up the game and admitted defeat, the most low-status thing you can do. “You couldn’t hack it here with the rest of us morons who pay $45 for brunch, so long the photos of the food look good in a Snapchat story, so you had to go and runaway to Texas.”

It’s difficult to understate just how powerful the pull of “keeping up with the Joneses” is. When I was 24 I had a six-figure job at Microsoft and was light years ahead of my peer group in terms of both earning power and status.

I didn’t think much about that at the time. So at the age of 26, I left Microsoft to found MarkedUp feeling like my process of self-realization was almost complete and I was in total control over it.

But things didn’t work out with MarkedUp. I failed, publicly, and brought down most of my personal savings and my investors’ dollars with it. Oops.

The thing that kept me motivated in the midst of 100 hour work weeks, grinding to save the company from going under, wasn’t so much the thought of losing this great opportunity. It was the fear of looking like a loser; having to lay off loyal employees who had done nothing but bust their ass to save the company, personally calling all of our investors to tell them I’d fucked up, telling vendors we owed money to that we wouldn’t be able to pay them, and worst of all: telling our thousands of users that we were going to have to cut off their service. I did all of those things and, miraculously, didn’t die from it.

However, it’s what happened afterwards that drove this story home for me. At the age of 29 I co-founded Petabridge with what little personal capital I had left. I knew I had an opportunity to build something special around Akka.NET and I wanted to take a chance on that rather than go back to work for the man. We self-funded that company this time around - no outside investors. Money was really scarce for the first couple of years in particular. I made barely enough to cover my rent.

At one point I went an entire year without buying a new pair of pants because I simply couldn’t afford them; all of the pairs of jeans I owned had ripped crotches and numerous coffee stains. It wasn’t until I told my mother about it that she stepped in and helped. I went from thinking I was pretty hot shit at 24 to not being able to buy a pair of Levi’s without help from mom and dad at 30. Welcome to the downsides of taking risk: hitting rock bottom and having to start over.

I felt like a complete and total fraud when I was out with my friends or my girlfriend’s friends. Someone who didn’t deserve a seat at the table. “Damaged goods.”

By this point in time my peer group was light years ahead of me. Getting married, buying homes, going on nice trips, nice cars… Few of these things, individually, mattered to me - but the thought that I couldn’t participate in any of these activities made me question my life choices up to this point. “Did I fuck up when I left Microsoft?” “Should I have taken a stable job after my first company failed?” “Am I cut out to be an entrepreneur?”

I understand why my generation is risk averse because I’ve been to the other side and back again. In an environment where the public projection of success and confidence is more common and important than ever, putting yourself in a situation where you’ll be exposed to real hardship and the distinct possibility of public humiliation is the very essence of millennial dread.

What We Leave Behind

If there’s a second thing I’d ding my generation for, it’d be for letting pervasive cynicism become a core part of our outlook.

For all of my fears, worries, and self-doubt there was an essential truth that I’d completely discounted and overlooked: no one thought any less of me for failing. Most people just admired that I had the balls to try in the first place and be upfront about it when the first business failed. At the time and for a long time afterwards, I couldn’t process that. Instead, I felt like I had lost face and status, branded with an “L” for loser on my forehead.

We assume by default that every one else assumes the worst about us, and that probably isn’t unique to millennials. My failure at launching a business must mean that my friends and family think I’m a failure. But that couldn’t be further from the truth.

We may humor each other by pretending that what we see others post on social media is who they really are, so long as they continue to do the same for us. But we’re not idiots. The 20-something girl posting a blurry Valentine’s Day photo of a bouquet of wilting flowers her boyfriend bought at the last minute off of 1800flowers.com with the “I’m so lucky!!!!” caption isn’t fooling anyone, despite the 400 likes on her Facebook feed. Neither is the 30-something guy posting photos of himself sitting in his company’s corporate booth at the Maverick’s game shoving nachos down his hatch; actual big shots don’t need to remind everyone that they’re a big shot on social media.

In an endless news feed of grandstanding bullshit we truly and deeply value authenticity when we see it. Seeing someone who takes a risk, fails, and get back up again awes and inspires us - because it stands clearly apart from the endless cynical facade of self-promotion and aggrandizement that surrounds us. It’s this authenticity and lived experience that will form relationships with the very people who will help you through the crests and troughs of life and help you emerge victorious, successful, happy, and surrounded with friends.

The truth is, our perception of existential risk is very different from the reality of it. Our peers judge us less harshly than we judge ourselves. And the real parts of the risk, flirting with financial disaster and lost time or opportunities? What about those?

I’ll answer your question with a question of my own: what do you want to leave behind after you’re gone? Children? Knowledge? Achievements in art or science? An organization? A company? Your acts of decency, charity, gratitude, and good nature told fondly by friends and family?

We escape the job we hate; the crushing interest of student loan and credit card debt; the dissatisfying relationship; our grief; loneliness; and the rest of inadequacies of our lives by pursuing something bigger and harder than our next Instagram story.

Risk aversion is fundamentally prioritizing our daily needs over long-term aims. Forgoing legacy for comfort.

Achievement, distinct from “social media achievement,” necessitates risk. Walking away from a “good enough” but not “great” relationship in pursuit of someone better is a risk. Leaving that comfy corporate job with its great benefits to start a company is a risk. Moving to an unfamiliar place with few lifelines is a risk. Letting your children fail and get back up on their own is a risk.

Hardship is an inevitability of risk; you will eventually take a risk that goes sideways. Rather than treat it like a terminating event for your career and life, adopt that attitude that risk taking requires practice in order to be done well. Failure is the greatest teacher and you will emerge stronger and better prepared for the next and bigger risks.

That has certainly been the case in my life. Petabridge is doing great and I’m happy to report that I can afford to buy my own pants, like a big boy, at the ripe old age of 32.

I “retreated” from California to Texas because it’s a stone on the path of my legacy, which I prioritize ahead of being able to surf on the beaches of Malibu or clinking flutes of champagne with other tech CEOs on the rooftop bars of Santa Monica.

My fellow millennials: do the same. Life is too short to live unintentionally. Choose legacy over comfort. It will lead you on a path that may include hardship, but who you’ll become when you emerge on the other side is someone who no longer needs to project success because that’s you actually are both on and beneath the surface.

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I'm the CTO and founder of Petabridge, where I'm making distributed programming for .NET developers easy by working on Akka.NET, Phobos, and more..

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