On procrastination
I fear the empty page, the digital void where my ideas are unborn. Four years since I wrote unfinished lines about my dramatic decision to slam the door on a job and a life that had brought me untold joy and some riches. Enter the dull flow of routine days in London, life streaming like water under the bridges of the languid river Thames.
The past is written in indelible letters but am I capable of comprehending the arc of my story without being blinded by the veil of my own revisionist thoughts and feelings? Can an objective truth be discerned when I watch the reel of my existence? Am I capable of detaching myself from misleading narratives rooted in my emotions?
For months I wanted to write this post but procrastinated, always finding feeble excuses that I knew wouldn’t stand to my own scrutiny. There was always another chore that couldn’t be postponed, lest cataclysmic events would occur. A pernicious game of delayed gratification where mind-numbing activities suffocate any spark of creative impulse.
Am I the only one feeling that obscure yet overwhelming presence? Lurking in the back of my mind, judging my every choice against my own towering standard of duty? Am I alone in hearing that sententious voice whispering guilt-inducing words when I fail to measure up against that unrealistic standard? How convenient is it then to flee into the calming embrace of hollow activities that fritter away the essence of life.
Setting the scene
But I digress, my apologies! Let me transport you to Medellin, Colombia, during the spring of 2021 as boxes and suitcases were piling up in the entrance of our newly built house, ready to be shipped to distant Albion. I sat in my bed, documenting a decision that had become irreversible: taking a job at Checkout.com in London, uprooting my wife and son from the soil of the Andes, jumping into the unknown as I was just about to turn 50.
Madness? Hubris? Post-pandemic dementia? An under-appreciated benefit of blogging - or keeping a journal - is the ability to time-travel and peek into one’s psyche in years past, trying to understand that “me” that is no more. A post-mortem practiced on one’s own ghost, a forensic exercise meant to yield insights about one’s mindset and decision making process, in the hope of self-improvement.
To my eternal regret, I never finished the post that you are about to read, reborn from the womb of Substack. The “me” from 2021 insisted on peppering every post with a myriad of links and citations, resembling more an academic article than a spontaneous story. There’s scant evidence that my vanishingly small number of followers were expecting such level of rigour. What is clear however, is that my pursuit of factfulness steadily sucked all pleasure out from the creative act of writing. Predictably, I only published a handful of posts since then.
It is said that authors enter an unspoken contract with their readers, a promise to deliver something worth their precious time - an experience, some knowledge even. Your reward, should you persevere through my laborious text, is the beginning of a merciless dissection of one of my life’s most momentous decisions. We will learn together from the mistakes I made and the consequences that befell me and my family.
(Time machine engaged. Traveling to...)
2021
I’m writing this post a few days before my resignation from Twilio is made public. I aim to answer the question why starting a job search while working for one of the most supportive and highly regarded SF Bay Area software companies made sense, from the perspective of a senior engineering leader.
Most of the content on the topic of software engineering careers is geared toward early to mid career professionals. Reading Quora articles or Blind posts, it seems like a mainstream career dream is to join Facebook or Google for the lavish compensation packages and planet-scale engineering problems offered.
While necessary, these two data points aren’t sufficient on their own. At this stage in my life, they must feed into a more complex and nuanced decision making process, which I will attempt to rationalise and explain here.
A job too good to leave
I joined Twilio on October 19th, 2015, when we were still a dashing startup of less than a thousand employees, rewriting the rules of business with a developer-first focus and a mission to fuel the future of communications.
It had taken me 20 years to hone my technical and leadership skills with a singular focus on telecoms. Getting hired by Twilio felt like reaching the summit of Mt. Everest via the demanding Southwest face route. No higher professional achievement existed for me.
To compound this accomplishment, the acquisition of Authy allowed me to work from Colombia, my country of choice, leading a small team of incredibly talented developers. Twilio’s subsequent IPO in 2016 showered unanticipated wealth upon Twilions. All the sudden it felt like life just couldn’t get any better.
Yet in the next few years Authy would be renamed Account Security, I would become the head of engineering for that business unit, while growing our engineering team 3x and supporting a 700x annual revenue expansion - living the type of non-linear success story that is usually explained by a combination of good fortune, hard work and a touch of talent.
With the benefit of 20/20 hindsight, here are some of the reasons why I stayed more than five years at Twilio:
Meaning
Jim Collins in his book Good to Great defined the hedgehog concept for companies which he later adapted to encompass individuals. In a nutshell, you want to work at the intersection of these three circles:
What you are deeply passionate about
What you can be the best in the world at
What drives your economic engine
Recent research from Facebook published by HBR confirmed that finding a meaningful job is essential to remain engaged. Employees don’t leave bad managers, they leave managers and organizations that fail to design meaningful roles.
Helping scale up the engineering practices of the Authy team was deeply meaningful to me. Witnessing how the adoption of disciplined Agile improved product delivery predictability and how better telemetry, dashboards, monitors and rigorous post-mortems drove down our incident frequency - earning the team respect from their peers at HQ and increased business from our customers - was truly satisfying.
Embarking on a quest to make Bogota a global engineering hub for Twilio also fired me up. Why look to Bangalore when you can find in Bogota skilled engineers at a fraction of the cost of San Francisco - in a timezone that makes it easy to collaborate closely without imposing silly working hours to remote staff? I’m proud to report that today Twilio employs 136 men and women from a richly diverse set of backgrounds in Colombia.
Growing
In my early days at Twilio I suffered from acute impostor syndrom. I was working with the world’s best developers and leaders - how could I add any value? I realized how woefully incomplete my knowledge was, to some extent as a result of years spent learning hapahazardly whatever was of immediate benefit to me - instead of adopting a long term professional development plan.
Consider, then, the sum total of our accumulated knowledge as constituting an island, which I call the “Island of Knowledge.” … A vast ocean surrounds the Island of Knowledge, the unexplored ocean of the unknown, hiding countless tantalizing mysteries. — The Island of Knowledge: The Limits of Science and the Search for Meaning, Marcelo Gleiser.
Fortunately, I was working with great mentors, like David Cuadrado, Pat Malatack, Marc Boroditsky and later Bharat Guruprakash. They were willing to help me grow my tiny island, challenging me to constantly improve, to push out those shores of ignorance.
I stopped feeling like a victim of my own incompetence and (re-)discovered a passion for lifelong learning. As Seth Godin puts it in The Dip, I embraced the long slow slog between starting and mastery.
Successful people don’t just ride out the Dip. They don’t just buckle down and survive it. No, they lean into the Dip. They push harder, changing the rules as they go. — The Dip, Seth Godin.
I learned to become a manager of managers, solving bigger and more ambiguous problems with less guidance, navigating through conflicting priorities and agendas. My professional growth pace was perfectly aligned with that of Account Security.
For your tenure, your hope is you keep learning and getting challenged by a growth rate that’s slightly faster than your own, pulling you forward. That might last a few years or could be much longer. — The Skip, Nikhyl Singhal
To measure my progress, I interview once a year for a role of equal or higher seniority and scope. I started this habit while at Livevox several years ago. An interview with the CTO of OpenTable had revealed how astonishingly little I knew about Agile. I promptly enrolled - on my own dime - into a Scrum training course to get my CSM - and later CSD - certifications, both of which proved invaluable when I started at Twilio. The purpose of those interviews is to discover what employers want and understand my competitive advantages - and gaps.
Even if your company culture emphasizes constant feedback and radical candor, you may focus on learning skills that are relevant to the narrow niche of your business and miss on new and important industry trends. Keep your head outside of your job bubble!
Living
Back in 2017, Silicon Valley VC Keith Rabois’ response to a tweet about work life balance sparked a debate on whether working smarter was enough to achieve success in tech - or working harder was indispensable. In a playing field full of ultra-smart and ultra-talented individuals, the ability to work hard is a critical success factor under your control. I firmly believe that you need grit in order to become the best in the world in your unique market niche.
Our potential is one thing. What we do with it is quite another. — Grit: The Power of Passion and Perseverance, Angela Duckworth.
Such work intensity will affect your personal life, forcing you to quit other pursuits to focus on what is essential. You will need the right set of conditions to even make it possible in the first place. Discipline will be crucial to get enough sleep, eat healthy and exercise regularly. Don’t neglect to nurture your soul as well, through whatever hobby that brings you joy.
When I joined Twilio I was training for the Ultrafjord race in Patagonia. I soon realized that 50% travel from Medellin to Bogota made it impossible to achieve my training goals. I settled into a pace of one week of 60+ hours office work from Bogota alternating with a 40+ hours work-week from home in Medellin. Call me crazy, but I actually enjoyed trying out a new hotel around Parque de la 93 every other week.
No longer was I experiencing work life balance - it became a work life blend. The IPO gave me much needed resources to build a house near my son’s school and invest in my wife’s ceramic workshop. We were fortunate to move into our new house one month before the pandemic lockdown started in Colombia, giving me an ideal work from home environment. My life and work values were perfectly aligned.
The key concept here is that life is non-linear, i.e. it doesn’t follow well defined stages. Twilio entered my life just when I felt the urge to accelerate my professional growth while spreading deeper roots in Colombia, offering new opportunities to my family. It was perfect timing.
Leaving that job now
Over a multi-year period even the most perfect life/work fit is bound to evolve and career choices that made perfect sense originally may look questionable.
Always remember that in a capitalist society a free worker sells his or her labour for an indeterminate time (from a few years to the entire career of the worker) in return for a money-wage or salary. There’s no notion that
you must unconditionally love your work, or that
your employer must always care for your success and happiness.
To steal a line from the Netflix culture, your company is a team, not a family:
A dream team is about pushing yourself to be the best teammate you can be, caring intensely about your teammates, and knowing that you may not be on the team forever.
(Reversing the direction of time travel, heading back to the present days…)
2025
Sure, working for Twilio was insanely cool, unreal and quintessentially perfect, the epitome of a Silicon Valley company that moves fast on its hockey stick trajectory toward startup stardom. I’m eternally grateful for the lifetime opportunity to freeze my butt together with hundreds of fellow Twilions in the bowels of an aircraft carrier moored in Oakland, shivering at every gust of wind until being handed a Patagonia vest to celebrate our 2016 kickoff. Death by pneumonia averted, I couldn’t wait to see what our customers would be building with our APIs.
However, my promise to you was to share some lessons I learned after abandoning the Twilio mothership 4 years ago. Wisdom acquired at great cost once I had crossed the pond to land on Old Blighty’s misty shores.
Any decision of such magnitude is necessarily multifaceted, comprising multiple bets with varying odds and time horizons. Some outcomes remain uncertain - the game is far from over yet.
Like any self-respecting soap opera, this life reboot in London will unfold in several acts. To whet your appetite, I will begin with the most indecent topics of all, money.
Equity jackpot
I have particularly fond memories of meals with my colleagues at Twilio in San Francisco and Bogota. During one of those dinners, a friend shared how grateful he was to have won the jackpot in the lottery of life: we had joined a startup that had gone public and seen its stock price skyrocket making many of us modestly wealthy.
Not all tech companies are as successful as Twilio post-IPO. They often see their stock price crash sooner or later after the lock-up period expires. Thus I decided to adopt a regret minimisation strategy and sell my vested options on a regular basis instead of trying to time the market. Others were HODL-ing. They saw their dreams fade like the mirage of an oasis in the Gobi desert during the 2022 stock market correction that affected countless cloud companies.
In April 2021 my pile of unvested Twilio RSUs amounted to quite a lot of money, as long as the stock price hovered around the stratospheric $400 mark. Paper money of course. Worthless, for sure! Yet this was a significant sum for someone whose first paycheque as a software engineer in 1995 was less than $2000.
Ceteris paribus, walking away from that mountain of RSUs beckoning me was an epic mistake that will haunt me for the rest of my life. Why did I do this?
I had become overconfident. I believed I could create an assembly line churning out profitable liquidity events. Yesterday LiveVox (SPAC), today Twilio (IPO), tomorrow Checkout.com - surely an IPO in waiting? I had the Midas touch, I was beating VCs at their own game, raking in money with no prior investment: join, grow, exit. Rinse and repeat.
Enduring a few more quarters at Twilio, like an oak tree withstanding a storm of ill-advised org changes as well as professional stagnation, would have done wonders to calm my financial anxiety. Oh, do not think for a second that having some money in the bank automatically brought zen-like calm to my heart. To the contrary! I became utterly frightened to lose it all and go back to square one.
My family has a history of attracting financial calamity. My grandparents’ home in Budapest was confiscated by the Soviet high command in 1944. They lost everything. Soon after my graduation, my parents and I were evicted from our house in Geneva. We lost everything - and ended up in a cockroach infested flat inside one of the world’s largest apartment complex. The view of the Jura mountains was magnificent though.
This is why I admire true risk takers, those who aren’t afraid to gamble their last $5k in Vegas to save their company from bankruptcy. I could never do that. My fear of poverty has shaped me.
The morale of this story can be summarised as follows:
Wealth generating events are exceedingly rare and must be exploited relentlessly.
Mental health be damned, financial freedom is worth a modicum of stress!
Always remain humble and eager to learn - this much can be controlled.
Life is about more than money
Relocating to London wasn’t a transcendental failure, as I shall explain in the next instalment of this chronicle - hopefully in less than 4 years from today, assuming I have been cured of my tendency to procrastinate.