The Entrepreneurial Bug

"Were there none who were discontented with what they have, the world would never reach anything better." Florence Nightingale, Founder of Nursing


On my first hour of return to Toronto I turned on the television to learn from the newswoman that on this day, October 1st 2008, hell was going to freeze over: The US Housing Crisis was unfolding.

I had just untangled my life of personal and professional dissatisfaction by backpacking solo in Europe, spending the first (and last) bit of money I had ever saved up to that point by working at Microsoft. I had blissfully forgotten about the boring stresses of the day to day existence; and now suddenly it was coming back full circle. No income. No job market. One month of financial runway left.

After a hurried and futile month of remote job search, I bought a one way ticket back to Seattle in November; back where my personal belongings were swept to a corner of the shared apartment I had left behind, by a woman whose only intellectual pleasure in our former three-year relationship was to belittle and mock my ambitions to grow above ordinary contentment. The dead weight of a desktop computer bearing the code for my first failed startup laid there, waking a stressful malice inside that grinned and whispered “the solo delusion is over pal, welcome to everyone’s reality."

In a last bid to keep the dream alive, I contacted every recruiter I knew and roamed every downtown street in Seattle interviewing with tens of startups. They all would love to hire someone with experience, but everyone was stressed out about parting with cash. Two weeks of living in the shadows of our (now her) apartment put an end to the bid for self-actualization. I reconsidered the startup obsession, and by December, nailed a tough interview for a 9-month contract with an amazing group of engineers back at Microsoft. I vacated the ex’s apartment, packed all of my broken dreams, and rented a cheap unfurnished and solitary place by the woods near downtown Redmond.


The role was exciting. Xbox was relaunching worldwide, and Microsoft was moving its most entertaining product lines to its shiniest new buildings, Studios West campus. I had to make sure the scale worked. Just by the caliber of the people around me, my skills doubled within a few months. But something wasn’t quite right: the wooden, cold and empty new apartment, which I refused to furnish, served as a constant reminder that I had abandoned a mission. And when you ignore the guiding light within, that’s when you’re headed for the frost.

I was passively signing up for in-mail grad school brochures while day-dreaming about entrepreneurship in January, when Microsoft announced 15,000 layoffs for the next 18 months. Effective immediately, co-workers were being pulled into private rooms, handed pink slips, and escorted out of the building by security personnel. This was going to be a cold Winter to remember.

The beautiful new office was thinning out by mid-March 2009, starting to resemble my cold unfurnished apartment. My mission-critical contract had another five months to expire. Another five months to carry water, bucket by bucket, while watching fellow bucket-carrying Type 1 co-workers being let go, one by one, from the village. At home I was bored, and at work I was stressed. The ropes of dissatisfaction were tangling themselves around the neck of my dreams once again.

I decorated my unlit fireplace with the 100th emptied bottle of wine consumed in the presence of that malice within: “This is real life buddy! If you don’t turn off this unreasonable ambition, you’re going to have to be alone and miserable. Nobody likes you. And you’re wrong. WRONG. I’m sorry that we’re trapped together in this ridiculous mockery of a wishful life that we’ve allowed to go on this far, but get over it. I’d rather have friends, fun evenings, relaxing weekends, and do as I’m told at the job. Who are you to have ambitions for the future of the world? How DARE you imagine yourself above the ordinary?”

There was a chilling resonance in the discouraging voice inside my head, as if I had heard it before. And a few of the words rang louder than others, as if they were from a dialog. I began to meet friends, current and former, male and female, searching for those words: “how DARE you imagine yourself above the ordinary?” And by the end of that Winter, I had relived my entire life. As with all searches, your answer is in the very last place you look. Those malicious words within were the very words, from the mouth of my ex, that had sucked the life out of my first startup and sent me on that backpacking journey. Not too many evenings later we met for dinner. I smiled, excited about the meeting, and she smiled, content with the food. We didn’t quarrel anymore. And that was when I told her, “this is the last time we’re ever meeting."

The recession kept on going. But my Winter was over.


I printed a couple of GMAT (graduate school exam) study booklets and brochures, created an online dating profile, and against all reason, in the middle of the worst recession since the Great Depression, started perusing Craigslist for jobs.

In May, I met a girl online who lived a thousand miles away. She was from Mid-West USA moving to small-town California to be a nurse. What would I, an overseas immigrant, and a mid-western girl have in common? I knew the answer the moment I saw the drive in her story: the desire to rise above ordinary contentment. We talked once on the phone. And that was all it took.

In June, on my birthday, while sitting in the empty Redmond office and hiding a browser tab with Craigslist jobs open, I received a strange call from a private number. I picked up the phone: “Hello?” … “Hello Amin, this is Jim Morris. Do you know who I am?” (I didn’t know how to take that. I thought wrong number probably, but he knows my name.) “Oh Hi, my apologies, should I?” (I said this as my fingers sought the answer by googling him. Imagine my nervous shock when a Wikipedia entry for James H. Morris came up.)

“I’m the Dean of Carnegie Mellon University in Silicon Valley,” (Holy mother of God, it’s THE Jim Morris, co-inventor of the search algorithm!) “… and I noticed you requested our brochure. I’m wondering why you didn’t actually submit an application?” (Me, almost gasping for air) “Oh, thank you, I’d love to. It’s just that your late deadline is only 20 days away, and I haven’t even written the GMAT exam yet.” (He chuckled) “You’re a smart guy, right? How much time do you need to prepare?” (I wasn’t sure, a few months?) “I’ll give you five days. Prove it.” (He hung up. And I kneeled in the office, holding the chair over my head like a manic who couldn’t speak human.)

I forced myself into a tight exam slot before the next week. Moments before getting in the car to make the 100 mile drive to the exam room, I took another strange phone call: “Hi, I’m a recruiter calling on behalf of (a startup near San Francisco). We recently got acquired for nearly half a billion dollars and are in hyper-growth hiring phase. You’re one of the few qualified people who applied. Do you have a minute?"


I terminated the Microsoft contract, paid penalty on breaking the apartment lease, and left Seattle, symbolically on July 4th, Independence Day, 2009. I interviewed at the first real startup company that launched my Type 2 career, got admission into Carnegie Mellon University inside NASA Ames Research Park for Type 2 studies, met my Type 2 best friend (whom I married after graduating) all on the same week, Independence Day — and I assure you, I’m not making this up.

The hammer of layoffs came down hard that week, disrupting all those who had completely suppressed boredom to content with their stressful situations. By the time they started their job search, they were competing against incredibly bad odds in a game of musical chairs. Their very play-it-safe Type 1 strategy, of silencing the internal desire to rise above ordinary contentment, became the recipe to lose that very ordinary contentment.

Boredom is the Type 2 worker’s guiding light through the catastrophic crises that Type 1 work unleashes on the world.

The story doesn’t end here. At the hyper-growth startup, I interviewed at least a hundred qualified applicants fleeing the scene of layoffs and under-employment. The ones I helped hire became my friends at work. They also became secret subjects of my personal case studies on the differences between the characteristics of Type 1 and Type 2 workers. But that is perhaps another chapter, when boredom and I meet for reminiscing over coffee again.

Amin A.

Written by

Amin Ariana

A software entrepreneur from San Francisco