It was 9 o’clock on a Wednesday morning when I took a deep breath, stepped into my boss’s office, and asked for a minute of his time.
“So, I’ve given this a bit of thought, and well, I’m going to take some time off. And uh, I’m gonna be leaving the company.” [deep gulp]
“WHAT? ARE YOU GOING TO AMAZON?”
“No, no, I just want some time to clear my head, travel for a while, and figure out what’s next for me in life.”
“Oh. Okay. Hard to compete with that. Have you thought about a leave of absence? And are you sure you don’t want to wait until September?”
“You mean, for the money?”
“Yeah.” [brief pause.] “It’s not about the money is it?”
“Nah. It’s not about the money.”
Ah, the money.
When I told a few coworkers what was going down, the most common reaction was something I’d describe as a cross between admiration and “Are you insane? You’re just gonna walk away from the paycheck? I could never do it.”
Or more bluntly, as a close friend still back there confessed on a long walk, reflecting on life with me recently, “I just really love the money.”
Looking back on my time at Microsoft it’s hard to nail down the exact point at which money entered the conversation. Words like “money,” “salary,” and “pay” were nowhere to be found in my first impressions and experiences.
My salary straight out of college 9 years ago was $75,000.
It was $10K-$15K over the computer science median at the time. I was ecstatic about the journey. I accepted on-the-spot without negotiation.
And then gradually, something happened.
Every 18 months there was a promotion to a new pay level, often paired with a “re-recruitment” effort — a 1:1 meeting with higher-level management, kind words of encouragement, and entrance into a “High-Potential” employee program.
Somewhere along the way we started referring to the pay as “golden handcuffs,” implying that were it not for the money, we’d be long-gone. My salary upon leaving Microsoft at the end of 9 years ultimately amounted to $254,895.
I’ll just say that to the child of an immigrant and middle class family, raised of sufficient but not excessive means, I can only describe that number as feeling both grossly obscene while at the same time a bit like:
“Well, I’ve made it.”
But the irony in having “made it” was that as my salary was rising, the intrinsic meaning I found in work had been falling.
Whereas the things I valued most early on in my career had been achieved, other ambitions in life were slipping further away with each year that went by.
Start something new; change the world
Though a bit cliché, changing the world was what originally sold me on creating products at Microsoft.
Over time though, I began to feel real differences between starting something on a team of hundreds, if not thousands of people within a big corporation, versus starting something where you personally pour your heart and soul into all that’s required to earn the business and trust of your first customers, employees, and investors/partners.
I’d had a small taste of the latter in past startup life, and found myself craving the unique experience, challenge, and exponential learning curve that are intrinsic in it.
Create your own destiny; no limits or constraints
I started out with insanely high aspirations and commitment level.
And there were multiple points in my career where I had the fortune to work with amazing teams on revolutionary projects, often only to see their potential limited in some way by inside forces — often broken corporate systems or endless re-orgs.
And after 9 years in the system, I was very ready to double down on creating something new, without the risk of an impending re-org or other self-imposed artificial constraint tearing it down.
Stay strong my Amazonian friend, we’ve all been there.
The #1 risk/fear of great engineers I’ve met at big corporations is “cancellation by re-org.”
When it happens there’s no pivot, no “let’s change a few things and try again” — just a token “thank you for your service, here’s your next project, better luck next time.”
There are startup risks, and then there are big company risks. The former can often be de-risked by means under your control, the latter cannot.
Create a ridiculously awesome place to work
This is mostly about surrounding yourself with a brilliant team of people you enjoy working with every single day — and I feel fortunate to have met many great people at Microsoft.
It’s also about laying down a mission, core values, and/or principles you believe in, and systems to support and scale them — something that was at times missing.
“Mission and values” have been removed from Microsoft’s about page. Remnants remain in meta description and search results only.
And then there was an idea
As time went on, much closer to the point of pulling the trigger, there was the beginning of an idea. It was an idea that once discovered became a sort of mission, one I just couldn’t shake.
And so I decided to pursue it.
From Golden Handcuffs to Startup Fuel
I’ve never known anyone who’s had a real “Jerry Maguire” moment. I sure haven’t.
In my own journey, making the decision to leave what was in many ways a very secure, financially rewarding job happened in 3 stages.
The first stage began 2-3 years before I gave notice — where I first began to notice and feel that something was missing in work and in life.
I wasn’t quite sure what it was yet, or what I truly needed to feel fulfilled again, but I started to suspect that it wasn’t something I was going to be able to find without taking a leap, a big one, and leaving the comfort of corporate life.
So without knowing exactly what I wanted to do or start next, I just began to save. I looked at my personal “burn rate” and set a Mint.com goal to stash away enough cash, on top of retirement and rainy day savings, to live comfortably for at least two years without a paycheck.
And all the while, I stayed super focused on my product work at Microsoft, often working 10–12 hour days, and trying to learn as many new and different things as possible that might be useful somewhere other than in corporate life.
“Am I still engaged?”
The second stage began 2-3 months before I gave notice — yet another re-org had hit our newly minted Operating Systems Group, and signs were emerging that the new product I’d spent the past year-or-so creating was going to be killed.
As a manager at Microsoft, I’d been trained to recognize the conditions or circumstances under which employees generally decide to leave their jobs — and it often boils down to a cross between low engagement and satisfaction (a book called The Carrot Principle has a great list of indicators here).
I realized that my engagement was quickly going down the tubes.
And so, on a rainy Seattle afternoon, curled up in a blanket at home, I reflected a bit on work and life and finally wrote out the reasons I’d stayed so long:
January 8, 2014
1) See through shipping product that will have awesome impact [canceled]
2) Smart people I like to work with every day.
3) Smart, capable boss who cuts through politics and minimizes overhead.
4) Loyalty to manager, employees, peers.
5) Money in the bank to fund my own thing down the road.
6) Feels nice to be recognized/appreciated for what I do.
And after writing it out, I decided not to jump ship. Yet.
I felt fortunate for having a job that afforded me all of the above. Morale across the team was low. I was running a team. I’d just received a promotion. There might be new challenges ahead. It just felt like the wrong time to leave, and I didn’t think I was ready to.
Over the next few months the people around me wanted to know I was committed to what was next. I told myself, and then I told them, that I was.
Tipping point
The day I decided to finally walk away from corporate life and leave the Microsoft-sized paycheck behind was Monday, March 17th.
Work had stabilized. I took a first-ever 4-day “staycation” and was spending the second-to-last day off with a friend who’s founded an awesome startup in Seattle’s Fremont neighborhood.
He’d jokingly egg me on: “just quit!” and I’d quickly respond “not ready!” and then later that evening sitting on my sofa, I did something one shouldn’t ever do on vacation from corporate life and tapped open the Outlook Web Access app on my iPad.
And as I started glancing through the stream of several hundred new messages as they arrived, provocative thoughts started crossing my mind, and for once I couldn’t shake them off:
This isn’t changing the world.
If I write more emails, I may never stop.
It started to sink in: The project timing was right. The personal timing was right.
If I still wasn’t ready to take the leap, then it was time to accept fate and resign myself to abandoning any bigger ambitions. There was nothing else to wait for.
And so 9 o’clock that Wednesday morning, I went into the office, and I leapt.
And I haven’t looked back since.
It’s now been 6 months since leaving Microsoft, and 3 months since my co-founder and I incorporated and began to talk to customers and create our first product.
Startup life so far is what I expected and more.
I feel appreciation towards all my friends & colleagues at Microsoft who gave me the opportunity to learn and grow, and to the company itself for the resources and opportunities it afforded me as well. This really can’t be overstated.
And at the same time, I know there are so many brilliant minds out there aspiring to start their own thing, change the world — who haven’t yet found the courage or opportune time to do so — particularly in the Seattle area where larger companies play a major role in the tech & business ecosystem. So, in honor of Seattle Startup Week, this post is dedicated to anyone who’s thought or is thinking about leaving your corporate job for startup land.
If your situation was anything like mine, I’d highly encourage it.
And as I continue my own journey, I promise to keep the posts coming here. If you enjoyed, feel free to follow, share, or reach out.
This post originally appeared on Medium, and has been reprinted with permission.
Photo via Heisenberg Media/Flickr (CC BY 2.0)
