Advice to My Twenty-something Startup Self

I’ve been involved in over a dozen startups since moving to Silicon Valley in 1996. When I moved here in my early twenties, I had seemingly endless stamina to pull all-nighters. I was pretty much immune to both sleep deprivation and caffeine overload. This made it very easy to throw myself into startup life, which looking back — I think I was addicted to: the thrill of building products that could disrupt then-giants like Microsoft and Yahoo! (ha!) fueled many of us to burn the midnight oil for years.

After LinkExchange was acquired by Microsoft in 1998, I stayed on for a short while to see if the ‘Microsoft Way’ would suit me, and I soon realized the answer was ‘no way’. I longed for the fun and fast-paced startup culture that surrounded me in San Francisco, so I joined one early stage startup after another. One in the mobile space (when WAP handsets were the thing), and another in the e-commerce space (a predecessor to Wag.com – which is cool now that Amazon’s doing it!). Both ran out of money and steam so I moved on to an enterprise-focused mobile startup called SEVEN.

The company seemed full of promise, it’s founder Bill Nguyen had recently sold Onebox to Phone.com for $850 million. They were going to redefine how enterprises accessed their corporate email on wireless handsets — this was before the iPhone or Android existed, and the only way to get your email was through a Blackberry. As the company’s first program manager, I was sent to London to build out a custom product for a wireless carrier partner. My first job as an international wireless project manager made me ideally suited to working with operators and managing large-scale projects. This one required mobilizing dozens of people who didn’t report to me to collaborate across several timezones and deliver a product under insane deadlines. I liked a good challenge!  I had also grown accustomed to falling asleep on long-haul flights while being able to wake up completely refreshed, so the travel didn’t daunt me. My secret? Melatonin and a good glass of port.

While I initially loved spending time in London, the cross-Atlantic trips and constant jetlag started to wear me out. It also became ridiculously expensive for the company to put us up in hotels for weeks at a time, so I volunteered to move my life to London, lease a flat, and stay until the project’s completion. What started out as ‘several months’ turned out to be more than a year.

As anyone from the West Coast who’s worked in Europe knows, the time difference is just convenient enough between London and San Francisco that you can practically work an entire two business day’s worth back to back! Just as my London day came to a close, the Silicon Valley office would open up and I’d spend hours on the phone or over email late into the night, collaborating with colleagues. It made for a gruelingly long work week, and ultimately my immunity to sleep deprivation wore out. So did my passion for startup life. There I was, in one of the most amazing metropolitan cities in the world, and all I wanted to do on the weekend was catch up on my sleep!

To console myself that I did actually have a life and this was all somehow worth it, I managed to take the train to Paris on the occasional weekend.  When I had a particularly good week at work and was feeling upbeat about living so far from my family and friends, I took several spontaneous trips on LastMinute.com. My criteria for a getaway was If I could get to a destination in under 3 hours for less than a $300 ticket and spend less than $300 all weekend, I’d book it. I saw Reykjavik, Seville, Santorini, Istanbul and Rome. They were great adventures, but ultimately I missed having friends to share them with.

Then on September 11, 2001 while en route to a work meeting in a London cab, the first breaking news report that the World Trade Center had been hit by an airplane came over the radio. I remember the moments after that vividly. Instead of having our team meeting we gathered to watch the BBC News and agreed we would all go home and call it a day. It was from my hotel room that I watched in disbelief as the second tower was hit live on television. At that moment, none of the startup glory mattered. My international adventures didn’t matter. My bank account didn’t matter, nor did my glorified options. Even the feeling of being really kick-ass awesome at my job paled in comparison to the feeling of wanting to go home, be with family, and see my friends. Something big shifted inside me that day, and though I couldn’t quite place it in the moment, it felt like a layer of illusion had been torn from my whole perception and that somehow, my life would not remain the same. On some level, I was done playing the game that somehow work was all that mattered in order to define my self worth in the world.

Six months later, I packed up my London apartment to take what would be my last London – SFO trip for a long time. Having wrapped up the first launch of the company’s project, my heart, head and body were no longer able to give any more. I decided to take a sabbatical from startup life and give myself time to just be. I figured since I had graduated a full year early from college to save on tuition and to start making a dent in the Universe, I had ‘banked’ at least a year’s worth or more of time to figure out the next phase of life. I was barely thirty years old.

What advice would I give to my twenty-something self, knowing what I know now? While I wouldn’t advise her to change a thing about the journey she took, I would urge her to savor the moments more. To ‘pursue’ and ‘do’ less, and just “be” more. To pay closer attention to life outside of the working world. To breathe more and to be still. To be aware of her body and to take care of it — feed it well, exercise, and don’t be fooled into thinking it is invincible and can’t be damaged by lack of sleep. To be kind to herself, even when being tough seems expected by the men in the room. And to know that life is teaching her something even through the moments that don’t deliver happiness. Especially those ones.

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In a future post, find out how I launched my own small business, became an expert in the wellness and maternity industry, then returned to startups on my own terms.

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