What Spending Six Days on a Train Taught Me About Life and Entrepreneurship

The other day I was connecting with a fellow alumnus over email and was caught off guard when he asked me: “What’s the most remarkable accomplishment you’ve achieved to date?”

Now that is a very loaded and deep question. It took me two months to get back to him. During those two months, I wrestled with this question, reflecting deeply on what could be deemed “remarkable.” Today, I finally got it: “Human resilience.” Here’s why:

I underwent retina repair surgery back in February 2012 while in my last semester of college (University of Virginia); needless to say, my fantasy of an epic college last semester came to abrupt halt. The news was nerve wracking and harrowing. I was angry, nervous and scared – I didn’t want to go blind at 21! To make matters worse, my entrepreneurship capstone class had planned to visit start-ups in the San Francisco bay area during Spring Break. Having preoccupied myself with entrepreneurial projects all year, I was very excited to experience Silicon Valley first-hand.

But my doctor did not clear me to fly.

Lesson 1: There is never a perfect time and you will never be “ready;” just pull the trigger and do it

As part of the surgery, I had a gas bubble injected in my eye – this prevented me from flying because a higher altitude will cause the bubble to expand and potentially render me blind. However, there were no solid, documented cases of this occurring; it was plain conjecture. But the trade-off was simple:

  1. Fly to San Francisco and risk going blind
  2. Don’t go at all, or
  3. Improvise

I wasn’t ready to fly but I knew I had to go on this trip.

So instead, I bit the bullet, pulled the trigger, and booked a three-day (74 hours to be exact) cross-country train ride. I left 3 days before my classmates, slept uncomfortably in coach class in upright seats for three nights next to total strangers, ate nothing but ramen and oranges and didn’t shower. And for those wondering – yes, I took the same three-day trip back (for a total of 148 hours spent on a train).


My meal: Ramen and an orange

How I slept in coach

When it comes to entrepreneurship, you will never find a perfect time to launch, you will never have a perfect product and you will never be fully prepared. What you will have is an opportunity to take a calculated risk. And if you believe in your cause enough, just do it. Despite whatever obstacles may come your way, you will improvise and make it happen.

Lesson 2: Take a risk; if you succeed you will be happy, if you fail you will be wise

My God was the trip it worth it.

Not only was visiting startups a great experience, the cross-country trip on an Amtrak was remarkable. I met so many people from different aspects of life, saw so many wonders tucked away in America and for once in a long time – reflected inwards.

The rain in West Virginia drummed out the silence on the train; the plains in Nebraska opened my eyes to America’s vast country; the snow in Colorado made me enjoy nature; the canyons and rivers in Nevada made me feel sublime and by the time I reached California, I realized even though we humans are more “connected” than before through social media, we are still very isolated from one another.

Train Station Colorado

Train Station in Colorado

Halfway there

Halfway to San Francisco

To be an entrepreneur you have to take risks. Even if they are small risks. As humans, we are anthropomorphically engineered to fear loss more than to appreciate gain. We’d rather shower in stability than to realize risk. But today’s dynamics have changed. People no longer work at companies for decades on end just to retire on a pension into their “golden years.” The time is NOW. “Safe is the new risky; risky is the new safe. The riskiest thing you can do is to play it safe” – Seth Godin. 

Lesson 3: Talk to a stranger

Instead of talking to their neighbors, people were talking to their screens. No one on the train interacted with each other; everyone was too busy on their smartphones or tablets although there was the occasional “may I sit here?” or “can I borrow your charger?”

Our society has become so plugged-in to our devices that interacting and making small talk with strangers has become somewhat taboo, making people question your intention at times and fear nonsensical ulterior motives. But sometimes, you just have to break the ice and say hello.

There were three individuals I met on the train that I won’t forget. The first was a retired army recruiter who was on his way to meet his wife in California; he recounted to me stories about memorable applicants and how San Francisco was like “in the old days.” He seemed so joyful and so full of life in his elderly state. And even though he wasn’t really paying attention to what I had to say, I listened. That’s the most someone can ask for – for you to listen, and to feel appreciated.

The second individual I met during dinner one night. He was from the Southwest and loved to camp outdoors. He told me tales of how he used to just pack up his bags, bring his tent, ride his horse out to the desert and canyons and spend the night watching the Milky Way in the sky. I was genuinely interested in his adventures and we had a great conversation.There was a nostalgic feel to it all.

The third individual was a mobile game app developer (for those who don’t know, my brother and I run a mobile app company – Endgame Apps). See? You never know who you’ll bump into if you don’t say hello. We spoke in depth about his experience at his company and as a game developer and I also shared with him my thoughts on strategy and monetization (putting that business degree to work).

A rule I tell all my friends and fellow entrepreneurs is to always look for opportunities to connect, connect, connect. And when doing so, listen; build rapport; and most importantly, give and share. You’ll never know who you’ll end up meeting; he or she could just be the catalyst for your idea!

Lesson 4: Slow down and appreciate the small things

If you thought three days on a train was long, try taking the same trip back. And yes, even though I slept uncomfortably for six nights in coach and didn’t shower, I wouldn’t trade those six days for anything. When you’re stuck somewhere for a long time, nothing else seems to matter. The outside world became separated from me and time seemed to slow down as my new world, the train, became more apparent.

For the first time in a long time, I had time to reflect. I was plucked away from my high-paced life in college stressing out about jobs or working on my entrepreneurial projects or thinking about parties that weekend and thrown into a sanctuary where I could put things into perspective. Those important items on my check list began to seem less and less important. I was able to relax, regather my attention and relish the moment.

For entrepreneurs, don’t get too caught up and stressed out abouteverything. Slow down, step back and take a deep breath. Oftentimes, we entrepreneurs give up because we create in our minds this grand plan of execution and stress out when we see how much farther we have to go. Instead, take a breather and reflect on how far we’ve come.

My six-day, 148 hour cross country trip and back was not ideal; it wasn’t preferable and it wasn’t my first choice…and yet it was everything I wanted it to be.

Lesson 5: Life will always be unfair at times, but don’t let that stop you from living your life and pursuing your dreams

I still see occasional flashes in my eye and still have to go to the opthamologist every 6 months but I don’t let that bring me down. I’ve accepted it and moved on; I’ve let it become part of my story of who I am. What is a good entrepreneur without stories of risk, failure and triumph?

So, what was my most remarkable accomplishment that I have achieved to date? It was an accomplishment all of us have experienced. We have all faced challenges and obstacles in our lives but the remarkable part is what you make of it. Human resilience is truly remarkable; we can change any series of unfortunate events life throws our way into an adventure and eye-opening experience.

Title Photo Credit: flickr