Some Difficult Questions..

I left my job in San Francisco recently and moved to New York City to start a company.  In the past several weeks, I’ve had numerous conversations with friends and family about my decision.  Their first question is always:  Why?  I can tell you that there’s no better gut-check than trying to explain to people you care about why being irrational actually makes sense.  Fumbling with my response a few times has motivated me to collect my thoughts and write down an answer to the most difficult questions I get asked.  My hope is that these thoughts will be interesting and helpful to you in some way. 

Why move to New York City and start a company?

I wrote this question on a blank screen and then stared at it for a half hour.  I didn’t know where to start.  I thought about my life up to this point;  my accomplishments, my failures.  I tried to imagine how hard this would be and reminded myself of everything that has inspired me.  Then the answer hit me – and it’s actually very simple.

Because I’d be pursuing my dream.

But wait.  That’s not an answer!  It still means I have to quit a great job, move to one of the most expensive cities in the world, and start something that statistically has a ridiculously low chance of success.  Basically, it means I have to be completely irrational.  So, it doesn’t really answer anything, right?  Or does it?

Why does pursuing our dreams feel so irrational?  Doesn’t accomplishing your dreams lead to happiness?  And shouldn’t the pursuit of happiness make sense to you?  It feels irrational because in order to accomplish our most ambitious goals, we have to face fears and take risks.  If we focus on the hurdles before success, any path towards our dreams will seem irrational.  Instead, if we focus on our dreams; all paths lead to happiness.

Bottom Line:  Focus on your dreams; and any path forward will make perfect sense.

Ok, focusing on your dreams is great.  How can you just forget about all the risks?

The most sobering aspect of the why-are-you-doing-this conversations is when you start to list the risks involved:  I won’t have any income if I leave my job.  What if my business idea sucks?  I spent long nights ranking each risk in terms of “degree of riskiness” (I’m an engineer, so this seemed like a good idea).  One night, I realized that I’d only been listing the risks of pursuing my dream.  What about the risks of NOT pursuing my dream!  If you consider that, then there’s really only one risk that matters.  Regret.

To me, regret was more terrifying than any of the other risks.  If you think about regret, you’ll see your focus shift.  I bet you will become more concerned with how to accomplish your goals and less worried about what is standing in your way.  You’ll begin to adapt to the discomfort of not knowing how it will turn out; and amazingly – the world will begin to make a tiny bit more sense.  I still felt the fear, but now it was the fear of not trying.  Somehow, that was motivating.  My approach had changed from, “how do I limit risk and avoid failure”, to “what do I need to do in order to succeed”.  It’s a subtle shift – but for me – it was monumental.

Bottom Line:  Acknowledge all the risks.  But remember, regret is the scariest risk of them all. You can use it as a renewable motivator.   Will you regret never trying?  If you fail, will you regret not trying again?  If the answer is yes; then you have everything you need.  If the answer is no; then your dreams have changed.

You do realize that this is going to be exponentially harder than you think, right?

Thinking about the immediate road ahead is very frightening.  All I can say is that there are two books I’ve read that have helped me deal with this question.  Maybe they will help you as well.

1.  Think and Grow Rich by Napolean Hill
2.  The Alchemist by Paulo Coelho

These books are different, but in many ways they paint the same picture.  To me, their message is that the unknown is a scary place, but also that there are ways to slowly conquer this fear.

The following quotes are two of my favorites and words that help me deal with fear and the unknown.

“Desire is the starting point of all achievement, not a hope, not a wish, but a keen pulsating desire which transcends everything”. – Napolean Hill

“And, when you want something, all the universe conspires in helping you to achieve it”. – Paulo Coelho

Some closing thoughts..

All the ideas above have helped me take the first big step.  But at the end of the day, they’re just words.  I admire all those brave people out there who have achieved their dreams.  You are amazing.

The purpose of this blog is to document my experiences, but also to engage with you and learn from your questions and comments.  I’d love to hear from you and it’s easy to comment here or send me a message.  So, please do.

Bottom Line:  Trying new things reminds you of how much you don’t know.  No matter what it is you want to learn, I bet someone out there can help.  Don’t forget to ask.  Don’t forget to listen.