Life is great. Arguably, I have done many things right in my past. I've had the luxury of attending college in the US, starting a great company with my roommate and travelling 35,000+ miles in the last 4 months alone. Along the way, I have met driven and passionate people, top notch in their respective fields, seen amazing places and made invaluable and diverse experiences. And I'm only 22.
By and large, I am near the top. I should be satisfied. I couldn't have possibly asked for more as I'm already stretching my luck. Succinctly, this was a comment on Facebook by a very good friend of mine earlier this month:
I want your life. You're not allowed to complain about anything, ever.
I'm here to say: Sorry to disappoint, Alex, but it has been a while since I have felt so lost. There, I have said it.
Fortunately, I have had amazing people to talk to who were giving me great advice. I wanted to take this opportunity to illustrate the journey of what it’s like to get doubts. Maybe someone will read this who is going through the same in the future.
Something just didn't feel right
I liken my experience of leaving Google to breaking up with my college boyfriend. He was brilliant, good looking, respected, and everyone loved him — I even loved him — but he wasn’t the one.
- Ellen Huerta - Why I left Google 
If you haven't found it yet, keep looking, and don't settle, as with all matters of the heart, you'll know when you find it.
- Steve Jobs - Stanford 2005 Commencement Address 
For the first time I ever, I felt like I wasn't where I'm supposed to be. Like quoted above, it was something from within. An inner voice telling you that something was wrong. For the longest time, I have tried to suppress that voice. I told myself I just wasn't trying hard enough and not being appreciative of what I had. Having doubts is for the weak. What was happening?
With Choice comes Responsibility
At the root of the problem was a mixture of two things: 1. Paralysis of choice and 2. External Expectations.
It is my theory, that paralysis of choice is the greatest when making the jump from Maslow's need for safety to the need for esteem (I think love is more basic than safety). It's a truly liberating feeling in a time of seemingly perpetual economic crisis. When people stress out about their careers. When you realize that you are not confined to these restrictions. When anything is possible. When commitment is not required anymore. What do you do?
Fact is that with great choice comes paralysis, the difficulty and delay to choose. In this paralysis of choice, external factors can serve as seemingly great tie breakers: Just go with what everyone else would be doing. On way too many occasions, I have literally asked dozens of friends and strangers: "What would you do if you could do anything?"
You could get lucky and you get to your true calling, or you could realize that it most certainly isn't it. But most likely, you will find something in the middle (I barely ever speak in absolutes). Surely, that does not make things easier.
I'll have what he is having
So I had this paralysis of choice, which by itself is a problem indeed, but nothing that isn’t widely known. However, combine that with increasing external expectation, and you got yourself a mess.
When I sat down and really thought about why I was resisting, I realized something about myself that I didn’t like, something that I’m ashamed to even admit now. The main reason I was resisting was because I would be giving up the safety and prestige associated with life as a Googler. When I reflected more, I realized that external recognition had unfortunately become a primary motivator for me.
The social human beings that we are, we care a lot about what others think. That's neither surprising nor a flaw. However, the higher up you go the “external recognition” ladder, the more you and society are telling yourself that your other problems aren’t real. Having doubts is such a non-problem, a true #firstworldproblem, which makes it so much worse. When your life is externally going great, it gets harder to admit that something is wrong.
Here is an exemplary and rather resentful comment on Ellen's piece:
When you frame your process [of leaving Google] as a courageous struggle, you're not only being narcissistic, you're being rude and disrespectful to people who are really struggling, which is pretty much everyone else.
- Ellen Huerta - Why I left Google 
You start to feel guilty for the way you feel It can’t possibly be a paralysis of choice, you are just being a coward, not focused enough, not appreciative enough. You'll end up blaming yourself.
Pseudo-Freedom and Dogma
I think this is especially true in the startup world (probably the same in finance from what I’ve heard). Obscurely, people pride themselves for personal misery, long work hours are glorified like nowhere else. You having emotional issues simply means that you are not cut for an entrepreneur.
What’s left is an incredible paradox for people: In our post-modern western fantasy world, we are obsessed with having the freedom to individualism and self-actualization. So obsessed that we actually get more self-conscious about external recognition as a quantification of our progress in achieving such freedom. Once our inner voice clash with these external influences, confusion is left. More often than not, we give into external pressure for the fear of being alone, of being truly different.
Your time is limited, so don't waste it living someone else's life. Don't be trapped by dogma - which is living with the results of other people's thinking.
It was easy to hide to believe that because I wasn't being trapped by the dogma of career, I wasn't trapped by dogma at all when in fact I was. And that realization made me afraid of what would happen once I took the courage to step out of that dogma.
On my way out
I liked to tell myself that I'm not afraid. And its true. I’m not afraid that I won’t find a job. I think when a lot of people think about leaving their job, they are not afraid that they won’t be able to find another job. They are not afraid that they won’t be able to sustain their lifestyle.
The biggest fear when making a change out of a feeling of incompleteness is that doing so won't change a thing, that it will be worthless. That it won't fill the void they are feeling. That there is a possibility that you might have to live with this feeling for the rest of your life. That you have failed “at life”.
How to address fear
We have a multitude of fears at hand in situations like mine:
- Fear of regret to make the wrong decision.
- Fear of being different and going your own way.
- Fear of failing “at life”.
Luckily, there are textbook solutions to address all these fears.
- Decide and don’t look back
- Just be yourself.
- Fail fast and early.
Like so much of the best advice out there: Incredibly obvious, yet so hard to follow. You just gotta do it. You gotta stop listen to everyone else. Embrace failure. The only way to clear the fear is to stop being afraid. The worst thing you can do is to be intimidated by it.
For as long as I can remember, I always knew what I wanted to do. I always had something I was passionate about. Once I lost interest, the next thing was usually just right around the corner. I was a total chemistry geek when the iPhone came out to prompt me to program. I had an awesome time being irresponsible and having fun when a link to the Thiel Fellowship popped up on my Facebook feed. Things always had a way of working out.
However that's looking backwards. In hindsight, I had the great luxury of decisions being magically made and fall right onto my lap just in time. Unfortunately, things don't always just happen and that's a first for me. There will be times where you won't know what to do. Your patience will be tested.
You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something: your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your heart ...
I for one, am grateful to have made those learnings on my path to “recovery”. I have a increased trust and belief in myself that feels incredibly refreshing. I’m gonna figure it out. Continue in my next post "Dropping back in" as why I would possibly think that college is going to help me with that.
Update: I found it
tl;dr: Life is hard, and is perceivingly even harder when you have absolute freedom of choice.