Unexpected learning from leaving my full-time job to run the company of my dreams.

About 9 months ago, I left Airbnb to focus full-time on The Passion Co.. Here are some of the unexpected learning.

Get Naked

I woke up in the middle of night sweating. I thought I was dying. I could not breathe. I opened the window and hung my head out of it, trying to capture any air that would make it into my lungs. After a few minutes I laid into my bed, and tried to return to my sleep.

The next morning I brushed the incident as isolated, and went on with my day. Two days later, the same thing happened. Another painful and isolated incident I thought.

When it happened for the third time, I knew there was something wrong. I was able to start looking at these incidents as data points to indicate some hidden anxiety.

The anxiety turns out started, when a friend was laid off from a new and on the surface successful start-up overnight. The first thought that came to mind was what if things do not go as planned and I have to do the same. When you do something from passion, the people that work with are not just employees. They become family, people you care deeply about. And as in any start-up, things did start going wrong.

What came next were the panic attacks. The solution? Getting naked.

I like to think of vulnerability as getting out in the freezing cold night, naked, jumping in the ocean. Someone stands outside watching you. Thy have the choice to help you on the way out. But you should be also be prepared for they may turn their back and never return.

I got naked with my team. I told them that things were not going as planned, and despite the uncertainty, I have their best interest at heart. My choice went against everything I was taught in all of my jobs, and even at business school. Being vulnerable with your employees is a no no, they said, it makes you look weak and you lose your allure as a leader.

I had to. I could not show up to work, pretending everything is a smooth sail when things were not. That was not me, and exactly why I left the corporate world. Besides bringing us closer, opening up meant having us work together towards a solution.

Do what you hate

When you start pursuing your passion full-time, you expect to be spending at least half of your time doing that exact thing you enjoy. Turns out the number 1 task of a business owner, whatever business you start, is selling. Selling to your potential employees, selling to customers and investors. Even selling to yourself on hard days.

I was caught off guard by how much I dreaded selling. I soon started coming up with excuses so I do not do it. One of them was deciding not to fundraise for the company. While I still think it was a good decision, I am now more honest with myself that the main reason was how much I could not stand selling.

It turns out, and after digging deeper, we hate selling because we fear rejection. And the rejection whiplash is greater when it is your own company or product. How to overcome that fear? Reframe and practice. Jia Jiang, the expert on rejection, now a friend, taught me to look at rejection as a win. That helped a lot, for example, in getting sponsorships for our conference.

But most importantly, I learned that I still had a decent amount of self-doubt, that made it harder to sell my dream. And not being an employee means you have to deal with your self-doubt. You cannot blame your boss or the system. You are the boss and the system.

How to measure success

Want to be popular and loved by everyone? Do not start a business.

You are going to make mistakes. Some people are going to view you as competition. You are going to let down an employee, a customer. You may not show compassion at all times. The difference between before and now that I am a full-time founder, is that I am held to a higher standard and therefore people judge me harsher, and I don’t blame them.

I used to measure success, with ensuring everyone is happy. After trying to constantly please everyone, I was exhausted and was spending energy on what could have been building the business. I finally accepted the fact that there are those who will not like my way and that is okay. I cannot sweat it constantly, take it personal and have it affect my self-worth.

The zone

Congratulations! said everyone when we launched the conference. I could not take it in, because how can you congratulate me if 99% of the work is yet to be done?

People from the outside are so excited for you, that they miss that doing what you love for a living means you have all of your skin in the game, and it is stressful and at times terrifying. But this time you cannot complain.

Because weren’t you the one who was talking non stop about how it is so important for you to pursue your dreams? and doing a soulless job should never be allowed? Well that same you is suddenly hanging out on the less greener side of passion. And you are left with your problems.

That was one unexpected situation I found myself in. The no complaint zone. Eventually, the no complaint zone served me well, and made me realize how easy, and cheap, well it is free, it is for us to complain about our jobs. It is after all a form of social bonding that I lost. And so I found another more efficient way: a close circle of other entrepreneurs I trusted that allowed me to both vent and brainstorm solutions.

The cup 100% full

Your cup. You must ensure your cup is refilled at all costs. Some people call it self-care, others self-love, I call it the #1 must. After all, you left stability to do something you believe in so do not lose you along the way. Because then what is the point? I say this, as I struggle to write this article. Why? Because I burned myself out.

Last week, 7 x 7 magazine wrote me that I was selected as one the top 20 movers and shakers of the Bay Area for 2015. What did I feel? Nothing. My cup is empty. And it gets harder to fill it when you have not for a while. Because even the water dries. So first, I am letting the ice melt. And slowly and gently I shall refill. So I can come back a better leader, entrepreneur and most importantly, human being.

Itfeels pertinent to go back to the original meaning of passion, in latin: suffering. And it is even more pertinent to go back to what we teach atThe Passion Co.: a passion is an expression of your life’s meaning. The truth is, I have never felt more fulfilled in my entire life as much as I feel today. The work I do brings meaning to my existence. And I will keep going because as Victor Frankl said: When you know your why, you can survive any how. To surviving, learning, thriving and keeping it real. Grateful for all those who supported me and continue to do so.