Are you a self-conscious entrepreneur? Why you need to own your decisions.

 

Last week I got a free ticket to Hustle Con in Oakland, CA.

The conference brings together some of Silicon Valley’s brightest minds for two days of TED-styled talks that feature founders and professionals.

I was slammed with work. So I figured I would take an Uber downtown, stay for a little bit and then head home. 

I got to the conference and took my seat.

I was enjoying myself but had this nagging feeling like I had to get going. 

I almost got up and left, but I saw that the Founder of Pandora was speaking at 3 PM… he was the last person to speak.

Okay I thought, I‘ll stick around. 

I picked a spot in the back and sat down with my back up against the wall.

When Tim entered the stage the first thing I thought was that he looked comfortable and content. He didn’t come off as “showy” or proud. He seemed humble and happy to be there.

Pandora’s history has a company is absolutely wild. 

“Then things got rough. We began running out of money and wound up in a long, grueling fight for survival. It took almost 4 years, a few business model changes, and 348 investor pitches before we were able to raise another venture capital round. By the time we got to the closing in March of 2004, we had deferred close to $2 million of salary, racked up massive credit card debt, battled lawsuits and eviction notices, and experienced just about every other imaginable challenge for a young business. It was a wild process that by all measures we should not have survived.”

(You can read the full story here.) 


Tim explained that he received a very simple and timely piece of advice during this period. His girlfriend, now wife, told him to, "stop being so self-conscious."

Straightforward. But the input really struck a chord. 

I paused and thought about my own self-consciousness.

Since moving to Oakland I’ve put myself in front of many new people. I’ve been dating, making new friends, and seeking new business opportunities.

It feels like I am always pitching myself. I make a case for business every single day. And somewhere along the way, I found myself exhausted. And perhaps a little self-conscious.

I looked at everyone else around me and wondered, “Have I done something wrong?”

These feelings brought me to a very difficult moment in my car last week. It was raining outside and tears welled up in my eyes. I felt immense pressure and anxiety come over my body.

I asked myself why I was feeling this way. Why was I questioning myself? Doubting my decisions?

And then it dawned on me.

I was measuring my life on the same yardstick as my peers. I was comparing myself. And it was affecting my spirit and making miserable.

As soon as I removed other people from my mind, I began to see everything more clearly. I actually had a profound sense of peace and assurance. 

I thought to myself, This is my life. These are my decisions. And this is the vision I have for my future.

I realized, sitting right there in my car, that if you invite other people into your own equation—you are bound to feel inadequate, inferior, and undervalued.

And while I believe you can learn from the wisdom and experiences of others, I also believe that you have to own your life and decisions with abandon. They are yours, and they will work only for you. No one else can determine your path, or tell you what is right. You must ultimately decide for yourself. 

I wiped my eyes and pulled my hair back into a ponytail. I felt calm for the first time in weeks.

From the outside looking in, perhaps I can look reckless. I put myself out there so much it’s embarrassing. I make bold moves and take big risks. Sometimes I tell myself, “Anna, you are fucking insane”.

But really, I couldn’t imagine my life another way. I couldn’t imagine doing this differently. I make mistakes, but they are my mistakes. And moving forward, I will own them and be thankful for them.


Are you a self-conscious entrepreneur? If so, I urge you to put the ruler away. Don’t compare yourself anymore. Step into your story—own your mistakes. 

There’s this quote by Cheryl Strayed. I love it so much. It goes,

“Whatever happens to you belongs to you. Make it yours. Feed it to yourself even if it feels impossible to swallow. Let it nurture you, because it will.”  ― Cheryl Strayed, Tiny Beautiful Things: Advice on Love and Life from Dear Sugar

 
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