Go Ahead, Be Naive

Plus, I'm launching a live course!

“It would be a lot easier to go and work for a company.” 

I received this well meaning advice recently from someone further along the entrepreneurship path than me. 

Was it recently? The message seems to be on repeat. Like the time I lost internet connection driving in the desert and was stuck listening to Jack Harlow’s CD for two hours.

It seems that every few months, someone wants to warn me that the writing path, the podcast path, or the entrepreneurship path is not worth pursuing because it’s difficult and unpredictable. 

Worse, sometimes they want me to explain how I’m going to make money or what my goals are. This is a trap. Whatever plan I scrape up in the moment is simply an opportunity to poke holes and discourage me. 

The interesting thing is that I find that these people are well intentioned strangers. I imagine the goal is to help me see that I should be more realistic. People who are successful are the exception, not the rule. You have to know somebody. You have to pay somebody. You have to get lucky. 

When people tell me to be realistic, what they are saying is that they do not think that I am resilient. I can’t handle seeing my savings go down. I can’t handle burning out. I can’t handle the same challenges they went through.

My biggest accomplishments came from the moments that I leaned into being unrealistic. I was naive. That was my superpower. That allowed me to aim higher than what others expected of me. I was one of the few students in my high school in Michigan that went out of state for college. I didn’t have the top grades. What I didn’t realize was that everyone else applied to one or two schools out of state. Harvard, Yale, University of Michigan. I applied to ten. I’m glad I didn’t ask anyone else for their thoughts on what I could accomplish. 

Now, I wish I could say I’ve never been this negative person, but I have. I have felt the need to protect someone else on their journey. “Most people quit,” I say, well intentioned. Luckily, the best people don’t listen. They smile politely and a few years later, I see they’ve done something incredible. Something shifts. I’m inspired by them. 

Sure, I get into trouble too. I have days where I’m nervous about money. I end up living in a desert in the middle of nowhere. But I survive and then I thrive. 

I meet cool people on the internet that I then get to meet in San Francisco, Palm Springs and Charleston. 

Online Friends Turned IRL Friends

People write to me and tell me that they relate to my essays on quitting alcohol, my sabbatical mindset or simply being an Indian woman that loves to dance. 

I’ve gotten paid opportunities from my writing. I’ve learned that success isn’t binary. I can freelance and support communities while I write. I apprentice with people who I admire. I know now that I can always go back to my old job in sales. That’s not a punishment, that’s a blessing. I also now know that has its challenges too. 

I worked in a safe corporate environment. For five years, I had so much fun working in tech and living in San Francisco. But I shifted from living my best life to feeling too comfortable and bored. 

I moved cities, I switched jobs. 

Surprise! A global pandemic.

I was fired. 

I learned that I am resilient. And if I am resilient, I can embrace naivety. Naive people go into new scenarios ignoring the warnings of other people. They don’t need to know all the problems they could encounter. They don’t account for everyone else’s pitfalls. They know somewhere deep inside that they will run into problems and still somehow move forward. 

I don’t need to be told to consider an easier path because there is no easier path. That’s not how life works. People become sick. People lose their jobs. People run out of money. Everyone runs into challenges. It doesn’t matter if we try to do everything “right” or if we go off doing our own thing, throwing the playbook out the window. 

I have embraced naivety. I follow my intuition and my interests. No one has to warn me that this journey will be difficult. It has already been difficult. 

But, we are resilient.

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Exciting News!

In March,

Tobi Ogunnaike

and I will be launching our first live course: “Turn Your Layoff Into a Sabbatical.”

I often write about my two year sabbatical that I took after I left my career in software sales. I was fired and was not ready to hop back into the interview circuit. On top of that, I was living in a new city during a global pandemic and I realized that I hadn’t built a life around the things I valued.

For me, my sabbatical allowed me the opportunity to live with my parents and sister for a year. After that, I moved to a desert in the middle of nowhere with my sister and worked on creative projects like my podcast and my writing. My sabbatical didn’t look like anyone else’s, but it was perfect for me.

One thing I’ve realized in writing about my experience is that the details of my sabbatical may have been unique, but the internal struggles were not. I’ve spoken to so many people in this past year who either left their job in tech or were unfortunately let go. There are certain themes that come up. For example, it took me months to not feel guilty that I wasn’t working from 9-5. I felt like I wasn’t “productive” because in the corporate world, I was so used to having to justify how I was spending my time. I learned to shift from a corporate mindset to a sabbatical mindset.

If you or someone you know has left your job recently and are looking to take a pause, come join Tobi, me and others who are on the same journey. I’m excited. It’ll be a container to share your feelings and experiences with others. At the same time, we’ll walk through some of the common scripts that pop up when you diverge off the well known path.