What I Learned from Breaking the 52 Cups of Coffee Rule in Half the Time

When I heard about the book, 52 Cups of Coffee by Megan Gebhart, the first thing that came to my mind was: That’s Exactly What I Do.

For those who are unfamiliar, in her book 52 Cups of Coffee, Megan explores the insights she gathered from over a year of learning from strangers. Each week that year, Megan had at least one cup of coffee with a person she didn’t know.

I have spent my business school career discovering what I want to do when I grow up. After discovering that where I did my summer internship was not the right fit, I went back to the drawing board. And this time, I committed to doing an extremely thorough search. I know there are worlds of opportunities that I haven’t discovered yet and I didn’t want to leave any stone unturned.

So I signed up for LinkedIn Premium and got to inMail-ing. If I thought your background, current job and/or story was interesting I wanted to talk to you. I set up coffee chat after coffee chat learning stories about people at Google.org to Safeway to LeapFrog to The Westly Group.

In total, I’ve had 55 coffee chats in over 7 months.

My biggest takeaways?

You Will Have More than 1 Dream Company

Have you ever taken the Myers Briggs test? Well I am an isfj with a capital F. I don’t do anything if it doesn’t feel just right. So for me, joining a company that I believe in is absolutely paramount. Through my coffee chats, I discovered that I am passionate about the opportunity to impact the next generation of businesses through joining a venture capital (VC) firm.

When I first explored this space, I thought this was a very small community so I shouldn’t get too excited about a real chance to work at a real VC. Not true. Once I began talking with people, I discovered that every “dream company” of mine, had a sister I didn’t know about. From The Westly Group, I learned about Collaborative Fund. From Collaborative Fund, I learned about First Round Capital. From First Round Capital, I learned about Omidyar Network. The list goes on.

What I’m trying to say to career and job switchers out there is: find a company you believe in. Connect with people who work there. If you fall in love with it, awesome. If you get a job there, perfect. If you don’t, use that passion and those connections to continue to explore other companies that are doing similar work — there are more options than you know!

There’s No Right Way of Doing Things

To be fair, I have been told this for years. But then I got to b-school and was told there is a rule book for everything. My first dream job was to get into the mission-driven Consumer Packaged Goods (CPG) space. So I was told, if you want to go into the mission-driven CPG space, first intern at an established CPG as an Assistant Brand Manager Intern, then once you get the offer stay in that company until you at least make Brand Manager (but no longer than 5 years), then consider exploring mission-driven CPGs.

I didn’t like these rules so I decided to find alternative ways of getting the same result.

And luckily for me, the world of work is changing. Some of the people I talked with had fallen into their line of work by accident and it was only once they got there that they realized they loved it. Others followed a traditional path for 20+ years until their dream job in a different career finally opened up. Then there were the few idealists who (shocker) sounded a little more like me. They had an idea — that seemed to others a bit wacky and unrealistic — pursued it fearlessly and eventually succeeded.

The one commonality? All of them ended up where they wanted to be.

Sometimes You Just Won’t Click — And That’s Ok

Throughout this journey, I had plenty of conversations that didn’t go so great.

In these scenarios it was always one of two things. 1) I was distracted and didn’t come prepared enough. Or 2) The person I was talking with was really busy and/or not that interested in talking with me.

I tried my hardest to make #1 extremely a rare occurrence. Unfortunately #2 was more frequent. However, neither 1 or 2 ever happened when I met with the person face-to-face. It’s so much easier to build an authentic connection with whoever you’re talking to when you’re meeting in person.

But I also learned to become ok with the fact that sometimes I just didn’t connect. One of the most valuable lessons I’ve learned is that not everyone is going to like you. But you need to like yourself. So be authentic every time you show up.