Fierce Founder Confession: I Ugly Cried Today

By Chris Olsen

A former coworker sent me a text message confessing that she was having doubts about her corporate management position. I found myself doing as I often do with friends sharing woes of corporate life—I shifted into blunt cheerleader mode. My message in response to her text was simple: You are awesome, the company is not the right culture fit, you need to move on and be awesome somewhere that appreciates your awesomeness or start your own business and sprinkle your awesome everywhere.

Suddenly, I was overwhelmed by emotion. I confessed to my friend that I was full-on ugly crying, gulping in air and uncontrollably blinking out big fat tears. At first because I wanted more than anything for her to experience the joy and satisfaction of building something all her own. And then the magnitude of launching my business hit me like a ton of bricks. I realized I’ve grown more, learned more, and experienced more in the past three years than in all of my time on the planet. For the first time in my life, I feel like I am doing the work I was meant to do.

That confession got me thinking about other revelations founders may not always share with the world—the aha moments that impact our personal and professional growth that we don’t really talk about. Here are a few of my founder confessions and the lessons I’ve learned from them:

I Obsess Over the Time/Money I Lose When I’m in the Car

I was born and raised in the Twin Cities, so when I moved to the country, it was a big deal for me. Living an hour away from the city didn’t bother me before I started my business, but now I obsess over my time spent in the car. I factor in losing two hours of work time on the days I have meetings in the city and consider how it’ll add up. The lesson: Video and teleconferencing works really well for some (not all) meetings.

I Don’t Love Talking on the Phone

So, the realization that connecting by video or phone rather than in person could save my business tens of thousands of dollars a year was powerful. However, the last time I loved talking on the phone was when I was a teenager. It’s weird, because I adore my clients, I’m super inspired by the work they do and I am passionate about helping them. But talking on the phone sometimes feels … awkward. The lesson: There are lots of things you won’t love about running a business (do them anyway).

I Have Fallen Asleep on the Job

Twice in the past year I have made the (questionable) decision to work while sitting on the sofa with my laptop (OK, and a blanket too). Both times I awoke two hours later with my dogs cuddled up next to me. While I felt a twinge of guilt, those may have been the best naps I have ever had. The lesson: If you don’t make time for self-care, your body will.

I Work a Minimum of 50 Hours a Week and at Least Three 12-Hour Days

Hmm, this may be the reason I have fallen asleep on the job. Seriously, though, I wonder if founders who say they started a business to free up time for family and friends and to live life on their terms are in an alternate universe. Because I work more now than I’ve ever worked in my life. And I love (almost) every minute of it. The lesson: Any time spent developing your business is time well spent.

I Wonder Why People Who Care About Me Don’t Care About My Business

I have friends and family members who haven’t uttered a word to me about my business. And others who’ve read my blogs and stories but have never liked, commented or shared. I don’t get it. However, I’ve been through enough therapy to know it’s not about me. And I’m grateful to have a very supportive partner. The lesson: There are plenty of people in your corner—surround yourself with those people.

I’ve Cried About My Business on More Than One Occasion

Entrepreneurship is a roller coaster. Some days are extremely rewarding and filled with the satisfaction of knowing I’m making a difference for clients. Other times, I don’t have time to feel anything because I’m so busy just getting shit done. And then there are days when I cry. Sometimes I cry because I’m overwhelmed or frustrated or sleep deprived. But almost always my tears represent sheer gratitude for the opportunity to live my best life and follow my passion and purpose. The lesson: Ugly crying is a beautiful thing.

About the author: Chris Olsen is a radio veteran turned communications consultant, educator and author of “Whyography: Building a Brand Fueled by Purpose”. Through her work as a consultant partnering with startups, Chris realized her WHY—to support women-owned businesses in confidently communicating their purpose and impact, setting them up for entrepreneurial success. She created My Founder Story and Publish Her as platforms for doing so.

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