My Story of Entrepreneurship…Thus Far

It was the best of times, it was the worst of times. I hate to steal a great line, but it’s just so true. It was exciting, fun, fulfilling, filled with soul and creativity. It was adventurous and beautiful things happened all the time. Wonderful people came into my life — customers and employees alike. And I like to think we were all made richer for the experience. It was frickin’ awesome.

It was also frickin’ horrible. I made devastating mistakes, got lost in flawed thinking and misadventures, breakdowns of expensive equipment, not enough money, not enough wisdom, patience or compassion, and never enough time. Sometimes it felt like I could be crushed by it all. Yet, I became so wedded with my business that I sacrifice almost anything to keep it going. After all, it was beautiful, almost exquisite at moments, bursting with joy and just general coolness…and an incredible heaviness. It was both — all at the same time.


I started this adventure almost 11 years ago now. I sold my business 10 years after opening, almost to the day. Opened January 5th in 2005 and sold January 1st 2015. It’s a marvel to me that a decade was spent in this adventure and I think it may have been an accelerated maturation process, like some bizarre sci-fi technological apparatus. Simply step into this seemingly innocuous contraption and you will step out a changed person — somewhat wizened, certainly older, but also hopefully wiser, too. Fingers crossed.

Entrepreneurship is something I’d recommend to anyone who wants a life-altering, soul-challenging crucible of an experience that will push you to new levels of development and growth at every step of the way. Just as it sounds, it’s not for the faint of heart. And perhaps this is part of the reason why we celebrate great entrepreneurs. We know it’s hard. Going into it, I knew it would be hard, but I had no idea why or for what reasons I would be so challenged. I thought going in that success would come down to hard work, smarts, good ideas, good execution of those ideas, and dedication. I was wrong.

I’m standing now on the opposite shore of a sea crossing that has changed my life and I want to tell you about what that sea crossing was actually like for me. There are plenty of people who in the middle of that same journey right now, thinking that they are all alone in their struggle because no one talks about what this adventure is actually like. I want to write my story for the sake of my learning, processing and reclaiming (or gaining) sanity. However, I’m making this public in case that my story may help other entrepreneurs feel less alone in their own journey of creation. I know that sharing our stories makes us stronger, wiser, happier and far more effective at whatever it is that we’re doing. Hiding is an anchor that sinks too many ships out there on the open seas of business.

The story
I was barely out of school before I was disenchanted with the whole work thing. I craved meaning in my work and a work environment that felt expansive, supportive and creative. I wanted work to be a platform which could enable me to become my best self in the world, as opposed to what it felt like — a transaction of my time and energy for money so that I could create my best self in the world elsewhere. It felt too small for me and I think, ultimately, that kind of transaction is too small for all of us.

After graduating college with a degree in Cell and Molecular Biology, I started working as a bench scientist. The plan was to work for two years and then start my PhD program in developmental biology. I loved the idea of science and studying how things come into being. However, my pull into the world has always been the discussion of ideas, being with people in conversations that matter in the trajectory of our lives. Big, juicy ideas and conversations that blow your world views to smithereens. I love that stuff and certainly scientific discovery has its share of world-view shattering tales. However, the pace of those tales, I discovered, was at the clip of years. My world of science had its level of focus at a layer of detail that was fascinating, but intricate when I craved big, immediate and socially powerful ideas. I felt stuck while working at a great job, in a great lab and a great future ahead of me. Stuck, unwilling to quit, but not wanting to move forward.

Then, a tragic death in our family of someone far too young and healthy to die changed my focus. If I should die young, too, then I wanted to be doing what my heart and soul were telling me to do before I had to cash in my chips. I didn’t want to still be flying low before the trip was over. I wanted to go where my heart wanted to take me. I just didn’t know where or what or how or anything. I just needed something different.

My boyfriend’s (now husband) mom, Caren, gave me a wonderful gift of a series of coaching sessions with her friend, Wendy. Caren knew I was lost in the woods and this great gift of coaching changed my life. Wendy helped me see a way forward and helped me manage the guilt of walking away from a perfectly promising career.

We moved to a town that both my boyfriend and I wanted to be in and started a new life. It was thrilling, but quite scary. In my work with Wendy, I had this idea that I wanted to open a cafe that was centered around community, the arts, and meaningful conversation. This idea totally caught my imagination. I could see how my place could be vibrant, fun, bold, and a meaningful center of community in people’s lives. In our new neighborhood, there was a little cafe that was like this. Funky, great set of regulars, sense of family between everyone. I got a job there so I could live the life a bit, see what it was like and whether this was something I wanted to pursue.

This is the part of the story that you’d think I’d be so inspired, meet so many great people, find backers for my idea, and launch. But, that’s not what happened. I got scared about money and wondered what in the world I was thinking, working for minimum wage plus tips when I could just as easily get a professional job with real money and benefits. After 3 months of my funky, fun cafe lifestyle, I went to work at a job that required sensible heels — a job in marketing scientific robots to lab folks like I was just a few months prior.

Can you feel it? The slowing of this locomotive train of my idea to the pace of a crawl? I don’t know that it ever stopped, exactly — just slowed to incremental, almost frozen change over the course of the next few years. However, this was not lost time. I learned about marketing and got a few tricks under my belt about promotions, press releases, design, web stuff and the like. I also got my MBA during this period, which my employer helped pay for. Bless their hearts! Working there, in an environment of conservative, controlled procedures and policies ultimately re-solidified my belief that there has to be a better way to run a business. There has to be a way for people to have fun, express themselves, invest their passion in the work and serve the company while serving their own development. I believed in this and I wanted to see if I could find a way to do that.

By this time I had given up on the cafe idea. I left my safe job to start a catalog company serving the needs of women athletes in mountain sports, including hand-picked clothing, accessories, and equipment. It was going to be an awesome place to work where everyone pulled together to get their jobs done, but also could take a bike ride at lunch, bring their dog in and have beer at the Friday staff meeting. Still sounds good, actually. However, I didn’t know anything about that kind of company and I didn’t want to be a first time entrepreneur while learning a whole new industry at the same time. That seemed like a very poor idea.

So, I started coffee carts as my practice business to learn how to be an entrepreneur. I wasn’t a barista. I didn’t know the industry from the inside out. But I was an avid consumer of coffee and a lover of coffee shops. I had certainly spent some serious time in coffee shops during college and I had my opinions and ideas. So, I became a student of the whole thing. Got training in being a barista, practiced on a commercial machine at home, went to a conference, read everything I could get my hands on, worked a business plan, talked to vendors. I went full throttle on this idea and making it work. I was excited. I was a believer. I was in it all the way and very excited. I knew that we’d make a ton of money and that all we had to do was open up. How could we not? It was going to be awesome, fun, and flowin’ in the money, because I had done my homework and I knew that my ducks were in order. I was ready to fly.

…and then…

What happened next was a much more complicated journey than I ever could have imagined. Did I fly? Yes, certainly there were moments that I felt my wings stretch, but it’s not that simple and that is what I’m using this space here to talk about — that complex journey that brought me from unflinching optimism to despair to love to gratitude to terror and back to joy.

The simple story of what happened is that I started a coffee cart in January 2005 and launched a second in March 2005. Eventually we added a third in 2007 and rented space in an off-site kitchen for baking, prep and catering work. In the midst of that I moved a cart and ultimately shut that one down in 2008. Left with all this equipment and stuff in storage, and with a commercial real estate market that was crashing due to the economic disaster of 2008, I negotiated a good deal on space and opened my cafe in 2009.

That’s when life got really interesting, both for the better and the worse. I finally had my cafe where I could facilitate the arts and great conversation! But, I also ultimately had a restaurant to run. The leap up in complexity from coffee cart operation to cafe was shocking. Add on top of that, I believed that our national and local economic stumbles would be short-lived and didn’t see the forming desert of small business capital.

These are the realities of entrepreneurship. You make the best decisions you can and all of a sudden, you find you’re not in Kansas anymore. But what do you do? You’ve just got to keep going. Ultimately, I sold my cafe and two kiosks in January 2015.

I had so many good times and magical moments with people who I loved and who loved me. I learned some huge lessons about what some of the traps were that I was caught in and what I should have done. I learned some great lessons about how to do some things right — things that worked for us and made my cafe special in the world. However, my biggest lessons were about the personal struggle of entrepreneurship — the difficulty of it, what made it so hard and something of what it takes to maneuver and even thrive through the minefields of entrepreneurship. These are the ideas that I want to share, because I hope it helps other entrepreneurs feel less isolated, help them find the supports they truly need, be more effective in their work and lives and create their most thrilling visions yet.