3 Things I’ve Learned from Being an Entrepreneur for 16 Months

I quit my last job in April 2018 and started Upfront Work in May 2018. The last 16 months has been an ocean of swells, calm waters and capsizing but I can’t imagine doing anything else. Here’s what I’ve learned:

Lesson Learned #1: It’s not enough to be flexible, you have to be liquid.

A female pilot told me that during a chance encounter at O’Hare while waiting for an elevator. The escalator was out, it was late at night, I had a heavy bag, and I just got off a long flight and wanted to go home. I complained out loud about the poor state of our airport’s infrastructure and she said at least we had that option.

As an entrepreneur, you’re always adjusting: to your client’s needs, the whims of the market, your partner’s schedule. Flexibility is bending without breaking, but liquidity is being able to take on the necessary shape. That’s not to say you should lose yourself and values in the process (more on that next) but the ability to quickly adjust to new information has helped me close deals, work through difficult issues and be a happier person.

Lesson Learned #2: Stand for something.

Product manager may be the buzziest title of 2019. According to LinkedIn, product owner job openings increased by 87% along with scrum master (67%) and product manager (29%). A quick search for “product management” now yields online certification ads and articles to help job seekers “become a product manager in 10 weeks.”

As a seasoned product manager, I think it’s great that the industry is growing because we need diverse people from every walk of life to develop solutions to big hairy problems. But how do I stand out when traditional consultancies are now hawking product management services? At first I tried to play their game: cozying up to other product leaders, speaking at events, aligning myself with brands. But at the end of the day I knew it was a big fake show that wasn’t authentically me. So I threw in the towel and I’m leaning into my values of creativity, curiosity, critical thinking, and adaptability. By leading with my values, I take a unique approach to my work that can’t be replicated.

Lesson Learned #3: If you’re not enjoying it then stop.

We live in a world of shoulds. You should go to college. You should get a job. You should climb the corporate ladder. You should go for the promotion. But what if those “shoulds” don’t resonate with you? For more than 10 years, I followed that advice but at the end of the decade I just wasn’t that happy so I left and started my entrepreneurial journey. But if I thought the “shoulds” had ended I was dead wrong.

As an entrepreneur, “you should go for the promotion” was replaced by: You should apply to speak at that event. You should network with more people. (And when sales are flat, “maybe you should apply for a full-time job.”) Recently, I started replacing “should” with “what do I want to do?” It’s a tough transition and I’m constantly taking two steps forward, one step back, but becoming more mindful and introspective has brought more meaning to my work.

Jess MeanComment