Entrepreneurship Happens Behind the Scenes

You can’t make this up…“The year was 2016! We were riding high off our first ever Create & Cultivate conference in Los Angeles and decided to bring it to Chicago. We were putting all the finishing touches on the event and the last item we needed was our decals; We had planned to dress up the nearly all white space with tons of colorful decals. With 12 hours till the day of the event the decals arrived and lo and behold all the files said, Cultivate & Create and #cultivatecreatechi — how this happened is for another time but beyond my initial paralyzing fear I looked at my head of events and we knew what we needed to do. We began cutting, moving, and re-doing all the decals in a complex puzzle to make them work. Our decal company didn’t want to do overtime so they left, leaving us to climb shaky ladders and haphazardly put all the decals up till 5 a.m.! When I hit the stage at 8 a.m., I, of course, noticed every small issue but the crowd was so happy and enthusiastic it quickly dissipated.” — Jaclyn Johnson, CEO and Founder of Create & Cultivate

The show must go on! Every event has one, or ten, of these moments. One of my most vivid is when an agent called two hours prior to our fashion show to say that two of our models were double booked and wouldn’t be walking ours. I was younger then and thought a forceful response - You will have them here, or else! - would reverse the outcome. Safe to say ‘Or else’ doesn’t intimidate an agent (or anyone), and definitely doesn’t solve problems. I’ve learned that being calm and ideating solutions is always the better option. 

Entrepreneurship is similar to being in the throes of planning an event...that never ends. You’re constantly putting out fires and working until the last minute before launches. Leadership is what happens behind the scenes, not what we see on stage. This week, we’re chatting with Jaclyn and Squad CEO and Founder Isa Watson about what they’ve learned rolling up their sleeves to overcome the unexpected challenges. 

We can all relate to the contrast of the beautiful Create & Cultivate summit versus Jaclyn and her head of events’ exhaustion at 5 a.m. It reminds me of our early trunk shows when showcasing our handbags might have looked glamorous. The reality is that our suppliers often ran out of hardware. So, I would drive to hardware stores in different states and fill suitcases with clasps and chain straps to maintain production. They’re totally different situations and the latter is rarely shared, even though it’s more representative of life as a founder. Imagine if we posted more of these pictures on our social media feeds instead. 

Scrappiness is vital in business. Every day brings its own set of challenges and you can’t survive unless you’re willing to do whatever it takes to get the job done. Jaclyn learned to prepare for the worst and hope for the best after the decal disaster. “Be prepared to get your hands dirty,” she says. “The saying if you want it done right you have to do it yourself has a lot of merit.”

A leader doing the job herself quite literally means doing different jobs, which Isa did when her head of engineering had to leave suddenly due to a family tragedy. Her first priority was, of course, her team member and then taking on a daunting role. “I had worked with a lot of engineers before, but hadn’t fully managed an engineering team end-to-end, but that is what I had to step in to do for a while,” she reflects. “I stepped in, stepped up, and began to manage engineering full time. I sought advice and insights from my founder CTO friends, and made it work until we could get someone into that role. It took a while to get the right arrangement.” 

No day as a leader is predictable and Jaclyn urges to “always have a Plan B” (This year, let’s add C, D, and E!) We’re less likely to be blindsided when we accept that things rarely go as planned. “The lesson here is to be ready for whatever,” Isa adds “There are so many things that will happen, and will be outside of my control but I have to think 10 steps ahead more actively. With people, that includes having more of a recruiting mindset all the time. I should have a slate of candidates at any given time that I can recruit into roles pretty quickly.” 

The confidence gained from leading through uncertainty is hard-won and instills the belief that you can handle whatever comes your way. These experiences stretch us and culminate in resilience and reward. The more crises you divert, the faster you respond, and the more likely you are to laugh (through the tears). 

Isa and Jaclyn illuminate the twists and turns of what it actually takes to navigate our careers, which I especially appreciate today when the path feels more like a maze...in a funhouse. Isa sums it up perfectly: “Founder life can seem sexy, but it is often full of surprises. I have learned some of my hardest lessons as a founder, and - while painful - I am so grateful for those lessons.” 

Let’s all reflect on our own hard-earned lessons and be proud of the situations when we’ve risen up and figured things out, even when the odds were stacked against us. This journey can be a grind and we all deserve to recognize the hustle. 

What is your best Instagram vs. reality leadership moment? Let me know in the comments and subscribe to receive the next edition!