Lessons in Leadership: Taking Risks & Not Looking Back

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By Leslie Vickrey, ClearEdge Marketing CEO & Founder; Solving IT Partner

I’ve never been afraid to take risks, but becoming an entrepreneur wasn’t something that I originally set out to do career wise. I spent a lot of my early career working in a typical corporate environment, from McDonald’s Corporation to Junior Achievement and a few others along the way. Then one day an idea came to me – based on my own personal experiences – that fast-growth companies could benefit from outsourced heads of marketing and teams to execute on strategy instead of carrying the overhead of a team and multiple agencies, and that was the beginning of where I am today, founder and CEO of ClearEdge Marketing.


Fast-forward several years later and in total, I’ve been part of five start-ups, including a mixed-martial arts gym with my husband and as of late, ARA, a group dedicated to attracting, retaining and advancing women in tech. Each of these experiences taught me a variety of key business and life lessons.


Probably one of the biggest lessons I’ve learned along the way is that when you take risks, you need to be prepared to cut your losses sooner than later before paying an ultimate price of business failure. Of course, that’s easier said than done.


During my early efforts to start these various businesses, I didn’t always do a great job of failing fast after the risks I took didn’t pan out. It was challenging to come to that realization. Now, however, I’m more disciplined to assess and then commit to making the necessary tough decisions. I try not to think of it as a failure or a loss, but instead as an invaluable learning opportunity I’ve just had. If I’m not learning, I’m not growing.


The risks I’ve chosen to take throughout my career have also inspired me to take my own personal passions to the next level. In 2013, I co-founded ARA and we’re now active in Chicago, Seattle, New York, Houston, Silicon Valley and Denver, and have reached over 2,500 women thus far. Through our work, we are seeing more women not only stay in the tech industry and help fill the talent gap, but also fight for equal pay and rise up in the ranks.


The risk for me in this situation was making sure I could balance between running operations at ClearEdge, while getting ARA successfully off the ground. People would ask me if I split my time 50/50 and I would say: There’s no such thing as 50/50 or even 100%. It’s more like 150%+ and every day priorities shift and change. I’m proud to say the risk paid off as ClearEdge is healthier than ever and ARA just hired its first Managing Director to run day-to-day operations. It wasn’t without sacrifice, but fortunately the risks and sacrifices paid off.


No matter what your job, company or personal goals, the risks we take are what drive us forward. Big and small, each day is a chance to try something new, and even fail. The lessons we learn along the way make us who we are. Risk-taking and entrepreneurship isn’t for everyone, and that’s OK too. No joke here, but my husband even has a tattoo that says: The only risk you’ll ever regret is the one you didn’t take. And I couldn’t agree more.


About Leslie:

Leslie Vickrey is the CEO and founder of ClearEdge Marketing, an agency specializing in outsourced marketing and PR services for high growth technology, HR tech and recruitment companies.


Leslie’s passion for creating meaningful connections extends beyond ClearEdge. In 2013, she co-founded ARA, an organization that aims to attract, retain and advance women in technology through mentoring. She is also a founding partner of the Chicago Executive Women’s Networking Group, which cultivates and nurtures relationships among senior-level women in IT leadership roles through quarterly dinner events. Beyond these initiatives, Leslie is actively involved in local Chicago tech organizations, serving on the Board of Directors for i.c.stars and the Chicago Innovation Awards. Leslie was named to the prestigious Techweek 100 list, The Blue Sky Vault featuring 100 of Chicago’s most compelling innovators and entrepreneurs, and Chicago’s 50 on Fire, which celebrates visionary individuals and companies across Chicago’s top industries. Leslie was also inducted into the UIC Entrepreneurship Hall of Fame, and named as one of the 2016 Enterprising Women of the Year, which recognizes the world’s top women entrepreneurs.


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One Response

  1. […] I reflect on my lessons in leadership and entrepreneurship in this guest post on the Solving IT blog. […]