Reflecting on Past Successes and Looking Into the Future with Leslie Vickrey

ARA Co-Founder and ClearEdge Marketing CEO Leslie Vickrey presented a five-minute lightning talk to a crowd of 200+ during a recent Women in Tech breakfast hosted by General Assembly. Each of five speakers were asked to answer a specific question. Here’s what Leslie had to answer along with her response. We hope you find it of value and consider for yourself, how would you answer this question?

What was the moment when you knew you had made it? How can we get more women to that feeling?

“The moment I knew I made it was when I was 21 years old, graduated college and pulled out of my driveway in Saginaw, MI, in a Pontiac T1000 with $300 in travelers checks (yes, travelers checks!) and a credit card with a $500 limit (which I thought was the most $$ ever). I was headed to Colorado with all of my belongings in the hatch of my car. I sang my heart out to Fleetwood Mac on my 23-hour drive. I had freedom. In my mind, I had made it.

On my way to Vail for a broadcasting gig my car broke down. I didn’t have enough money to make it there, so I slept on my friend’s couch in Denver and waited tables until I got on my feet.

Little did I know that moment was the beginning of one of many chapters in my life, and the start of my adult personal and professional journey. From a professional ski bum/waitress to an intern at McDonalds to PR at Junior Achievement, and then several years later owning my own company, I have come to realize that the definition of “making it” changes for me as I go through different stages in my life and probably means something very different to me than it does to you.

To some “making it” means financial gains. To others job titles. Selling a company. Winning an award. Having a family. Whatever it is, it’s different for everyone. And many people never feel like they made it. Which is why I’m here to share my story.

Fast forward from my experience in Colorado to current state. People often ask me, did you always want to own your own company? It wasn’t that I didn’t want to, I just didn’t think about it. I always worked for other people, but one day an idea came to me and I decided to go for it. I didn’t spend months writing a business plan and working on financials. I didn’t get investors. I landed a client and took another leap of faith. Similar to how I went out West, but this time I was a little wiser in my approach.

I launched ClearEdge Marketing in Chicago over 10 years ago and on that day, I thought to myself “I made it.” Again.

I have spent the past 10 years really focused on building my network, and pinpointing organizations to associate with that were both personally and professionally important and rewarding to me, my company, our clients and our team. ARA, The Chicago Innovation Awards and i.c.stars are my three primary areas of focus. Where I spend most of my “extra” time. And I’ve met some pretty terrific people along the way.

Last year was a big year for me. For the first time in my career, I was being recognized for my achievements. I’m used to helping get clients recognized or recognizing people on our team, but not me. People say women never take the time to slow down and celebrate their accomplishments. I am certainly one of those women.

I won a few industry awards last year, made lists of the Who’s Who in Tech, got inducted into the UIC Entrepreneurial Hall of Fame, was named Enterprising Women Magazine Woman of the Year. I was nominated to the Chicago Innovation Awards and i.c.stars Boards of Directors. I was frequently speaking at events. I even questioned one of the awards as I thought it was a scam until I found out it was not only legit, but several people had nominated me. I didn’t believe it. I didn’t see in myself what others saw in me. That said, one could say, last year, I made it.

Then July of last year came along. I spent my entire ClearEdge life building a company with a flexible model and work environment. We have 30 people on our team across 10 states and service clients across the U.S. and throughout Europe/Asia Pac. I don’t care where people work. It doesn’t matter to me. Talent – accountability – giving people, men and women alike, a chance to have a career AND raise a family AND take care of their parents AND care for special needs kids AND travel the world… that’s what matters to me. But what I didn’t realize over the years of building this company, was how that model would in the end be what changed my life forever. Last year I really came into my own in Chicago. I thought wow, all of this hard work – my networking, my community involvement has really paid off.

Then something crazy happened to me. After 7 years of marriage and turning 42 years old, I found out I was pregnant. My son is now five months old and I’m about to turn 44. We weren’t expecting to have a kid. I started turning down board roles. Slowing down my travel. Wondering what was going to become of me. The life we had. My career. People questioned me left and right – and notice I said questioned, not encouraged.

Then I realized while all of the awards and recognition meant the world to me, my biggest challenge AND accomplishment was still ahead. I was going to be a mom. My flexible model, the one I fought to make work for everyone else BUT me, would now actually work FOR me. My team stepped up, forced me to take time off, told me they wanted more responsibility. Begged me in fact. I slowly started stepping away from the day-to-day. I had to start acting like a CEO. A CEO who is a wife and a mom and driven by my career. I thrive for it.

So you see, there are many ways you can make it. And I’m fortunate to have made it a few different times in my life. But it’s going to be different for you, than it was for me.

That said, I do have a few pieces of advice I learned along the way. Lord knows I get a lot of advice, some I take and other advice I listen to and don’t necessarily follow. I would expect the same of you…

It’s OK to celebrate success. Even the smallest of success. Be proud of who you are and the woman you have become. We often feel guilty or not worthy or that if we celebrate, something bad will certainly happen.

Try not to let fear get the best of you. And for the love of God, be confident in yourself. The second you hear an inner voice telling you anything negative, pinpoint where that voice is coming from and TURN IT OFF. SHUT IT DOWN. Be the best you can…

Build a network. Try not to focus only on your day job and family. Believe me, I know first-hand it’s hard. If something happens to your company or your job and you don’t have any connections or a network, it will be more difficult to land somewhere. It’s super important. Try to build it around what you love. It will help make it better.

A mantra I stick by all the time now, something someone said during an ARA event: If you don’t ask, you won’t get YES. I truly take that to heart. What’s the worst thing someone will say to me when I reach out to connect, network on behalf of an organization I’m associated with. NO. Who cares? It isn’t personal. It’s just business. Make the ask.

Stay humble. You can make it one day and the next day just when you thought you “made it”, what you thought was one thing could change on a dime. It’s just life. Be prepared to pivot. Don’t give up. And most importantly, always be true to yourself and your beliefs.

Take care of yourself. People who know me know I’m crazy about working out. It’s something I do for ME. I don’t care if it’s 6 a.m., 3 p.m. or 9 p.m., I’m going to make it happen. If you let years go by and start saying what about me, I’ve lost myself – my kids are now off to college and I’m stuck. You have one person to blame…you. Again, it’s not easy, I realize. But whatever small thing you can do– reading a book, listening to music, meditating, working out – do it. For YOU. A happy you = more happiness around you.

My vision for ClearEdge and ARA couldn’t be more clear than it is today. So for me, I’m still making it happen and I don’t see that slowing down. It will certainly change along the way, and I’m OK with that.

My 21-year-old self will always be a part of me. Inspiring me to keep pushing ahead.

To bring the story full circle. My husband and I bought a second home in Breckenridge when we thought kids wouldn’t be in the picture, just wasn’t happening for us. He worked ski patrol in Keystone back in the day and we already covered my moment in CO. Talk about thinking I made it. Back to where my heart was in the mountains. Little did I know my next chapter was just beginning in a way I never thought was possible.

Thank you for listening…”

You can learn more about Leslie here: A frequent speaker on women in tech and IT and marketing trends, Leslie loves inspiring those around her and realizes her opinions and ideas aren’t for everyone – but hopes people take away at least one piece of information that will help them along their own path in life.