Lessons in Failure, Growth and Resiliency

Walker Tracker Leadership Team (from left to right): Stephanie Green, VP of Business Development; Ben Parzybok, CTO & Founder; Taylor Welsh, CEO & President; Blanca Garcia-Rinder, VP of Customer Success.

Walker Tracker Leadership Team (from left to right): Stephanie Green, VP of Business Development; Ben Parzybok, CTO & Founder; Taylor Welsh, CEO & President; Blanca Garcia-Rinder, VP of Customer Success.

As a little girl, I wished to be a ballerina when I grew up. Then, a nurse. Then, a teacher…and on and on. These were the women I looked up to, the footsteps I thought I should follow.

Never in my wildest dreams did I imagine I’d be the leader of a company, let alone a CEO working in tech.

When I look back on this journey, there is one thing that made it possible: resilience. I cannot stress enough the importance of being persistent through adversity and learning how to bounce back after (inevitable) failures.

The ups and downs as a revenue-funded tech company were enough for me to think about jumping ship more than a couple of times. It’s never been easy. It’s been trying, it’s been fun, but never easy. Between bouts of imposter syndrome and chronic sleep deprivation — the truth of the matter is that it’s not at all glamorous. It’s uncomfortable, ugly, exhausting and defeating, and that’s just typical for a CEO. Being a (relatively young) female CEO in tech comes with even more challenges. When I leave the comforts of my office (where women make up over 50% of our team and 75% of our leadership team), I experience the extreme loneliness that is this role.

Below are five of the most important lessons I’ve learned in my time as CEO. I hope these will reassure you, be useful in your journey, or inspire you!

1. Learn how to be comfortable in uncomfortable spaces.

Outside of my office, I find I’m often the only woman in the room. I don’t seek out events particularly to find gender parity. I seek spaces that interest me and will be useful to my business, and as it happens, these spaces are dominated by men. No matter what every other person in that space is actually thinking, I immediately assume they’re questioning, “Is she lost?” That’s a really hard place to start from if you want to ask questions, seek advice and altogether be taken seriously. Building a shield of confidence (real or not) and letting go of fear is imperative. Hey, what do you have to lose? Not near as much as you have to gain!

To get to this place, I recommend Mark Manson’s book The Subtle Art of Not Giving a F*ck; while it may lack elegance, it offers some valuable insights on living your life more freely.  As a culture we are stunted by the chatter of our monkey minds (negative self-talk, attachment to our fears, and deep concern about how others will perceive us). I find myself here often, and reading this book was extremely useful. It stirred me to pose my “dumb“ questions, ask for advice that I should probably already know and chime in with my two cents. So far, this has been an amazing way to learn. Before I walk in to any room, I take a moment, stand up tall (power posing is no joke, people!), let go of any self defeating mental clutter and walk in like I own the space. Who is going to take me seriously if I don’t?

I’m not suggesting you stop caring about how you show up in the world, because that is so very important. I’m suggesting you give yourself the gift of letting go of all the preconceived thoughts, assumptions and judgements you place on yourself — even if just for a moment. The more you practice this, the easier it gets.

2. Have conversations that terrify you.

Stress and anxiety squash creativity and disable us from speaking our truth with confidence. When I feel threatened, it’s hard to be inspired. I also tend to ramble when I’m nervous. The narrative in my head goes a little something like: “Taylor, shut up, stop talking, you’re digging yourself deeper. Oh my gosh, what did you even just say? Why are you talking about spaghettification now…?” (true story).

Joking and rambling aside, I’ve used a few tools to make myself more comfortable having these conversations:

  • Let them speak. Listening, you can gain insight. People like to be heard, and generally if they spoke up in a meeting, they will walk away feeling good about how it went. This one is entry level and may help you get to the place where participating feels more comfortable. Be an observer first, then a participant when you’re ready.

  • Prepare, read, research. Come with questions and/or objectives.

  • Be unapologetically you. You can’t go wrong with being yourself. If you don’t connect with the audience, it probably wasn’t meant to be. You won’t be everyone’s favorite flavor, and being OK with that will set you free.

  • Don’t settle for manterruptions. Men interrupt women at a higher frequency than they do men — 33 percent more according to a study done at George Washington University. Here’s a link to 7 other studies that examine this. It’s not just men; we all interrupt, so come prepared to redirect. Either be OK with them taking over the conversation or finish your thought, even if it means speaking over them. Decide how you’d like to assert yourself (it may not be the most important thing to finish your thought on spaghettification, but it also may be just as important you let them know that you won’t be interrupted).

3. Get over your ego for the sake of learning.

At the beginning, I had a hard time admitting I had no clue what I was doing. I was on a mission to prove myself. I quickly learned that you cannot fake this. I had to fail to grow. Once I started asking the “stupid” questions, I started solving problems. The best thing I’ve done this year is make a fool of myself for the sake of learning. So don’t be afraid to say “no” when someone asks if you’re following or if you understand. Clarification is king (or queen). One short question now could save you a whole lot of pain down the road.

4. It doesn’t get easier, you just get better.  

It’s hard not to focus on what we should have done better and what we hope we can do in the future. Don’t get me wrong. It’s imperative to learn from the past and to plan for the future. But don’t think that just over this hill things will level out.

Once we have X, everything will be better.

After client Y is onboard, we’ll have the revenue to do all the things.

Hiring Z will make all our lives easy.

After XYZ, you will find there is another mountain for you to climb, bigger than the one you just ascended. Take solace in the fact that you are better prepared for each challenge you face every time you conquer the previous one. Yes, plan for the future (duh) and learn from the past, but don’t forget that life, creativity, and genius are happening right now.

5.  You’re already enough.

You may have a lot to learn. We all do. It’s exciting to listen to inspiring entrepreneurs, take notes from their journey and apply tips to your own adventure. But don’t forget that last part: this is your own adventure. No one can do it for you, no one can make it like you will, no one will care as much as you do.

Don’t get so caught up in trying to be like your heroes that you forget who you are.

Be wild, get comfortable with being uncomfortable, and be unapologetically YOU! Don’t forget that making a fool of yourself along the way is not only inevitable, but part of growth.

Taylor Welsh is the CEO and President of Walker Tracker, a platform that enables organizations to build a culture of wellbeing through wellness challenges, team building, and social engagement. She is passionate about creating equity in wellness and making healthy behaviors accessible and fun. Find her on LinkedIn or follow @walkertracker on Twitter.



Megan Bigelow