From Hats to Heartfelt Advice: Takeaways from a Fireside Chat with CISO @ Crocs

I recently had the opportunity to sit down for a fireside-chat–style event in beautiful Denver, Colorado. Truly, the city is absolutely stunning. I had only been once before for a conference, but as we all know, when you are conferencing you are unfortunately often bound to the convention center or whatever hotel is hosting the event. Regardless, the combination of company, location, and conversation made this one of my favorite events I have had the pleasure of participating in to date.

It took place at the very unique Rancher Hat Bar, which gave attendees the ability not only to chat over snacks and drinks, but also to complete an activity together: choosing and designing their own cowboy or rancher hat. It was so fun for both men and women alike. Although this was a “Women in Cybersecurity” event hosted by Seemplicity, we were joined by several of our male allies as well. Including them in the conversation is so important.

The highlight of the night, and what the event was centered around, was my conversation with Lena Taylor, the Chief Information Security Officer at Crocs. And as you might expect, she showed up rocking the coolest pair of Crocs I have ever seen, a platformed black pair adorned with charms and chains. I knew right away the conversation was going to be awesome because clearly, she was. The event was truly electric. People who walked in shyly, not knowing anyone, were hugging and laughing by the end of the night.

For those of you who could not make it all the way to Denver to join us at the hat bar, I wanted to share some of the key points Lena made during our conversation, or at least the topics that really resonated with me and that I am still sitting with now. Enjoy!

Grounding Yourself in What Really Matters

Even though this was one of the last things we covered, I feel compelled to start with a book recommendation Lena shared. The book is titled Ikigai: The Japanese Secret to a Joyful Life.

Ikigai explores the Japanese concept of having a reason to get up in the morning, how a meaningful life comes from blending what you love, what you are good at, what the world needs, and what actually pays the bills. The authors spend time in Okinawa, where it is normal for people to live well into their 90s and often past 100, and they highlight the everyday habits that help people stay healthy and happy for so long. The book embraces slow, steady routines, staying connected, moving your body, and doing work that feels natural. It has a warm, easy vibe that nudges you to pay attention to the small things and build a life that feels meaningful in your own way.

Man, that is beautiful. In a culture where we are inundated with lists of things to do and things to buy, we cannot forget to slow down. Our minds and bodies will thank us.

You Are Absolutely Capable, But Be Real With Yourself About Timing

Since entering the corporate world, especially as a woman, a mother, and a manager, I have heard about the elusive concept of work life balance for my entire career. The “Lean In” movement made it an even hotter topic. When Lena was asked about work life balance, or more poignantly how she knew it was the right time to go for it, I loved her take and respect her so much for it.

I am summarizing, but essentially she said this: when you are given an opportunity, take stock of what you have going on in your life and be honest with yourself about whether now is the right time. For example, if you are in a season of life where you are raising young children, pursuing higher education, or caring for an elderly or sick family member, ask yourself whether you are truly in a position to take on more responsibility at work. And if you think you are, ask yourself if you are comfortable with the reality of adding more stress, and to be real, burden, to your existing situation.

It is okay if the answer is no. Sometimes the answer is not “never,” it is “not right now.” Opportunities often appear at inconvenient times, but we have to be honest about whether they are worth the potential impact on our mental and physical health.

In Lena’s case, she said she could never have done the job she is doing now when her children were young. But now that they are older and have flown the nest, it is the perfect time for her to lean into her career and give more of herself to her work. I love this. Sometimes just hearing someone say out loud that it is okay to say “not right now” is cathartic. We do not have to be cut-throat or relentlessly ambitious in every season of life. That does not mean we are not doing an excellent job where we currently are, but it is okay to be content with the status quo for a little while. Give yourself grace. We are not all built the same.ol.

Find Advocates and Use Them

No matter what gender you identify with, Lena emphasized the importance of finding mentors and advocates along the way. Yes, it is valuable to have people you can call to vent to or get advice from. But also find the people who will go to bat for you. The ones who will open doors, bring you opportunities, and take meaningful action to include you in conversations and roles. Those who will give you a seat at the table.

Most of us have one, maybe two if we are really lucky, people we can look back on and say, “They helped me get my big break. They helped me get my foot in the door so I could pry it the rest of the way open.” And if nobody comes to mind yet, that is okay. It is coming. I am confident of that. 

Learn to make the most of the relationships people are able to offer you, and maybe even more importantly, when you have the opportunity to do the same for someone else, take it. Life is so much more meaningful when we look out for others and share success with the rest of the table.

Summary

Nights like this are such a good reminder of why these kinds of gatherings matter. Most of us spend our days heads-down, juggling deadlines, solving tough problems, and carrying a bunch of responsibilities no one else ever really sees. But when you get a group of people together who are willing to be honest, open, and generous with their experiences, it hits differently. It fills your cup in a way no Slack message or Zoom call ever could.

What Lena shared wasn’t just career advice, it was real-life wisdom. Slow down. Check in with yourself about what you can actually take on. Let people support you. And when you get the chance, be that person for someone else. If we hold onto even a couple of those ideas, I honestly think our work and our lives will feel a little steadier and a lot more connected.

I hope some of this gives you even a fraction of the inspiration we all felt in that room. Here’s to more conversations like this, more community, and more moments where we lift each other up.