251: 10 Lessons I Wish I Knew 20 Years Ago: Elisabeth Bykoff’s Advice for Women in Leadership

What if the only thing standing between you and the career you dream of… is the belief that you're not ready yet?

Far too many brilliant women delay bold moves, silenced by doubt or the weight of invisible barriers. In this powerful episode, Elisabeth Bykoff—seasoned consultant, startup leader, and now founder—opens up about the 10 game-changing lessons she wishes she knew two decades ago. From navigating bias in male-dominated industries and silencing self-doubt, to building a strong network of mentors and allies, Elisabeth shares the candid truths behind her leadership journey, the confidence she had to cultivate, and the bold decisions that changed everything.

“If you are thinking about making a change, do it. Find help and support. Don't be afraid.” — Elisabeth Bykoff

What You’ll Learn in This Episode:

• Why confidence is a career skill—and how to build it before you feel ready
• How Elisabeth navigated bias and found allies in male-dominated spaces
• The critical role of mentorship and allyship for women in leadership
• Her advice to her younger self—and how it can accelerate your growth
• What it takes to confront self-doubt and make high-stakes career moves
• How she transitioned from corporate operator to first-time founder
• The mindset shifts that helped her stop second-guessing and start owning her path
• And more!

Navigating doubt doesn’t mean eliminating it—it means moving through it with power and purpose.

🎙️ Let’s chat about breaking barriers and making bold career moves. If you’re a woman navigating leadership—or aspiring to—this episode is your blueprint for moving forward with confidence.

**Useful links**

• Connect with today’s guest and sponsor, Elisabeth:
  • Visit Boxsy:  
    • https://www.boxsy.io 
    • https://www.linkedin.com/company/boxsy
  • Connected with Elisabeth on LinkedIn: https://www.linkedin.com/in/elisabethbykoff 
• Elisabeth’s current read: Mythos: The Greek Myths Retold by Stephen Fry
• If you are ready to uplevel your career, get unstuck or you are simply ready to unlock those leadership time-management techniques then join us in my monthly career & leadership coaching program exclusively for women in tech: https://www.tonicollis.com/academy 
• Catch the show notes, and more details about today's episode here: https://tonicollis.com/episode251 
• Check us out on Youtube.
• Join the Leading Women in Tech community in Slack where we discuss all-the-things for women’s tech leadership, covering everything from early-career leadership to C-level executives.