Erin Lydon: From Fear of Failure to Fearless Leadership

• Erin Lydon’s childhood instilled perseverance and honesty, shaping her leadership journey.
• Navigating multiple industries led to embracing challenges, leading with action, setting clear goals, and building strong relationships.
• Erin Lydon champions diversity, pay transparency, and early career advancement for women in leadership roles.
• Confidence, resilience, and continuous learning remain key to driving impact and pushing boundaries.

1. How did your early years shape who you are today?

I grew up in Maine, a small town of 5,000, where everyone knew each other. My childhood in the 1970s and ‘80s was idyllic—we had enormous freedom, riding bikes with friends, sailing along the coast and playing sports. My mother’s family had deep roots in Maine, while my dad, from Colorado, was an outsider. My grandmother was the matriarch of our family, setting high expectations for all of us. From a young age, I had to call my grandparents and read them my report card. Achievement and perseverance were non-negotiable. Academically, I excelled—valedictorian, great colleges—but I feared failure. For 30 years, I avoided risks, trying to meet family expectations over personal growth. When I finally entered startups in 2012, I embraced it. Now, I believe there’s nothing I can’t do. The sooner you get comfortable with risk, the better. I was late to the game, but it changed my life.

2. What core memory has helped you stay true to your values?

My core values of honesty, hard work, and empathy, stay with me. Growing up, I had very strong examples of the importance of serving others and leaving a place better than I found it. I also wasn’t allowed to quit, even when I wanted to. That integrity crystallized while raising my daughters, who are now in college. Seeing them develop the same caring, hard working attitude and resilience shows they came from me, my mother, and my grandmother. True values are passed from one generation to the next. No matter the situation, you already know what to do. Life gets complex, but if you step back and reflect on your values, you’ll know the answer. It may be hard, but listen to your gut, and you’ll know the right choice.

3. You’ve described your career as a “scatter plot.” How has this unconventional journey shaped your leadership and decision-making?

I think “scatter plot” is a great way to describe my professional life. At my 25th Kellogg reunion, I compared my path to my classmates’, whose careers steadily climbed upward. Had I stayed in banking, mine might have too, but I left to raise my children and later pursued new challenges working in startups. I thrive on doing things I don’t know how to do, and once I recognized that as a forte, moving between industries became less scary.

My leadership has always been collaborative. At 25, I led a team while fundraising for Northwestern Memorial Hospital, working with top executives. I learned to listen first, take in ideas, and then drive action with clear steps and metrics. I’m very biased toward action—once a decision is made, I want to achieve measurable goals.

In early startups, constant pivots are necessary—most things fail, but breakthroughs reenergize teams and clarify the path forward. Over time, I’ve become comfortable admitting when I don’t know something and I build teams where everyone’s input is valuable. Leadership means bringing in the best people, trusting them, setting clear goals, and keeping the team focused on the mission.

4. What are some leadership and organizational strategies that help you stay on track?

I have a trait where I become very single minded particularly in the early stages of doing something new; candidly, I don’t do a very good job of having a balanced life, and I’ve accepted this in myself and others. I don’t believe in strict work-life separation. Forgiveness for yourself is important because if you’re like me, you’ll work too much and miss things.

Communicating better on needs, I think, is critical. Asking for help is difficult for me, especially in personal settings, but being open with loved ones makes a difference. Whether it’s delegating the smallest tasks or recognizing when I need space to focus, better communication helps.

I always say that life comes in phases: sometimes focused on work, other times on rest and rejuvenation. Try as best as you can to prioritize what matters most, which we all know is family and health and those good things. I recently took time off, traveled, and spent time with my daughters and parents, but now I’m ready to get busy again. I find joy and confidence in work, so I’ve accepted that my balance won’t look like everyone else’s.

5. How have the industries you’ve worked in evolved in terms of diversity, equity, and inclusion over the past 15 years?

This is personal to me and incredibly important in my work. I started in finance at JP Morgan, then moved into wellness, gaming, and edtech. Across industries, the constant is clear: not enough women are in leadership, decision-making roles, or CEO positions.

The gap starts much earlier in our careers. Women and men enter the workforce in equal numbers, but the first step up to manager around three to four years in, is where men advance faster. It’s not just about motherhood; it’s about early promotions. Women stay in individual roles longer while men get promoted at higher rates. They’re missing chances to manage teams and move toward the C-suite.

Not everyone wants to run the world, and that’s okay. But young women need to advocate for themselves, take risks, and say yes to opportunities. Mentors are great, but sponsors are critical. They say your name in rooms where you aren’t present and decisions are made. Career growth starts with you.

Networking and relationship-building take effort but are worth it. I was given leadership roles beyond my skillset because I built strong relationships. More women are entering male-dominated fields, but the leadership gap remains. Closing it means being visible, gaining access, and seizing opportunities. You need access and opportunities which means building skills, confidence, and having the right people advocating for you.

6. What steps can organizations take to close the gender pay gap, especially in male-dominated industries?

This is so important because we have so far to go. Closing the gender pay gap requires a collective effort. Not just HR, the CEO, or employees, but everyone. Early in my career, I was shocked to learn male colleagues earned significantly more for doing the same role. I blamed myself for not negotiating, not realizing men already knew to ask for more. That experience was an eye-opener. I hadn’t even known a game was being played. But I learned, and made it my mission to empower others so it never happened again.

A major issue is pay transparency. Men talk about salaries, sharing insights over golf or through casual conversations by the water cooler, while women often don’t. Without this knowledge, women don’t know what to ask for. Another challenge is hesitancy to self-advocate. Many assume hard work alone will lead to recognition, but leaders expect employees to speak up for themselves.

When asking for a raise, expect to hear “no.” But no never means never. it just means not right now. The key is following up: “What do I need to do?” Keep asking. Keep proving your value. And don’t forget, if you aren’t being paid equitably, then it’s time to move elsewhere. We need to get paid right, and we deserve it.

7. How can companies foster a positive workplace culture?

Building a positive workplace culture isn’t the job of one person. It’s the whole team, the whole company. The first person who comes to mind is Lauren Fay, a woman I worked with and deeply admired. I’ve hired many women throughout my career and feel responsible for their growth, but some naturally bring positivity into any situation. Lauren was one of them.

In the early days of the startup, with limited funds and many pressing needs, Lauren had a clear sense of what was worth spending on and what wasn’t. But she delivered it in a way that never felt negative, just practical and aligned with where we were as a business. Even over Zoom, during the pandemic, her optimism and energy were contagious.

Energy matters. And I think when you’re building a small company, that’s a critical factor because it’s going to impact everybody else. Leaders matter a lot. You have to always have that passion and enthusiasm for what you’re doing. But you need other people around you who radiate the same positivity. When you find them, keep them.

8. How do you incorporate empathy into your leadership style to better connect with your team?

Empathy, compassion, and the ability to see the world through others are critical leadership traits. I reflect on the pandemic. It was difficult, sad, and lonely. During that time, while building a company, I learned that others have different needs and respond to the world in their own way. That understanding has come with time, especially working with diverse populations.

I think it’s really hard to lead well and not have empathy. You can be financially astute, build a great product, or have a brilliant marketing mind, but leadership is about setting a vision and delivering real impact. If the impact you make is only through your own lens to achieve success, have you really left a positive mark on people?

At the end of the day, what matters most is the impact you leave whether that’s on your team, your family, and the world. We all must keep working at it. Your way of thinking is not the only way and embracing that makes you a better leader and a better person.

9. How do you approach networking and cultivating relationships that support your personal and professional growth?

Networking takes effort. You have to make it a line item in your day or week to build your professional network. You often give more than you get, especially at the start. If you’re a junior, you might wonder what you bring to the table—one of the most valuable things is feedback.

I’ve worked with senior leaders who often surround themselves with like-minded people. A fresh perspective challenges them in valuable ways. If you hesitate to speak in meetings, follow up afterward: thank them, share your thoughts, and offer insights from your position and perspective.

I’m also not a big fan of assigned mentors. It doesn’t work out because you have nothing in common, feels very structured and just doesn’t feel genuine. Instead, seek out people you admire, ask for 15 minutes of their time, and come prepared. 

Follow-up matters. It’s on you to maintain contact. Put yourself where these people are, attend events, engage in conversations, and stay visible. You want people to keep seeing you, recognizing your value, and remembering your name when opportunities arise. Practice your ‘elevator pitch’ so that when someone asks how they can help, you already have a concise and actionable response.

10. What is one value you believe is crucial for young professionals with big aspirations?

Confidence is the first value that comes to mind. It’s a hard answer because so many factors shape a person’s confidence, but I truly believe in its importance.

I think back to when I was four years old, a gymnast, staring at a rope hanging from the ceiling. The six-year-olds were climbing it, and I thought, I can do that. And I did, but when I got to the top, I was terrified. I didn’t know how to climb down. That was my first memory of believing in myself, figuring it out, and pushing through fear.

That mindset has stayed with me. I recently became an advisor to The Bioplanning Institute, where we are building a harmonious and ecological solution to hyperurbanism. I have no background in sustainability and climate change, but I said yes because I believe in the vision and in my ability to learn quickly, add value, and make a meaningful impact. That takes confidence.

But this confidence must be tempered. Overconfidence leads to hubris. I’ve always believed in myself, but I also recognize I can’t do everything and there is much for me to learn from others. The best outcomes usually come from collaboration. Knowing that keeps me humble while still striving to break through the next challenge.

11. What is something you are grateful for, professionally or personally?

I am most grateful for my health. I’ve been a runner my entire life. A sprinter in college, later running marathons, and now sticking to three to five miles a day. Running has always been a constant for me.

As I get older, I see friends facing health challenges. Chronic illnesses, cancer, and it makes me appreciate my ability to stay active even more. Running keeps me mentally sharp and gives me space to decompress. Some people meditate, do yoga, or go to the bar. I run. It’s my quiet time, my way to think. I never run on treadmills; I go outside, even when it’s freezing.

When I run, I solve problems, practice speeches, and clear my mind. I even prepared for my TED talk, Equal Pay: From Head Nodding to Hand Clapping, this way. I told myself, if I could deliver it while running, I could do it on stage. Running makes me feel strong, sharp, and far from middle age. And that’s something I never want to lose.

Erin Lydon’s journey reflects resilience, adaptability, and fearless leadership. From navigating a non-linear career path to advocating for women in leadership, she embraces risk, values honesty, and believes in the power of mentorship and sponsorship. Her passion for financial accessibility and workplace inclusion continues to drive her impact. Whether leading teams, breaking barriers in male-dominated industries, or running to clear her mind, Erin embodies the mindset of lifelong growth. Through confidence, empathy, and action, she not only inspires others but actively shapes a more inclusive and equitable professional landscape.