We caught up with the brilliant and insightful Megan Gilmore a few weeks ago and have shared our conversation below.

Megan , thanks for joining us, excited to have you contributing your stories and insights. One of our favorite things to brainstorm about with friends who’ve built something entrepreneurial is what they would do differently if they were to start over today. Surely, there are things you’ve learned that would allow you to do it over faster, more efficiently. We’d love to hear how you would go about setting things up if you were starting over today, knowing everything that you already know.

If I were to start over today, knowing what I know now, I would focus less on efficiency and profitability and more on key performance indicators for collective well-being, wholehearted reciprocity in partnerships, and developing curiosity and a growth-mindset around decolonizing my organization’s systems and processes and equitable, accessible practices and spaces. I would also focus on developing unique rhythms of care, support and accountability for myself and my team based on our needs, personalities, and preferences. While I think there is always room for growth and development in both of these areas, it makes our work more dignified, compassionate, efficient and sustainable long-term to start with a great foundational place to function.

Megan , love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

Since I was a young child, I have been drawn to alleviating suffering and developing potential in the world around me. I had three near-death experiences by the time I was 16 and grew up as the oldest of five children in a home that cultivated a deep sense of responsibility for how my character and actions impacted the world around me and a beautiful appreciation for my own creativity and leadership pursuits. I was the first person in my family to graduate from college and then to go on to graduate school and graduate there as well. I studied, researched, and worked in the fields of psychology, leadership studies, and addictions counseling in the 2000s. During this time, positive psychology was developing a robust amount of research and seemed incredibly hopeful to me as a methodology for both alleviating suffering and moving toward flourishing by partnering with people to reach their own goals by developing their potential. I pursued my international certification as a professional coach, and my life has never been the safe. After working and teaching in higher education for 5 years, I knew it was time to move into my community and apply these principles and practices to real problems in the real world in challenging places – because what good would it be if this stuff only worked for the most privileged and elite? I started a private coaching practice that quickly grew through client referrals and expanded into a coaching collective agency with four professional coaches who then built an incredible certified coach training program with me – and Lark’s Song was born.
Lark’s Song LLC was established in 2013 and became Lark’s Song Inc. (a 501(c)3 non-profit organization) in 2015. Our vision is to courageously co-create a more fulfilled and flourishing world by activating our mission to provide excellent and evidence-based educational programs and services in well-being education, certified coach training, and culture care. We have been celebrating a lot lately as we hit the 10-year mark on several programs and accomplishments.
As far as our programs and services go, I think I am most proud of our work cascading cultures of well-being with brave and bold organizations that bring us in to advance their staff and processes through curriculum development, team coaching, and leadership training. My favorite things that we do on a regular basis are 1) our Lark’s Song Certified Coach training program which participants consistently say not only prepares them as competent, excellent coaches but also transforms their lives personally, 2) our Made Wild wilderness coaching excursions, and 3) our 5-day Superhero Camp for 5-10 year olds.
But even more than that, I’m proud of HOW we do the work we do. The community that has emerged at Lark’s Song over the past 10 years is more beautiful, skillful and supportive than I ever could have imagined was possible. We are committed to doing this work together in a way that supports each other’s mutual flourishing through “powering with” — and while that requires a great deal of creativity and listening on a regular basis, we get so much further together as a result. Our clients and colleagues are now stretch over the North America and are located in four other continents and multiple cultures.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

I used to believe that my worth as a person was inextricably linked to the success of my professional pursuits and the meaningful impact that I could make on the world as one person. I felt like it was my responsibility to prove my worth as a person, a friend, a team member, and a leader in some way or another – so I did not want to be in the same neighborhood or township with failure. Two mentors spoke into my life in ways that I will forever be grateful for.
The first mentor moment occurred back when I was working in higher education, I led a team of coaches, professors and researchers that served the students on campus that were unclear on their course of study. We invested in these students lives to help them find clarity and a resonant academic path forward. We were getting ready to send some team members on for some intense and expensive training, and I told my supervisor that we should send two other team members – not me. He was curious about this and asked why I wouldn’t be the first one we should send. I told him that I wasn’t sure how long I would be working at the university, and it might not be the best return on investment if they sent me. His response floored me. He said, “Megan, we don’t invest in you so we can see the return. We invest in you because we are confident there will be a return – whether we get to see it here or not.”
The second mentor moment occurred after I start Lark’s Song and was grappling with whether or not we should start a massive global education initiative in the Chilanga district of Zambia, Africa or focus on growing our coach training programs here in the Midwest of the U.S. the initiative was risky and scary and frankly, a pivot in our primary focus as an organization that was going to cost us a lot and be difficult to explain fully to stakeholders and partners. Sticking with what we started with and focusing on growing that was easy to explain, had a lot of support behind it already, and while challenging, wasn’t risky or scary. I was in a state of overwhelm and anxiety when I met with my mentor, really uncertain about what the “right” decision was. She asked me two questions, “Well, Megan. Are you more afraid of failure or regret? And, if you could choose, what do you want to be more afraid of?” In that moment, and from then on, I wanted to be more afraid of regret.
While the limiting beliefs around proving myself and my worth being tied up in my performance still pop up here and there, I have learned so much and gained so much freedom from leaning into pursuing failure experiments as an opportunity to learn and trusting there will be a return on my investment of resource and energy – whether I get credit for it or get to see it or not.

What’s been the most effective strategy for growing your clientele?

The most effective strategy for growing our clientele has hands-down been relationship-based referrals. While there are a lot of people that find us in a variety of ways, well over 50% of our clientele finds us because they hear a story from someone they trust about the impact that Lark’s Song has had on their life, their team, or their business. We have tried to pay attention to this and lean into it as a strength by growing referral benefits, investing time in our current community, and following up or continuing to offer valuable resources to our past clients, as well.

Contact Info:

• Website: https://www.larkssong.com
• Instagram: @larks_song
• Facebook: https://www.facebook.com/LarksSong
• Linkedin: https://www.linkedin.com/company/lark’s-song-inc-/
• Youtube: https://www.youtube.com/LarksSong

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