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Sydney Guerrette on Life, Lessons & Legacy

We recently had the chance to connect with Sydney Guerrette and have shared our conversation below.

Sydney , really appreciate you sharing your stories and insights with us. The world would have so much more understanding and empathy if we all were a bit more open about our stories and how they have helped shaped our journey and worldview. Let’s jump in with a fun one: Are you walking a path—or wandering?
Honestly, I feel like I’m creating a path, which is a little more labor intensive than walking. For the longest time, my biggest hope was that I would find someone who could help me navigate the journey. But I’ve come to realize that following a map laid out by someone else doesn’t always lead where you need to go, especially if you’re trying to do things differently. At the end of the day, I guess I clearing a path for other youth, expending a whole lot of energy in clearing the way for them to do great things in their communities.

Can you briefly introduce yourself and share what makes you or your brand unique?
I’m a singer-songwriter and storyteller with the band In The Company Of Wolves and I’m also the Founder and President of Be The Change Youth Initiative, an organization dedicated to empowering young people to create positive change in their communities. In both my music and my work with BTCYI, I focus on connecting with people on a real, human level—whether that’s through songs that explore emotion and experience, or programs that equip and inspire youth to take meaningful action. What makes my journey unique is that I see myself not just following a path, but creating one—step by step, learning as I go, and leaving small traces of hope, care, and encouragement for others along the way. Right now, I’m focused on projects that combine creativity, community, and collaboration, helping others discover their gifts and use them to make a difference.

Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. What was your earliest memory of feeling powerful?
For my 15th birthday, I wanted to celebrate by raising $7,000 to grant a wish for a child in Maine through a partnership with Make-A-Wish America. I reached out to members of my youth group, hoping they might join me in supporting this cause. However, when our youth pastor found out about the project he told the other students not to help with the fundraising. Even now, eight years later, it still feels almost unbelievable. At the time, I couldn’t understand why someone entrusted with the responsibility of encouraging and uplifting young people would discourage an act of kindness and service. That experience was confusing and hurtful, but it also taught me a quiet lesson: sometimes the most important support and encouragement has to come from within, and from those who truly share your vision and values. Thankfully, the other students saw the value of this work and together we granted that wish. This was also the catalyst for starting Be The Change Youth Initiative.

Was there ever a time you almost gave up?
At least once a week!

Right now, leading a youth mental health advocacy and youth empowerment organization is incredibly difficult. There are days when the challenges feel overwhelming—balancing limited resources, navigating complex community needs, and trying to reach young people in meaningful ways can feel exhausting. But even in the hardest moments, giving up isn’t really an option. The young people we work with deserve persistence, guidance, and care, and I’ve seen firsthand how small acts of support and encouragement can transform lives. The work is demanding, but it’s also deeply rewarding—every story of growth, courage, or connection reminds me why I started and why I need to keep going, even when it feels like the path is steep.

Next, maybe we can discuss some of your foundational philosophies and views? Whom do you admire for their character, not their power?
As a musician, I really admire Mumford & Sons, as well as Maggie Rogers and Noah Kahan. What stands out to me is how uncompromising they are when it comes to making music—they stay true to their vision, their sound, and their message, even when it might be easier to follow trends or chase commercial success. They prioritize authenticity over popularity, and that kind of integrity is something I deeply respect. It’s a reminder that character often shows itself in the choices we make when no one is forcing us to compromise, and that staying true to who you are can have a far greater impact than chasing recognition or influence.

Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. How do you know when you’re out of your depth?
I’ve been out of my depth since I was 15. At that age, I took on projects and responsibilities that felt way bigger than me—raising funds for Make-A-Wish, leading initiatives, trying to make a difference in ways I didn’t fully understand yet. I still feel that way sometimes, like the challenges are bigger than my experience or my skills. But over time, I’ve learned that being out of your depth isn’t a sign to stop—it’s a sign that you’re growing. You know you’re out of your depth when you feel stretched, uncertain, or a little scared. And the key is to keep moving anyway, learning as you go, asking for help when you need it, and trusting that the work matters even if it’s hard. That’s when real growth—and real impact—happens.

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Image Credits
Justin Brickler

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