The intersection of philanthropy and travel with Maryann Fernandez

By Kristen Oliveri 

Success alone does not guarantee fulfillment. Many high performers reach milestones only to realize they are craving something deeper like alignment between ambition, wellbeing and purpose. Jessica Li has built her work around helping leaders close that gap.

As the founder of Align Impact and a trusted executive coach for more than 15 years, Li guides ambitious individuals through pivotal decisions across career, relationships, and wellbeing with a rare combination of analytical precision and human insight. With a background in behavioral finance, psychology, and business economics from NYU Stern, she integrates strategy with intuition to help clients move toward lives that feel not only successful, but truly alive.

In this conversation, Li shares her perspective on alignment, leadership and what it means to live well.

Q: You’ve built a career at the intersection of ambition and wellbeing. What personal experiences first led you to this path of executive coaching?

A: Ever since grade school, I was the person parents, peers, and teachers went to for advice — on academics, focus, balance, and relationships. People would say, “You should do this for a living,” and I’d think, what is this, a hotline?

In high school, I saw a Tony Robbins video and it was like lightning struck. I knew this was who I was meant to be and how I could add value to the world. That desire to help people live their best lives followed me through NYU Stern and into my career in finance. I started coaching quietly behind the scenes, growing through referrals.

Then 2020 hit, and my coaching conversations began to mirror my fundraising conversations. People were sharing their deepest fears, desires, and truths. I kept hearing the same theme: misalignment. “I’m in the wrong job, the wrong relationship, or I put my head down for 10 years and forgot who I was.”

I knew I couldn’t keep hiding this gift. So I founded Align Experience in 2020, my executive coaching platform focused on helping ambitious individuals through bespoke coaching, team work, and transformational experiences.

Q: Your background in behavioral finance, psychology, and business economics gives you a rare lens on human behavior. How does that shape the way you work with high-performers?

A: I’m a blend of traits: IQ and EQ. Masculine energy — focus, results, direction — paired with feminine energy — empathy, intuition, openness. Clients often describe me as East Coast hustle meets West Coast soul.

I look at every client holistically. My work isn’t just about career and purpose — it also includes relationships, mindset, and vitality. A multidisciplinary perspective allows me to untangle complex challenges and pinpoint core drivers. Once we understand how someone got where they are, we can create a clear path toward where they want to go next.

Q: Many of your clients are successful on paper but still feel out of alignment. What does “alignment” actually mean in your work?

A: Alignment is when the way you live matches who you truly are — your values, your purpose, and the lifestyle you desire. When that happens, you come fully alive. I explored this more deeply in my article “The Great Re-Alignment,” which examines why so many people are moving beyond hustle culture and searching for something more authentic.

Q: When someone begins an Align coaching experience with you, what are they typically coming in with, and what do they most often walk away with?

A: Clients come for many reasons related to career and purpose, relationships, or wellbeing. But the common denominator is closing the gap between where they are and where they want to be. While they may think they’re pursuing external goals, they’re really seeking to evolve into a higher version of themselves. They want alignment with their true nature and gifts so they can live a life they’re proud of and deeply enjoy.

Q: You’re known for helping people make pivotal decisions across career, purpose, relationships, and wellbeing. What patterns do you see when someone is ready for real change?

A: It always comes down to courage.

Courage to admit they’re done with their current state. Courage to want more — and believe they deserve it. Courage to seek guidance. Courage to move forward despite fear. And courage to let go of the ego’s belief that asking for help is weakness.

The strongest, most successful people are always learning and evolving.

Q: Your coaching style blends precision with empathy. How do you balance being supportive while also challenging clients to grow?

A: My attention is fully on the client. I notice body language, tone, and energy shifts that often say more than words. When you’re truly present, it becomes clear whether someone needs compassion or a push.

Sometimes I’m the empathetic listener. Sometimes I’m the athletic coach. The balance comes naturally when you’re deeply attuned to the person in front of you.

Q: What makes your approach different from more traditional executive coaching?

Clients often describe me as a one-stop resource for clarity across life — career, relationships, and wellbeing. My coaching is completely bespoke because every person and team is unique. I don’t apply a fixed system or template.

People feel fully seen and understood, and the guidance is tailored to their personality, motivation style, and goals. I also believe joy matters. Learning happens best when people are engaged and energized, so even serious topics are approached with warmth, humor, and meaningful experiences.

Q: How would you describe the energy of an Align experience? What does it feel like to be coached by you or attend one of your events?

A: I’ll let clients speak for themselves:

“Jessica is one of those rare people whose energy lifts everyone around her. She truly sees you. With the right balance of encouragement and tough love, she pushes you forward. In a few months, I became the best version of myself.”

“It felt like a mini personal development workshop — think Tony Robbins-style coaching, but fresh and emotionally resonant. You’re laughing, crying, and learning so much. People leave with powerful insights and real clarity.”

Other guests have described the experience as mind-opening, fun and enlightening, and even “Alice in Wonderland meets self-development.”

Q: And just for fun: what’s your personal superpower, or one thing you do that helps you stay grounded and joyful outside of work?

A: My superpower is helping people discover and own their gifts so they can positively impact humanity. Imagine how incredible our world would be if everyone unlocked their gifts and used them to serve others. That’s the world I wake up to help create every day.