Jackie Leon: From Borders to Breakthroughs

How one woman’s journey through displacement, loss, and reinvention became a calling to guide others through their own turning points.

Jackie Leon never set out to become a coach. Her path wasn’t paved with strategy decks or five-year plans—it was shaped by quiet resilience, cross-continental moves, and a deep reverence for the human experience. Born to a Hong Kong Chinese father and a Guatemalan mother, Jackie’s life has been a tapestry of cultures, transitions, and hard-won clarity. From arriving in North America on forged papers to building and rebuilding businesses, navigating grief, and raising two visionary daughters, her story is one of fire, freedom, and fierce compassion. Today, through her coaching practice, she creates space for soul-led leaders to realign, reflect, and rise. This is not just her journey—it’s an invitation to come home to yourself.

What inspired you to move from engineering and control systems into Transformative Coaching and personal growth?

It’s been a 44-year journey, shaped by life’s ups and downs. I didn’t call it coaching back then, but I’ve always loved being with people, hearing their stories, supporting their growth, and walking with them through moments of change.

Even in technical roles, I was never just focused on systems or performance. I formed deep connections with the people I worked with. I’m a soul person.  I feel things deeply, read people easily, and create space for honest conversations. That came naturally, long before I had language for it.

Engineering alone never fulfilled me. It sharpened my mind, but it didn’t feed my spirit.

Over time, those deeper moments became the work. Coaching wasn’t a pivot, it was a path I’d quietly been walking all along. Today, I still bring my engineering mind, but what drives me is helping people find alignment, truth, and the courage to lead from who they are.

Was there a moment in your life when everything shifted—when you knew things had to change?

There wasn’t one single moment, but there was a season where everything became undeniable. I had spent years showing up for my relationship, for my family, for our shared life. And yet, I felt stuck. Uncomfortable. Not just with my circumstances, but with myself.

I kept asking, “Is this it? This can’t be it.”

Deep down, I knew I wasn’t living the life I was meant to live. I didn’t accept my situation. I couldn’t. Something in me needed to break free.

I’m someone who carries a lot of love, energy, and courage, but over time, I felt myself dimming, dying bit by bit.  Not because I stopped being me, but because there was no longer room for me to exist as I truly was. I asked for support. I tried to hold it all together, as a mother, a partner, a woman quietly longing to return to her purpose. But the help I needed didn’t arrive in the way I hoped.

And I realized, we were moving in different directions. He was growing, and I was standing still.

Then, in 2023, our family business collapsed. We lost our home. And as painful as it was, I felt something unexpected: relief. A quiet, sacred breath. It was as if life said, “You’re free now.”
That collapse wasn’t just an ending. It was a beginning. It permitted me to start over, not from fear, but from truth. To reclaim my life. To live on my terms. Fully awake. Fully myself.

You’ve lived across different cultures. How has that shaped who you are today?

It’s shaped everything. I was born into a rich blend of cultures, Hong Kong Chinese and Guatemalan, and raised across continents, languages, and traditions. I’ve lived in New York City, Montreal, Paris, Hong Kong, and London, each place expanding my perspective, deepening my appreciation for diversity, and adding another layer to how I see the world.

From an early age, I felt at home in difference. I’ve always been drawn to people, to their stories, their rituals, their ways of loving and connecting. Inclusivity isn’t something I had to learn; I was born with that spirit. My heart has always been open.

Growing up, our home reflected those values. My father would often say, “Where two can eat, three can eat,” and we lived by it. Everyone was welcome. We were taught to share, to respect, to celebrate the richness of others and to love, freely and fully.

That spirit is at the core of everything I do today. Whether I’m coaching a client or meeting someone new, I lead with curiosity, warmth, and a deep reverence for each person’s lived experience. Culture, language, and faith inspire me, always have, always will.

What do you think people are searching for when they feel stuck or burned out?

Burnout is very real and it wears many faces. Sometimes it comes through life-shifting events like immigration, illness, loss, or the collapse of a business. Other times, it’s the slow erosion of daily responsibilities that feel misaligned, monotonous, or invisible. Both can be equally exhausting. Both deserve to be acknowledged.

Whether someone is crossing borders undocumented or showing up to a job that drains their spirit, the weight is real. The external circumstances may look different, but the longing inside is the same.

At the heart of it, people are searching for something simple and deeply human:
Their purpose.
Themselves.
To be seen, accepted, and loved.

Where you are physically is just geography. The real journey is the one between your heart and your mind.

How do you help someone reconnect with themselves when they’ve been in “go mode” for so long?

It takes time. It’s a process, one that asks for patience, love, and care. When someone has been in “go mode” for too long, there’s often a quiet sense that something’s off. They feel depleted, overwhelmed, disconnected. That constant motion isn’t natural, it’s noisy, eroding, and unsustainable.

So the first thing I offer is space. Space to pause, to breathe, and to simply be. Then presence. Sitting with them and saying, I see you. I feel you. You’re not alone. Let’s do this together. I believe in you.

And maybe most importantly, I hold the vision for them, that it’s possible. That they’re not broken or lost. That there’s another way to live, one that feels more true, more grounded, more whole.

We all go through these seasons. Crossroads are part of being human. And when we stop resisting them and begin to welcome new possibilities, something shifts.

Because life is bigger than all of this.
Bigger than the hustle. Bigger than the pressure to keep going.
Life wants to meet us somewhere softer, more honest, more alive.

What does real success mean to you now?

I have the best transformative life coach who reminds me how powerful it is to be accepted, fully, honestly, for who you are and who you are not. That presence opened something in me. It gave language to a truth I’ve been living into for a long time:

Real success, to me now, means being able to accept someone for who they are and who they are not.

It’s not easy. It takes presence, maturity, and a soft kind of strength. But that’s the stage I’m in, learning to live and lead with that kind of depth.

Success means treating everyone with the utmost respect. It means standing in my values, honoring my boundaries, and showing up as a human being who can inspire, uplift, and remind others that life is still beautiful, even when it’s hard.

It’s the message I most want to leave for my daughters:
To lead with love.
To see people for who they are.
To stay curious, to listen deeply, and to honor connection.
To remember that relationships, not achievements, are the most meaningful part of life.

I’m grateful to my coach for reflecting that back to me so clearly, his presence reminds me of the kind of leader I strive to be.

Because real success isn’t about status or striving.
It’s about how we live, how we love, and how we walk beside others while they find their way.

What have you learned about starting over, personally or professionally?

I’ve had to start over many, many times, across cultures, countries, careers, and seasons of life. At this point, I often say I’m fluent in the language of starting over.

For a long time, I did it unconsciously, responding to change instinctively, automatically. But now, I’m working toward doing it consciously. I want to master how I start over, so I can teach it clearly and offer others a simple, human roadmap to navigate their own transitions.

Because starting over isn’t a single moment, it’s a journey with many phases. It begins with a loss, often uninvited. Then comes the transition phase, the in-between, that messy, disorienting stretch where everything feels up in the air. That’s where people tend to feel lost, impatient, uncertain. But eventually, the new beginning arrives. The fog starts to lift. And we begin to see what’s possible again.

Starting over takes strength, perseverance, and a whole lot of compassion. You can’t do it all at once. You have to break it down, one step at a time, one breath, one day. And most importantly, you never do it alone.

There’s always someone, a guide, a friend, a stranger, a transformative life coach, who offers you direction, or presence, or simply believes in you when you can’t yet believe in yourself. Don’t be afraid to ask for help. We are meant to rise together.

What’s one thing you wish more leaders understood about true, lasting change?

I wish more leaders understood that real change is not only possible, it’s inevitable when we allow it. But it’s not instant. It takes time. It unfolds in phases. And each phase has its own purpose.

Change often begins with something situational, a shift in circumstance, a loss, a new opportunity, or a disruption. But that’s just the surface. What follows is the transition period, the psychological part, the messy middle, the part we rarely talk about, but where most of the transformation truly happens.

It’s the in-between, where things are uncertain, where identities are shifting, and where old frameworks no longer fit. It can feel disorienting, but it’s also incredibly fertile. Because when everything is up in the air… anything becomes possible.

That’s the beauty of the transition phase. It’s not about control. It’s about presence, patience, and permission to not have it all figured out. True, lasting change happens when we stop trying to force a clear outcome and instead allow the next version of ourselves, our work, or our leadership to emerge.

What does it look like when someone leads from a place of alignment?

When someone leads from alignment, people feel it. There’s a quiet strength, a grounded presence that draws others in, not through force, but through truth. People listen. They follow. They mirror that energy. They rise with it.

Alignment brings clarity, not just for the leader, but for everyone around them. Communication is cleaner. Decisions are clearer. Even the hard choices feel honest and necessary, because they come from a place of deep inner truth.

Martha Beck speaks beautifully to this. She says that when we’re in integrity, when our thoughts, actions, and words are in harmony with who we really are, everything begins to flow. We stop resisting life, and life stops resisting us. From that space, leadership becomes less about control, and more about coherence.

Aligned leadership builds trust. It creates safety. It’s expansive, it opens up space for people to share openly, to try without fear, to grow and flourish. It invites others into their own alignment, without pressure or performance.

And in return, your life, your business, and everything around you grows, not through effort alone, but through truth, trust, and connection.

For someone standing at a crossroads, unsure of what’s next, what would you say to them?

I would say: You are never alone. And it’s okay to feel everything you’re feeling right now. All of it is valid, the fear, the confusion, the hope, the grief, the relief. Crossroads are emotional territory. They ask you to stretch, to choose, to grow.

So be courageous. Make a decision, any decision. Even if it turns out to be the wrong one, it doesn’t matter. You can always course-correct. Life is fluid. What matters is that you don’t stay stagnant. Keep moving forward, even if it’s just one small step.

Doors will open. The fog will lift. But motion is what calls clarity forward.

And whatever this moment is asking of you, whether it’s terrifying or liberating, trust that you’ve been given it for a reason. 

Life, God, the universe, however you name it, handed you this threshold because you are capable of walking through it.

You’ve got this. Keep going. Your next chapter is already waiting for you.