Navigating Life and Career Transitions
How to Move Through Transitions with Clarity and Courage
Life transitions—whether in business, career, or personal identity—can feel like walking a tightrope between who you were and who you’re becoming. You’re not stuck, but you’re not quite free. You’re no longer aligned with the old path, but the new one hasn’t fully appeared yet.
This is the in-between. And if you’re navigating a major transition—quitting your job, starting a business, shifting your identity, or reinventing your career—you’re not alone.
As a business coach, fractional CMO, and advisor to purpose-driven entrepreneurs, I work with people who are right here in this liminal space. They’re craving clarity, confidence, and a roadmap through the unknown.
Here’s how I break down the three stages of transition—and the questions I guide my clients through to help them move forward with intention.
Stage 1: The Ending – Letting Go of What Was
Every new beginning starts with an ending. And endings are emotional—sometimes heartbreaking, sometimes relieving, often both.
You might be here if:
You’re questioning whether your current job, role, or identity still fits
You feel the quiet nudge to release something that once defined you
You’re grieving something you haven’t yet named
Reflective questions for this phase:
Will your future self sleep more peacefully knowing you let this go?
What emotions still need to be felt, expressed, or released before you can move on?
How can you mark this ending in a way that honors it—through ritual, writing, or symbolic action?
Endings deserve to be acknowledged. Without honoring the goodbye, we carry that emotional weight into what’s next.
Stage 2: The Messy Middle – Embracing the In-Between
This is the most uncomfortable phase—and the one most of us try to skip. It’s uncertain. It’s awkward. You’re no longer your “old self,” but you haven’t quite grown into the new one.
You might be here if:
You’ve made the leap… but now feel lost or unsure
You’re doing the work, but nothing feels clear yet
You’re questioning everything and wondering if you made the wrong move
Reflective questions for this phase:
Who can support you with objectivity and compassion without rushing your process?
What hard-won lessons are you taking from the past chapter that are shaping your next one?
If you looked back ten years from now, how might this moment be the very turning point that changed everything?
This is where the real growth happens. It’s not glamorous, but it’s powerful. The messy middle is where clarity is earned.
Stage 3: The New Beginning – Becoming Who You’re Meant to Be
Eventually, something clicks. You’ve released what no longer fits. You’ve sat in the space between. And then—you begin to build again.
You might be here if:
You’re taking your first steps in a new role, business, or identity
You’re finding your voice again, and it sounds different this time
You’re excited—but nervous—to be seen in a new way
Reflective questions for this phase:
Can you allow yourself to be a beginner, even if it means making mistakes or feeling unsure?
What beliefs need to shift so you can show up fully—confident, capable, and evolving?
How can you celebrate your growth as you go, instead of waiting for some final “arrival”?
Beginnings don’t have to be bold. They just have to be real.
A Final Reflection: What Will You Regret Not Doing?
One of the most powerful questions I use in my coaching practice is this:
Ten years from now, what will you regret not starting, saying, or exploring right now?
Anticipated regret is a form of wisdom. It’s your inner knowing trying to get your attention.
Ready to Move Through Your Next Chapter?
If you're navigating a personal or professional transition and want structured support with heart, I’d love to help. Whether you're pivoting careers, launching a new offer, or simply craving clarity, my coaching and advisory work is built for this moment.
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Let’s make the next chapter the one that feels most aligned for you.