ADULT GAP YEAR SERIES: The Courage to Change Your Path With Lori Stephenson

Michelle Dittmer
May 31
2 min read

Michelle spoke with Lori Stephenson, a career coach and leadership developer, about how to navigate life's transitions with curiosity and courage. Drawing on her own career pivot and years of coaching experience, Lori shared practical tools for self-reflection, reframing fear, and taking meaningful action toward change.

About Lori

Founder of My Big Sky — supports students, mid-career professionals, and those approaching retirement
Background in leadership development, career coaching, and career transition
Former communications and talent development professional at Accenture
Coaches individuals on self-awareness, career direction, and how to lead others

Key Themes

Knowing Yourself Before Making a Move

Lori encouraged people to dig into three core areas before pursuing change:

Interests — what keeps showing up that you genuinely enjoy?
Capabilities — what are you actually good at, separate from what you like?
Environment — where do you thrive? Who do you need around you? Do you prefer collaboration or independence?

Self-Reflection Questions to Get Started

What were my peak moments over the last 10–15 years — what was I doing, who was I with?
What energizes me? What do I dread?
What do people continually thank me or recognize me for?
How do I want to contribute?
What am I putting off or waiting for — and do I really have to wait?

Practical Tools

Do a peaks and valleys exercise across your career
Write everything down — get it out of your head and onto paper
Use AI or psychometric tools to help spot patterns you might miss
Look for non-negotiables — things you will never compromise on again
Pick one small action, give it a deadline, and find someone to hold you accountable

On Fear and Discomfort

Lori referenced the work of Susan David (Emotional Agility):

"Discomfort is the price of admission to a meaningful life."

Fear is often a signal to pause and consider — not a reason to stop
Challenge the stories you tell yourself about why change is impossible
Be selective about whose input you take in — limiting perspectives often come from other people's fears, not yours

Moving from Thinking to Action

Stop waiting to have it all figured out
Go from big thinking → distilled insights → one concrete step
Connect with people in person — buy someone a coffee, ask questions, get out of your own world
Ask yourself: If time, money, and approval weren't factors, what would I be doing?

Lori's Personal Story

After 10 years at Accenture, Lori felt misaligned and burned out. She proactively put herself on a restructuring list, took 12–18 months to recover and reflect, and used that time to discover her passion for career coaching. She describes it as one of her proudest decisions — and proof that you don't need to have the full plan before you take the first step.