The ONE question that changed everything for me
And gave my clients the clarity they’d been searching for.
In August 2024, I was knee-deep in planning a summit for my nonprofit…
balancing a demanding full-time job…
mothering a toddler…
and still beating myself up for not scaling the one thing I truly cared about:
Coaching.
That year, I had only coached four people.
I knew I wanted to do more, but every passing day made it feel even more impossible.
My life felt like it was moving in every direction at once, and I couldn’t imagine adding one more thing to my plate.
Then one day, I decided to take a break from my typical WFH routine and work from a co-working space.
And that’s where I met Oba (a gentleman in his mid-forties).
I’d noticed him earlier. He sat a few metres away - calm, focused, intentional.
When we finally got talking, what started as a quick “hi” turned into a deep 2-hour conversation about life, work, and everything.
He had just left his 15-year career as a Learning & Development Director to build his own thing.
So I finally admitted how much I also wanted to build my coaching practice but kept pushing it down the priority list.
He listened. Then he said:
“You’re acting like you’re afraid of your own success.”
And it stopped me.
Then he asked me one question - the same question I’m now asking you:
“Think a year from now. Picture your ideal life. What’s the one thing you’ll regret not doing?”
That question became a compass for me.
And it made me appreciate something about my own meandering career journey:
I know what it feels like to want more but feel stuck. I’ve walked through the same uncertainty my clients face.
And I deeply want more people to succeed - to stop settling and start building a career they’re proud of.
That moment with Oba is what pushed me to set a bold goal:
Help 120 people in one year.
Today, I’m at 100+, through quick 1:1 sessions and group AMAs - supporting people who, like me back then, were standing at the edge of clarity but afraid to jump.
And as we close out the year, I’m hosting my final live AMA session on November 29th - a space for anyone who’s ready to face the uncertainty they’ve been avoiding.
30 seats only. 4 left.
If you’ve been waiting for a sign, this is it.
In my AMA, we’ll dig into honest, practical conversations around:
Finding clarity when life feels unclear
The four pillars of a fulfilling career
Making courageous career decisions
Repositioning your skills with confidence
And the mindset shifts that help you grow with intention
🎟️ Reserve your spot here → wamide.com/ask-me-anything
Want to go even deeper? Here are two more ways to grow:
1:1 Career Coaching – Ready to transition but not sure where to start? Book a career transition coaching session and get the clarity, strategy, and confidence you need to make your next move - without the overwhelm. Apply for coaching.
Personal SWOT Workbook – Not ready for coaching? Start here. Use this self-paced workbook (trusted by 300+ professionals) to assess your strengths, weaknesses, opportunities, and threats - so you can make smarter moves and stop guessing your next step. Download the workbook.
Till next week,
Keep growing 💜