You Can't Win If You Need Certainty Before You Start | April Cunningham | Ep 964

Outlier's Edge Podcast with Niiamah Ashong · May 19, 2026 · 47m

"I trust myself and I don't trust myself; complicitly. These two are partners in crime keeping you exactly where you are." – Niiamah Ashong

Join Niiamah (@niiamahashong) and April Cunningham for a live coaching conversation that goes somewhere neither of them planned. April came in talking about dating. What surfaced was a paradox she had never named: she wants adventure, free fall, and full uncertainty in love and that desire is exactly what makes her shut down. Niiamah coaches her through the trap in real time, shares his own version of the same paradox, and leaves her with a question more…