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

EPISODE · May 19, 2026 · 47 MIN

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

from Outlier's Edge Podcast with Niiamah Ashong

"I trust myself and I don't trust myself; complicitly. These two are partners in crime keeping you exactly where you are." – Niiamah AshongJoin 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 powerful than any answer. This is what it looks like when a leader stops performing and starts telling the truth.Welcome to the Outlier's Edge Podcast, hosted by Niiamah Ashong, Founder of Outlier's Edge and Sherpa of the World of Difference. On this podcast, you'll join other high-performing unconventional leaders and entrepreneurs (aka Outliers) as they talk about leveraging what makes them different to make a difference in the world.--Check out the video episode on YouTube!--Timestamps:00:00 Welcome and play begins00:53 Gravitas vs heaviness explained05:38 April's two playing fields08:57 Admitting love already happened13:37 It isn't fear — it's resistance18:28 "I don't want to play"22:20 What love actually looks like28:45 The paradox named clearly38:50 Niiamah shares his own paradox42:00 Walking out of the trapFollow Outlier's Edge Socials:Facebook | Instagram | LinkedIn | Youtube | Website | Guild Community

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

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How long is this episode of Outlier's Edge Podcast with Niiamah Ashong?

This episode is 47 minutes long.

When was this Outlier's Edge Podcast with Niiamah Ashong episode published?

This episode was published on May 19, 2026.

What is this episode about?

"I trust myself and I don't trust myself; complicitly. These two are partners in crime keeping you exactly where you are." – Niiamah AshongJoin Niiamah (@niiamahashong) and April Cunningham for a live coaching conversation that goes somewhere...

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