Chosen Suffering: Make Sales Feel Easy Through Hard Life Habits

Stephen Clifford (Cliff), Managing Director of East Coast Client Partnerships at Infillion, thinks a lot of sales professionals spend too much time behind a screen — and not enough of it getting in front of their clients.

Cliff shares how creative outreach (like a game of pickleball) and empathy-driven approaches can help sellers connect with even the toughest decision-makers. He also discusses the importance of asking tough questions, managing rejection, and balancing healthy paranoia, grace, and humility in a high-stakes career.

Tune in for practical advice and powerful anecdotes from a sales veteran who knows how to turn connections into long-term partnerships.

Join us as we discuss:

• [4:00] Building a long-term relationship by getting whipped in pickleball 

• [14:37] How being too nice can backfire in sales meetings

• [19:24] Approaching sales relationships with a pizza delivery mindset

• [26:40] Why Cliff does hard activities to make sales feel easier
  

Check out these resources we mentioned during the podcast:

• Forgotten Wisdom Books
  

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