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 easierCheck out these resources we mentioned during the podcast:Forgotten Wisdom BooksFor more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player.Hosted on Ausha. See ausha.co/privacy-policy for more information.