Why Success Makes Dating Harder Than You Think

Why Success Makes Dating Harder Than You Think

From The Journey Podcast by Zachary Cummings, Jake Moscato, and John Scafiddi Jr.

May 4, 2026 · 1h 4m · Episode 193

About this episode

This episode explores the challenges of dating as a successful individual and the impact of wealth on happiness and relationships.

Why does dating get harder the more successful you become and does money actually make you happier? In this episode, we break down the reality of leveling up, from building wealth and realizing money doesn’t fix everything to what really changes once you make it. We also dive into women in business, why women have a natural edge in sales through confidence and communication, and how that can unlock massive opportunities. On the dating side, we talk about what it’s like being a successful woman, higher standards, fewer options, and the truth about loyalty, ambition, and modern relationships, giving you a new perspective on money, success, and your potential. The Journey Podcast Merch https://thejourneypodcast.shopEXCLUSIVE AD FREE EPISODES https://www.patreon.com/c/TheJourneyPodINSTAGRAM https://www.instagram.com/zacharycummings_ https://www.instagram.com/thejourneypodcast https://www.instagram.com/itsjesschangTik Tok https://www.tiktok.com/thejourneypodcast__ #dating #relationships #modernrelationships #datingadvice #success #money #selfimprovement #womeninbusiness

People in this episode

Hosts: Zachary Cummings, Jake Moscato, John Scafiddi Jr.

Topics covered

  • success
  • dating
  • women in business
  • relationships
  • money
  • self improvement

Keywords

  • dating
  • success
  • money
  • women in business
  • relationships
  • self improvement

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