Midlife Remix

When Success Isn’t Enough: Redefining What Truly Matters

Nov 11, 2025
Keith Lawrence, executive coach focused on designing purposeful next chapters. Bruno Del Ama, leader critiquing the hedonic treadmill and external metrics. Brett Wright, leadership practitioner who centers listening and vulnerability. Jack Swift, entrepreneur who left corporate for value-aligned ventures. They discuss walking away from prestige, listening to your inner voice, human-centered leadership, redefining success, and choosing time over status.
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INSIGHT

Three Buckets Of Fear Make Decisions Tractable

  • Jack Swift buckets fear into three types: fear of failure, fear of success, and fear of judgment to make it approachable.
  • He asks successive "why" questions until the emotional loop dissolves, turning fear into learnable practice.
ANECDOTE

Walking Away From Prestige Led To New Ventures

  • Jack Swift recounted leaving Janus and Tiffin despite huge growth, then joining Vantage Discovery which sold to Shopify in 12 months.
  • He uses these pivots as examples of following heart alignment leading to unexpected new ventures like GridAero.
ADVICE

Listen To Your Heart Because Security Follows

  • Jack Swift advises listening to your heart because it will bring more meaningful success and calm the ego that chases money.
  • He would tell his younger self "it's going to be okay" and that you don't need all the money to be fine.
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