Alan and I catch up over coffee and martinis, talk weather and travel (including his Nantucket trip), and share updates on upcoming books and family projects. We dive into “you made it, now what?”—how successful people start asking “how much is enough?” and why the better question is “enough of what?” Alan argues success is about purpose, not endless accumulation, and warns about scarcity mindset, low self-esteem, and normative pressure to “beat the Joneses.” He shares practical markers of “enough”: living without financial anxiety, protecting family, pursuing opportunities by choice, being generous without risk, buying back time, and walking away from bad clients and deals. We discuss hobbies, using talents beyond work, the survive–alive–arrive–thrive model, shutting “watertight doors,” and organizing life selfishly to gain freedom and reduce guilt.
00:00 Cold Open Banter
00:31 Vacation Tan Talk
01:45 Books and Life Updates
03:15 You Made It Now What
03:57 Enough Money vs Purpose
05:47 Bucket Lists and Iceland Rant
07:05 Bigger Boat Syndrome
09:00 Bored After Success
10:13 Retired for 25 Years
11:23 Why Hobbies Matter
12:51 Talents And Recognition
13:21 Beyond Success Buying Time
15:10 Enough Metrics For Success
16:16 Purpose Shifts With Age
18:08 Avoid Purpose Fanaticism
18:58 Watertight Doors Model
20:30 Coaching Scarcity Mindset
21:26 Generosity Of Spirit
22:56 Staying Challenged In Retirement
25:49 Calling Personal Metrics
26:47 Systems Healthy Selfishness
27:34 Final Thanks And Wrap
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