Don and Tom examine Kiplinger’s list of top retirement side gigs and separate practical ideas from pipe dreams, questioning whether executive coaching, IT consulting, online reselling, and landlord life truly offer “passive” or realistic income. They highlight more viable options like tutoring, handyman work, and tour guiding while emphasizing purpose over paycheck. Listener questions cover the risks of private credit and alternative investments, plus smart strategies for consolidating multiple 401(k) accounts without triggering unintended tax consequences.

0:04 Old guys still podcasting intro

1:38 Kiplinger’s retiree side-gig list

3:26 Executive coaching reality check

4:40 AI and tech consulting skepticism

6:32 Consulting and client ego problems

7:53 AI vs. content writers

9:06 Bookkeeping for small businesses

9:29 Online selling isn’t easy money

11:19 Tutoring as a steady option

12:17 Handyman work pays well

13:44 Tour guide opportunities

14:17 Landlord myth of “passive” income

16:00 Where to find side gigs

16:47 Bridge jobs for healthcare

17:08 Purpose-driven retirement

19:14 Private credit and alternative risks

23:46 Consolidating multiple 401(k)s

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