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 Learn more about your ad choices. Visit megaphone.fm/adchoices