Kylen picked the topic and went first, which meant Kenda had to go second.

His example is small and he refuses to let it be small. He stays up for one more hour of a day he is enjoying, and he pays for it with the whole of the next one. Not a little sleep. A lot of him.

Hers is six nights in Paris and Champagne for her sister-in-law’s 40th, and she spent most of it anxious in beautiful rooms. Kenda grew up in a VW van on the beach, on welfare, then in an apartment with a rug she can still describe. She and Brian built the exact opposite of that. The part of her that remembers the van never agreed to any of it, and it is the part holding the bill.

So the two of them spend an hour on what self betrayal actually is: whether it is your values you are betraying or just an identity that has gone out of date, whether cutting a corner counts, and whether anybody grows without struggle. They also agree, out loud, that they should not judge anybody, and then judge everybody — a sommelier, a room full of diamonds, a man in a VIP booth pointing at the dance floor, and a stranger in the Galapagos who did nothing worse than dress well.

The Kylen and Kenda Show. Kenda is the mentor. Kylen is the mentee. Neither of them comes out of this one clean.

00:00 Cold open
00:58 Today’s topic is self betrayal
01:10 Kylen: the tomorrow he keeps trading away
04:51 The tape Kenda’s mother recorded for her
08:02 Paris, Champagne, and a knot in her stomach
09:42 The VW van, welfare, and the rug
10:50 Do you feel broke, or do you identify as broke?
11:51 Dripping diamonds, flip flops, and the cheapest wine on the menu
14:55 Salt of the earth: where the discomfort with money came from
16:31 Brian cries at the Eiffel Tower while she argues with herself
18:45 The shoes her grandma would not let her buy
22:11 Outdated values, or an outdated identity?
23:19 The best moments cost nothing
24:34 Sabering champagne, and nobody wanted to do it
26:35 "I know how to open beers with other beers"
29:19 What she actually wants from a hotel now
30:31 Pretentious, ego, and an opinion that costs other people
32:07 "I don’t want to judge anybody" / "Let’s judge the fuck out of them"
32:28 Exclusivity buys privacy and loses connection
35:33 The VIP booth, and the guy pointing at the dance floor
37:55 Stock market syndrome
39:26 Latchkey kids and what the struggle was for
42:19 Is there growth without struggle?
43:40 When everything is abundant, nothing is special
47:00 The thing she needs to work on is gratitude
48:57 Aleem, three outfit changes a day, and the verdict she reached early
52:22 "You almost robbed yourself of the experience"
52:44 High waters, sneaker heels, and dressing for yourself
55:35 Out of the running early, and the day his mother won
59:15 Why the backpack is always packed