🎯 Deeper Conversations: Goals & Aspirations

Do you crave inspiring conversations? This month's topic is your invitation to think outside the box and get inspired for 2026!

“Deeper Conversations” is a monthly event series where we gather in a semi-quiet space to discuss a different theme each month. I will bring a curated list of conversation starter questions inspired by the card decks sold by popular YouTube channels that foster deep conversations, including Diary of a CEO, Yes Theory, and Eamon & Bec. These questions are vetted to be non-political and non-religious, while sparking meaningful, uplifting, or intellectual conversations. They will be roughly sequenced from lighter to deeper questions, so we can warm up and get to know each other before diving in. Each month's theme will be matched to the season whenever possible…

January's Theme: Goals & Aspirations
New Year's resolutions may be on your mind, but this conversation will be much bigger than that. This is a chance to reflect, celebrate, dream, identify what you really want, and discover what might already be possible. Example questions include: "What is one thing you’re afraid to do, but suspect if you did it, you’d be glad you did?" AND "If you never needed to work or worry about money again, what would you do to fill your time on a typical day?"

VENUE
I’ve chosen the Harry Waugh Dessert Room at Bern's Steakhouse for its old money vibes and large tables in private booth rooms made out of wine casks (see Photos section). It's very conducive to aspirational ideas and feeling like you've already reached your financial goals. This room is an experience unlike any other in the world! The dessert room is upstairs and totally separate from Bern's dining rooms downstairs. It offers an extensive dessert menu of cakes, flambees, ice creams, sorbets, chocolates, cheeses, coffees, teas, dessert cocktails, and one of the largest wine and port menus and largest spirits menus in the country! Sometimes there is a live pianist, and each booth comes with its own speaker system of music tracks and volume control to choose from. It's a must-do experience for every Tampan.

Note there is no dinner food offered in this dessert room, but you can go early and eat dinner at the bar downstairs or any of the great restaurants nearby.

IMPORTANT: As usual, RSVPs close 25 hours before the event, so please make any changes before then. No-shows and cancellations after RSVPs close will be removed from this Meetup.