Ep. 216 – Dr. Jennifer Dragonette – How to Thrive, Not Survive, The Holiday Season Financially & Emotionally

Podcast

Nov 24

Are you trying to survive, or do you want to thrive this holiday season?

I welcome back our resident psychologist, Dr. Jennifer Dragonette, to tackle the emotional whirlwind of the year-end holiday season.

Both Dr. Jen and I felt it was time to reframe the usual “surviving the holidays” narrative. Instead of just getting through it, we talk about how you can actually enjoy and find meaning in this busy, sometimes stressful time.

Together, we dig into four areas that create holiday pressure: financial strain, tricky family dynamics, the pain of losing a loved one, and dealing with career changes, especially job loss—all of which are heightened by the expectations we set for ourselves and others.

Please enjoy my conversation with Dr. Jennifer Dragonette.

Connect with Paul

Contact Paul here or schedule a time to meet with Paul here.

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And feel free to email Paul at pfenner@tammacapital.com with any feedback, questions, or ideas for future guests and topics.

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1 Big Idea to Think About

Shifting holiday conversations from just "surviving" to openly discussing values, boundaries, and expectations with family can transform the season from a pressure-filled endurance test into a more enjoyable and meaningful experience for everyone.

1 Way You Can Apply This

Start by having open conversations with your closest family about what truly matters to each person and set clear intentions together. By focusing on shared values rather than unspoken expectations or trying to appease everyone, you can reduce stress, set healthy boundaries, and create meaningful experiences that allow everyone to feel heard and included—transforming the holidays from something to survive into something to savor.

1 Question to Ask

What would make the holidays truly enjoyable and meaningful for my loved ones and me this year, and how can I communicate those priorities clearly?

Key Moments From the Show

00:10 “Surviving” the holidays feels negative. Can we do better?
00:47 Four holiday stressors: finances, family dynamics, loss, and job changes.
01:48 Holidays heighten emotions—especially after personal or professional loss.
03:05 Want to enjoy—not just survive—the season; rethink expectations.
04:19 Expectations make December harder than June, regardless of the stress.
05:10 Holidays aren’t a sprint: stress accumulates over weeks/months.
06:12 Distinguishing values from expectations is key to enjoying holidays.
07:07 Start honest conversations—challenge by choice—for a holiday that fits.
08:18 “Ask vs. guess” culture: don’t assume; explicitly discuss needs and wishes.
09:34 Fear or avoidance keeps us from real conversations, fueling resentment.
10:44 Mind reading about what others want rarely works.
11:31 As families grow, trying to please everyone drains joy.
13:22 Childhood holiday rituals had pros/cons; flexibility can be a positive lesson.
14:22 Ask: is it the date that matters, or the togetherness?
16:54 Being clear and direct (“clear is kind”) avoids anxiety and misunderstanding.
17:37 Family harmony is hard in bigger groups—fewer moments left adds pressure.
20:46 Setting boundaries isn’t exclusion; it’s about comfort—let in what matters.
21:59 Set ground rules to keep the peace; not everyone enjoys debates or conflict.
24:31 No one ever asks how much to spend on holidays; financial friction rises.
25:47 Less is more with gifts and spending—experiences outlast stuff.
29:41 Budget not just money, but time and self-care; breaks are essential.
31:34 Supporting someone through grief: be present, listen, welcome their feelings.
34:00 Grief is non-linear; all feelings are valid and must be felt to heal.
35:49 When supporting others: be curious about their story and avoid clichés.
38:28 Create new rituals to honor those lost, rather than comparing to others.
39:18 Job loss (like grief) brings a roller coaster—don’t mistake now for forever.
41:24 Supporting others: avoid “at least…”; simple presence and validation matter.
44:11 Boundaries are for you; how others react is not your business.
46:11 Don’t settle for survival—choose to thrive during the holidays.