Ep.205 – Dr. Jennifer Dragonette – Finding Satisfaction Beyond Winning: Enjoying the Journey in Life, Sports, and Finances
"That's something that I wrestle with on a daily basis. It's like showing up at the Masters every year; it's like why do I want to win this golf tournament so badly? Why do I want to win the Open Championship so badly? I don't know because, if I win, it's going to be awesome for two minutes."
That is a quote from the world's top golfer, Scottie Scheffler, before he tees it up to try and win another major golf tournament. Scottie's point is also the topic of conversation today with our resident psychologist expert, Dr. Jennifer Dragonette.
Dr. Jen and I explore how the thrill of big wins fades quickly and why major milestones, whether in sports, career, or personal life, rarely satisfy us for long. Together, we also unpack common traps around goal-setting, retirement, and the pursuit of "enough," all while examining the importance of focusing on values over simple achievements.
There are many great personal stories we share in this discussion, so I hope you can take away a few strategies from the conversation to help you along your journey.
Please enjoy my conversation with Dr. Jennifer Dragonette.
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ADDITIONAL RESOURCES YOU MAY LIKE
1 Big Idea to Think About
True fulfillment comes not from achieving big, fleeting goals, but from aligning with our values and recognizing the small, meaningful moments of growth and pride in our everyday journey.
1 Way You Can Apply This
To build a deeper sense of fulfillment and resilience along your personal or financial journey, try a daily “pride practice”—at the end of each day, jot down three things you’re proud of, big or small, and challenge yourself not to repeat them. This simple reflection helps you recognize growth, appreciate incremental achievements, and shift your focus from chasing fleeting milestones to enjoying the ongoing process, ultimately cultivating a more balanced and satisfying outlook.
1 Question to Ask
What are three things I can be proud of myself for today, no matter how big or small?
Key Moments From the Show
00:05 Dr. Jen celebrates her birthday on the podcast, setting a lighthearted and personal tone.
00:47 Host Paul introduces Scotty Scheffler’s quote about fleeting satisfaction after winning, comparing sports milestones to life goals.
03:15 Dr. Jen discusses how achieving goals can lead to disappointment and even post-goal depression—goals don’t guarantee lasting happiness.
04:14 The importance of values versus goals: values as ongoing directions, while goals are binary and fleeting.
06:12 Paul raises the core struggle: finding enjoyment in the journey versus focusing only on end goals, using parenting and sports as examples.
07:18 Dr. Jen discusses the difference between a fixed and growth mindset; focusing on continuous learning rather than achievement alone.
09:32 The “power of compounding” in life and finances—celebrating small, consistent growth over time.
11:04 Dr. Jen and Paul explore the concept of “enough” and how external goals rarely satisfy our deeper needs.
13:14 Dr. Jen emphasizes the importance of understanding the true meaning behind our goals—what are we really seeking?
15:34 Enjoying the process and practice (as with golf or swimming) versus chasing accolades; recognizing intrinsic motivation.
16:25 Identity and achievement—warning against equating self-worth with success, especially in sports and career.
18:55 Dr. Jen introduces the “pride practice”: daily journaling about three things you’re proud of, big or small, to build real self-worth.
22:44 Finding satisfaction in the day-to-day—acknowledging the power of small actions and mindful reflection.
23:31 Paul asks how to make goals instructive rather than destructive, particularly for kids in competitive activities.
24:58 Dr. Jen advocates for breaking goals into smaller steps, focusing on learning, and using setbacks as growth opportunities.
27:50 Paul summarizes the actionable takeaway: try the pride practice daily to support emotional growth and resilience.
29:35 Dr. Jen explains how practices like pride journaling help rewire our focus from danger to daily wins—building emotional balance.
30:55 Episode closes with appreciation for the ongoing dialogue between therapy, financial planning, and life’s big questions.
Resources Featured in This Episode:
Scottie Scheffler's take on success in golf: 'What's the point?'