Chasing Happiness: Why Success Never Feels Like Enough

Why does happiness always feel one step away? In this episode, we welcome back positive psychology expert Jodi Wellman to explore why so many of us keep “moving the goalposts” on our own success, and learn why accomplishments that once thrilled us eventually feel ordinary.

Jodi breaks down why we convince ourselves that one more thing — a new job, a relationship, a move, a big purchase — will finally deliver lasting happiness. Using Gabe’s own podcasting journey as a case study, the conversation exposes a mental trap familiar to anyone who’s ever felt like their wins “don’t count” for long.

But this episode isn’t just about naming the problem — it’s about fixing it. Jodi offers practical, research-backed strategies to help you savor your accomplishments, find a healthier balance between ambition and contentment, and stop letting your inner critic erase your progress.

Listener takeaways

• why humans believe they’re always “one thing away” from feeling fulfilled

• what the hedonic treadmill is and how it sabotages our happiness

• how to balance ambition with genuine joy so you can grow without feeling miserable

If you’ve ever wondered, “Why don’t I feel successful?” this is the episode that can finally help you understand.

“We like to dupe ourselves. It's just one of the features of our psychology. It all comes down to this idea called the hedonic treadmill. We think, and we go for it. We'll buy the pill, we'll make the move, we'll take the job, we'll buy the car, we'll do a thing. And usually it's external stuff, but sometimes it's internal, like, I will become the person that I've been meant to be and that will make me happy. But then, because we adapt so well, this is this hedonic adaptation, hedonic treadmill, we adapt so reliably, damn it. And we end up, over time, some of us shorter than others. Naturally, meh. Okay, well, how come it's not doing it for me anymore?” ~Jodi Wellman, MAPP

Our guest, Jodi Wellman, MAPP is a speaker, author, and facilitator on living lives worth living. She founded Four Thousand Mondays to help people make the most of the time they are lucky to be above ground. 

With 25 years of corporate leadership experience (most recently as Senior Vice President of Operations at a leading health and lifestyle organization), Jodi has led private CEO advisory boards and coaches teams to work well and live even better.

Jodi has a Master’s of Applied Positive Psychology from the University of Pennsylvania, where she is also an Assistant Instructor and facilitator in the Penn Resilience Program. She is an ICF Professional Certified Coach. Her book, "You Only Die Once: How to Make It to the End with No Regrets," made Adam Grant’s Summer Reading List and was a “Top 3 Psychology Book of 2024” by the Next Big Idea Club (curated by Malcolm Gladwell, Susan Cain, Adam Grant, and Dan Pink). Jodi has been featured in The New York Times, Oprah Daily, Fast Company, CNBC, Forbes, Psychology Today, The Los Angeles Times, and more. Jodi’s TEDx talk is called How Death Can Bring You Back to Life; with over 1.3 million views, it is the 14th most-watched TEDx talk released in 2022, out of 15,900!

Our host, Gabe Howard, is an award-winning writer and speaker who lives with bipolar disorder. He is the author of the popular book, "Mental Illness is an Asshole and other Observations," available from Amazon; signed copies are also available directly from the author. Gabe is also the host of the "Inside Bipolar" podcast with Dr. Nicole Washington.

Gabe makes his home in the suburbs of Columbus, Ohio. He lives with his supportive wife, Kendall, and a Miniature Schnauzer dog that he never wanted, but now can’t imagine life without. To book Gabe for your next event or learn more about him, please visit gabehoward.com.

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