Q: Jay, have you ever reached a goal you thought would change everything, only to realise it didn’t change how you felt inside?

Great question. In my life, as well as the lives of the very successful people I’ve spoken to on my podcast or worked with as a coach, one thing has consistently surprised us:

Success doesn’t guarantee fulfillment.

And yet, as humans, we often think the promotion, the big achievement, the new relationship (our “successes”) will fix all our problems. Think about it: how many times have you set aside your own day-to-day needs because you believe that whatever big future thing you’re pouring yourself into will eventually make those smaller problems go away?

When, in reality, it rarely ever does.

Think back to those big achievements you’ve had in your life. Maybe you got your bachelor’s degree. Or you made a certain amount of money. Or you finally got accepted by that friend group you always looked at enviously. Did those moments make you feel fulfilled?

A lot of the time, the answer is going to be “not really.” Or maybe a little.

But I want you to pay attention to those achievements that did fulfill you. I’m talking about a deep inner sense of peace and meaning. Because success can lead to fulfillment.

  • If a value of yours is health, and you achieve a major fitness goal, that can be fulfilling.

  • If you value knowledge, mastery of a new skill can be fulfilling.

  • If you value love, reconnecting with family can bring deep, beautiful fulfillment.

If what you seek to achieve is in alignment with your purpose, you will be fulfilled.

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On Purpose

On Monday’s episode of On Purpose, I sat down with my friend Roxie Nafousi to talk about what confidence really feels like on the inside, not the glossy highlight-reel version. Roxie opened up about her lifelong struggle with body dysmorphia and the quiet, relentless self-criticism that came with it, and we explored how many of us are carrying similar stories in our own heads. We talk about letting go of the need to be liked by everyone, breaking patterns of people-pleasing, managing comparison before it controls you, and learning to speak to yourself with compassion instead of judgment. If you’ve ever questioned your worth when you walk into a room, this conversation will help you start building a steadier, kinder kind of confidence from the inside out.

Listen on

Today’s Wiser Choice

Are you working in alignment with your values? Do you even know what your values are?

Try This: Put together a list of the achievements in your life that brought you the most personal fulfillment. Notice I didn’t say money, or fame, or followers (though any of those could be part of it as well!). These personal milestones are what can teach us what our values are.

Let’s say you’re really proud of learning Spanish. You might value learning. Or maybe you’re proud of a trip you took. That could mean you value exploration.

As you reflect on your values, ask yourself: Am I working on anything that’s in alignment with my values? And if the answer is no… what can you do to change that?

Brought to you by Poppy AI

Bringing wisdom to the world takes partners who share our belief in its purpose. We’re deeply grateful to today’s partner, Poppy AI. Without their support, our message wouldn’t reach as far or as wide as it’s needed. Please help us share our gratitude by checking out their work.*

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