The Unhappy Achiever

Always moving, never quite arriving.?

Constantly achieving but never satisfied.

Outwardly successful, but internally it’s dreadful.?

“Unhappy Achievers”, as defined by Yale Psychotherapist Heather Silvestri in this article, “are people who regularly achieve what they strive for, but still feel empty, maybe even anxious, or depressed. Those around them believe they have it all together and on the surface they do but deep down, they’re miserable.”

The sad part for me in all of this is, “Unhappy Achievers are often embarrassed to admit that they’re struggling and because it’s so counterintuitive, many of them can’t seem to figure out why they feel the way they do and so they go it alone.?

It’s a feeling that in and of itself can be so isolating...I know because I've been there.

It's feeling like there’s something shameful or broken about us or at a minimum that we’re ungrateful for feeling the way we do and so we deny ourselves of our own truth and because we deny our truth, we suffer in silence and it eats away at us perpetuating our unhappiness.?

This Sunday Reset, I’d like to offer you some of the most common (albeit not exhaustive) reasons why you may be an “Unhappy Achiever”.

1. The Perfectionist’s Trap

Perfectionism often masquerades as a strength. While it drives excellence, it also sets impossible standards. When perfection becomes the goal, fulfillment takes a backseat. This relentless striving creates a cycle: achieve, feel empty, repeat. The irony? Despite outward success, many achievers feel unseen, as though their worth is tethered solely to their productivity.

2. Living Someone Else’s Dream / Definition of Success

When you follow the life of “ought to”—what you should do, who you should be—you risk losing touch with your truth, with your authenticity. The expectations of others or societal norms often pull us away from who we are truly meant to be. Living someone else’s version of success, we fill our lives with checkboxes of other people’s expectations leaving ourselves empty in the process.?

3. The “I’m Only as Worthy as my Achievement” Syndrome

For many high achievers, self-worth is a learned behavior tied to achievement. This belief—“I must achieve to be valuable”—can drive extraordinary results, but it also fosters deep insecurity. Achievements become less about growth and more about proving your worth, creating an endless cycle of striving that rarely feels satisfying.

4. A Lack of Purpose / Vision for your Life

Purpose is the antidote to the emptiness of high achievement. Not only is purpose one of three determinants of happiness, it’s what transforms the endless hustle into meaningful progress. Without purpose, success becomes a hollow and meaningless exercise of meeting external standards, rather than an internally driven journey and it’s exhausting, depleting, and erosive to our soul. When your efforts are aligned with a vision that resonates deeply, achievement stops being a metric of worth and becomes a byproduct of passion…it just hits different! Purpose aligns and fuels effort with a greater vision, providing direction, fulfillment, and joy in the process.

What you can name, you can tame so I’m curious, if you’re willing to share, drop in the comments which one (or more) of these resonate for you??

And if you’re wondering ‘What do I do next?” my offer to you is

3 simple steps:

1?? Ground in your purpose and build a vision for your life that defines success on your?terms!

2?? Deepen your awareness of the driving forces fueling your ambitions…are they yours or someone else’s ? Are you fueled by fear of unworthiness or driven by passion ?

3?? Reclaim your life with a set of high performance habits that condition you to be in your most authentic, and joyfully productive state more often than not.

These are the 3 steps of the Relaxed Hustle formula that helps high achieving leaders shift from Unhappy Achievement to Satisfying Success!

It’s not about working less, it’s about working better!

On December 3rd, we’re coming together as a group of high achieving leaders to ground ourselves in our purpose creating a vision for our lives that excites us!

Let’s end the year with anticipation so we can start the year in execution!

?I hope you join us.

All my love,

Sky

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