Leadership Digest: Attention Hyper-Achievers
Edition 107: Weekly leadership fuel—tools, frameworks, and reflections for leaders serious about growth, from the inside out.
Last month, I wrote a Deep Dive on the Enneagram.
In it, I shared some of my struggles as an Enneagram 3 — The Achiever (though I often call this part of me the “Hyper-Achiever”). I got a lot of messages about that piece. Some from fellow Type 3s, of course. But mostly from people who recognized the feeling underneath it. They might not call themselves Hyper-Achievers, but they know what it feels like to always be pushing, striving, and proving - all while quietly wondering if there is another way to work (and live).
A lot of people told me some version of the same thing: I’m just really tired.
Tired of hustling. Tired of always feeling behind. Tired of getting to the milestone only to move the goalpost again. They still want to achieve. They just want to enjoy their actual lives a bit more along the way.
That was certainly true for me.
Many of the questions I got were about what to do. Which is exactly where Type 3 / Hyper-Achievers go: Give me the tactical plan or framework so I can optimize my way out of this.
Unfortunately, deep work doesn’t quite work like this. And believe me, I went into doing mode for years before I understood that much of the work was actually about being.
For me, that meant slowing down enough to understand what was actually driving me — the patterns, beliefs, and stories underneath the constant striving. Coaching, therapy, Parts work, Somatic Experiencing (to get me out of my head and into my body), and, of course The Enneagram, all played roles in my journey.
And while no book changes you, there are a few that have genuinely helped me on this journey and that I wanted to pass along to you.
📚 Books of the Week
Radical Acceptance
I recommend this one often. It masterfully addresses feelings of “not enoughness” and our tendency to constantly prove our value.
Never Enough
Especially resonant for anyone thinking about achievement, pressure, and the messages we absorb about worth.
The Gifts of Imperfection
A thoughtful companion for anyone trying to loosen the grip of perfectionism, proving, and performance.
4000 Weeks
A good reminder that life is not something waiting for us on the other side of productivity.
🪞 Reflections of the Week
Where in your life have you moved the goalpost so many times that you no longer let yourself enjoy what you’ve already built?
What is your drive giving you right now? What might it quietly be costing you — at work, at home, or internally?
Where are you chasing something because you deeply want it versus because an old story says you should?
If achievement became one part of your identity rather than the whole thing, what else might have room to emerge?
What would “success” look like if it included enjoying the actual day-to-day — not just reaching the next milestone?