Self-Sabotage at the Top: Why Smart People Get in Their Own Way
Here's the thing about self-sabotage at the executive level—it doesn't look like what you'd expect.
It's not missing deadlines or dropping the ball. For most high performers, it shows up as staying busy, perfecting everything to death, or saying yes to too many things. Your calendar is packed, the business looks good on paper, but something feels... off. Like you're running hard but not actually moving forward.
I've been thinking about this a lot lately, especially after re-reading two books that completely changed how I see this pattern: Atomic Habits by James Clear and Breaking the Habit of Being Yourself by Dr. Joe Dispenza. (If you haven't read these yet, seriously—grab them. I'll drop the links at the end.)
What really gets me is how these two books tackle the same problem from different angles and somehow meet in the middle.
It's Not About Willpower—It's About Systems
James Clear has this line that hit me like a ton of bricks:
"You do not rise to the level of your goals. You fall to the level of your systems."
Think about that for a second. As a leader or solopreneur, you've got big visions. You know where you want to go. But if your daily systems—how you actually spend your time, what you prioritize, how you structure your work—don't match that vision? You're basically voting against yourself every single day.
I see this all the time (and look, I've done it too). You overload your schedule "just for this quarter." You put off the strategic thinking because everything feels urgent. You stay reactive instead of proactive. You keep doing what got you here, even though you know it won't get you there.
Clear puts it another way that really lands:
"Every action you take is a vote for the type of person you wish to become."
So when your calendar is jammed with back-to-back meetings but you say you want to be more strategic... when you're always in your inbox but you claim you want to lead more thoughtfully... there's a disconnect. And that friction? It eventually shows up as burnout, avoidance, or just feeling stuck.
Your Body Might Be Addicted to Stress
This is where Joe Dispenza's work comes in, and honestly, it's a bit mind-blowing.
In Breaking the Habit of Being Yourself, he explains how we're basically wired to repeat familiar emotional patterns—even the ones that hold us back. Your brain and body get so used to operating in a certain state (urgency, pressure, constantly proving yourself) that anything else feels wrong.
He says it like this:
"Your personality creates your personal reality."
If your default setting is urgency and control, your nervous system will actually resist the behaviors you need for growth—like delegating, taking recovery time, or thinking long-term. It's not that you don't know what to do. It's that your body literally feels uncomfortable doing it.
And here's the kicker:
"To change is to think greater than how you feel."
You might logically know you need fewer meetings and better boundaries. But if your body is addicted to the chemistry of stress? Those new habits won't stick. They'll feel "off" even when they're exactly what you need.
Why Success Makes This Harder
The irony is that the more successful you become, the sneakier self-sabotage gets.
You have more autonomy, so there's no one telling you to slow down or set boundaries. Your identity gets wrapped up in performance. The stakes feel higher, so you avoid things in more sophisticated ways. And because your old habits got you this far, you keep them way longer than you should.
At this level, self-sabotage isn't about being lazy. It's about protecting who you've always been—even when that version of you is outdated.
Real change means working at both levels: fixing your systems (habits, schedule, environment) and rewiring your internal responses (thought patterns, stress chemistry, emotional defaults).
That's why productivity hacks don't work for high performers. You can't hack your way out of a nervous system that's stuck in the past.
Questions Worth Sitting With
I like to think of these as a private audit for yourself. Not affirmations—just honest awareness:
Where does my schedule reflect who I used to be, not who I'm becoming?
What habits got me here but are now quietly holding me back?
Which emotional states do I rely on to feel productive or valuable?
If my calendar showed my highest-value work, what would I cut first?
What would change if I built systems that support calm, not just results?
Grab a journal and sit with these. Even better if you're reading through Atomic Habits or Breaking the Habit of Being Yourself at the same time—the insights will hit different.
The Real Work
Self-sabotage isn't a character flaw. It's what happens when who you are, what you do, and how you feel are out of sync.
The good news? You don't fix it by pushing harder. You fix it by redesigning your systems and updating your internal operating system to match.
The next level isn't about doing more. It's about becoming someone whose habits and nervous system can actually hold it.
Want to dive deeper? Check out [Atomic Habits by James Clear] and [Breaking the Habit of Being Yourself by Dr. Joe Dispenza]. Both are game-changers.