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Let’s be real: if ambition alone was enough, you’d already be “there.” But for so many neurodivergent entrepreneurs—especially those of us with ADHD—there’s a gap between what we want and what we actually do.

That’s the sticky middle: where you’re smart, driven, full of ideas… but still somehow stuck.

In this episode of The Optimization Toolbox, I sat down with Olivia Slavosky, a certified self-sabotage coach, to unpack why that happens and how to move through it.

This episode is for you if:

* You’re always “about to start” something but don’t follow through

* You overthink or over-prepare and call it being responsible (when really it’s fear)

* You feel like you’ve done all the inner work and still don’t act

* You’re ambitious and self-aware… but tired of your own BS

⏱️ What We Cover (Timestamps)

00:00 – Why we’re talking about self-sabotage (especially for ADHD brains)

01:35 – Olivia’s story: Starting over, again and again

04:30 – What self-sabotage really looks like (and why it’s not laziness)

06:45 – Perfectionism, people-pleasing, and “procrastivity”

10:20 – Messy action: the antidote to fear-based stuckness

15:15 – How ADHD brains self-sabotage through busyness + overcommitting

20:30 – Real tools to interrupt the cycle: pattern tracking, love/fear dialogue

24:50 – Coaching vs. therapy: which one do you need?

31:20 – Olivia’s take on identity shifts + healing burnout

💡 Standout Moments & Quotes

“You can’t out-strategize self-sabotage.”

Even the best plan won’t work if your nervous system is screaming “this isn’t safe.” Self-sabotage isn’t a time management issue—it’s a fearmanagement issue.

“Perfectionism is just procrastination in a prettier outfit.”

Or as I call it, procrastivity—when you’re tweaking, refining, or “prepping” instead of just doing the thing. It feels productive,

but it’s really avoidance.

“The only way out… is through.”

Resistance isn’t a red light—it’s an invitation. When we stop trying to avoid the hard stuff and actually move through it, everything shifts.

“I forgive myself for buying into the misunderstanding that I should be further along.”

One of the most powerful tools Olivia shared: a compassionate self-forgiveness practice. You fill in the blank with your inner criticism—and then reframe it with truth.

“You already have the answers—you just have to get quiet enough to hear them.”

Whether through journaling, bodywork, or a love/fear dialogue, so much of this work is about coming back to yourself—not outsourcing your clarity.

📣 Why I Made This Episode

Honestly? Because I needed it too.

I’m an ADHD entrepreneur who can talk systems and strategy all day—but if I’m not addressing what’s underneath the stuckness, I’ll still spiral in my own patterns.

And I know I’m not alone.

This episode is for the smart, self-aware folks who’ve read the books, taken the courses, made the to-do lists—and are still wondering why they can’t get out of their own way.

🎧 Listen if you’re tired of spinning in place. Share it if you know someone who needs this.

Go follow Olivia on IG @oliviajoancoaching (we are going live together in August!)

🎯 Feeling stuck in your marketing? Let’s untangle it.

If you’re spinning out on content ideas, overwhelmed by platforms, or procrastinating on showing up—my 90-minute Untangle Clarity Session is for you.

This isn’t just a brainstorm—it’s a reset.

In this session, we’ll:

* Untangle your current marketing mess (strategy, offers, messaging, content)

* Identify where you’re stuck—and why it’s happening (hello, perfectionism + self-sabotage)

* Clarify what actually matters for your visibility, audience, and next steps

* Leave you with a simple, ADHD-friendly plan to move forward with ease

👉 Perfect if you’re a coach, creative, or service provider who’s tired of second-guessing every post or pivot.

⚡️This is the session I wish I had every time I was overthinking my own marketing.

→ Book your 90-minute Untangle Clarity Session here

Jenna

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