11. How to Stop Overthinking and Start Doing — with Deborah Hurwitz

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What if your biggest barrier to success isn’t lack of strategy—but a nervous system that’s been trained to fear action, visibility, and imperfection?

If you’ve ever felt overwhelmed by your own ambition, buried in unfinished ideas, or stuck in a loop of overthinking while nothing actually gets done… this episode is about to feel very personal.

In this deeply honest and high-impact conversation, Hailey sits down with Deborah Hurwitz—Broadway music director turned mindset and productivity coach—to explore how high-achieving creatives can break through the paralysis of perfectionism and finally take aligned, powerful, messy action.

Deborah doesn’t just talk about the theory—she lived it. From performing at the White House and conducting Broadway hits like Miss Saigon and Jersey Boys to hitting a wall of burnout, Deborah’s story is one of reinvention, raw honesty, and building a business by doing the exact opposite of what she’d been taught.

The Wake-Up Call: Glamour, Exhaustion, and Nothing to Show for It

Deborah opens up about what it really looked like to be “successful” in show business—on paper, she had it all. But behind the scenes, she was overworked, under-rested, and disconnected from her purpose.

Her dream job? It ended abruptly. Her next step? Unknown.

That breakdown became the breakthrough. And it’s what led her to discover the work she does now: helping other perfectionists stop hiding behind high standards and start finishing the things that matter.

Why Perfectionism Isn’t a Personality Trait—It’s a Safety Response

Deborah breaks down how perfectionism often masks fear: fear of judgment, fear of failure, and most of all—fear of being truly seen.

She shares how perfectionists can reframe their tendencies not as flaws, but as protective strategies… ones that worked in the past but are now holding them back. And she offers a reframe: you’re not lazy. You’re not flaky. You’re just protecting yourself. Let’s give that part of you a better job.

Her Game-Changing Framework: 20 Minutes at a Time

One of the most practical (and immediately doable) takeaways? You don’t need a 3-hour time block to make progress. You just need 20 focused, imperfect minutes.

Deborah explains how short, strategic work sprints help quiet the inner critic and build momentum—especially for overthinkers who wait to start until everything is “ready.”

From Resistance to Results: The Power of Starting Messy

This episode is a masterclass in creative courage. Deborah walks us through how she went from hiding behind production value and industry accolades… to launching a coaching business without a niche, a website, or a clue what she was even selling.

She made her first $10,000 sale on a phone call with a Stripe account she’d opened the day before. That’s what happens when you stop planning and start doing.

Redefining Success: What Really Matters Now

For Deborah, success isn’t about applause anymore—it’s about freedom.
Freedom of time. Freedom of geography. Freedom to say yes to lunch in the sunshine or no to the wrong client. And freedom to create a business that honors her whole self: the creative, the coach, the human.

Her mission? Help smart, capable perfectionists stop stalling and start finishing what they care about.

Episode Timestamps

00:03:45 – Deborah’s Broadway beginnings and the burnout that followed
00:10:00 – The surprising crash of her dream job—and what came next
00:17:30 – Why perfectionism is actually a trauma response
00:22:15 – “You’re not going to feel ready. Do it anyway.”
00:28:45 – The power of consistent 20-minute work sprints
00:34:00 – Starting a business without a niche, offer, or clue
00:40:50 – From $0 coach to $10K sales calls: how she did it
00:47:30 – How to dismantle the fear of being seen and judged
00:54:00 – What success really looks like: agency, creativity, peace
01:02:00 – Her signature masterclass and what to do next

Want to Work with Deborah?

Watch the Free Masterclass:
How to Get Big Things Done
Available for 5 days after signup!

Follow Deborah on Instagram: @cobalt.coaching
Learn more: Cobalt Coaching

Loved this episode?

Screenshot and share it to Instagram—tag @hails.krajewski + @cobalt.coaching to let us know your favorite takeaway. Let’s normalize success that feels as good as it looks.

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