Ever wonder what’s really happening behind the scenes of a coach who’s scaling toward a million dollars?

In this episode, Debbie Shadid shares the real story—no sugarcoating, no "just work 10 hours a week and it'll happen" myths. 

We talk about how she built her business from the ground up (before digital ads even existed!), what she’s had to rework to hit her next goals, and why it’s not about finding the “perfect” automation—it’s about showing up, building skills, and doing the work.

Debbie also gets honest about switching industries, embracing tech even when it was hard, and the mental shifts she had to make to stop "dabbling" and step fully into leadership. Plus, she gives practical advice for how YOU can start thinking about your business like a brick-and-mortar boutique—and why that mindset will change everything.

Here’s what we dive into:

For all the notes, links, and more, go to:  https://simplysquaredaway.com/109

What if I told you that you could build a thriving business and grow your email list—all without using social media?

In this episode, I sit down with Kylie Kelly, host of the No Socials, No Worries podcast and founder of The Email Collab, who helps coaches, course creators, and service providers grow their email lists through relationship-based strategies, not reels and DMs. Kylie shares her personal journey from burnt-out wedding photographer to email marketing pro—and exactly how she makes collaborations her growth superpower.

We dive into how to ditch social without ditching your growth, how to use bundles, summits, and freebie swaps to grow your list, and how Kylie organizes it all without a team. Plus, we cover her “V2 Collaboration Framework” and how to choose the right strategies for long- and short-term list-building wins.

Thinking about quitting Instagram? This is your permission slip.

What you’ll learn:

How Kylie grew her email list from zero to 600 in one event (without social media)

Why social media made her feel stuck—and how she finally let it go

What a 9-grid is and how she uses it as a digital storefront

Her favorite high-converting collab strategies (summits, bundles, swaps)

The #1 mistake people make when joining bundles (and how to avoid it)

Kylie’s “V2 Collaboration Framework” for choosing smart list-building strategies

How she organizes all her collaborations with a simple Google Sheet

The real talk on FOMO, unsubscribes, and promo fatigue—and how to manage them

For the notes, links, and more -->  https://simplysquaredaway.com/108

Work with me: https://simplysquaredaway.com/appointments

Learn the only five folders I use to organize my business: https://simplysquaredaway.com/5files

Do you ever feel like your computer is one big junk drawer?

If you're constantly hunting down files, re-downloading things, or wondering where in the world you saved that doc, this episode is your digital rescue plan.

I'm sharing the two simple habits I’ve been coaching on over and over lately—and they’ll help you actually stay organized after your initial digital cleanup. Whether you're just starting your organizing journey or you've got a shiny new file structure, these tips are your maintenance BFFs.

Plus, I’m breaking down:

Why organizing is a project AND a lifestyle (yep, like eating veggies and flossing)

The foundational mindset shift to think of organizing like a 12-week sprint

My go-to Google Drive tip to save time and reduce decision fatigue

What to do if your desktop is turning into a clutter crime scene

How to download smarter (not just dump everything in "Downloads")

And if you’ve ever felt guilty seeing 94 PDFs piled on your screen...you’re not alone. But this episode gives you a no-shame plan to fix it.

💡What You’ll Learn:

The two habits that will help you maintain your digital organization long-term

Why you don’t need to be perfect—just consistent

How to “name and home” like a pro

How to adjust your habits based on your clutter tolerance

Why maintenance routines (just like brushing your teeth) matter for your digital life

How to use Tracy’s File Naming Formula and 5-File System to simplify everything

For the full transcript, notes, links, and more, go to: https://simplysquaredaway.com/107

Ever feel like your coaching business is stuck in no-man’s-land? You’ve got your offer, your socials are active, maybe you've even had a few clients—but now it’s crickets. No one’s buying, and you're starting to question... everything.

In this episode, I sit down with business coach Candy Motzek to unpack what’s really going on when the clients stop coming. From the real reason people don’t want “coaching” (spoiler: no one does) to the mindset shifts that get you back into momentum, this conversation is equal parts strategy and soul-search.

Whether you’re in a dry spell or just need to reignite your belief in your offer, Candy offers the wisdom, tools, and compassion every coach needs to hear.

We cover:

How to shift out of discouragement and get back into aligned action

Why people aren’t buying your “coaching package” (and what they do want)

How to market research the right way (hint: use Amazon!)

What gamifying your client-getting strategy might do for your energy

Mindset hacks to fall back in love with your business again

The surprising power of journaling and how to use it to get unstuck

When to pivot your offer (and how to know it’s the right time)

What You’ll Learn:

Why even great coaches hit dry spells—and how to handle them

The #1 shift that will make your offer more sellable instantly

What to ask your dream client to uncover irresistible copy

The simple journaling prompt Candy swears by

How to know if it’s time to pivot (or just repackage your offer)

For the full transcript, notes, links, and to connect with Candy Motzek, go to:  https://simplysquaredaway.com/106

Have you ever felt like your creativity thrives—but your systems are falling apart behind the scenes? 😬

If so, you are going to LOVE this conversation with my past one-on-one coaching client, Laurie Smith.

Laurie is an author, a workshop leader, and a fierce advocate for flow. She lights up when she talks about creativity—but struggled behind the scenes to organize her growing business, especially as she landed a book deal with a major publisher (hello, Hay House!).

In this episode, Laurie gets real about what it’s like to run a creative business that’s scaling fast—and how disorganization was costing her more than just time. We talk about the emotional impact of digital clutter, the power of honoring how you're wired (instead of fighting it), and how she shifted into a CEO mindset… complete with a sticky-note wall, a customized bookmarks bar, and a little Beyoncé alter ego energy. 

Get ready for a warm, honest, and super-inspiring conversation that’ll make you want to spend the weekend organizing your bookmarks—and maybe your life.

What you'll hear in this episode:

How Laurie knew it was time to invest in organization for business growth and how it impacted her creativity

The surprising link between being organized and helping people feel safe

Laurie’s “book baby” metaphor—and how she wanted to prepare for her third "child"

Why the ability to find things is more important than having a Pinterest-perfect system

What happened when she started building systems her way (she carried herself differently is one thing)

The mindset shift that helped her stop judging herself for how she works

Post-it walls, branding audits, and CEO alter egos (we cover it ALL)

For the notes, links, and more, go to:  https://simplysquaredaway.com/105

You’re not alone. In this episode, I’m sharing one simple yet powerful strategy that has been a total game-changer in my own business this week. It’s about reducing decision fatigue, staying laser-focused, and actually finishing tasks. (Yes, even when your brain wants to jump ship every 10 seconds.)

But first—a little reminder: the doors to Organized Coach Academy are officially OPEN. This is your sign if you’re craving calm, order, and confidence in your business. Want to stop wasting time, find what you need fast, and finally get that scribbly mess out of your brain? Then, let’s do this together.

Organized Coach Academy's deal of the century ends today, so join now by clicking here.

I even pulled out some recent student wins to give you a peek behind the scenes (and to show you what’s possible when you organize your biz like a pro).

Then, we dive into the power of one—one tab, one task, one Post-it. I walk you through how this approach helps you ditch distractions and get stuff DONE. Think of this as your brain’s best friend, especially if you're prone to hopping from idea to idea like it's your job.

If you're ready to feel in control and love your systems, this episode is for you.

For the full transcript, notes, links, and more, go to:  https://simplysquaredaway.com/104

Time Sensitive Links:

Feeling like there’s never enough time in the day? Struggling to get (and stay) organized? You’re not alone!

In this episode, I’m pulling back the curtain on how AI can be a game-changer in productivity—but only if your business is organized first. I’m sharing my proven three-part organizing framework and showing you exactly how to layer AI on top to 10X your efficiency.

Here’s what we cover:

If you’ve ever wasted time searching for a file, felt overwhelmed by decision fatigue, or wondered how to use AI without adding more chaos to your business, this episode is a must-listen!

🎧 Tune in and let’s get your business streamlined!

Grab your seat at the FREE AI-Powered Productivity Training: https://simplysquaredaway.com/ai

For the full transcript, notes, links, and more, go to:  https://simplysquaredaway.com/103

Are you making this mistake when trying to be more productive with AI?

If you've been adding AI into your workflow but still feel overwhelmed and scattered, you're not alone. In fact, most coaches are making one major mistake that’s keeping them stuck in a cycle of busywork instead of true productivity.

In this episode, I’m diving into what productivity really means and why jumping into AI tools without an organized business is actually making things worse. If you feel like you’re spinning your wheels despite all the automation hacks out there, this episode is for you.

And—if you’re catching this episode live—my AI-Powered Productivity Training is happening tomorrow, March 19! Don’t miss it: https://simplysquaredaway.com/ai

Sign up for my free class on March 19th, AI-Powered Productivity: How Coaches and Online Business Owners Can Organize Without the Overwhelm: https://simplysquaredaway.com/ai

For the full transcript, notes, links, and more, go to:  https://simplysquaredaway.com/102

What if your course had its own personal assistant working 24/7 to help your students finish what they started... and actually have fun doing it?

That's exactly what I'm building inside Organized Coach Academy—custom AI bots in every module guiding my students step by step, making the whole process smoother, faster, and way less overwhelming.

And today? I'm pulling back the curtain to show you exactly how I'm doing it.

In this episode, I'm sharing how ChatGPT helped me brainstorm custom AI bots for each module of my program, how I'm integrating them to make the course 10x more helpful, and how YOU can use this same strategy to create an incredible, guided experience inside your own course or coaching program.

Because here's the truth:

This episode is going to fire you up with ideas to fix that.

For the full transcript, notes, links, and more, go to:   https://simplysquaredaway.com/101

AI is everywhere—but is it actually useful for online business owners and coaches?

In this episode, I’m breaking down AI from an organizer’s perspective. I’ll share

Plus, I’ll explain how I finally upgraded from the free version of ChatGPT (spoiler: I resisted for a while!) and why I created a custom GPT to write podcast scripts for me… except when it totally backfired. 🤦‍♀️

And don’t forget—registration is open for my upcoming workshop:

✅ The biggest pros and cons of using AI as an online business owner