Why Your To-Do List Is Keeping You Stuck (and What Actually Moves the Needle)

You’re not behind — you’re just building your days around the wrong kind of work. In this episode, Jacqueline breaks down why your planner isn’t the problem… your strategy is. She shares the real reason entrepreneurs stay overwhelmed (hint: it’s not a lack of hustle) and how to finally separate the busy work from the needle-movers. If your to-do list feels endless but your business isn’t moving — this one's for you. 

💡 Want to go deeper?
Everything you need — the podcast, courses, Launchpad Kit, and our social links — is in one place:
👉 thestrategichustle.com/links-hub

📲 Follow us on social:
Instagram — @strategichustle_society
Facebook — The Strategic Hustle Society

© 2025 The Strategic Hustle. All rights reserved.

Transcript

INTRO

🎵 [Opening music fades in]

You know that feeling when you sit down to “get things done” — and somehow, even after hours of work, you can’t actually name what moved forward?

Yeah. That’s not just a time problem — it’s a system problem.

Welcome to The Strategic Hustle Podcast — a space for real people trying to juggle business, life, caregiving, responsibilities… and still somehow move forward without burning out.

I’m Jacqueline — systems strategist, founder of The Strategic Hustle, and someone who spent nearly 40 years building high-stakes quality systems in the corporate world before walking away to create something better.
 Now I help entrepreneurs and everyday people build clarity, structure, and calm into the chaos — without needing 12 apps or a 5 a.m. routine.

And if you’re anything like me — running a business, managing a household, leading with intention — then you’ve probably already noticed something’s off.

Your brain doesn’t operate like a factory.
Your days aren’t a neat little schedule.
And your to-do list?
Let’s just say it wasn’t designed for entrepreneurs juggling everything from strategy to snack duty.

So today, we’re going deeper than productivity hacks.

We’re talking about why your current planner might be failing you — and how to build a system that finally gives your big-picture work the attention it deserves.

Because the goal isn’t just to feel productive.
It’s to feel clear.

It’s to feel in control.
And it starts by flipping your list upside down.

🎵 [Music fades out]

🎵 [Soft transition music fades in]

I want to take a minute to speak to those of you who might be listening and thinking…
 “This sounds great, Jacqueline, but I’m not an entrepreneur.”

Maybe you’re not building a business.
Maybe you’re managing a household, raising a family, navigating a full-time job, caring for others, or trying to keep your own life from spinning out.
And you’ve heard me talk about systems, structure, and strategy — and thought, “Is this really for me?”

Let me tell you something: Yes. It absolutely is.

Because what I’ve learned — after almost 40 years in high-pressure environments and now running a life that includes both business and family with complex needs — is that everyone benefits from structure.
Everyone needs margin.
Everyone deserves to feel less overwhelmed.

You don’t need to be chasing revenue or building a brand to deserve peace.
You just need to be a human carrying a lot… and ready to feel more clear, more in control, and more supported.

That’s why I built the Launchpad Course.
Yes, it works for entrepreneurs. But it was also designed for people who are simply trying to manage their days without feeling buried.
It gives you tools that work — even when life is loud, even when you’re tired, even when things feel messy.

Because you don’t need a perfect planner.
You need something that actually helps.

So if you’ve been listening and quietly wondering if this space is for you — I want you to hear me clearly:
It is.
And I’m so glad you’re here.

🎵 [Soft outro music fades back into the episode]

🎵 [Opening music fades in]

You know that feeling when you sit down to “get things done” — and somehow, even after hours of work, you can’t actually name what moved forward?

Yeah. That’s not just a time problem — it’s a system problem.

Welcome to The Strategic Hustle Podcast — a space for real people trying to juggle business, life, caregiving, responsibilities… and still somehow move forward without burning out.

I’m Jacqueline — systems strategist, founder of The Strategic Hustle, and someone who spent nearly 40 years building high-stakes quality systems in the corporate world before walking away to create something better.
Now I help entrepreneurs and everyday people build clarity, structure, and calm into the chaos — without needing 12 apps or a 5 a.m. routine.

And if you’re anything like me — running a business, managing a household, leading with intention — then you’ve probably already noticed something’s off.

Your brain doesn’t operate like a factory.
Your days aren’t a neat little schedule.
And your to-do list?
Let’s just say it wasn’t designed for entrepreneurs juggling everything from strategy to snack duty.

So today, we’re going deeper than productivity hacks.

We’re talking about why your current planner might be failing you — and how to build a system that finally gives your big-picture work the attention it deserves.

Because the goal isn’t just to feel productive.
It’s to feel clear.

It’s to feel in control.
And it starts by flipping your list upside down.

🎵 [Music fades out]

🎵 [Opening music fades in]

Hey there — welcome back to The Strategic Hustle Podcast.

I’m Jacqueline — founder of The Strategic Hustle and a systems strategist with nearly 40 years of experience in high-stakes industries like automotive and medical devices.

After decades in corporate leadership, I stepped away to build something more personal — two purpose-driven businesses that reflect what really matters: structure, clarity, and people.

And let me just say it up front:
If you’re building a business and tired of drowning in your to-do list, you’re going to want to hang with me for this one.

Because today we’re talking about why your current planner — and your entire approach to your to-do list — probably isn’t working.
And more importantly, what to do instead.

🎵 [Music fades out]

PART 1 — WHY MOST TO-DO LISTS FAIL ENTREPRENEURS

Let’s start here.
Most planners?
They’re built for people living a pretty straightforward life.

Get up. Go to work. Come home. Handle dinner, laundry, maybe a workout.

They’re not designed for entrepreneurs who have 47 spinning plates, constant fires, unpredictable demands, and revenue tied directly to what they focus on.

Your brain — and your business — simply don’t work like a regular 9-to-5.

So if you’re trying to fit your business reality into a standard planner system, of course you feel scattered.
Of course you feel like you never catch up.

It’s not because you’re lazy or bad at time management.
It’s because you’re using the wrong tool for the wrong job.

PART 2 — THE PROBLEM WITH MASHED-UP LISTS

Here’s one of the biggest mistakes I see:
Most people create mashed-up to-do lists.

They’ll have things like:

• Send proposal to new client
• Buy paper towels
• Finish module 3 slides
• RSVP to kid’s field trip
• Update website privacy policy

All sitting on the same list.
Equal weight.
Equal urgency.

Your brain can’t naturally prioritize that.
It sees everything on the same level — and panics.
Or it does the easiest thing first just to get a dopamine hit.

A LITTLE PERSONAL CONFESSION

Listen, I’ve been there.
Years ago — when I first launched POSSiBiLiTEEs, my screen printing shop — I had these giant sticky notes plastered all over my office wall.

Some were about customers, some were about t-shirt inventory, some were about social media posts.

It was chaos.
Every day I’d come in, stand there with my coffee, and just feel this wash of overwhelm.

Because there was no structure.
No separation of what was truly moving the business forward vs. what was just daily maintenance.

So I did what most people do:
I stayed busy.
Checked off the easy things.
Felt productive — but never actually made progress on the stuff that would grow the business.

Sound familiar?

PART 3 — THE DIFFERENCE BETWEEN STRATEGIC & SUPPORT TASKS

Here’s the critical shift.

As an entrepreneur, you have two kinds of work:

1. Strategic work — the work that moves your business forward.
   It’s building your offers, tightening your delivery, creating marketing assets that keep working while you sleep, developing systems that free you up.
2. Support work — the work that keeps the machine running.
   It’s responding to emails, posting content, ordering supplies, sending invoices.

Both matter.
But they’re not equal.

Your planner doesn’t usually distinguish between them.
So you end up spending 80% of your time on support work because it’s loud, it’s immediate, and it feels good to check off.

Meanwhile, your strategic work sits untouched.

A QUICK STORY FROM MY CORPORATE DAYS

I remember back when I was leading global quality initiatives, we’d do these massive audits.
We’d spend weeks prepping for them — tightening documentation, training teams, running internal mock reviews.

Some people would grumble, “This doesn’t directly make us money. Why are we wasting time on it?”

But here’s the truth — that was the strategic work.
Because passing those audits kept us certified.
It meant we could continue manufacturing.
Which meant we could keep our contracts — and keep the entire business alive.

If we only did the loud work — shipping parts, handling customer complaints — we might have made short-term dollars but long-term we’d have lost everything.

Same principle in your business.

PART 4 — HOW TO BUILD A STRATEGIC TO-DO LIST

Alright — so let’s talk solutions.

Here’s how I want you to build your new to-do list.

Split it into two clear columns.
Get a piece of paper — or open a new note on your phone.

On the left side, write:
 ✅ Strategic Work

On the right side, write:
 ✅ Support Work

Now start dumping everything that’s on your mental load into one of these two columns.

Examples

Strategic:

• Outline your next course module 
• Build your lead magnet
• Set up client onboarding emails
• Create an SOP for your delivery process

Support:

• Check DMs
• Print labels
• Follow up on small invoices
• Post a quick story on Instagram

When you see it laid out like this, it becomes painfully obvious where your time should go.

PART 5 — SCHEDULE THE QUIET WORK FIRST

Now here’s the key.

The strategic work will almost never scream for your attention.
That’s why it has to be scheduled first.

Literally block off time for it on your calendar.
Protect it like it’s a sales meeting with your biggest customer.

Because it is.
Your future business is your biggest customer.

If you don’t prioritize this work, the loud stuff will always eat your day.

PART 6 — A MINI EXERCISE (DO THIS WITH ME NOW)

Let’s do a 30-second exercise right now.

Close your eyes — unless you’re driving — and think about the last week.

Where did most of your time go?
Was it on strategic work — building assets, creating systems, tightening your offers?
Or was it on support work — emails, tiny admin fires, feeling busy?

Just notice it. No shame.
This is about awareness, not beating yourself up.

Now pick one strategic task you’ve been avoiding.
Maybe it’s recording a sales video.
Maybe it’s drafting your client onboarding process.
Maybe it’s mapping out your next quarter.

Promise yourself you’ll schedule it this week.
And actually show up for it.

PART 7 — WHY THIS MATTERS MORE THAN YOU THINK

I want to leave you with this.

Most entrepreneurs stay stuck not because they’re not working hard enough — but because they’re working on the wrong things.

They’re stuck in a loop of support work, thinking if they can just get “caught up,” then they’ll focus on the big stuff.

But here’s the truth — you’re never going to be caught up.
The inbox will never be empty.
There’s always another tiny thing to handle.

Growth comes when you flip the script.
When you build your days around the quiet work — the strategic moves — and let the support work fill in around it.

Not the other way around.

CLOSING & CTA

🎵 [Soft outro music fades in]

If this clicked for you — if you’re realizing maybe your list has been upside down — I’ve got tools that can help.

At thestrategichustle.com, you’ll find simple systems, guided workbooks, and my Launchpad Course that walks you through building a foundation so you can grow without burning out.

Because I promise you — it doesn’t have to feel like you’re running on chaos and caffeine every single day.

Alright — in our next episode, we’re going to dive into something big:
The difference between the right work and the loud work, and how to finally break out of that busy trap.

Until then, keep it simple, keep it strategic — and keep going.

I’m Jacqueline, and this was The Strategic Hustle Podcast.

🎵 [Music up and out]

🎵 [Soft outro music fades in]

Whether you're here as a business owner, a caregiver, or just someone trying to make life work a little better — I want to thank you for spending time with me today.

This podcast isn’t just about systems and structure — it’s about creating margin for the things that matter.

So if something clicked, if you felt seen or supported, or if you're walking away with a little more clarity than you came in with — that’s the win.

And if you’re ready to take the next step — whether that’s exploring the Launchpad Course, grabbing one of our tools, or simply joining the conversation — head to thestrategichustle.com.

Because you don’t need more noise.

You need space to think, room to breathe, and systems that actually serve your life.

I’m Jacqueline — and this is The Strategic Hustle.

Until next time… keep it simple, keep it strategic, and keep showing up.

🎵 [Music swells and fades out]