Why This Multimillion-Dollar CEO Starts the Year Doing Nothing: A Four-Part Sabbatical Series

The first time I took a sabbatical, it wasn’t strategic.

It was desperate.

It was 1:00 a.m., the house was quiet, my toddler was asleep, and my husband was already in bed. I was sitting alone, overstimulated, exhausted, and angry in a way I hadn’t let myself admit yet.

Not angry at my clients.

Not angry at my business.

Angry at myself.

I had built a company that looked successful from the outside—but internally, I was running on fumes. I was over-delivering to a fault, saying yes when I should’ve said no, and tolerating behavior from a few wild clients that I would never accept today. That’s rare now—but back then, I hadn’t earned my boundaries yet.

I wasn’t taking care of my body.

I wasn’t listening to my nervous system.

I was driven almost exclusively by achievement.

And it was working—until it wasn’t.

So I did something impulsive.

At one in the morning, without a spreadsheet, without a plan, without asking permission from logic—I booked a 30-day international trip for my husband, my toddler, and myself.

Flights. Lodging. Everything.

Not because it was smart.

But because I was done.

I handed the company over.

Trusted the systems more than my fear.

And left.

That trip wasn’t rest—it was recovery.

It was the moment I realized that success without self-regulation is just slow-motion self-destruction.

Fast forward to now—and the difference is this:

I don’t wait for burnout anymore.

I leave on cue.

I step away before my body forces me to.

I listen to the early signals instead of ignoring them.

And when I get on a plane now, it’s not to escape pressure—it’s to preserve clarity.

That’s the evolution.

That’s the work.

And that’s why this time looks completely different.

My name is Ashley Kirkwood.

I’m the founder and CEO of Speak Your Way To Cash®—a company that helps experts, consultants, and leaders sell at the top of the market through speaking, positioning, and strategic sales systems.

Last year, we ran 20 live launches.

We crossed multiple seven figures.

We scaled without chaos.

And we did it without building a business that eats its founder alive.

This is my first Substack article, and I want to be clear about what you’re reading—and why I’m writing it.

This is not content.

This is not a highlight reel.

This is not a “soft life” essay.

This is a four-part journaled series on what happens when a CEO with a real company, real employees, and real revenue chooses to step back on purpose.

What This Series Is (And Isn’t)

This series documents a sabbatical—not as an escape, but as a strategic act.

A sabbatical, as I define it, is:

A deliberate, time-bound withdrawal from day-to-day execution in order to restore decision quality, perspective, and long-term capacity.

This is important:

My business is open.

My team is working.

Revenue is still being generated.

Clients are still being served.

I am not “gone.”

I am personally off.

That distinction matters.

Because the goal of leadership is not to be constantly active.

The goal is to build something that does not require your nervous system as the bottleneck.

Why Every CEO Should Take a Sabbatical—When They Can

Most founders wait until they’re exhausted to step away. That used to be me, but this is now our third 30-45 day sabbatical.

That’s backward.

The most dangerous time to not pause is when:

The business is working

Revenue is flowing

Momentum is high

Your calendar is full

That’s when poor decisions get disguised as confidence.

That’s when speed replaces precision.

That’s when identity starts running the business instead of strategy.

A sabbatical—when done correctly—is not about rest for rest’s sake.

It’s about:

Testing the strength of your systems

Removing adrenaline from decision-making

Seeing your business without emotional noise

Regaining authority over how and why you grow next

Every CEO should take one when:

The business can sustain it

The team is capable

The systems are proven

The founder is no longer required for daily survival

That’s not privilege.

That’s good leadership.

Why I’m Sharing This Publicly

I teach leadership, strategy, and scale.

That means I don’t just explain concepts—I model them.

My clients don’t only listen to what I say.

They watch what I do.

They want to know:

When to push

When to pause

When restraint is wisdom, not fear

When doing less creates more

I cannot teach that from theory.

So I tested it.

This sabbatical will cost close to $100,000 all in.

Flights were covered with points.

Hotels, food, logistics, time—real money.

And it is one of the best investments I’ve ever made.

This series exists because:

I don’t teach what I haven’t lived

I don’t recommend what I haven’t tested

And I don’t believe leadership is proven by exhaustion

What’s Coming in This Four-Part Series

This is not chronological travel journaling.

This is strategic reflection, shared weekly.

Part 1: Why I Started the Year Doing Nothing (This Article)

The philosophy, the numbers, and why stillness sharpened—not slowed—my business.

Part 2: What Stepping Away Revealed About My Business

What held. What broke. What surprised me when I removed myself from execution.

Part 3: The Identity Shift That Happens When You Stop Performing

Why many founders sabotage scale because they don’t know who they are without urgency.

Part 4: How This Changes the Way I’ll Build, Sell, and Scale Going Forward

What I’m keeping. What I’m eliminating. And what this unlocks for the next phase.

If you’re building a real business—

If you lead people—

If your decisions affect others—

This series is for you.

Not because you should disappear.

But because at some point, you must prove the business works without you gripping it.

And now—this time—I’m only 2/6 of the way through this sabbatical.

We’re moving through Bangkok, Manila, Nigeria, Ghana, and Indonesia.

And I’m already learning things I didn’t know I needed to learn.

I’ve learned that I can spend two hours in the gym and not feel guilty.

I can spend an hour (sometimes two) reading and praying and still be sharp.

I can be so present that I can literally just… sit.

No phone. No multitasking. No “What’s next?”

I’ve learned what it feels like to look my husband in the eyes long enough to actually see him again.

Not as my partner in logistics.

Not as the person helping me hold life together.

But as my husband.

And I’ve fallen more in love with him out here.

That alone would’ve been worth it.

But rest has also made me ruthless—in the best way.

Because when you’re not drowning, you can finally tell the truth.

I’ve already decided to sunset some programs.

Not because they’re not good.

Not because they don’t make money.

But because I can feel—clearly—what I love, what I don’t, and what I’m no longer available for.

This is what rest gives you:

Not laziness.

Not softness.

Discernment.

And discernment is expensive.

Which is why I invest in it.

Anyways, drop in the comments how I can make this series valuable for you? Want to know how to keep your business for this? Where we were when we started this? How I do check ins while away? Hint: I get daily reports. Or something else? Nothing is off limits….