How We Defined Our Version of “Livin’ the Dream” (and How It Changed the Way We Built Our Business)

vapostol
4 days ago
5 min read

Why success didn’t come from working harder—but from deciding what success actually meant to us

For a long time, we chased a version of success that wasn’t fully defined.

We were building businesses.

We were growing revenue.

We were solving problems and making things work.

From the outside, it all looked successful.

But internally, something was missing.

We were busy—often exhausted—and while there were moments of freedom, they felt fragile. Like something that could disappear the moment the business needed us again.

And that’s when we realized something fundamental:

We had built a successful business—but we hadn’t clearly defined what “Livin’ the Dream” actually meant for us.

Until that moment, success had been measured in outputs.

Revenue.

Growth.

Momentum.

What we hadn’t done was define success in terms of how we wanted to live.

That single shift changed everything.

The Moment We Stopped Accepting Someone Else’s Definition of Success

Entrepreneurs are surrounded by other people’s definitions of success.

More growth.

More hustle.

More scale.

More visibility.

More pressure.

And while there’s nothing wrong with ambition, there is a problem when we pursue goals without questioning whether they align with the life we actually want.

At one point, we had a realization that stopped us in our tracks:

If the business required us to be constantly present, constantly available, constantly solving problems—then we hadn’t built freedom. We had built a very demanding job.

That was not the dream.

The dream was never about escaping responsibility.

It was about choice.

Choice over where we spent our time.

Choice over how involved we needed to be.

Choice over when we worked—and when we didn’t.

Choice over travel, family, and lifestyle.

Once we named that clearly, it became obvious that the way we were building the business had to change.

Why Clarity Precedes Freedom

Before we defined our version of “Livin’ the Dream,” we were making decisions reactively.

We said yes because opportunities came up.

We stayed involved because it felt safer.

We held onto tasks because no system existed yet.

We postponed changes because the business was “working.”

But “working” isn’t the same as working for us.

Defining the dream gave us a filter.

Instead of asking:

“Can we do this?”

We started asking:

“Does this support the life we’re intentionally building?”

That question became a strategic tool.

It guided how we hired.

How we delegated.

How we structured operations.

How we designed systems.How we decided what not to do.

Freedom didn’t come from scaling faster.

It came from building intentionally.

Selling a Business Didn’t End the Dream—It Proved the System

One of the clearest confirmations that we were on the right path came years later, when we sold a business we had built with intention and systems in place.

We didn’t walk away completely.

We didn’t abandon it.

We didn’t “check out.”

The business was still our baby—but it was walking on its own.

That was the point.

Because when a business can operate without your constant presence, you gain options.

After that sale, we didn’t stop being entrepreneurs.

We built other businesses.

We grew them.

We sold them.

And throughout all of it, we continued living our version of the dream.

We traveled.

We chose when to work.

We chose when not to.

We lived a “work hard, play hard” lifestyle—but on our terms.

That’s the distinction most entrepreneurs miss.

The Owner vs. Operator Shift That Made It Possible

Defining “Livin’ the Dream” forced us to confront a hard truth:

We were still operating too much like operators—even when we were technically owners.

Operators solve.

Owners design.

Operators react.

Owners plan.

Operators are needed daily.

Owners build systems so they’re not.

Once we clarified that our dream involved freedom, we were able to make choices that allowed us to step more fully into the owner role vs the operator role.

That meant:

Letting go of control before we felt fully ready
Writing things down instead of keeping them in our heads
Training people instead of “just doing it faster ourselves.”
Accepting short-term discomfort for long-term leverage

None of that was easy.

But all of it was necessary.

Why Systems Were the Bridge Between Vision and Reality

A dream without structure is just a wish.

What allowed us to live the dream wasn’t luck or timing—it was systems.

Systems allowed the business to operate consistently.

Systems allowed other people to step in.

Systems reduced dependence on us.

Systems made delegation realistic instead of risky.

When systems are absent, freedom is temporary.

When systems are strong, freedom is sustainable.

That’s why we don’t teach systems as a productivity tool.

We teach them as a lifestyle tool.

Every process we documented.

Every role we clarified.

Every policy we defined.

Each one bought us time, energy, and peace of mind.

Redefining Success Changed How We Made Decisions

Once we defined our version of “Livin’ the Dream,” decision-making became simpler.

Not easier—but clearer.

We didn’t chase every opportunity.

We didn’t say yes to everything.

We didn’t build for ego or appearances.

We built for:

Sustainability
Flexibility
Transferability
Enjoyment
Alignment

That meant sometimes turning down “good” ideas.

Sometimes slowing growth.

Sometimes, restructuring things that already worked.

But those decisions compounded.

Over time, the business became something that supported us—not something that consumed us.

Why We Believe Every Entrepreneur Needs Their Own Definition

One of the biggest mistakes entrepreneurs make is assuming the dream looks the same for everyone.

It doesn’t.

For some, it’s travel.

For others, it’s time with family.

For others, it’s creative freedom.

For others, it’s flexibility or impact.

There is no universal dream.

But there is a universal problem when the dream is undefined.

When we don’t define it ourselves, we default to someone else’s version—and build a business that quietly pulls us away from what matters most to us.

A Simple Reflection We Come Back to Often

Whenever things feel heavy or misaligned, we return to a simple reflection:

Is the way we’re running the business still supporting the life we said we wanted?

If the answer is no, that’s not a failure.

It’s feedback.

And feedback allows us to realign.

Sometimes that means adjusting systems.

Sometimes it means redefining roles.

Sometimes it means saying no.

Sometimes it means redesigning the business model.

But it always starts with clarity.

Expert Spotlight

G. Mick “The Doctor of Digital” Smith, PhD, helps thought leaders turn ideas into published books that build authority, influence, and leverage. As a Chief Story Strategist, Book Coach, and Ghostwriter, he works with purpose-driven entrepreneurs, educators, and creatives to transform lived experience into clear, compelling narratives.

Founder of the Idea-to-Author Coaching Community, G. Mick Smith guides clients through a proven end-to-end process—from concept and outline to publishing and launch—helping them finish with confidence and create new opportunities through their books.

With more than 20 years in educational leadership and digital strategy, Mick brings both structure and storytelling mastery to every project. His clients don’t just write books—they create platforms.

Learn more or connect here:

TheDoctorOfDigital@proton.me