Ashleigh Jessica Taylor

Creative Entrepreneur

Where business meets freedom, and creativity knows no borders.

Ashleigh Jessica Taylor

Creative Entrepreneur

Where business meets freedom, and creativity knows no borders.

How I Got Here: The Naked Version of My Creative Entrepreneur Journey

There’s the version of my story that sounds nice on paper. And then there’s the real version — the one built from pivots, risks, random jobs, and figuring it out one lesson at a time.

If we’re going to hang out on this blog together — you should probably know the real version of my story and how exactly I got here – so let me bare it all.

Because truthfully… I didn’t grow up knowing I wanted to do this – be a mix mash of entrepreneur and creative.

I didn’t come from a family of business owners. I didn’t have some master plan. What I did know was that I never quite fit the mold.

I tried the “right” paths — college, 9-to-5 jobs, the corporate ladder life. I worked in big environments, supported C-suite executives, managed complex projects…and still felt like I was playing small.

Not because those jobs weren’t good.

But because I knew I was built for something else.


What I really wanted?

Freedom. Flexibility. Creativity. Impact.

I didn’t want to ask permission to take a day off.

I didn’t want to squeeze my life into weekends and vacation days.

I didn’t want to build someone else’s dream while leaving mine on the back burner.

But wanting that life — and actually building it — are two very different things.

I had weeks of absolute euphoria — like this is it, I’m really doing it.

And I had nights where I cried non-stop wondering what I got myself into.

There were days I felt like a genius — unstoppable, clear, on fire with ideas.

And there were days I genuinely thought I was an idiot for thinking I could do this at all.

That’s the part nobody talks about enough.

Not just the strategy or the hustle… but the emotional whiplash of chasing a dream and betting on yourself every single day.

So I did what most people don’t see…

I took on random freelance jobs.

I built websites for friends-of-friends.

I learned skills on YouTube and Google at 1AM.

I launched things that flopped.

I launched things that quietly worked.

And piece by piece, project by project… I built something real.

Something mine.


That’s what led me here.

To this blog. To this space.

A place to document the messy middle.

To tell the real stories behind building a business and life that actually feels like you.

Not just the wins. But the figuring-it-out parts too.

Because here’s what I know for sure — we’ll never be in this exact moment again.

Same lessons. Same struggles. Same dreams swirling around in your Notes app.

That’s why I’m writing.

To jot it down before it passes.

To remind myself (and maybe you) that the figuring-it-out stage is the story.

To not document the struggle-the process, is to not tell the whole story.

If you’re new here — welcome.

This blog is for the dreamers, the doers, the late-night Googlers, the “is it just me?” thinkers.

I’m glad you’re here.

Let’s figure it out — one note at a time.

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