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.

When to Pivot, When to Hold On — And How I Learned The Difference

Maybe you’re standing at a crossroads right now — wondering if it’s time to let go, shift directions, or try something new. This is your reminder: Pivoting isn’t failure. Sometimes it’s the smartest, bravest thing you’ll ever do.

There’s this idea floating around that if you pivot, it means you’ve failed.

That changing direction means you didn’t stick it out long enough.

But let me tell you — some of the smartest, most successful, most creative people I know… got there because they knew when to pivot.

I’ve been pivoting my whole life.

Not because I’m flaky.

Not because I couldn’t commit.

But because sometimes life makes the decision for you — and sometimes you realize staying still costs you more than moving forward ever could.


Growing up, I was a competitive dancer.

That was the dream. The focus. The thing I thought I’d do forever.

But then I got injured.

And just like that, life forced me into my first pivot. I couldn’t dance the way I used to, and suddenly, I had to ask myself a terrifying question:

If I’m not this thing I’ve been my whole life… then who am I?


That question led me to acting.

And that dream led me to NYU Tisch.

Acting became my new outlet, my new obsession, my new plan.

But the thing about being a curious person in a creative environment is… your interests start to expand fast.

While I was in acting school, I found myself fascinated by filmmaking — not just being in front of the camera, but behind it too.

I started making short films. Producing music videos. Writing stories. Building worlds.


College wasn’t cheap. New York definitely wasn’t cheap.

So I worked.

And without realizing it, every random skill I picked up along the way started stacking up:

→ Website design

→ Photography

→ Social media content creation

→ Video editing

→ Marketing

→ Copywriting

I didn’t know it then, but I was building an entire creative skillset that would end up serving me way beyond the stage or screen.

Every job. Every skill. Every pivot.

All of it gave me something bigger than a title — it gave me perspective.

It allowed me to see the bigger picture.

To see patterns. To connect ideas. To understand story in a way that went beyond characters or scripts.

It shaped how I think.

It shaped the kind of creator I became.

And ultimately — it shaped the story I wanted to tell… not just on a stage, but in my life, in my work, in everything I build now.

And Now? Another Pivot.

I still love storytelling.

I still love creating.

Acting is still a part of me — and maybe always will be.

But let’s be real…

I ‘m Black. And let’s just say — in the entertainment industry, especially with this new government administration, certain doors will stay closed a little longer for people who look like me.

So I pivoted. Not because I wasn’t good enough. But because I got tired of waiting for a seat at a table, I could build myself – sure it would take longer, but at least I’m taking my destiny in my own hands .


I pivoted into entrepreneurship.

Into content creation.

Into brand strategy.

Into building my own thing from scratch.

What I’ve Learned About Pivoting

→ Pivot when life forces you to.

→ Pivot when your curiosity leads you somewhere new.

→ Pivot when staying still starts to feel like shrinking.

→ But never be afraid to circle back to the thing you love when the timing feels right.

The goal isn’t to “pick one thing” forever.

The goal is to keep growing. Keep learning. Keep building a life with range.

And trust me — every pivot teaches you something you’ll need later.

Every single one.

What’s a pivot you made that shaped who you are today? Tell me below — I’d love to know.

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