How Playing It Safe Almost Cost Me My Future

For midlife women entrepreneurs ready to step out of their comfort zone, learn from those who’ve walked the path, and use proven prompts to reclaim clarity and momentum.

The Safety Trap

If you had asked me in early 2021 how I was doing, I probably would’ve said something like, “I’m fine,” or “It’s just the change of the buy-out.” But the truth is, everything in my life was slowly shutting down.

It started in February, out of nowhere, with pain that didn’t make sense. A deep radiating pain that shot from my neck down my arm. At first, I brushed it off.

“Just a strain.”
“It’ll go away.”
“I just need to rest.”

But it didn’t go away.

Within weeks, the pain spread. I couldn’t sleep. I couldn’t focus. I couldn’t think clearly. Every part of my day felt like walking through heavy fog.

And it wasn’t just physical.
The pain chipped away at my confidence.
At my drive.
Looking back, I see now that the pain started after a long stretch of time where, little by little, I stopped doing the things that make me me.

I wasn’t reading anymore.
I wasn’t growing.
I wasn’t stretching myself.
I wasn’t curious.
I wasn’t planning.

For years, I had been teling myself, “I just need to get through this. I don’t have the energy to add more to my plate.”

I thought I was minimizing stress. Doing less. But what I was really doing was playing small.

I had lost the spark I’d always had, the part of me that loved learning, planning, dreaming, building.

It felt safer to stay still.

But here’s the truth I couldn’t see at the time:

Staying still was quietly costing me my life.

There’s a quote I love now but wasn’t ready for back then:
“Nothing changes if nothing changes.”

But I wasn’t changing anything.
I couldn’t see what I couldn’t see, and I had no idea where to start.
I was shrinking.

The Quiet Collapse

The part that still surprises me is how subtle it all was.

You don’t wake up one day and say, “My life has collapsed.”
It happens slowly, one choice, one fear, one hesitation at a time.

My world shrank month by month.

A “no” to activities became my default.
My social world got smaller.
My professional world got quieter.
My confidence got thinner.
And the part of me that used to feel unstoppable… disappeared.

It's strange how staying stuck feels safe, and how fear can disguise itself as “being responsible.”

There’s research showing that when people stop challenging themselves, life satisfaction drops and regret increases. People avoid growth not because they’re lazy, but because fear feels familiar.

And that was me.
Fear was running the show.

I kept thinking:

“What if it gets worse?”
“What if I push too hard?”
“What if I can’t handle it?”

I was thinking about my arm, but now I see this was also a reflection of my personal thoughts about my career.

So I stayed small.
I stayed quiet.
I stayed safe.

But nothing about that season felt safe.
It felt like I was disappearing.

The Moment Everything Shifted

There wasn’t a dramatic turning point; no bold declaration or inspirational epiphany.

It was more like a whisper.
A moment where I realized:

It wasn’t the pain that derailed me…
It was the stopping.

The stopping of growth.
The stopping of learning.
The stopping of listening to people who had walked this path before.
The stopping of trusting my ability to figure things out.

That was the real villain.
Stagnation.
Shrinking.
Avoidance disguised as safety.

Once I saw that, something inside me cracked open.

And I made one small choice, the first step back to myself:

I started learning again.

Not big learning. Not dramatic.
Tiny steps.

I picked up a book.
I listened to someone who inspired me.
I allowed myself to be guided.
I opened my mind again.
I gave myself permission to be a beginner during a painful season.

That one little decision was the start of everything good that came after.

What Staying Stuck Really Costs

When we stop learning, our world stops expanding.

There’s research showing that people who keep learning throughout life have:

• higher confidence

• greater life satisfaction

• stronger emotional resilience

• and fewer regrets

Meanwhile, staying stuck, even for “good reasons”, slowly erodes your sense of possibility.

When I stopped growing, I didn’t just lose direction.
I lost connection with the woman I had been.

For midlife women, especially, staying in the comfort zone feels responsible… until it isn’t.

Because all growth requires discomfort.
And discomfort is a sign of expansion. Not danger.

Learning From Those Who’ve Walked Before You

There’s something powerful about learning from someone who has lived the journey you’re about to take.

Before I built Elevate 50+ or Achieve Greatness Daily, I spent years as the Head of Business & Commercial Analytics. My entire world was:

• digging into data

• spotting patterns

• understanding behavior

• predicting future outcomes

• building business strategies

• and presenting strategic options to leadership

Nothing we did was based on guessing.
We used insight to determine the smartest path forward.

I lived in the world of:

“What’s the story the numbers are telling?”
“What trend do we need to pay attention to?”
“What decision will move us forward with the least friction and the biggest return?”

What I realized during my “stuck” season was this:

I had stopped treating my life the way I used to treat multi-million-dollar business decisions.

I wasn’t analyzing my thoughts.
I wasn’t planning.
I wasn’t designing my path.
I wasn’t listening to people who knew how to help me grow.
When I finally reconnected to that part of me, the learning part, the curious part, everything started shifting.

Learning again cracked the door open.
Planning blew it wide open.

Planning Breaks the “Stuck” Cycle

Planning gives you direction.
Direction gives you energy.
Energy gives you identity.
Identity gives you confidence.

There’s research showing:

• Writing down goals significantly increases your chance of achieving them

• Accountability partners can raise your success rate up to 95%

• Flexible planning (not rigid planning) leads to stronger long-term outcomes

Then why do more business owners not plan? I have been asking this question a lot, and what I have learned is that

It’s not because they don’t care.
It’s not because they don’t want to.
But it’s because no one ever showed them a simple way to do it that actually works.

So I reviewed the processes I have been using to plan for years successfully and I created the:

The AI-Powered Planning Starter Kit

Five simple, powerful prompts that:

• pull you out of the fog by helping you name who you are becoming and what actually matters in the next 12 months

• reconnect you to your identity through your own reflections, values, and future-self direction

• clarify what you want by revealing the themes, patterns, and truths already present in your background

• reveal your real capacity by mapping your personal seasons, commitments, and emotional bandwidth

• determine the direction your business needs you to go next using identity, revenue drivers, capacity logic, and aligned Q1 milestones

These prompts don’t give you random answers. They extract the answers you already know, organize them, and turn them into identity statements, revenue clarity, capacity boundaries, and Q1 priorities you can actually use to plan your year.

They’re the first five of the eight personal prompts I use in the upcoming 2026 Annual Business Blueprint Workshop.

And they make planning feel doable again, especially when life feels heavy or uncertain.

Why I’m Leading This Work

I didn’t rebuild my life through luck.

I rebuilt it through:

• learning again

• asking for help

• listening to people who had walked this path

• using the strategic planning frameworks I spent years perfecting in a high-level corporate role

I’ve rebuilt confidence.
I’ve rebuilt direction.
I’ve rebuilt momentum.
I’ve rebuilt identity.

And I now help other midlife women entrepreneurs do the same, with structure, clarity, and compassion.

There’s a quote I love:
“A goal without a plan is just a wish.”

My life started changing the moment I stopped wishing and started planning.

Your Invitation

If you’ve felt stuck…
If you’ve been shrinking…
If you’ve been avoiding growth because “safe” feels easier…

This is your moment to shift.

Just like I did.

Comment “PLANNING” and I’ll send you the

AI-Powered Planning Starter Kit

so you can reconnect to your clarity and direction without the overwhelm.

And when you’re ready to go deeper…

You’re invited to the

2026 Annual Business Blueprint Workshop

where we go through all eight prompts, build your custom roadmap, use custom AI tools strategically, and plan Q1 together, with a supportive community walking beside you.

Because learning alongside your peers doesn’t just speed up success, it makes the journey feel lighter.

And you deserve a year built with intention, clarity, strategy, and support.

The link for the workshop is included in the AI-Powered Planning Starter Kit.