Jess with starting at 40's

🎉 Why I’m Not “Behind” at 49 — And You’re Not Either

January 16, 2026•3 min read

What turning 49 taught me about success, peace, and the business I’m building in 2026

Jess Birthday

Yesterday, I turned 49.

No big party.

No “birthday bash” or over-the-top celebration.

Just my husband, our besties, and a reservation at The White Horse — a restaurant I’ve wanted to try for over a decade.

As I sat there, wine glass in hand, I realized how far we’ve come.

We weren’t just celebrating another year of life…

We were celebrating a life we’ve built — with intention, strategy, and a whole lot of hard work.


A Life With Margin

The older I get, the more I crave simplicity.

Jess with husband

Peace. Margin. Room to think and breathe.

And that doesn’t happen by accident — especially not when you’re growing a business.

So much of my 30s and early 40s was hustle.

Build the thing. Fix the thing. Sell the thing.

Spin every plate. Answer every message. Be available 24/7.

But now?

Now I build on purpose.

I make room for birthday lunches with people I love.

I take actual vacations.

I say no to chaos, yes to systems, and I’m building a multiple 7-figure business with peace and profit as the metric — not burnout.


A Big Audacious Goal for 2026

This year, we’re taking Self Made™ into its biggest chapter yet.

We’re scaling to multiple 7-figures.

We’re expanding our mentor team, launching the full Tech-Savvy School™, and pouring into female entrepreneurs who are done duct-taping tech and finally ready to build a business that runs while they live their life.

That’s our mission.
That’s our momentum.

And the best part?

I feel more ready than I ever have — at 49.


If You’re Feeling “Behind” — Read This

So many women I talk to feel like they’ve missed their window.

They tell me things like:

“I should’ve started sooner.”

“I’m already in my 40s — is it too late to pivot?”

“Everyone else seems to have it figured out.”

But let me hit you with a little reality check (and some stats to back it up):

  • ✅ The average self-made millionaire is 45+

  • ✅ Most CEOs hit their career stride around age 54

  • ✅ The average age of “I feel successful” is between 45 and 55

So if you’re in your 40s or 50s thinking you’re behind?

You’re not. You’re just getting started.

Your life experience is your edge.

Your timing is divine.

And your success story might just be right on time — even if it doesn’t look like someone else’s.


We’re Headed to Islamorada Next…

And to keep the celebration going, we’ve got a beach house in Islamorada booked with some of our closest friends. One week of salt air, sunsets, and soul-deep laughter.

That’s the why behind the business.

That’s the real ROI I measure.

Yes, we’ll be growing.

Yes, we’ll be scaling.

But we’ll be living while we do it.

Because that’s the whole point of building a business like this — one that makes money while you sleep, sends emails while you sip sangria, and keeps growing even when you’re off the grid.


Final Thought:

If you’re feeling behind, rushed, or like you should’ve figured it out by now — breathe.

Your next best chapter may not come with a birthday candle or big milestone.

It may come in a quiet decision to keep going.

To simplify.

To get support.

To stop overthinking it and just start.

And trust me — 49 has never looked so good. 😉

Here’s to your version of success, however and whenever it comes.


Want help mapping your 2026 business strategy with peace, systems, and real momentum?

🎧 Listen to Episode 58: Your 2026 Game Plan

Or better yet…

📩 Subscribe to the Self Made Memo — where we share behind-the-scenes business moves, real-life lessons, and weekly strategies to build your own automated, profitable business.


Jessica Green and Natasha Roberson are the dynamic duo of tech mentorship—combining strategy, systems, and soul to help entrepreneurs win with Go High Level. Jess brings the big-picture vision and automation strategies, while Natasha makes the tech feel simple and doable. Together, they’ve built a mentorship model that takes the overwhelm out of digital business and replaces it with clarity, confidence, and growth.

Self Made Mentors

Jessica Green and Natasha Roberson are the dynamic duo of tech mentorship—combining strategy, systems, and soul to help entrepreneurs win with Go High Level. Jess brings the big-picture vision and automation strategies, while Natasha makes the tech feel simple and doable. Together, they’ve built a mentorship model that takes the overwhelm out of digital business and replaces it with clarity, confidence, and growth.

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