leadership

The Mentor You Didn't Know You Needed

February 03, 20263 min read

Leadership confidence doesn’t disappear overnight.

It fades quietly.

And this week’s Self-Made Memo is about something we don’t talk about enough — what to do when your leadership spark goes dim, even when you’re still showing up and doing the work.

Because yes… even strong leaders lose their confidence sometimes.

And I watched it happen to someone I love more than anything.


🏀 Jacoby: From Confident Leader to Quiet Observer

Jacoby has always been a confident leader on the court.

Smart.
Strategic.
Poised.

But after a major injury, a long recovery, and stepping onto a new team with a new coach…

Something shifted.

INJURY

His skills were still sharp.
His court IQ was solid.
His confidence as a player stayed intact.

But his leadership?

That part went quiet.

He played well — but he didn’t lead.

He hesitated.
He hung back.
And the spark that once defined him just wasn’t there.


Until One Practice Changed Everything

This week, Jacoby was invited to stay after shootaround and join the top 8th-grade team’s practice.

A faster group.
A more intense environment.
A completely unfamiliar room.

He didn’t know the players.
He wasn’t their point guard.
He was the youngest — and smallest — kid on the court.

And at first?

CONFIDENT

He was shy.
Quiet.
Observing.
Unsure.

Then something powerful happened.

A coach — not even his coach — pulled him aside.

He gave him feedback.
He poured into him.
And he did it repeatedly throughout the two-hour practice.

That coach saw something in Jacoby.

And slowly… Jacoby started to see it in himself again.

By the end of practice, we saw the old Jacoby return.

The confident one.
The leader.
The kid who commands the court no matter where he plays.

Just three days later, he’s coming home from practice talking about how he stepped into leadership again — not because someone gave him a title, but because someone reminded him who he already was.


So What’s the Business Lesson Here?

If you’ve been moving through your business quietly lately…

If your confidence feels dulled…

If your leadership presence feels a little off…

Here’s the truth:

Maybe what’s missing isn’t skill or strategy.
Maybe it’s mentorship.

Sometimes all it takes is one person

With the right energy.
The right question.
Or the right feedback.

Someone who helps you realign with who you were always meant to be.

You’re not broken.
You’re not behind.

You may just need someone to help you remember your power.


Leadership Isn’t a Title — It’s a Presence

This week, pause and ask yourself:

  • Do I have a mentor right now who sees my next level?

  • Am I actively leading — or quietly coasting?

  • What support or shift could reignite my spark?

Because whether you’re a CEO, contractor, partner, or employee — leadership isn’t about position.

It’s about presence.

And if you’ve lost yours, I promise — it can return.

You just need the right coach in your corner.

Jacoby found his.

Are you ready to find yours?


📩 Leadership isn’t built alone — and neither is a business that lasts.

🎧 Continue the journey inside The Digital Shift™ Podcasthttps://www.self-made.biz/podcast

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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