Letting Go to Let Them Grow: Leadership Evolution in Parenting and Entrepreneurship

In a few days, my daughter will head off to college.

I’ve caught myself laughing because I’ve been “nesting” — cleaning out storage, organizing closets, donating things we don’t use. The same flurry of preparation I did before she was born… just in reverse.

This is my third child to leave for college (though my first girl), so I’m more level-headed than I was the first time. I know she’ll be okay. I know I’ll be okay. But that doesn’t make the shift any less real.

The truth is, my role as her mom is about to change.

When she lived here, I was part of her everyday life. I knew where she was, who she was with, what time she’d be home. I was hands-on, guiding, managing, making decisions with her and sometimes for her.

Now, she won’t need me in that way.

She doesn’t need a manager — she needs an advisor. A sounding board. A safe place to land. Someone to help her see options and perspective when she asks. My job is to trust the values, judgment, and resilience she’s developed, and give her the space to put them into practice.

And as I’ve been preparing myself for this change, I’ve been reminded of something I see with business owners all the time.

The Parenting–Entrepreneurship Parallel

In the Entrepreneurial Evolution™️, there’s a point where your role must change for your business to keep growing.

In the early days, you are the business. Every decision runs through you. Every success and every problem bears your fingerprints. You’re the doer, the fixer, the one holding it all together.

But just like parenting, there comes a stage where staying in that role will actually hold them back.

Your business doesn’t need you to approve every proposal or solve every client problem.
It needs you to set direction, to protect the vision, and to mentor the people you’ve trusted with execution.

If you keep doing for them what they can do for themselves, you’ll slow their growth — and burn yourself out.

What It Takes to Evolve as a Leader

Whether you’re sending a daughter to college or guiding your company into its next phase, the work is similar:

  • Trust the preparation. You’ve taught your child — or your team — the skills and values they need. Let them use them.

  • Redefine your role. Move from being the operator to the strategist. In parenting, that means less daily management, more perspective-giving. In business, it means less firefighting, more architecting the future.

  • Let go of the hero role. It’s tempting to keep swooping in to save the day. But the real mark of leadership is building something that thrives without you being the center of it all.

The Gift of Letting Go

Yes, it’s bittersweet. Yes, there will be moments where you miss being so needed.

But letting go isn’t abandoning — it’s believing in what you’ve built.

When we evolve alongside those we’ve nurtured — whether it’s a child stepping into adulthood or a business stepping into its next stage — we create space for them to grow into their full potential. And we grow, too.

Because the next level — for them and for us — requires a different kind of leader than we’ve been before.

If we want them to soar, we have to rise, too.

Jen Eckhardt

I created Entrepreneurial Freedom to solve a problem most business owners don’t recognize until it’s too late. Our work focuses on both the operational systems and the personal transitions that make true freedom possible.

Even with a great team, most businesses still rely on the owner in ways that quietly limit growth—and ultimately reduce value at exit.

We help owners design a business that runs and grows without them, so when the time comes to exit, they have options—and peace of mind.

Next
Next

Quiet Truths, Part 2: “I’ve created success that doesn’t feel successful.”