What I Would Tell My 25-Year-Old Self

Lessons From My First 50 Years

Turning 50 has made me think about a lot of things.

Not just where I am today… but how I got here.

The dreams I had.
The mistakes I made.
The lessons I learned the hard way.

And if I could sit across the table from my 25-year-old self, or maybe even you, and just have a conversation, I know some things I would say.

Honestly, life doesn’t always go the way you plan.

Sometimes it’s beautiful.
Sometimes it’s hard.
And sometimes it breaks you in ways you never saw coming.

But if I’ve learned anything over the last 50 years, it’s this:

The small things matter more than you think.

I would start here.

Dream bigger.

When I was in my early 20s, I told myself I wanted to own 10 rental properties free and clear.

And I did it.

I reached that goal before I was even 40.

But looking back now, I realize something…

If I had written down 20, I probably would have achieved that too.

Because we move toward what we believe is possible.

We build our lives around the goals we set.

So don’t shrink your dreams to fit your current situation.

Expand your vision to match what’s actually possible.

Then I would tell her…

Be more present.

I had my son when I was 14, and from that moment on, I feel like I lived in hustle mode.

Trying to build a life.
Trying to provide.
Trying to get ahead.

And I was there… but my mind wasn’t always there.

Now, at 50, with my grandson, I see it differently.

I can put my phone down.
I can be fully present.

Because I’ve learned that the next call, the next lead, the next opportunity… it’s not as urgent as it feels.

And if I miss it, and they go somewhere else… then they probably weren’t meant to work with me anyway.

But the moments with your family?

You don’t get those back.

I would also say…

Take care of your body and don’t live in extremes.

We used to think low-fat bagels and fat-free cream cheese were the answer. 😂

And while that’s funny now, the real lesson is this:

I tend to go all in.

All or nothing.

And while discipline is a strength, extremes aren’t sustainable.

So be consistent. Be intentional. But give yourself grace.

Because real results don’t come from perfection.

They come from consistency over time.

And then I’d say something that took me years to understand:

Redefine fun.

When I was younger, fun often meant being entertained, staying busy, doing what everyone else was doing.

But now?

Fun looks different.

It can be reading a book.
Writing a blog.
Spending time with family.
Working toward something meaningful.

Because not all fun is equal.

Some fun drains you.

And some fun builds your life.

And I wish I had understood earlier that how you define fun will shape the direction of your life.

And finally…

I would talk about faith.

Because faith isn’t what I thought it was when I was younger.

Faith isn’t just believing everything will work out.

Faith is what you hold onto when your world falls apart.

When life doesn’t make sense.
When the pain is overwhelming.

Faith is waking up and saying,

“I’m just going to get through today.”

And then doing it again tomorrow.

And then stacking another day.

And slowly… over time… healing begins.

Breathing gets easier.

Not all at once.

Not in a straight line.

But it happens.

And somewhere along the way, you realize something…

You may never fully understand why certain things happened.

But when you’re ready, you can begin to find purpose in the pain.

You can take the hardest thing you’ve walked through, the thing you would never wish on anyone, and use it to help someone else find their way through the dark.

That doesn’t make it okay.

But it gives it some type of purpose.

At 50, I don’t have everything figured out.

But I do know this:

The life you’re building tomorrow is shaped by the small choices you make every single day.

So choose wisely.

Stay consistent.

Stay present.

Dream bigger.

And have faith… even when it’s hard.

Especially then.

The 3-2-1

3 Things to Remember

Dream bigger than feels comfortable.
Be present for the people who matter most.
Small, consistent habits will shape your life more than big moments.

2 Questions to Ask Yourself

What kind of life are you building with your daily choices?
And are your priorities aligned with what truly matters?

1 Thought to Carry With You

Stay faithful in the small things… because they are building a life far greater than you can see.

One More Thing… Try This

Before you move on with your day, I want you to do something simple.

Grab a piece of paper.

Turn on some music.

And imagine your life 25 years from now.

Do not use guardrails and think of what is safe or “realistic”.

Instead, create a version where you really, truly went for it.

Now write a letter from your future self back to you today.

Write it as if you set big goals… and then spent the next 25 years chasing them.

What does your life look like?
Who are you surrounded by?
What have you built?
How do you feel?

Then read it.

And ask yourself one question:

What would have to change starting today to make that life real?

And then…

Go get it.

Dream big.

So big it feels uncomfortable.

Because the life you’re meant to live is built by the courage to believe it’s possible first.

My son used to tell me “I am glad you were born”

So hear me today…..I am glad you were born…now go be ALL you are created to be. Climb to the top of your mountain (see photo).

Love, Jenn