The Wonder Years: Broke, Booked & Figuring Shiiiii Out.

December 5, 2025

Before the business, the experience, and the expensive lessons, there was a girl with a laptop who thought she knew what she was doing.

You know you're getting older when you start watching television shows from your childhood and suddenly understand the adults.

Remember The Wonder Years?

Kevin Arnold. Winnie Cooper. Paul Pfeiffer.

The awkwardness. The friendships. The heartbreak. And that grown man narrating his childhood like every embarrassing experience deserved its own documentary.

I loved that show.

And the older I get, the more I appreciate the concept.

Because if somebody had followed me around during my early freelancing years with a camera, I could've given Kevin Arnold a run for his money.

Except my version would've featured questionable pricing decisions, disappearing clients, and an alarming amount of unpaid work.

Cue the theme song.

Everybody Has Their Wonder Years

When I first started freelancing, I was figuring things out as I went.

And by figuring things out, I mean occasionally making decisions that present-day Monica would strongly advise against.

I was ambitious.

I was excited.

And I was absolutely convinced that working hard would eventually solve everything.

Oh, honey.

If only somebody had warned me.

Those early years were full of experiences that taught me what it actually meant to run a business.

Some clients disappeared after projects.

Others taught me why contracts and professional boundaries exist.

And then there were the assignments I accepted for prices that should've been considered charitable donations.

I remember finishing certain projects and wondering why I'd worked so hard just to end up exhausted.

Apparently, being talented doesn't automatically mean you're good at pricing your services.

Who knew?

Well, probably everybody who'd been freelancing longer than me.

But I had to find out personally.

My First Business Degree Came From the School of Absolutely Not

There's something particularly humbling about undercharging for a project and then discovering that the client has approximately 900 additional requests.

Suddenly, that exciting new opportunity becomes a hostage situation involving your calendar.

And because you're inexperienced, you start questioning yourself.

Maybe I should've charged more.

Maybe I should've explained what was included.

Maybe I should've stopped answering emails three hours ago.

I had plenty of those moments.

But I also had to acknowledge that some of my problems came from decisions I'd made.

I hadn't always communicated expectations properly.

I didn't have every system figured out.

And sometimes I was so excited that somebody wanted to hire me that I forgot to consider whether I actually wanted the assignment.

Experience is an expensive teacher.

Especially when you're the one sending the invoices.

Eventually, I learned to establish boundaries, reconsider my pricing, and approach my business with a little more intention.

Although I'm fairly certain I could've purchased a small island with the money I left on the table.

Winnie Had Kevin. I Had Clients Who Actually Liked Me.

One of my favorite things about The Wonder Years was the relationships.

Kevin had Winnie and Paul.

They annoyed each other, disappointed each other, and occasionally made decisions that had me yelling at the television.

But those relationships were what made the story worth watching.

And looking back, relationships played a pretty important role in my business, too.

Early on, I thought success meant working harder than everybody else.

More projects.

More hours.

More clients.

And preferably enough coffee to survive all three.

But one of my earliest significant referrals came from a client I'd taken the time to build a genuine relationship with.

Imagine that.

Someone recommended me because they enjoyed working with me.

There was no elaborate marketing campaign involved.

No complicated sales funnel.

Just somebody who trusted me enough to introduce me to someone else.

That experience stayed with me.

Because clients remember how you make their lives easier.

They remember whether you communicate.

And they remember whether working with you feels like a partnership or another responsibility they have to manage.

Those relationships became some of the most valuable parts of my business.

And unlike my early pricing decisions, they were actually worth what I invested in them.

Can Somebody Please Roll the Childhood Montage?

One of the things I appreciated about The Wonder Years was how ordinary experiences became meaningful when Kevin looked back on them.

At the time, he was just a kid trying to survive adolescence.

Years later, those moments became stories about the person he'd become.

I understand that a lot better now.

Because when I think about my early freelancing years, I remember things differently.

The late nights.

The projects I probably shouldn't have accepted.

The excitement of getting paid.

The disappointment when a client disappeared.

And those tiny victories that felt absolutely enormous at the time.

I didn't have everything figured out.

Far from it.

But I was doing something I'd wanted to do.

I was building a business.

And every mistake, unexpected opportunity, and professional relationship was giving me experience I couldn't have purchased in a classroom.

Sometimes I wish I could visit that younger version of myself.

I'd probably tell her to raise her rates.

Then I'd tell her to stop accepting assignments without proper agreements.

And finally, I'd ask why the hell she thought she needed to do everything herself.

She probably wouldn't listen.

But I'd try.

Turns Out, My Embarrassing Stories Are Actually Useful

For a long time, I thought being an experienced professional meant having all the answers.

You know, presenting yourself as the woman who has everything under control.

The business.

The clients.

The systems.

The perfectly organized calendar.

Meanwhile, I had enough stories about my professional mistakes to produce several seasons of television.

And eventually, I started sharing them.

The difficult clients.

The pricing mistakes.

The relationships that didn't work out.

The business decisions I wish I'd handled differently.

And something interesting happened.

People connected with those experiences.

Other freelancers recognized themselves in my stories.

Some had made the same mistakes.

Others were dealing with situations I'd already experienced.

And suddenly, those embarrassing moments became useful.

I didn't have to pretend I'd been born knowing how to run a business.

I could simply explain what happened, what I'd learned, and what I'd do differently today.

Apparently, my younger self had been producing educational content without realizing it.

Very inconsiderate of her not to monetize it sooner.

The Woman Behind the Business Has Quite a Few Stories

This is one of the reasons I've grown to appreciate personal storytelling.

My professional experience is part of who I am.

But it isn't the entire story.

There's the woman who worked her way through difficult situations.

The woman who questioned herself.

The woman who celebrated her first meaningful referral.

And the woman who occasionally made decisions that deserved an immediate intervention.

Those experiences shaped the way I approach business today.

They're also the reason I enjoy helping other people develop their own professional identities.

Because I remember what it felt like to be starting out.

And I remember how much I would've appreciated somebody explaining the things nobody tells you until you've already made an expensive mistake.

Now I get to be that person.

Preferably without sending anybody an invoice for the emotional damage.

Kevin Arnold Would've Made an Excellent Freelancer

Think about it.

He spent years figuring out relationships, dealing with disappointment, questioning his decisions, and learning that the world didn't always operate according to his expectations.

Sounds suspiciously like entrepreneurship.

And just like Kevin, I can look back at certain experiences and appreciate them more now than I did while they were happening.

Even the uncomfortable ones.

Because I can see how much I've changed.

I understand my value differently.

I approach professional relationships differently.

And I have a much better understanding of the kind of business I actually want to operate.

Do I still make mistakes?

Absolutely.

But at least now I have enough experience to recognize some of them before they become particularly expensive.

Progress, darling.

Progress.

And perhaps that's what I appreciate most about getting older.

You get to look back at the woman you used to be and recognize how hard she was trying.

Even when she had absolutely no idea what she was doing.

I'd like to think she'd be pretty impressed with how things turned out.

Although she'd probably be wondering why I'm still working when I said I was going to take the afternoon off.

Some things never change.

CURRENT MOOD

"With a Little Help from My Friends" by Joe Cocker

Of course, we're going with the theme song from The Wonder Years.

It reminds me of growing up, figuring things out, and realizing how important the people around us become.

And considering how much of my business grew through relationships, unexpected referrals, and people who believed in me, it feels particularly appropriate.

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