I Wear a Lot of Hats… Literally: What Running a Flea Market Actually Looks Like Behind the Counter

If you follow The Old Pioneer on social media, you may have seen the picture of me wearing approximately 947 different hats.

Boss Lady.Social Media Manager.Price Tagger.Cashier.Vendor Coordinator.Inventory Detective.Decorator.Cleanup Crew.Event Planner.Problem Solver.Treasure Hunter.Photographer.

And, perhaps most importantly:

Coffee Fueled.

It was supposed to be funny.

And it is. 😂

But the longer I looked at it, the more I realized…

Good Lord, this is actually my life.

So I thought maybe it was time for another peek behind the counter.

Not the pretty, staged, "Look at all the beautiful treasures at The Old Pioneer!" version.

The real one.

The version where I have six things in my hands, someone is calling my name from across the building, my phone is ringing, there's a vendor waiting to talk to me, Facebook needs a post, somebody found an item without a price tag, and I suddenly remember the paperwork I promised someone would be ready yesterday.

Welcome to owning a flea market.

And before I go any further, I need to make something very clear:

I don't actually do this alone.

My mom, Bobbie Jo, owns The Old Pioneer with me, and she carries plenty of hats of her own.

The difference is that she also works a full-time job outside of the Market.

So while a lot of the day-to-day chaos falls into my lap simply because I'm able to be more available to the Market, there is another person behind the scenes answering my calls, listening to my newest idea, helping make decisions, working at the Market when she can, shopping for it from hundreds of miles away when necessary 😂, and generally doing everything she possibly can while ALSO working an entirely separate full-time job.

If you think my hat rack is crowded, you should see hers.

There Isn't Really a "Boss Lady" Job

Before owning The Old Pioneer, I think I imagined being a business owner meant eventually reaching a point where you mostly… managed the business.

Cute.

😂

What I've actually discovered is that "Owner" is less of a job title and more of a giant umbrella covering every job nobody else is currently doing.

Between Mom and me, somebody has to handle all of it.

And because she's at another job much of the week, during Market hours that "somebody" is very often me.

On any given day, I might be:

• Cashier

• Marketer

• Photographer

• Decorator

• Janitor

• Bookkeeper

• Vendor Coordinator

• Customer Service

• Event Planner

• Furniture Mover

• Social Media Manager

• Maintenance Assistant

• Sign Maker

• Conflict Resolver

• Treasure Hunter

• Price Tagger

• Inventory Detective

• Website Editor

• Blogger — apparently we're doing that now too 😂

• Professional Answerer of "Do you know where I saw that one thing three weeks ago?"

• Chief Finder of Things That Were Definitely Right Here Five Minutes Ago

And those are just the ones I could think of while writing this.

Some of those hats belong primarily to me.

Some belong primarily to Mom.

And plenty of them get tossed back and forth depending on which one of us has the time, energy, information—or simply happens to be standing closest to the problem when it occurs. 😂

Ashley's Two Cents

If you're thinking about opening a flea market, antique mall, or vendor market because you want to "be your own boss," just know your new boss is an absolute lunatic.

She will schedule you for every department.

And if you go into business with your mom, there's a good chance you'll call her approximately 14 times a day.

Ask Bobbie Jo.

She has receipts. 😂

But Those Are Only My Market Hats

Here's the part that really puts that list into perspective:

Those are only my Market Owner hats.

Because when I lock the doors at The Old Pioneer, the hat rack doesn't magically disappear.

There are two other umbrellas hanging over everything I do, and they hold the hats that matter to me more than any of the ones I just listed:

Momma. ❤️

and

Wifey. ❤️

Under Momma lives an entirely different collection.

Chauffeur. Calendar Keeper. Baseball Mom. Biggest Fan. Homework Helper. Appointment Maker. Snack Provider. Life Advice Giver. Professional Worrier. Cheerleader. Keeper of All the Important Dates. Finder of Lost Things. And the person who's somehow supposed to know what everybody needs before they know they need it.

Then there's Wifey.

Partner. Best Friend. Sounding Board. Schedule Coordinator. Household Manager. Fellow Bill Payer. Dreamer. Teammate. Date-Night Planner-Who-Rarely-Actually-Plans-Date-Night. And occasionally the woman who realizes at 9:47 p.m. that I haven't actually had a real conversation with my husband all day because we've both been running in twelve different directions.

And here's the kicker:

I don't wear those hats after I'm finished being a business owner.

I wear them all at the same time.

There isn't a neat little switch where I clock out of being Momma so I can run the Market.

There isn't another one where I stop being a wife because vendor paperwork needs finished.

My kids still need their mom when I'm working.

My husband still deserves his wife when the Market has taken every ounce of energy I have.

And The Old Pioneer still needs its owner when life outside those doors gets busy.

And in a funny way, watching my own mom juggle her responsibilities has probably taught me more about this than I realize.

Because she's doing the same thing.

She's my business partner.

She's an employee somewhere else.

She's a wife.

She's a mom.

She's a grandma.

She's Bobbie Jo.

And somehow all of those people are expected to exist in the same 24-hour day.

So while Boss Lady might be one of the hats everybody sees…

Momma and Wifey will always be my favorite—and most important—ones.

Everything else has to learn how to fit around them. ❤️

So… About Those Missing Price Tags

Here's a little confession.

Sometimes you'll find something that belongs to me and…

there's no price on it.

🤦‍♀️

I KNOW.

I own a flea market.

I tell vendors all the time how important it is to have items clearly priced.

And then somebody walks up to the counter holding one of my items and asks:

"How much is this?"

There is no tag.

Of course there isn't.

And somewhere deep inside, I can hear every vendor I've ever reminded about tagging their merchandise laughing at me.

The truth is, I am often pricing things between doing twelve other jobs.

I may get halfway through a tote before someone needs me.

Then I set it down.

Then someone else needs something.

Then the phone rings.

Then I remember I need to make a Facebook post.

Then somebody brings in a load of furniture.

Then one of my kids needs something.

Then a vendor needs me.

Then I need to call Mom and ask her about something.

Then I call Mom.

She is, you know, AT HER ACTUAL JOB.

So she doesn't answer.

Then I forget why I called her.

Then she calls me back two hours later and I have absolutely no idea what I needed.

This is a real system we have developed.

It works beautifully. 😂

Eventually it's three hours later and I walk past that tote and think:

"Oh yeah. I was doing that."

This isn't an excuse for things being imperfect.

It's just the reality behind the imperfection.

And That Paperwork I Said I'd Have Ready…

Yeah.

About that.

😂

There are days I sit down at my computer with ONE goal.

"Today I am finishing this paperwork."

Thirty minutes later I've answered four vendor questions, checked out six customers, investigated a missing tag, taken pictures for Facebook, moved a chair, answered the phone twice, dealt with something completely unexpected, texted Mom about three things we need to discuss later, and somehow ended up upstairs looking for a Christmas decoration.

The paperwork?

Still open on my computer.

I promise I haven't forgotten about you.

Well…

Okay.

Sometimes I have temporarily forgotten about you.

But I remembered eventually! 😂

That's one of the weirdest things about running a business like this.

Your to-do list doesn't necessarily determine what you do that day.

Whatever happens determines what you do that day.

You can walk in with Plan A and be on Plan Q by lunchtime.

And when you have two owners with two different schedules, sometimes things have to wait until Mom and I can actually sit down together.

There are decisions I don't want to make without her.

There are things she knows more about than I do.

There are things I know more about than she does.

And there are plenty of times when one of us says:

"Wait. I thought YOU were doing that."

Nope.

Apparently neither of us was doing that.

Add it to the list. 😂

Why I Don't Always Answer Right Away

This one is important to me because I never want someone to think I'm intentionally ignoring them.

There are a lot of people connected to The Old Pioneer.

Vendors. Shoppers. People interested in booths. People selling things. People looking for things. Facebook followers. People calling the store. People messaging the business page. People messaging me personally.

And I genuinely want to help all of them.

But I've also had to learn something that I think every small-business owner eventually has to learn:

Being reachable does not mean being available every second of every day.

Sometimes I'm helping the person physically standing in front of me.

Sometimes I'm buried in another Market project.

Sometimes I'm dealing with something at home.

Sometimes I'm being Momma.

Sometimes I'm being Wifey.

Sometimes I need to check with Bobbie Jo before I can give someone an answer—and Bobbie Jo may currently be working at the job that actually expects her to concentrate on THAT job instead of whatever fresh chaos I've created at The Old Pioneer.

Rude, honestly.

😂

Sometimes I see a message and think, "I'll answer that when I can actually give it my full attention."

And sometimes…

I am completely honest with myself and realize I do not have one more ounce of brainpower left for that day.

That doesn't mean your question isn't important.

It doesn't mean I'm mad at you.

It doesn't mean I don't care.

It means there is only one of me.

And there is only one Bobbie Jo.

And despite extensive research, apparently cloning either of us is still frowned upon.

When Wearing Too Many Hats Starts to Show

But here's the other side of all of this—and I think it's especially important for other business owners to hear.

Sometimes wearing all the hats isn't funny anymore.

Sometimes you're stretched too thin.

You're frustrated.

You're rushing from one thing to another.

Your brain is six steps ahead of your body.

And even if you don't mean for it to happen…

It shows.

I know there have been times when I've walked through the Market at approximately 97 miles per hour with a frazzled look on my face because I'm mentally running through the next fifteen things I need to do.

There have probably been times when someone smiled at me and got a distracted smile back instead of the warm greeting I normally would have given them.

There have absolutely been times when I've been frustrated about something completely unrelated to the person standing in front of me and probably wasn't wearing my very best Customer Service Face.

And that's something I have to own.

Because here's the thing:

The person walking through our doors doesn't know what's going on behind the scenes.

They don't know that three things went wrong five minutes ago.

They don't know that I'm trying to solve a vendor issue, answer a message, remember something I forgot at home, get information from Mom when she's at work and deal with my teenage helpers who are currently being…

Well…

Teenagers.

If you know, you know. 😂

They only know the interaction they had with me.

And as the owner, that's important.

Being overwhelmed might explain why I'm not at my best in a particular moment.

But it doesn't automatically excuse it.

That's a lesson I'm learning.

Very, VERY slowly.

Knowing When You're Stretched Too Thin

I think one of the most important skills a business owner can learn is recognizing when you've crossed the line from:

"I'm busy, but I've got this."

to:

"I am currently one minor inconvenience away from needing to hide in the storage room."

😂

Because once you get there, you're not doing yourself—or your business—any favors.

That's when patience gets shorter.

Little problems feel enormous.

Your face starts saying things your mouth isn't saying.

You rush.

You forget things.

You become less approachable without even realizing you're doing it.

And, probably most importantly, someone who has absolutely nothing to do with whatever has you frazzled can end up on the receiving end of it.

Maybe you don't say anything rude.

Maybe you don't even interact with them.

Maybe you're simply rushing through the building with a look on your face that says "FOR THE LOVE OF EVERYTHING, NOBODY ASK ME ONE MORE QUESTION" while you're actually thinking about the printer that isn't working.

😂

But they can't read your mind.

They only know what they see.

And perception matters when you're the face of your business.

I am learning that sometimes the best thing I can do for The Old Pioneer is stop.

Go home.

Delegate something.

Ask for help.

Say no.

Move something to tomorrow's list.

Admit that something can wait.

Or recognize that maybe I don't personally have to be the one doing every single thing.

And that last one is probably especially important because I do have help.

I have Mom.

I have people at the Market who help keep things moving.

I have family who pitches in.

The problem isn't always that nobody else can do something.

Sometimes the problem is that I haven't learned to let somebody else do it.

That's different.

And I'm working on it.

I also have to remember that Bobbie Jo can't be my automatic solution to everything either.

She would probably try.

That's who she is.

But she's already stretching herself between The Old Pioneer and a full-time job of her own.

Part of being a good business partner—and a good daughter—is remembering that her plate has a limit too.

I wish I could tell you I've mastered any of this.

I have not.

In fact, I say all of this while actively adding "write a blog" to the approximately 472 other things I have apparently decided I need to do.

The irony is not lost on me. 😂

But I am slowly learning.

I'm learning that working myself into the ground isn't necessarily proof that I'm dedicated.

I'm learning that being a good business owner doesn't mean being available to everybody at every moment.

I'm learning that saying "I can't get to that today" is sometimes better than trying to squeeze it in and doing it poorly.

I'm learning to ask for help.

I'm learning to accept help.

And I'm learning that protecting a little bit of my own bandwidth isn't selfish.

It helps me show up as the version of myself I actually want our shoppers, vendors, employees—and my own family—to get.

Ashley's Two Cents

There is a difference between wearing a lot of hats and trying to wear every hat at the exact same time.

I'm still learning when to take a few off.

I'm also learning that sometimes I can hand one to somebody else.

Very slowly.

Apparently while simultaneously buying myself another one labeled BLOGGER.

We'll get there. 😂❤️

The Part People Don't See

Social media tends to show the fun parts.

The incredible antique we just found.

The booth that looks amazing.

The new vendor moving in.

The giant sale.

The funny thing that happened at the counter.

The new display we worked on.

The treasure I couldn't believe somebody brought through the door.

What you don't see is everything happening between those moments.

The texts between Mom and me.

The phone calls.

The paperwork.

The bookkeeping.

The cleaning.

The repairs.

The planning.

The difficult conversations.

The late nights.

The thousand tiny decisions.

The times Mom gets off work from one job and still has something waiting for her from this one.

The nights spent designing something on the computer when I probably should have gone to bed two hours ago.

The ideas scribbled down because maybe this one will bring five more people through the door.

The times something doesn't work and we have to figure out why.

The times we try something completely new with absolutely no idea whether it's going to work.

And the constant question Mom and I have been asking since this adventure began:

"What can we do to make this place better?"

Because that's the hat underneath all of the Market hats.

Market Owner.

And that one means we care about the whole thing.

Not just our merchandise.

Not just today's sales.

We care about the vendors who trusted us with a piece of their businesses.

The shoppers who choose to spend their time and money here.

The building.

The atmosphere.

The reputation.

The community we've created.

And the future.

All of it.

Sometimes Caring About Everything Means Something Gets Dropped

I think this is the part I want people to understand most.

If something at The Old Pioneer isn't perfect, it isn't because nobody cares.

Sometimes it's actually the opposite.

It's because we're trying to care about everything.

The missing price tag might be there because I stopped pricing to help a vendor.

The unfinished paperwork might be because a customer needed me.

The unanswered message might be because I was sitting in the stands being Momma instead of Market Owner.

Something might have to wait because I need to talk it over with my business partner—and my business partner is busy working another full-time job.

The social media post might be late because something happened at home.

The thing I told you I'd do Tuesday might not happen until Wednesday because Tuesday decided it had other plans for me.

And sometimes I might simply have taken on too much.

That's mine to recognize too.

I want to do all of it well.

But I am learning that I can't do all of it perfectly.

And those are two very different things.

If You Own a Market Too…

Here's something I wish more small-business owners talked about:

You are probably never going to have everything completely caught up.

There will always be another email.

Another repair.

Another idea.

Another event.

Another piece of paperwork.

Another item that somehow escaped without a price tag.

And another part of your life outside your business that deserves you, too.

You can create systems.

You should create systems.

You can delegate.

You can organize.

You can improve.

You can have a wonderful business partner.

You can have people who love you and are willing to help.

And you can still feel completely overwhelmed sometimes.

But don't mistake "not finished" for "failing."

At the same time, don't wear being overwhelmed like it's a badge of honor.

That's one I'm working on.

There's nothing admirable about stretching yourself so thin that the people around you only get the exhausted, distracted, frazzled version of you.

Sometimes your business looks imperfect because you're actively building it.

Sometimes you're behind on one thing because something more urgent needed you.

Sometimes you're wearing the Cleanup Crew hat when you really needed to be wearing the Bookkeeper hat.

Sometimes your business partner can't swoop in and save you because she's busy wearing an entirely different set of hats herself.

And sometimes the most important thing you can do for your business is take the Boss Lady hat off entirely and go be Momma, Wifey, Daughter—or just Ashley—for a while.

Tomorrow, you put another hat back on.

Would I Change It?

There are days when you could ask me that question at precisely the wrong moment and I might hand you the keys.

😂

Although I suppose I'd have to ask Mom first.

She'd probably tell me to quit being dramatic and get back to work.

😂❤️

But really?

No.

Because underneath all the chaos is something I am incredibly proud of.

And something we are incredibly proud of.

The Old Pioneer isn't just a building full of stuff.

It's more than a hundred vendors and small businesses under one roof.

It's vendors becoming friends.

It's customers we've gotten to know by name.

It's people walking through the door and yelling hello before they've even made it to the counter.

It's finding something you've been hunting for forever.

It's hearing the story behind an old photograph or piece of furniture.

It's conversations.

It's community.

It's family.

And in our case, it really is family.

I get to build this crazy thing with my mom.

We don't always agree.

We don't always have enough hours in the day.

Sometimes I'm calling her while she's at work.

Sometimes she's trying to figure out what in the world I've volunteered us for now.

Sometimes I'm running around the Market like a lunatic while she's somewhere else working an entirely separate job and still trying to help me hold this one together from afar.

But she's there.

She helps every way she can.

She believes in what we're building.

And I hope she knows how much of what we've accomplished at The Old Pioneer belongs to her too.

Because it does.

For me, there's something else I'm proud of too.

My kids are watching their mom build something.

And I'm watching my mom do the same.

They're watching us try things we don't know how to do.

They're watching things work.

They're watching things fail.

They're watching us get back up and try something different.

They're also watching us make mistakes.

And hopefully they're watching us learn from those too.

Maybe that's one of my favorite parts of this whole crazy adventure.

Three generations of our family get to see what it looks like to build something you believe in.

Not perfectly.

Not gracefully.

And definitely not without a whole lot of coffee.

But together.

I'm not trying to convince anyone that I have business ownership figured out.

I absolutely do not.

I'm figuring it out as I go.

I'm learning where I need better systems.

I'm learning what I can delegate.

I'm learning that I don't have to personally fix every problem.

I'm learning that sometimes my family needs more of me than the Market does.

I'm learning that sometimes the Market needs a better version of me than the exhausted one I'm trying to give it.

I'm learning to lean on my business partner without forgetting that she has a whole life and workload of her own.

And apparently I'm learning all of this while starting a blog about what I'm learning.

That feels very on-brand for me. 😂

Ashley's Two Cents

Maybe that's the real secret nobody tells you about "wearing a lot of hats."

You don't actually get to take one off before putting the next one on.

Most days, you're just stacking them on top of each other and hoping nobody notices they're crooked.

But maybe the goal isn't to become really good at balancing 47 hats on your head.

Maybe the goal is learning which ones actually need to be on your head right now.

And maybe it's also learning that you don't have to wear every single one yourself.

Some days you can hand one to somebody who loves you enough to help carry it.

I'm pretty lucky to have one of those people.

I just happen to call mine Mom. ❤️

So yes…

I wear a lot of hats.

A LOT.

Some say Boss Lady.

Some say Cashier.

Some say Vendor Coordinator.

Some apparently say Blogger now.

But the two I'm proudest to wear will always be Momma and Wifey.

And somewhere nearby, Bobbie Jo has a stack of her own.

So if you see me running around The Old Pioneer looking like I've forgotten what I was doing…

There's a pretty good chance I have.

Give me a second.

I'm probably just changing hats. ❤️

— Ashley