Raising Sassholes

— How to Survive the Attitude and Accidentally Raise a Future CEO (or Crime Boss) at the Same Time

Let’s talk about raising sassholes—you know, the kids who came into this world with opinions, objections, and what feels like a fully licensed law degree. We all have at least one in the lot. The one you wait for to walk by so you can silently flip them off behind their backs in solidarity with your own sanity.

Yeah. I’ve got two.

Mine will either be gang leaders or the first woman president and vice president sister duo. On their own, they’re unstoppable. Together? Absolutely a force to be reckoned with.

The words, the thoughts, the rapid-fire jabs that come out of nowhere—it’s honestly impressive. Like… where is this even coming from? How are their brains working this fast? I mean, I KNOOOOW where they get it from… but let’s not say that out loud.

One of my all-time favorite moments was when one of my twins was about three. Her dad was playing with them and said something that clearly offended her entire existence. She stops, looks him dead in the eye, and says:
“Yeah, well you look like a dog… and YOU AREN’T EVEN A DOG!”

The conviction. The delivery. The absolute confidence in a completely illogical insult.

I still laugh about it to this day.

And if you think I’m exaggerating—on my last hospital visit, these kids tried to negotiate with hospital nurses to get me discharged early. Mind you, I was basically being held hostage for low blood pressure and dizzy spells, waiting for a doctor to see me, and they’re over there like:
“Okay, but what if we just… go home anyway?”
Plotting escape routes like a low-budget prison break. Looking down the hall for any signs of the nurses. Trying to figure out how to hide my I.V.

Then came the bribery attempt. One of them goes, “Fine, will $50 work?”
They are TEN.
And apparently under the impression I walk around with emergency bribe cash at all times. Honestly, they would’ve tried the doctor too… if he would have ever shown up.

Don’t get me started on the bartering skills the other twin has at the Saturday market!

So yeah… this is the level we’re working with.

How I Handle It (Without Backing Down)

1. Pick Your Battles — Because You Will Not Win Them All

Not every comment needs a response. Some are boundary tests. Some are just background noise with attitude. If I engaged with every single one, I’d be living in a full-time debate club I never signed up for.

Also, let’s be honest—I’d just be arguing with smaller, louder versions of myself… and I already know who wins those battles.

2. Respond, Don’t React

They come in hot—I stay… tepid. Not cold, not warm—just emotionally Switzerland. It keeps the environment stable and prevents things from escalating into a full courtroom drama.

“Errrr… restart.”

Surprisingly effective. Annoying for them. Peaceful for me.

3. Boundaries Still Exist (Despite Their Objections)

Sass? Allowed.
Disrespect? Absolutely not.

You can argue your point—you just can’t be a jerk while doing it.

Quick side story: when my oldest was in middle school, another mom asked what I do when my kid screams at me. I blinked a few times like… “We’re just letting that happen now?”

I told her mine don’t scream at me—and honestly, they wouldn’t. She gave me the classic eye roll, like I was either lying or completely out of touch with reality.

Now, we weren’t rich by any stretch, but we did live in a pretty bougie school district—one where barely-teen girls were getting the newest iPhone and a MacBook for Christmas… because they demanded it.

Look, I get it—there’s a trend right now, and it has been around for some time now, where we’ve normalized parents who are afraid to tell their child no, leading to kids acting like tiny, unregulated sticky-fingered tyrants. But letting them run wild with no boundaries or responsibility, doesn’t prepare them for real life. And if you’ve been out in the adult world lately… you already know it’s not exactly gentle.

Which brings me to the next one…

4. Acknowledge and Respect Who They Are

At the end of the day, they want what we all want—to be heard and accepted. Even when it comes out sideways.

When you acknowledge their thoughts and emotions (yes, even the dramatic ones), you’re helping shape that strong personality into something powerful—instead of just a stream of perfectly timed, quick-witted jabs that are somehow both savage and hilarious. Not me trying not to laugh because they are straight up knee slappers sometimes!

5. Validate First, Then Redirect

“I hear you. Still no.”

Clean. Clear. Effective.
Drives them absolutely insane—which, honestly, is a bonus.

6. Use Humor as a Survival Tool

Sometimes the only thing standing between me and absolutely losing it is a well-timed:
“Wow, your attitude is fire, bruh.”

Or my personal favorite:
“Do you need to poop?”

Because somehow—potty jokes will outlast the ends of times.

And honestly? If it breaks the tension, I’m using it.

Also… is “fire bruh” still a thing, or did I just age myself mid-discipline?

Why Sass Isn’t the Enemy

Here’s the part nobody wants to admit:
That attitude you’re trying to survive? It’s helping to serve them later.

Giving them:

  • Confidence – They won’t be easily intimidated
  • Critical Thinking – They question everything… especially you
  • Resilience – They push back instead of folding
  • Leadership – People follow kids like this (for better or worse… still TBD)

These are not quiet, compliant kids.
These are the ones who will speak up, challenge everything, and refuse to be walked over—or let anyone else be, either.

And in today’s world? That’s not a weakness. That’s power.

When It’s Not Just Sass

There is such a thing as too much sass—there’s a line, afterall.

If it turns into:
• Constant meltdowns
• Aggression or cruelty
• Trouble regulating emotions
• Issues in school or friendships

That’s not just personality—that’s a signal.

Behavior is communication.

Sometimes that “attitude” is really anxiety, overwhelm, ADHD, or something deeper waving a tiny red flag and hoping someone notices.

And no, getting help doesn’t mean you failed.
It means you’re paying attention—and choosing to break cycles instead of repeating them.

We all need support sometimes.
Kids are no different.

The Bottom Line

Yes, I’m raising sassholes.
Yes, they test me like it’s their full-time job.
Yes, they have already attempted to bribe medical professionals and negotiate hospital policies.

But I’m not here to break them.

I’m here to shape them into humans who can:
• Speak up without tearing people down
• Challenge things that don’t make sense
• Stand their ground and know when to soften

Because if I do this right…

I’m not just raising difficult kids.
I’m raising future leaders.

Whether that’s in a boardroom, the White House…
or a very well-organized underground operation—we’ll circle back.

For now, I’ll take the small wins.

Even if they still call me “bruh.”

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About Me

Howdy! I’m Holli Ann.
I’m a mom who thought she was almost done raising kids… and then life said, “Surprise! Here’s twins.”
So yes—I hit the restart button on motherhood when my youngest was 15. Highly recommend if you enjoy chaos, caffeine, and questioning your life choices in the best possible way.

I am a west coast girl but live in Georgia now, where I somehow became a deacon at a Cooperative Baptist Fellowship church after spending years away from church altogether. Turns out you can walk through church trauma, come out the other side, and still find a version of faith that feels honest, safe, and a little less… performative.

I live with chronic pain, which means my body and I are in a long-term, mildly hostile relationship. On top of that, I’m currently navigating a cancer journey—because apparently my life likes to keep things interesting. Around here, we cope with dark humor, real talk, and the understanding that some days are for fighting and some days are for just getting through.

I’m the kind of person who is aggressively kind—like, you might be a little too scared there is an underlining reason. But trust me there’s not.

I talk to animals like they’re people (because honestly, some of them have better personalities), and I’m currently working on befriending a family of crows that have decided to visit our house. They’re not fully convinced yet, but they seem to love the snacks, so I guess we’re building something.

When I’m not doing all of that, you’ll find me crafting, relaxing outside, (except in summer) or just existing as myself—which took a long time to feel like something I was allowed to do.

This space is where I share the messy, funny, hard, and unexpectedly beautiful parts of life—without pretending any of it is easy or perfectly put together.

If you’re here for honesty, a little sarcasm, and the occasional emotional gut-punch wrapped in humor… you’re in the right place.

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