THE BLOG

Why You Keep Starting Over Monday — And What Actually Helps Instead

There are few things more humbling than realizing your childhood hair was being managed by people who absolutely did not know what they were dealing with.

Especially if you had curls in the 70’s or 80’s.

No conditioner in sight. Detangler? What that even a thing yet?

Just a brush, a determined mother, and a tiny curly-haired child (me!) being sent into public with what can only be described as triangle hair.

You’ll find the full “Triangle Hair” story in this week’s #weirdandwitty newsletter, including the dry-brushed curls, the hidden platform situation, and the deeply unfortunate visual evidence that survived decades. You can read the full email story here: She Dry Brushed My Curls.

But the part that really stuck?

Curly hair was never the problem. It was being treated like something that needed to be forced, fought, flattened, and aggressively brushed into submission.

And that’s where I turn my curly hair experience from the 80’s into an explanation of why we keep starting over every Monday.

Starting Over Every Monday Usually Starts With One Tiny “Mistake”

At the café, people say the most revealing things when they’re ordering a cinnamon bun, cookie, date square, or dessert in general.

Not because they’re doing anything wrong.

Because before the treat even hits the plate, the explanation arrives.

“I’m being bad today.”
“I’ll start fresh Monday.”
“I’ll have to be extra good tomorrow.”

It’s a cinnamon bun, not a felony.

But also? Most of us get it.

Because we’ve been trained to treat food, movement, health, aging, energy, and habits like they only count when they’re done perfectly.

One cookie becomes “I blew it.”
One missed walk becomes “I’m off track.”
One busy weekend becomes “I need to get my life together.”

Suddenly, we’re not making one human choice. We’re building a whole dramatic scene around it, complete with guilt, evidence, and a fresh start scheduled for Monday morning.

No wonder we’re tired. But…

…The Problem Isn’t the Cinnamon Bun

The cinnamon bun is just sitting there minding its business.

The real issue is the story we attach to it.

That story usually sounds like this:

“I have zero willpower.”
“I messed up, so the day is ruined.”
“I’ll enjoy everything now because Monday is coming.”
“I need stricter rules next time.”

That all-or-nothing mindset is sneaky because it pretends to be discipline when it’s really ALL LIES.

Our perfection mind says, “Do it exactly right or don’t bother.”
Real life says, “The school called, supper is late, your energy crashed at 3pm, and someone left one spoonful of yogurt in the container.”

Which one do you think your habits need to survive?

EXACTLY!

And if that mid-afternoon energy crash is part of the cycle for you, this post is a good one to read next: Why You’re So Tired by 3pm.

Why Starting Over Monday Feels So Tempting

Monday has somehow become the imaginary wellness fairy.

She arrives with clean counters, matching containers, a new grocery plan, a perfect mood, better sleep, fewer cravings, and a version of you who never gets annoyed, busy, hungry, bored, rushed, emotional, or snacky.

Adorable. Completely unrealistic, but adorable.

The reason starting over Monday feels so good in the moment is because it gives you relief.

For a few days, you don’t have to think about balance.
You don’t have to practice moderation.
There’s no need to make a decent next choice.

You can just write the whole week off and hand the problem to Future Monday You.

Poor Future Monday You. She’s exhausted.

But here’s the shift I talk about in this week’s Walk With Me audio:

The people who feel the best long term are usually not the people obsessing over every tiny choice.

They’re the ones who have stopped quitting on themselves every few days.

• They walk.
• Eat decent most of the time
• Enjoy dessert sometimes
• Fit movement into their actual life.
• And don’t let messy days define them

It’s not flashy and nobody’s going to make a dramatic before-and-after montage of “woman calmly continues with her normal habits after eating a cookie.”

But that’s the stuff that works.

Because your body responds better to consistency than chaos.

Not punishment. Not panic. And not another Monday restart.

Just simple habits repeated often enough that they become part of your real life.

A Better Way to Handle the “I Blew It” Moment

So, the next time your brain tries to turn one “bad” choice into a wellness faux-pas, pause before you grab the emotional hairbrush and try asking:

“What would help me feel a little better next?”

Not perfect; BETTER.

Maybe it’s a walk around the block.
Maybe it’s drinking water because your body is basically running on coffee and vibes.
Perhaps it’s eating an actual lunch instead of standing near the fridge staring into the void.

Remind yourself that small choices count even when the day has been messy.

Actually, they matter most when the day has been messy.

Because anyone can follow a routine when life is behaving.

The useful habits are the ones soft enough to bend and strong enough to stay.

Listen to the Walk With Me Audio for the Deeper Version

The walk is the real conversation.

In this week’s Walk With Me episode, I talk you through why we keep starting over every Monday, how food guilt shows up in everyday café conversations, and why walking can become one of the simplest ways back to yourself.

You’ll hear the gravel under my sneakers, the real-life stuff, the slightly congested voice, the form checks, the reminders to unclench your jaw, and the kind of honest conversation that feels less like a lecture and more like walking beside a friend.

Listen here: Walk With Me Audio

And yes, go for an actual walk while you listen.

Nat – your 70’s curly haired survivor

P.S. Want the full walk-and-talk version of this conversation? Pop in your earbuds, grab your sneakers, and listen to this week’s Walk With Me here: Listen to the audio.

For more weird life lessons that somehow become useful, make sure you’re subscribed to the #weirdandwitty newsletter.