When the “perfect” plan just… doesn’t work.

Hi friend,

Most weeks, I walk into this space with a rough idea of what I want to say—never a script, but at least a loose frame.

This week? I recorded a full seven-plus minutes of an episode on mentorship and ethics… stopped… listened… and said out loud:

“This sucks.”

And then I deleted it.

Not because the topic didn’t matter (it does), but because I was trying to force something that needed to be individualized into a “one size fits all” conversation. My body knew it didn’t feel right. My energy knew it didn’t feel honest.

So I scrapped the plan and started again.

Sometimes the bravest thing you can do is stop mid-plan and say:

• This isn’t working.
  
• This isn’t honest.
  
• This isn’t what’s needed right now.
  

That’s true in business.
And it’s very, very true in parenting.

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A little life update: seasons changing (inside and out)

As I’m recording this, it’s December 5th in Colorado. We just had a huge snowstorm—real snow, real sledding, the whole thing.

We:

• ran around town hunting down snow boots
  
• re-stocked on winter gear after seasons in California and Brazil
  
• have been living our best sledding-hill life across from the park in downtown Denver
  

This is also our last month in this house.

We’ve been hunting for our next place to live, and in my mind I was so sure it would be another walkable downtown spot. Spoiler: it’s not.

We ended up renting a home:

• about 10–15 minutes from where I grew up
  
• surrounded by old familiar grocery stores and streets
  
• with mountain views and more space than I thought I wanted
  

If you’d told me a few months ago this would be “home,” I probably would’ve laughed. And yet—here we are. Moving on January 1st. New year, new home, same school for the kids… and a very different landscape for my nervous system.

Life loves to remind us:
You think you know the plan. Then life says, actually… try this.

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When your child brings you their pain

Underneath all the logistics and moving boxes, there’s been something much heavier on my heart:

I’m having a really tough time emotionally with my oldest son right now.

Not because he is difficult or “bad.”
But because of what he’s facing:

• feeling like the new kid in an already developed fifth-grade ecosystem
  
• worrying about what people think of him
  
• trying to find where he fits
  
• being in a body that’s changing rapidly and uncomfortably
  

He’s been in therapy since we landed in Colorado—something that was non-negotiable for me. We always wanted our son, especially as a boy, to know that:

• feeling is allowed
  
• talking is allowed
  
• support is allowed
  

And still… nothing prepares you for the moment your child looks at you and shares something so heavy that your stomach drops.

Recently, after a particularly hard evening, I had to ask my son one of the most terrifying questions I’ve ever asked him:

“Have you ever thought about hurting yourself?”

I wouldn’t be sharing this if his answer had been yes.
I’m incredibly grateful that his answer was no.

But I’m sharing this because:

• most parents are terrified to ask that question
  
• many don’t realize they should be asking it
  
• even with my therapy background, that question shook me
  

The fear that gripped my chest while I waited for his answer was unlike anything else. But this is what it means to be the safe parent:

You ask the question.
You hold the answer.
You let your child know nothing they say will make you leave.

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Why asking the hard questions matters

I’ve sat across from too many kids in therapy rooms who:

• didn’t have somewhere safe to take their feelings
  
• didn’t have adults asking the questions
  
• were carrying adult-level pain in child-sized bodies
  

Our kids:

• might look small (or taller than us 🙃)
  
• but their emotional worlds are not small
  
• are navigating social media, comparison, and pressure we never had at their age
  

As a parent, it is so tempting to:

• avoid your own discomfort
  
• not ask what you’re afraid to hear
  
• assume “they’re fine” because you want them to be
  

But avoiding the hard questions doesn’t protect them.
It just isolates them.

---

Parenting through values, not fear

When my son told me he had a girlfriend—a 13-year-old, while he’s 11—my first internal reaction was:

“Absolutely not. No. Nope. No thank you.”

But when I slowed down and came back to my values as a parent, things shifted.

My core parenting values include:

• Open communication
  
• Mutual respect
  
• Emotional safety
  
• Personal responsibility
  

I asked myself:

• If I say “no,” will he just do this behind my back? (Knowing him: probably.)
  
• What kind of relationship do I want us to have five, ten years from now?
  
• What matters more: my comfort, or his trust?
  

So I told him the truth:

• I don’t love this.
  
• I respect that this matters to you.
  
• My condition is that you stay open with me and keep talking.
  

And yes, we went back over sex, consent, boundaries—the whole thing.
Again.

Because parenting isn’t avoiding what makes you uncomfortable.
It’s protecting their safety more than your comfort.

---

“Because I said so” isn’t a value

One of the parenting hills I will die on:

“Because I said so” is not a value.

Your child deserves to understand:

• why rules exist
  
• what you’re trying to protect
  
• how your decisions connect to your deeper beliefs
  

Last night, after our really tender conversation, my son said:

“But… I thought I wouldn’t be grounded anymore.”

We’d just had a beautiful moment of connection. He’d opened up, I’d held space. And also… he had beat up his little brother.

So I told him:

• Yes, we had a really important moment.
  
• Yes, I am so proud of you for sharing your feelings.
  
• And also: your actions still have consequences.
  

Both can be true:

• I can be your safe place to land.
  
• And I can still hold boundaries and follow through.
  

My value isn’t “keep everyone happy at all costs.”
It’s: raise humans who understand that love and accountability can coexist.

---

Curiosity as a parenting tool

One of my greatest tools in parenting is curiosity.

Not the “How was your day?” kind of curiosity—because we all know the answer to that is almost always “fine.”

I ask questions like:

• “What was the most surprising part of your day?”
  
• “What happened today that completely shocked you?”
  
• “If you could redo one part of today, what would you change?”
  
• “Was there any moment today that made you feel really proud of yourself?”
  

Curiosity does a few things:

• shows your kids you actually care about their inner world
  
• gives them specific entry points to start talking
  
• keeps your nervous system in observing mode instead of fixing mode
  

Sometimes I’ll also use self-disclosure—a therapy term that basically means sharing a piece of my own story to soften the space.

Last night, I told my son:

“My biggest fear is that I won’t get this right as your mom.”

And then I asked him:

“What’s your biggest fear?”

He said:

“That everyone will hate me.”

And in that moment, I saw:

• my 11-year-old son
  
• my 11-year-old self
  
• and honestly, my 38-year-old self
  

We never outgrow the desire to belong.
We just get better (hopefully) at holding it.

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You can’t parent the way you want to from a fried nervous system

If there’s one sentence I want you to remember, it’s this:

I cannot be the mom I want to be from a dysregulated state.

Even with:

• all my tools
  
• all my training
  
• all my values
  

…I still:

• snap
  
• hand over screens when I’m exhausted
  
• say the wrong thing
  
• have days where I’m not proud of how I showed up
  

I’m human. You’re human.

The goal isn’t perfect parenting.
The goal is resourced parenting.

That looks like:

• catching yourself faster
  
• repairing more often
  
• asking for support sooner
  
• letting your body come back to calm before you tackle the big conversations
  

Our kids don’t need flawless parents.
They need parents who are willing to self-reflect, apologize, and keep learning.

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When your plan falls apart (in life, business, or motherhood)

You might be listening to this in a season where:

• your business plan didn’t go the way you thought
  
• your parenting feels like a series of “What the hell am I doing?”
  
• you’re having to ask questions you never wanted to ask
  

If that’s you, here’s what I want you to know:

• You are not supposed to know how to do this already.
  
• Every day is the first day you’ve ever parented your child at this exact age with this exact set of circumstances.
  
• It’s okay to scrap the plan and start over—on an episode, on a conversation, on a way of doing things.
  

Come back to:

• your values
  
• your nervous system
  
• your willingness to ask the hard questions
  

Those three things will carry you farther than any perfect parenting strategy ever will.

Thanks for being here with me in this very real, very imperfect episode.
I hope it met you where you needed it.

xx, Ash

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