The Wishing Well Trap: A Parent Leader’s Guide to Turning Hopes Into Action (Part 1)

On Monday of this week on The Business of Parenting Podcast, we explored this topic and I'm happy to expound upon it in the TBOP blog today. I encourage you to check out the podcast episode below.

I loved the idea of wishing wells when I was a little girl. You could make as many wishes as you wanted, toss in a coin, and feel that spark of excitement about the possibility of it coming true. And while I still think the idea — both the physical well and the abstract act of wishing — has value and helps us exercise our “hope muscles,” I’ve realized something as a parent leader: wishing wells are bottomless. They never fill up. They can hold all of our I wish statements without ever delivering a path forward.

With the start of a new school year, I think a lot of us find ourselves in “wishing well” mode. You know, wishing for more time, wishing for smoother mornings, wishing for easier homework routines, wishing for stronger connections with our kids.

As parents, our wishes often sound like this:

• I wish I had more time for my kids.

• I wish I could focus on them instead of everything else pulling at me.

• I wish I had more money to create experiences for them.

• I wish I could build better routines at home.

• I wish my relationships with my kids were stronger.

  
  

And usually those sentences come with a “then.” If I had more time, then I could help my kids get organized. If I had more energy, then I could be more patient and present. If I had more money, then I could give them more opportunities. I’m not pointing fingers here. Believe me, I’m right in the wishing well with you — probably more often than I’d like to admit. But here’s the problem: the well has no bottom. There’s no mechanism that gets you from the “wish” to the “then.” And that’s the parent leader trap. We can spend years wishing for better family rhythms instead of building them.

From Wishing Well to Wishing Jar

So here’s the idea I’ve been playing with: what if, instead of a well, we had a jar?

A jar has a bottom. A jar has limits. You can actually see what’s in it.

Here’s how it works:

• You write down your wish and put it in the jar.

• Then you reflect on your present — what you already have around you — and you put those things in the jar too.

Now your future is surrounded by present possibilities. And as you add more and more of those, your wish rises toward the top until eventually it overflows into reality.

But for it to work, you have to be clear on your “then.” What is it you actually want as a parent leader? What’s the real reason behind the wish? Because sometimes we think the wish is about time or money, but really it’s about connection, health, purpose, or trust within our families.

My Weeklong Experiment: Day 1

And because I’m me, I decided to test this. What good is an idea if it doesn’t hold up in the mess of real life parenting?

So here’s Day 1 of my weeklong wishing jar experiment.

Wish: I wish I had more time to help my newly minted middle schooler navigate the big academic changes.

Then:

• I could help him get organized.

• I could keep up with what he’s learning.

• I could prepare him to excel academically and socially — both by understanding how he learns and by teaching him when and how to ask for help.

So far, so normal. “If only I had more time, then I could…” Classic parent leader wishing well. But instead of throwing another coin down there, I turned to my jar and asked: What are my present possibilities?

Here’s what went in:

• I have knowledge of learning styles and motivation.

• I know how to make learning fun.

• He has a dedicated workspace at home.

• We can get notebooks and tools to help with organization.

• We have markers, paper, and all kinds of supplies to make that workspace personal.

• He loves spending time with me — games, movies, ice cream, popcorn.

• I usually get home by 5:00, and I don’t go to bed until 9:30 or 10:00. At least three nights a week, that’s four to five hours I can choose how to use.

• We have a big family wall calendar.

• His school sends weekly and daily updates.

• I can sign up for Guardian updates on Google Classroom.

• He has a watch that lets me message him.

• I even set him up with his own email.

Once I wrote them all down, I realized — I don’t actually need more time. I already have tools, resources, and moments of connection I wasn’t fully using.

So I grabbed sticky notes, wrote each possibility down, and started grouping them under my three outcomes. Suddenly, I could see a picture forming. I could see how the puzzle pieces fit.

And just like that, I stepped out of the parent wishing well and into my role as a parent leader — moving from “I wish” to “I can.”

Try It Yourself

Here’s the challenge:

1. Write down one wish you’ve been carrying as a parent.

2. Write down the “then” that follows it.

3. Make a list of present possibilities — skills, resources, moments, tools — that already surround you.

4. Put them together and see what new picture emerges.

You may be surprised by how much you already have to work with. Wishing alone won’t change our families but when we, as parent leaders, surround our wishes with the present possibilities already in our hands, we shift from hoping to leading. And that’s how strong families are built.

✨ In Part 2, I’ll share what happened after a full week of living with the wishing jar — and what I learned about purposeful parenting leadership along the way.

Jackie M

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