The slight difference between ambition and obligation.
When my kids were little, they loved asking “Would you rather?” questions.
Would you rather be able to fly or be invisible? Would you rather eat a bug or…well, something equally disgusting?
And while the questions were cute, they could get old fast. (Pete and Repeat were in a boat, anyone?)
But there was something fun about the way they asked them. With excitement, imagination, and absolutely no concern for whether the possibilities were realistic.
I was reminded of that recently when I heard someone share a question they regularly ask themselves. And I haven’t stopped thinking about it.
“Wouldn’t it be crazy if…?”
They shared how, when they were first starting their business, they would ask themselves things like, “Wouldn’t it be crazy if we made $100,000?”
And when they reached that milestone, they’d dare themselves to go a little further.
“Wouldn’t it be crazy if we made $250,000?”
And then a little further.
What struck me wasn’t necessarily the goals themselves (although who wouldn’t love $250,000?). It was the way they were framing them.
They were still being strategic and doing the work, but they weren’t waiting until every detail was figured out to give themselves permission to imagine something bigger.
They were approaching ambition with a little childlike wonder, taking steps in that direction, and seeing what might happen.
In a way, they were creating micro-goals disguised as possibilities.
And I love that.
Somewhere along the way, I think many of us lose a little of that childlike imagination.
A kid sees a cardboard box and wonders what they could build with it. An adult sees the same box and thinks, I need to recycle that.
And I wonder if we do something similar with our goals.
We set timelines. We create plans. We measure progress. And while there’s absolutely a place for all of that, sometimes the minute we turn something into a formal goal, we attach a whole lot of pressure to it.
Suddenly, we’re worrying about how we’ll get there, whether we’re qualified, what other people might think, and what happens if we fail.
Before we’ve even started, we’ve managed to talk ourselves out of the possibility.
But “Wouldn’t it be crazy if…?” feels different.
It feels curious. Mischievous. Hopeful.
It’s a challenge without all the heaviness. An invitation to explore rather than another expectation to meet.
And perhaps most importantly, it makes something that might otherwise feel impossible seem just possible enough to try.
Wouldn’t it be crazy if you started that thing you’ve been thinking about for years?
Wouldn’t it be crazy if you applied for the opportunity you weren’t quite sure you were qualified for?
Wouldn’t it be crazy if you finally made time for something you’ve always wanted to learn?
Wouldn’t it be crazy if you actually succeeded?
That last one gets me.
Because we spend an awful lot of time imagining what could go wrong. We can come up with a dozen reasons something might not work before we’ve even given it a chance.
But how often do we give the same amount of energy to imagining what could go right?
What if it works? What if you surprise yourself? What if the first step leads to an opportunity you couldn’t have planned for?
I’m all for having goals and making plans. But I also believe we can spend so much time trying to figure out exactly how something will happen that we never give ourselves the opportunity to find out what could happen.
And maybe that’s the beauty of this question. It gives us permission to experiment.
Not everything has to become a lifelong commitment or a measure of our success. Sometimes we can simply try something, learn a little, adjust, and decide whether we want to keep going.
And if it works? Maybe we dare ourselves to go a little further.
What if we made ambition feel a little more like adventure and a little less like obligation?
I wonder how many more things we’d be willing to try. How many ideas we’d pursue. How many opportunities we’d say yes to.
And how much more interesting life might become along the way.
So here’s my question for you this week: Wouldn’t it be crazy if __________?
Fill in the blank.
And then, instead of immediately listing all the reasons it might not work, ask yourself one more question:
What’s one small thing I could do to see if it might?
You don’t have to know exactly where it will lead.
You just have to be willing to find out.
Have Good Ripple Effect,
Lisa