Permission to Experiment
You don’t need a plan. You need a small experiment.
When I first thought about starting Carving Her Path, I didn’t start. I had been coaching, noticing patterns, collecting leadership lessons for years, and people kept telling me I should share what I was seeing more broadly. And instead of starting, I sat with the idea. I wanted to know exactly what the newsletter was before I wrote the first word. I wanted clarity, a plan, and some assurance that it would actually be good. In other words, I wanted certainty before I started.
What finally got it going wasn’t a better plan. It was publishing the first post before I felt ready, and then doing it again the next week, and the week after that. Thirty-seven weeks later, most of what I know about doing this newsletter, I learned by writing it, not by planning it. And if I’m honest, that same feeling of “this isn’t quite ready” shows up most weeks, right before I hit publish. It hasn’t gone away. I’ve just gotten more willing to feel it and post anyway.
I don’t think this is unique to writing. I think it’s true of most things that matter: careers, leadership, relationships, businesses. They don’t reveal themselves from the sidelines. The next step isn’t a more perfect plan. It’s a small experiment.
Why we resist experimenting
There’s a version of this that sounds like high standards. We want to know the right answer before we commit to it. We want to avoid wasted effort. We want complete information before we move. It sounds responsible.
But underneath it is usually something simpler: we’re afraid of getting it wrong, and we’ve quietly decided that if we just think a little longer, or gather a little more information, or revise it one more time, we’ll arrive at a version of the decision that can’t fail.
We treat these moments as permanent decisions when most of them are really just opportunities to collect data.
We picture the finished result in perfect detail, but we don’t let ourselves imagine, or trust, the messy middle that has to happen to get there. And perfectionism, in particular, is very good at disguising itself as patience. It tells you you’re being careful. Really, it’s delaying the moment you’ll discover whether your assumptions were right.
The truth is we don’t need a more certain picture of the ending. We need more evidence. And evidence only comes from diving in and doing the thing.
Action creates clarity
Looking back at my own path, I honestly can’t think of a time I thought or planned my way into clarity. Whatever clarity I have now came from acting, adjusting, and acting again.
Thinking produces theories. Action produces data and insights.
This is part of why action is one of the best antidotes to anxiety I know. Anxiety feeds on uncertainty, and it will happily keep you circling the same unanswered question forever if you let it. Action interrupts that loop. It doesn’t hand you certainty, but it hands you information, and information is what anxiety actually wants. You can’t out-think your way to knowing how a program will land with people, whether a proposal will resonate, or whether you’re ready for something. You can only find out by taking action.
Calling it a pilot
Years ago, while I was still in my corporate leadership role, I launched a group coaching program for women leaders. We had an external partner lined up to run it, and when we opened it up for sign-ups, the response was overwhelming. We had far more interest than our partner had capacity to take on.
The obvious response would have been to build entry criteria and turn people away. Instead, I asked a different question: what if I just tried something?
I decided to have my team build and run a second, parallel version of the program, and I called it a “pilot.” I asked the women who’d signed up what topics they most wanted covered, then brought in senior executives to lead sessions on exactly those things. There was no polished, pre-tested curriculum behind it, just a real question, a fast build, and a group of people willing to be part of something still taking shape.
When the program wrapped, the pilot cohort’s feedback was rated even higher than the original. If I’d waited until I had a fully worked-out version of that program, it simply wouldn’t have existed. Calling it a pilot gave us permission to build while we were still figuring out what it needed to be.
That instinct came back a few years later, when I was designing a returnship program to bring women back into the workforce after a career break. Almost everything about it was new: a new external partner, a new job classification for returning employees, a new training and mentorship model, criteria for converting participants to full-time roles that didn’t exist yet anywhere in the company. I proposed to my leadership that we launch the first cohort as a pilot, which gave the whole team room to experiment and adjust as we went rather than pretending we already had it figured out. That program went on to run several successful cohorts.
Neither of these worked because I had a better plan than anyone else. They worked because “pilot” lowered the bar enough that we could actually start and learn along the way.
Experimentation has gotten cheaper
There’s another reason this matters right now: the cost of trying things has collapsed.
You can draft a business idea in an afternoon. Build a website in a weekend. Learn the basics of a new skill in days instead of months. AI and new tools have dramatically shortened the distance between an idea and a first attempt.
Which means the advantage increasingly goes to people who are willing to run more experiments.
The people waiting for certainty may find themselves being outpaced by people willing to try, learn, and iterate.
And in a world where the cost of trying things has never been lower, experimentation may be one of the most valuable skills we can build.
Experimenting in leadership
I see this same pattern constantly in my coaching work. One client was working on sharing her perspective more visibly with senior leadership — speaking up in meetings, offering her point of view before it was fully formed, putting her thinking out in the room instead of holding it until she’d built the complete analysis. What helped wasn’t a plan for becoming a more vocal leader. It was permission to experiment with it: try speaking up in this one meeting, see what happens, adjust for the next one.
An experiment carries a completely different emotional weight than a permanent change. “I’ll try this for two weeks and see” feels safe in a way that “I’m going to become a different kind of person” never does. An experiment is just curiosity, given somewhere to go.
The experiment waiting for you
Even as I finish writing this, there’s a part of me that wants another day with it. Another pass. A few more edits.
Maybe it would be better. Or maybe it’s simply time to learn what happens when I hit publish.
Because that’s the thing about experiments: eventually you have to run them.
So I’ll ask you the question I’m asking myself:
What’s the experiment you’ve been waiting for permission to try?
Send the email.
Raise your hand.
Share the idea.
Publish the post.
Have the conversation.
Apply for the role.
Start before you’re ready.
You don’t need certainty to move forward.
You need curiosity.
You need a willingness to learn.
And sometimes, all you need is permission to experiment.
Keep carving your path.
-Tracy