When the Plan Isn’t the Plan Anymore

I was good at my career.

And honestly, that made leaving it harder.

I had spent years in education. Teacher. Administrator. Superintendent. I earned the degrees. Took on greater responsibilities. Built a career I was proud of.

From the outside, it looked like I was doing exactly what I was supposed to be doing.

There was just one problem.

It didn’t feel like I was supposed to be doing it anymore.

That realization didn’t arrive wrapped neatly in clarity. There wasn’t one magical morning when I woke up, dramatically announced my new purpose, and walked confidently into my next chapter.

It was messy.

There were questions. Doubt. Fear. And probably more than a few moments of, “What in the WORLD am I doing?”

Because walking away from something you are bad at is one thing.

Walking away from something you are GOOD at is entirely different.

I had invested years building that version of my life. My education, experience, identity, and even how other people saw me were wrapped up in my career.

Starting something new meant becoming a beginner again.

And I stumbled.

I didn’t know everything about running a business. I made mistakes. I tried things that didn’t work. I said yes when I probably needed to say no. I underestimated some things and overestimated others.

There were moments when returning to what was familiar would have been much easier.

But somewhere along the way, I realized that stumbling didn’t necessarily mean I had taken the wrong path.

Sometimes stumbling simply means you’re walking somewhere you’ve never been before.

That distinction has stayed with me.

We often interpret discomfort as evidence that something is wrong. We assume uncertainty means we made a bad decision. We see struggle and think, “Maybe I’m not supposed to be doing this.”

But growth is awkward.

New things require new muscles.

And sometimes the life that is most aligned with who you are becoming requires releasing a life that made perfect sense for who you used to be.

I still stumble.

I still make decisions that don’t work out exactly as planned. I still occasionally wonder what the heck I’m doing.

The difference is that I no longer automatically interpret stumbling as failure.

Sometimes I just need to regain my footing.

And keep walking.

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Reader interactions

3 Replies to “When the Plan Isn’t the Plan Anymore”

  1. As someone who has been attempting to figure out exactly what my business is and who my people are (it has changed so many times), reading this is very reassuring. Honestly, I think we have to pick some of the wrong things sometimes to help us figure out what is the right thing. Thanks for sharing!

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  2. I get it. Especially the reminder that stumbling doesn’t necessarily mean we’ve chosen the wrong path. Sometimes we’re simply doing something we’ve never done before. Great reminder!

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  3. I was just saying today that I look at this entrepreneurial journey differently. Instead of getting anxious when things go off book — I understand it’s just part of the process. Let’s enjoy stumbling into the unknown. It hasn’t let me down yet.

    I also deeply relate to leaving something you were GOOD at. I felt crazy, and I had to get rid of imaginary guilt… But I am happier. We know what we need.

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