Need to Burn Your Boats? Here's How I Unexpectedly Burned Mine

“Aren’t you going to regret getting rid of all of this stuff when you want to come back to teaching someday?”

The janitor said it casually, the way you’d comment on the weather.

He was watching me load folding tables with years of teaching materials — laminated anchor charts, carefully organized binders, manipulatives I’d built from scratch at 10 p.m. on a Sunday. All of these things were not making the trip with me into my next venture as an entrepreneur.

Nine years of a very successful career, priced at fifty cents and a dollar.

I stopped what I was doing and looked him in the eye. “I’m not coming back,” I told him.

But his question followed me around for the rest of the afternoon. It settled somewhere in my chest and stayed there.

I wasn’t sad about leaving teaching. I had made a decision to start my own business and was excited for the entrepreneurial journey ahead of me.

What unsettled me was something harder to name.

It was the feeling that those boxes weren’t just full of lesson plans of successful school days long passed.

They were full of proof:

     Proof that I was good at something.

     Proof that I’d earned my place.

     Proof of who I had been for a very long time.

And I was selling it all for fifty cents a piece.

We Don’t Hold Onto Things. We Hold Onto Identities.

There’s something nobody talks about when they talk about career transitions, business pivots, or stepping into something new.

The hardest part isn’t the logistics.

It’s the letting go of of a version of yourself that no longer exists.

Those materials I was selling weren’t just tools.

They were evidence.

Evidence that I was good – and highly effective – at what I did.

Those materials helped me earn Teacher of the Year awards and landed me leadership positions at my school.

They helped me deliver science units where my students built rollercoasters in the hallways out of plastic tubing and bb pellets to learn about energy and math units where we turned our classroom into a fraction field.

They held my creativity, my scholarship, and my pride.

They helped me feel good about my abilities and led me to be labeled a “highly effective teacher.’

For years, they had given me something to point to when I needed to prove that my time in education was well spent, even if I was only proving it to myself.

But I realized that unsettling feeling I carried that day wasn’t about sentimentality.

It was about releasing an old identity.

As humans, we do this constantly, whether we realize it or not.

We keep the degree on the wall long after it stopped defining us. We hold onto the title, the client roster, the portfolio from a version of ourselves we’ve already outgrown.

We keep the boxes stacked in a corner of our basement for years because putting them in the sale pile means admitting we’re not that person anymore.

The Primal Brain Doesn’t Care About Your Goals

Your primal mind, the part of your brain responsible for keeping you safe, is only doing its job when it makes you nervous about moving on to your next level.

Unfortunately, it doesn’t know the difference between a real threat to your physical safety and a threat to your identity.

Both register the same way and activate your self-doubt with the goal of keeping you from leaving your Comfort Cave.

The primal mind is also brilliant at disguising avoidance as practicality as it wraps hesitation into sensible-sounding reasons.

     “I’ll hold onto this just in case.”

     “Someday I might need this.”

     “I worked hard on this. I should hold onto it.”

Those phrases can be true. But they can also be the primal mind doing what it was designed to do: keeping you from changing.

That pull to stay in your Comfort Cave doesn’t disappear when you start a business. It just looks different.

The Real Cost of Staying Who You Were

One of the most consistent patterns I see in the entrepreneurs and founders I work with is this: they’ve built real success in one identity, and now they’re trying to grow into a new one — but they’re still carrying the old one with them everywhere they go, putting a drag on their business growth.

Often, they were a high-performing employee before they launched their business, and they’re still measuring themselves by employee metrics: hours worked, tasks completed, and whether someone else told them they did a good job.

Maybe they were considered an ‘expert’ at their former job, and now they’re learning to trust themselves in new rooms with new, often unknown expectations. Their imposter fear show up, making them long more for who they were than who they’re becoming.

Add to this that it’s easy for new entrepreneurs to get stuck working in their business, handling the day-to-day operations, rather than on their business, which keeps them tied to their employee identity even longer.

Holding onto the old employee identity often happens without us even realizing it, making the gap between who we were and who we’re becoming even harder to cross.

Sometimes this shows up in the mementos we keep from our past, but most often it shows up in how we continue to think about ourselves.

Because you can’t fully step into who you’re becoming while you’re still holding tight to who you were.

At some point, you have to set the boxes down – both literally and figuratively.

Not because the past wasn’t real or wasn’t worthy — it was.

But because you’ve outgrown it and your next-level self doesn’t stand a chance until you do.

What Actually Happened After the Sale

I remember looking around my classroom on the last day of the sale and realizing that I felt lighter than I had in years.

Sure, I was nervous about the next step into entrepreneurship, but I had also just made a major deposit in my Self-Trust Bank.

Selling my supplies was a clean break between who I was and where I was headed and put my full support behind my future. There was no turning back.

Without a doubt, my career in education shaped me and still shows up in the work today.

Not in the mementos and supplies that could be occupying space in my basement, but in how I listen, how I build structure for my clients, and how I meet people exactly where they are.

All of these things are real about me. Just because I’m no longer clocking in and out of a classroom every day doesn’t mean they no longer apply.

What I left behind that day was the weight of needing my past to be a lifeboat for my future – a Plan B if Plan A didn’t work out.

What I gained was a little more space to trust what was coming next.

That’s a huge deal.

For a lot of us entrepreneurs, that’s the whole work.

What Are You Still Carrying?

You don’t have to hold a rummage sale, but most of us are carrying around something — a title, a version of ourselves, a definition of “good enough” — that we’ve already outgrown.

What would it feel like to put it in the sale pile?

Not to erase where you’ve been. But to stop letting it be the reason you’re not fully showing up to where you’re going.

The next version of you doesn’t need you to have figured everything out first.

It just needs you to put down what you’ve already finished carrying.

That’s where momentum starts.

Jen Laffin is the Chief Momentum Officer for women entrepreneurs and the creator of Accountability Without the Angst™. She helps women business owners build consistent follow-through and self-trust in her group program, The Momentum Room, and private coaching. Learn more about Jen at www.JenLaffin.com.

The Momentum Room is Jen's small group program for women entrepreneurs who are ready to take action on the things they're avoiding.