Two years ago, I closed the door to the retail business I thought would define me forever.

I sold my store...the one I built from scratch, poured my energy into, and made a second home for more than a decade. People love to talk about selling like it’s the pinnacle of entrepreneurship and I do consider myself very fortunate. 

More freedom, more time, a chance to reinvent yourself. BUT...while there is freedom on the other side, let’s be clear: it’s a freedom that comes with its own complicated layers. Because no matter how prepared you think you are, life after selling your business hits differently.

If you’re considering stepping away, whether it’s next month or five years from now, let me pull back the curtain on life after selling your business....or at least some of the things I experienced (or realized) that I least expected.

These are the five biggest lessons I learned after selling my retail business...things I wish someone had told me before I handed over the keys.

1. Letting Go Feels Like a Death And You’ll Need to Grieve It

I don’t think enough people talk about this. Letting go isn’t just a transaction. It’s an ending and it feels, in many ways, like a death. You’re saying goodbye to the place you spent birthdays, holidays, late nights, and early mornings. You’re closing a chapter that held not just your career but your identity, your routines, and in some cases, your closest relationships.

Even though I knew selling was the right decision, I still needed time to mourn it.

I remember the first day after the sale went through. I repeatedly checked my phone for emails...but there was nothing. My phone was strangely quiet and for the first time in years, I had no one to touch base with. No sales to look at at the end of the day.  No meetings to schedule. 

There’s no feeling quite like handing over the keys.  No one prepared me for this moment. Signing the paperwork is one thing.  But the day I handed over the keys, it felt like time slowed down.

I remember walking through every aisle, noticing every dent and scratch on the shelves, every little sign that this place had been lived in.

Before I turned the lock for the last time, I took a final look around. My hands were shaking, not because I doubted my decision, but because I finally realized this was really happening.

It was closure and heartbreak, all at once.

And if you’re thinking about selling, know that final goodbye is going to hit you harder than you expect, but it’s also the start of something you can’t even imagine yet.

If you find yourself grieving after you walk away, know this: you’re not failing at “moving on.” 

You’re simply human.  Give yourself space to feel it. Grief is part of the process of creating space for what comes next.

I left the country on a trip just days after I sold my business and I am so glad I did.  I was able to keep my time and my mind busy with other things.

2. Your Identity Is Tied to Your Business (Even if You Pretend It Isn’t)

I used to tell myself I could separate who I was from what I built. I thought that once I sold, I’d wake up feeling weightless, ready to reinvent myself overnight. Instead, I learned that your business, especially one you built from nothing, becomes part of how you see yourself, and how others see you, too.

I used to be the owner of Cravings and even now instead, I hear:

“She used to own Cravings.”

3. No Matter How Much You Plan, The Transition Likely Won’t Look Exactly Like You Imagined

Just like childbirth, you can have the best plan and visualize exactly how it’s going to unfold.
You can map out the timeline, document every process, and picture the smooth handover to whoever takes over.

But when it actually happens, some pieces will fall into place seamlessly and others won’t look anything like you expected.

I thought I knew exactly how the relationships with suppliers, customers, and even my former team would continue. I assumed I’d still feel connected to the business in a predictable way, like an observer watching something I’d created flourish from a comfortable distance.

The reality was more nuanced.

Some relationships faded quickly, while others remained stronger than I expected.
Certain aspects of the business evolved in ways I hadn’t pictured, and I had to be ok with not controlling how it looked from the outside.

It takes time to get used to seeing something you built take on a new shape without your involvement in every detail.

If you’re planning to sell, give yourself space to accept that the transition likely won’t mirror the picture you had in your head and that’s okay. It doesn’t mean it was the wrong decision. It just means it’s real life, not a script. 

4. Starting Over in a New Field Challenged Me in Completely New Ways

One of the hardest adjustments was going from being at the top of my game, knowing my business inside and out, to stepping into something brand new. I moved into coaching and creating digital programs.

Even after years of learning as a retail owner, this transition to creating digital assets humbled me.

When I launched my first course, I remember staring at the checkout page wondering if anyone would buy. I had decades of experience behind me, but suddenly, I felt like a beginner all over again. The learning curve was steep. The technology felt overwhelming most days.

But every time I help another business owner find clarity, I feel the same pride I used to feel unlocking my store in the morning.

This chapter has proven that no matter how much experience you have, growth happens when you stretch beyond what’s comfortable. Starting over wasn’t always easy, but it was worth every uncomfortable moment.

5. Goodbyes Are Really Hard...REALLY Freaking Hard

I’ve always been the kind of person who struggles with endings. I’m great at starting things...new projects, new ideas, big dreams.

But goodbyes?
I’ve never been good at those and even when you think you're ready...it can be REALLY hard.

When I first opened my store, I didn’t really think about what the finish line would look like. I never pictured selling. I never pictured handing over the keys or saying, “This chapter is done.”

It just wasn’t on my radar.

So when the time came to walk away, it felt surreal...like I was living someone else’s story.

I’m not retired, I still work...just differently now.

I work fewer hours, doing work that lights me up, and helping other small business owners build something they can eventually step back from without guilt. And while I still don’t love goodbyes, I’ve learned that sometimes the bravest thing you can do isn’t launching something new.
It’s having the courage to close a door you once thought you’d never walk away from because that’s when you finally discover what’s waiting on the other side.

Selling your business doesn’t magically erase your need for purpose, growth, or validation. It doesn’t mean you’re done learning. It doesn’t mean everyone will understand your decision and it definitely doesn’t mean you won’t second-guess yourself at times.

But it does give you something rare...a chance to rebuild a life you choose intentionally, not out of habit or obligation.

If you’re standing at the edge, wondering whether to take the leap, I hope my story helps you see what my experience with selling was like...not just the highlight reel.

Ready to Create a Business That Doesn’t Own You?

If you’re dreaming about eventually stepping back, or selling someday, but your business feels too chaotic to imagine letting go, I’d love to help.

I’m opening up a limited number of coaching spots this September for business owners ready to reclaim their time, streamline their operations, and build something that thrives without them.

Because here’s what I know for sure...

Freedom isn’t something you stumble into. It’s something you design on purpose.

Send an email to [email protected] and I'll add you to my waitlist. 🖤