July 21, 2026

#194 ​​​​How to Know When It’s Time to Pivot Your Business

I sat with a heavy decision for a long time this year before I finally said it out loud: I’m retiring the STR Virtual Summit for Women. As your host, Stacey St. John, I had to look closely at my own STR business strategy and admit that our most popular annual event wasn’t serving the community the way it needed to. It’s incredibly difficult to walk away from something that looks like a massive success on paper.

Year after year, you’d tell me the summit was the highlight of your year. Right alongside that praise, you’d also admit you were completely exhausted by the end of those three days. That surface-level fatigue revealed a much deeper problem I couldn’t ignore. We were handing you a fire hose when what you actually needed was a faucet.

There’s a quiet trap in running a short-term rental business. We often confuse consuming information with actual implementation. I had to get brutally honest about what happens after the excitement fades.

Most of that brilliant summit content never got implemented. It wasn’t because you weren’t capable. It’s because there was simply too much to act on all at once.

The Difference Between Information and Implementation in Your STR Business

I know overwhelm that masquerades itself as productivity. I lived it for years on the corporate hamster wheel with the 4:00 AM alarms and the work that never ended. The last thing I want to do is build a platform that puts you back on that wheel and calls it a gift.

Many of the women who needed the summit’s content the most couldn’t even attend. Taking three full days away from your business, your W-2, or your family just isn’t realistic for everyone. Information was never the bottleneck. The real bottleneck was giving you the space to do the work.

You need something you can turn on every month, learn one thing, do the work, and watch it move your STR business strategy forward. Then, you come back and do the next thing.

Identifying the Bottleneck: Why the Summit Had to Go

When you change direction on something people love, there’s a quiet voice that whispers you got it wrong. It feels like giving up. I felt that voice loudly when deciding to close the doors on the summit.

But I’ve learned a critical lesson about pivoting. As I always say, “Having to pivot does not mean you have failed; it means you’re paying attention.” Real failure is staying loyal to a project that quietly stopped working just because you’re afraid of what people will think if you let it go.

That’s just fear wearing a convincing disguise. I wasn’t willing to keep operating from that zone, and you shouldn’t either.

The Discipline of Strategic Pruning

In business, we often hear about “scaling” and “adding.” We rarely hear about the necessity of cutting. This process is called strategic pruning. It’s not about getting rid of things because they’re broken; it’s about getting rid of things because they aren’t the most effective way to reach your goals.

As Greg McKeown explores in his work on Essentialism, the disciplined pursuit of less is often the only path to meaningful progress. It’s the difference between doing everything and doing the right thing.

When you prune a branch that’s healthy but stagnant, you’re making room for new growth. I had to use my own shears on the summit so I could focus on what comes next for the STR Sisterhood. It feels like a loss in the moment, but it’s the only way to ensure the tree stays healthy and continues to produce fruit.

Three Questions to Audit Your Current Focus

Once I saw that the summit was blocking our actual goal, I couldn’t unsee it. I want you to run your current operations, properties, and commitments through the same three questions I used for my own STR business strategy:

1. Does this move my most important priority forward?
2. Am I truly the right person to own this?
3. What would actually happen if it simply went away?

You’ll be surprised by that last answer. Often, the answer is “not much.” Those are the exact branches you need to cut first.

Building the New STR Sisterhood Around Action

I’m genuinely excited about what’s growing in the summit’s place. The STR Sisterhood is being rebuilt from the ground up to focus entirely on action. Instead of one overwhelming week a year, we’re going to learn and build together every single month in doable pieces.

Each month, we’ll tackle a two-day challenge where you get real work done in your business. We’re adding express trainings for one-hour deep dives. My live time is now reserved for a real Zoom room where we work together, not a webinar where you just watch me talk.

Pruning what you love isn’t failing. It’s exactly how you make room for what comes next. Grab the shears. It feels like a loss at the moment, but it looks like growth within months.

Click here now to listen to the full podcast.

HIGHLIGHTS AND KEY POINTS:

Golden Nuggets:

• •“You get in life what you have the courage to ask for.”
• “Having to pivot does not mean you have failed; it means you’re paying attention. Real failure isn’t changing course. Real failure is staying loyal to something that has quietly stopped working just because you’re afraid of what people will think if you let it go.”
• “Letting go of something good, so something better has room to grow, has a name. It’s called Strategic Pruning, and it’s one of the hardest disciplines there is for a high achieving woman to practice.”
• “A good thing that pulls your focus is more dangerous than a bad thing you could easily walk away from.”
• “Pruning what you love is not failing, it is how you make room for what comes next.”

Connect With Stacey:

Instagram : https://www.instagram.com/stacey_st.john/

Full Episode Transcript:

Stacey: Welcome to another episode of the STR Sisterhood. I’m your host, Stacey St. John, and I am so glad to be spending a few minutes with you today. Now, before we jump into this episode, I’m gonna share a quote with you that I recently read, and it says, “You get in life what you have the courage to ask for.” And those inspiring words come to us from the one and only Oprah Winfrey. Now, I wanna share with you something that’s deeply personal. I made a decision this year that I sat with for a long time before I could say it out loud. I’m retiring my favorite event The Short-Term Rental Virtual Summit for Women, the one so many of you tell me is the highlight of your year, will not be coming back in 2027. And if you’re someone who looks forward to it every single year, I want you to hear the whole story directly from me because this is not me walking away from you. This is me walking towards something I believe is gonna serve you a whole lot better. And by the end of this episode, you’ll know exactly why I made this call, what’s taking its place, and if you run a business of your own, the lesson you can carry into the next hard decision so let’s start there, because this whole episode is really a lesson disguised as an announcement. This is me taking my own medicine in public. I spend my days coaching women to make the hard calls in their businesses, the ones that feel scary, the ones that feel like loss. And today, I’m gonna walk you through one of mine while it’s still fresh. Here’s the thing nobody tells you about pivoting. It feels like failing. When you change direction on something you built, something people loved, there’s this quiet little voice that whispers, “See? You got it wrong. You’re giving up.” I felt that voice loudly on this one. But I want every woman listening to hear me say this clearly. Having to pivot does not mean you have failed. It means you’re paying attention. Real failure isn’t changing course. Real failure is staying loyal to something that has quietly stopped working just because you’re afraid of what people will think if you let it go. That’s not loyalty. That’s the fear zone wearing a really convincing disguise, and I wasn’t willing to keep living there. So let me tell you the real reason, because it has everything to do with you. The summit was never broken. Year after year, women would come out of those three days absolutely lit up. The feedback I got most often was some version of, “This is my favorite event of the entire year.” And right alongside it, almost every time, was a second sentence, “I’m completely exhausted by the end.” And there was even a quieter truth underneath that one, and I had to be honest with myself about it. So much of that brilliant content never actually got implemented. Not because the women in the room weren’t capable, they are some of the most capable women I know, but because there was simply too much to act on all at once. You cannot drink from a fire hose, my friend, And so many women who actually needed that content most often couldn’t even be in the room. Why? Because they couldn’t take three full days away from their business or their W-2 or their families so they could attend. So I had to sit with a hard truth. Information was never the bottleneck. Implementation was. I had been handing you a fire hose when what you actually needed was a faucet, Something you could turn on every month. Learn one thing, do the work, watch it move your business. Then come back and do the next thing. And honestly, I of all people should have seen it sooner. I know overwhelm that masquerades itself as productivity almost better than anyone. I lived it for years on the corporate hamster wheel. The 4:00 AM alarms, the work that never ended right up until the Sunday morning I finally broke down in bed crying to my husband. The last thing on earth I want to build is something that puts you back on that wheel and calls it a gift. Here’s where the lesson comes in, and this is the part I want you to take with you no matter what you do the rest of this episode. What I just described, letting go of something good so something better has room to grow, has a name. It’s called strategic pruning, and it’s one of the hardest disciplines there is for a high-achieving woman to practice because here’s the trap. Anybody can cut the thing that’s clearly broken. That’s easy. The real discipline shows up when you have to cut something that is working, something people love, something that still looks successful from the outside. That’s the branch we’re all afraid to touch, and this is the line I personally had to wrestle with. A good thing that pulls your focus is more dangerous than a bad thing you could easily walk away from. The summit wasn’t a failure. People adored it. And that’s exactly what made it so hard to pick up the shears and cut it. But people love this, and this is the best way for me to serve them turned out to be two completely different sentences. And once I saw that, I couldn’t unsee it. So if you take one thing from me today, take these three questions and run something in your own business through them this week. Number one, does this move my most important priority forward? Number two, am I truly the right person to own this? And number three, what would actually happen if it simply went away? You’ll be surprised about that last answer. Honestly, not much. Those are the branches to cut first. Now, for the part I’m genuinely excited about is what’s growing in its place. The STR Sisterhood is being reborn, simpler, cleaner, and built from the ground up to get the work done with you all year long. We’re giving it a smoother home, so the whole experience just feels better to be a part of. Instead of one overwhelming week a year where we’re tied together as a summit, we are going to learn and build together every single month in smaller, doable pieces. The kind where you leave with the work actually done, not just a notebook full of things you hope to get to someday. The faucet, not the fire hose. And the way we connect is also changing in the best way. The live time you get with me is no longer a webinar where you sit back and watch me talk at a screen. It’s a real Zoom room where we are on together, learning, working, and connecting with each other and with other women who are building exactly what you’re building. That’s real connection. And I’ll be honest with you about the boundary in that And I’ll be honest with you about the boundary in that because I teach boundaries. My live time, my hands-on time with you is now reserved for the women who are ready to roll up their sleeves and do the work alongside me. Let me walk you through how it actually works very simply. Each month, there’s a two-day challenge, a brand-new topic every time where you don’t just learn, you get real work done in your business while we’re together. There are also monthly express trainings, quick one-hour focused deep dives on one specific thing to sharpen in your short-term rental business. And then there’s the membership, which simply wraps it all together. Every challenge, every training, all the recordings, plus two Zoom calls with me each and every month. Everything all year in one place. And here’s a small detail that tells you everything about where my head is at with this change. The live price is always the better price. When you show up and do the work with us in real time, you pay less. When you grab the recordings later after the fact, a little more. This is not me being clever about pricing. That is me putting my money where my mouth is on the entire point of this pivot. I want you in the room doing the work, not quietly collecting recordings you’re planning to watch someday. Because we both know what actually happens to someday. Now, I know some of you are wondering where that leaves you if you’re not ready to jump into a paid room yet. So hear me clearly. The front door is still wide open, and it’s still free. The podcast you’re listening to right now isn’t going anywhere. Neither is the Female Short-Term Rental Investors Facebook group. Neither is my blog or my YouTube channel. If you’re here to learn, there is so much waiting for you completely free every single week. What’s changing is simply this: My live in-the-room time is now reserved for the women who are ready to build with me. And to my current STR Sisterhood members, I want to say something directly to you. You heard about all of this from me first before this episode ever aired, and that was completely on purpose. You showed up for this community when it was something totally different, and you will always be the first in line. Thank you for trusting me through the change. So let me bring this all the way back around, because it was never just about a summit or a membership. If you’re sitting on a hard call in your own business right now, some beautiful thing you love, that if you’re truly honest with yourself, you already know isn’t the right thing anymore, let this episode be your permission slip. Pruning what you love is not failing. It is how you make room for what comes next. The shears are in your hands, and I promise you, from someone who just used hers, it feels like a loss in the moment, and it looks like growth within months. So take a breath and make the brave cut. And before you go, do something for me. Send me a message and tell me one hard call you’re sitting on right now. I read them, and I would love to walk through it with you. Until next time, keep choosing courage over comfort, and I’ll see you soon.

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