
Sometimes the business that got you here can’t take you where you want to go!
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Blockbuster just kept trying to ignore that people were spending more time on the Internet. The people wanted more convenience. And they're like, we're sticking with our model. People can come to us. That clearly didn't work out for them.
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Welcome to the Strategy Hour podcast brought to you by Boss Project. I'm your host, Abigail Pumphrey, and I'm dedicated to supporting online businesses.
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I don't believe in one right way to build a business.
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I'm here to help you build business your way. One that supports not only the life.
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You have, but the life you want.
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I'm on a personal mission to help you become financially free. I'm taking all the lessons learned as I turned a layoff into a seven figure online business. I'm here to help you prioritize your life every step of the way, whether.
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You'Re creating your first digital product, growing.
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An email list, or scaling an already profitable business. Settle in. It's time to talk strategy.
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In the last episode, we talked a lot about seasons and how for you to recognize what season you're in and how to make decisions that are in alignment with what you have to give. This is a little bit different today. We're talking about when it's time for experimentation and reinvention because this is less about the energy you have to give to it and more about how you know when you need to make a change. A few years ago, I had hit one of these seasons for myself and I noticed that I was feeling less enthusiastic about showing up. I didn't care to teach or share as much about this particular subject. And it wasn't that I didn't care and it wasn't that I wasn't the expert and it wasn't that I didn't know the answers, but I found myself less and less drawn to it now for this in particular, I had spent years, about eight, eight and a half years talking to almost exclusively service providers, people who had been building businesses online and providing some sort of one on one professional service. And while I have a lot of knowledge around that topic and have lots to share around those strategies, I found that I felt disingenuous because it had been a long time since I had run a truly service based business. And so the last time this feeling had come up for me, my way to address it was to get back into the game. So a couple years prior to that more recent feeling, I said, okay, I'm gonna just, just like, it's no big deal. I'm just gonna reopen my agency quietly and take some One on one service based clients. At the time we were doing high end custom web design and that gave me the ability to get my feet wet and really know and understand what my clients were going through and how I could better help them and how I could give them better strategies and better sales, things that were going to work in today's economy, in the world we were living in right then. And that felt like an awesome way to create that realignment. But this time when it had rolled back around, I didn't want to do that. I could. I knew how. I had the skill set for it. But instead I felt like I have been teaching and sharing what I've known online for years and years and years and I've never taught someone how to do that, how to pivot away from exclusively selling services one to one and add in other layers that allow someone to diversify. And I was getting plenty of questions about that. I had clients who would be like, how do I add a digital offer to this? Or how do I sell a course on top of also doing this other thing? And I wanted to help them, but I hadn't built out any of that infrastructure. And instead of saying, you know, I can't do that because that's not what I've been doing and that's not who I've been serving or how I've been showing up, I didn't say that to myself. I was excited about that. I was ready and willing and looking forward to that evolution. And it wasn't chaotic. It was creative and fun and exciting and everything I needed in that season. And I loved building out new curriculum. I loved being able to show up in a new way and share different strategies. And you guys loved it too. I was hearing so much incredible feedback and loving seeing people jump into this world. Now. This wasn't changing how I was showing up necessarily. Like, I was still going to be on the same channels, I was still talking to the same email list. I was still doing all of those things. I wasn't editing that strategy. I was innovating. Because often innovation is showing up disguised as discomfort. And when we're resisting it, we're uncomfortable. When we are kind of putting aside what could be, we grow uncomfortable and sometimes just simply leaning into it. It's going to be a positive thing. It's of course scary to make changes. We want to be loyal to our audience or our brand or our offer or our identity or all of those things. But if we've outgrown them, we're going to stay really stagnant and we're going to become increasingly not fun to be around. Frankly, so many people stay stuck in it because they are bought into the sunk cost fallacy. But I've spent so much time building this. I've spent so much time, you know, pouring into this direction. I've done all of these things. And is it better from a business perspective to have one offer that you're consistently pouring into that you don't change major direction in and that you keep building on top of? Top up? Yes. Financially, yes. If your plan is scale, if you have VC funding and you're growing a team and you're pouring a lot of time and energy into that, you making a pivot like this could cost you a ton of money and a lot of lost years of momentum. But when it's just you or you in a very small team, if you've lost your momentum and you are bored and you are resistant and you are uninspired and you keep doing this thing, you're going to create a really unhappy, unfun place to work. We get this false sense of security around what worked before, but that can quietly become a cage where we are not even allowing ourselves to consider other options. Sometimes the business that got you here can't take you to where you're trying to go. And that can be so incredibly uncomfortable. I'm curious. Just curious. Okay. What are you maintaining because it feels safer, not because it's still working. Oh, I know. I have my list. I won't tell you what my list is, but I have my list. What am I maintaining because I feel safer? I don't even like how that sentence makes me feel. So I can only imagine how you're feeling right now. Now the signs that it's time to experiment are actually pretty recognizable and they have some really practical cues. So that's exciting. So let's go over those. The first one is going to sound kind of obvious, but I think we often try to put band aids on this. You're uninspired. You start dreading doing what you used to love. Red flag, number one. Number two, you've hit a plateau. Maybe your growth, financially especially, has stalled out. Even though your effort hasn't. You keep showing up and it feels like you're going against the grain. An even bigger red flag if it started to go backwards. Like if you're no longer even just maintaining, but you're starting to shrink. Oof. Big, big red flag that you need to be paying attention to. Maybe your audience has evolved, but your messaging or your offer or your content hasn't kept up. Like for example, an obvious one that we're all familiar with. Blockbuster, right? Blockbuster just kept trying to ignore that people were spending more time on the Internet. The people wanted more convenience. And they're like, we're sticking with our model. People can come to us. That clearly didn't work out for them. Now I can think of other things that are even more absurd. Like my mom, when I was a kid, for years she carried around like a Hallmark calendar that she wrote all of our stuff down in. And then she got a Palm Pilot. And for those of you unfamiliar, it was like the first smart device, but it didn't have the Internet and it definitely wasn't a cell phone. Palm Pilot, for example, could have just said, we're just going to keep doing what we're doing. But obviously smartphones came on the market and that tanked them. And I don't know much about PalmPilot to know if they got purchased or if they closed or what. But that's the sort of thinking I want you to be kind of on the wavelength of is this even what people want anymore? Or has technology changed so much that what I'm offering is no longer relevant? And maybe it's more subtle than that. I realize those are very extreme cases, but if we're not paying attention to that, like that's the kind of thing that will really, really throw you off.
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You may already be sort of aware you're like, I'm craving more alignment. I want this to feel better. Like something has got to change. Maybe you don't know what yet because something that once felt like freedom and excitement and something you were looking forward to now feels like an obligation. And let's be honest, most obligations are not fun. Obviously there's exceptions to that rule, but still. And the fifth sign that it's time to experiment is that you might be feeling a little jealous or a little curious, which are not necessarily the same, but I think they're coming from the same place. If we're feeling jealous, it's usually coming from an unhealthy mindset. And if you're feeling curious, I think there's a lot of health behind that thought process. But it's the same thing. It's coming from the same place. You have a quiet desire to explore something new and it is tugging at you. Reinvention is going to start when curiosity starts to outweigh that certainty that you once had. Now I'll be honest, there have been times in this business where burning it all down and walking away and doing this or doing that have felt like the easiest thing to do. And that's not what I'm talking about here. I want you to be strategic, not chaotic. We're not making decisions from emotional. What am I going for? Emotional, like you being unregulated. Like this can't be a blip in time, right? This has to be something that you're feeling for a while. But you can start with like micro experiments. Maybe you test a little bit of a different message or you start a new platform, or you put something out in a different format, or you try a new price point, or you sell in a new model. I think the thing that helps make this feel less crazy is if you start to think of it more like testing than pivoting, because pivoting feels final. And not to say you won't pivot eventually, but in the beginning, you need to experiment so you have more data and you can discover more and you can figure more things out, because things that might feel sexy or exciting might not be it. Reinvention is going to come after clarity. We need to emphasize those safe to fail testing opportunities where we're sandboxing things before we commit to them, before, God forbid, before try one new thing, track those results, tweak, make some adjustments, and trust what data and energy is telling you. It's really that simple. One successful experiment can become the blueprint for your next chapter. I remember a couple of years ago, I didn't feel right about my pricing. And it's not to say that I couldn't charge as much as I was charging. I could have charged 10 times what I was charging, but that's not how I wanted to show up. It felt off to me. I wanted things to be more accessible, but I'm like, if I'm going to make things more accessible, I need more income from somewhere else. And so I started going back to a strategy that I've used previously and spent more time and attention on developing brand deals to really bridge the gap for me. And it worked in a really big way. It really helped me make room for the space I wanted to get, for the way I wanted to show up for my community. And I felt this new sort of creativity rebirth from me. I felt new energy that I could show up from. Reinvention can come at the beginning or an end of a chapter, but it doesn't necessarily mean that the decisions you're making are good or bad. Sometimes they're just choices. If you're listening to all of this and you're like, yep, that's where I'm at. I don't like how it makes me feel. This is uncomfortable. I want to be inspired. I want to have those things come up for me. I need you to know the difference between when that means you just need rest and you need to call and, like, do a little bit less, and when it actually means you're excited and ready for something new, because those are not the same. And if you do the opposite in that season, I don't think it'll help you in the way that you want it to. Because sometimes reinvention is like a band aid because you want to be in a growing season, and you can't be in a growing season. And this is you feeling like, well, I could grow if I did it this way. Are you sure you don't need rest first? Are you sure? Have you been running a marathon and you haven't stopped? I don't know. So you have to really be able to judge. Now, it's not to say that maybe you've been through that harvesting phase. You know, you're going into a resting phase, and in rest, you found that to really get excited about planting and growing again, that you have to make some adjustments, that you have to have some reinvention that's likely coming from a much healthier place. One way that really helps me integrate this and, like, know if the direction I'm heading towards is actually what's gonna work is including points in which I'm doing that reflection. If you have not done a debrief before for an experiment or for a launch or for anything new that you're trying, like, you're missing a big step. Debriefs can be such a learning opportunity. We don't have to be focused on what were the results of XYZ experiment. We could say, what did we learn from XYZ experiment? Because if you focus on results, like, I sold in this way, and I got X number of people who signed up and X number converted, and I made this amount of money. But if you don't write down, well, I started this process and I realized I actually hate webinars, or I actually hate selling in DMs. And it worked, and I sold a bunch. But I can't do this again, like, energetically. It was so draining. I don't want to launch in this way again. If you'd been focused on results and you saw the shiny number on the paper, but you didn't reflect on the fact that it was actually horrible, then you're just going to be miserable every time you do the thing, right? And so we have to be thinking about the whole picture, because sometimes it's not worth it. Like, the reward we get from it is not outweighing the cost. Change can be scary, but change isn't punishment. It doesn't mean you did something wrong. It doesn't mean you failed. It doesn't mean all of those things that you've been putting in your head, right? It doesn't mean that it's an invitation. It is an opportunity. It is giving you permission to take that next step and go in that direction. Ask yourself, what's one thing that no longer excites me, but what do I want to try instead? What would my business look like if I started fresh today? You don't have to change everything, okay? You don't have to throw it out with the kitchen sink. I want you to to take one step, one small experiment and then report back and tag me with those results. I want to hear how it went. I want you to send me a dm. I want you to say, I made this change and this is how it felt and this is what I'm excited about doing moving forward. Every business is going to hit a point where the rules that got you here stop working and the ones who are going to thrive are the ones that are brave enough to write new ones.
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Title: How to Know When It’s Time for Experimentation & Reinvention
Host: Abagail Pumphrey
Date: October 28, 2025
In this solo episode, Abagail Pumphrey explores the signs that indicate it’s time for experimentation and reinvention within your online business. Drawing on her own experiences as a business strategist and CEO of Boss Project, she addresses how discomfort, boredom, and stagnation can be important signals to pivot or try new approaches. The episode delivers practical cues, underscores the importance of curiosity over blind loyalty to the status quo, and provides actionable advice for testing new ideas without risking stability.
Difference between “seasons” and reinvention:
Personal story of losing enthusiasm:
Experiencing resistance as a sign:
“We get this false sense of security around what worked before, but that can quietly become a cage.” ([06:13])
Small-scale testing:
“If you start to think of it more like testing than pivoting—because pivoting feels final… in the beginning, you need to experiment so you have more data.” ([15:10])
Importance of data and reflection:
“If you don’t write down, well, I started this process and I realized I actually hate webinars… then you’re just going to be miserable every time you do the thing, right?” ([19:16])
Regular check-ins:
Encouragement to take one small, brave step:
“Ask yourself, what’s one thing that no longer excites me, but what do I want to try instead? What would my business look like if I started fresh today?” ([22:13])
On resisting needed change:
“Innovation is showing up disguised as discomfort.” – Abagail ([04:47])
On false security:
“We get this false sense of security around what worked before, but that can quietly become a cage.” ([06:13])
Bold audience reflection:
“What are you maintaining because it feels safer, not because it’s still working?” ([06:28])
Business as evolution:
“Sometimes the business that got you here can’t take you to where you’re trying to go. And that can be so incredibly uncomfortable.” ([06:49])
Practical encouragement:
“One successful experiment can become the blueprint for your next chapter.” ([16:55])
Abagail affirms that every business, at some point, will meet a crossroads where following old rules leads to stagnation. The entrepreneurs who flourish are those willing to bravely test, reflect, and evolve. The episode is a practical, empathetic invitation to listen to discomfort, reflect honestly, and take actionable, incremental steps toward authentic growth—reminding listeners that change isn’t a failure, but an opportunity.
(All timestamps reflect MM:SS from the start of content. Ads and non-content sections are omitted.)