996: How to Know When It’s Time for Experimentation & Reinvention - Strategy Hour | Online Marketing for Business Growth

Podcast Summary: Strategy Hour | Episode 996

Title: How to Know When It’s Time for Experimentation & Reinvention
Host: Abagail Pumphrey
Date: October 28, 2025

Episode Overview

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.

Key Discussion Points & Insights

1. Recognizing the Need for Change

Difference between “seasons” and reinvention:
- Last episode focused on recognizing personal seasons in business; this episode hones in on knowing when it's time to innovate ([01:00]).
Personal story of losing enthusiasm:
- Abagail recounts getting burnt out discussing the same topics for years and describes feeling "disingenuous" after moving beyond the service-based business she originally taught ([01:15]).
- Her solution years ago: quietly restarting her agency to get “back in the game” with service clients. But the next time around, she leaned into creating new content and resources for business pivots rather than reverting to old models ([02:15]).
Experiencing resistance as a sign:
- "Innovation is showing up disguised as discomfort." – Abagail ([04:47])
- She stresses that resistance and boredom can be potent cues—not something to be ignored or simply patched over.

2. The Sunk Cost Fallacy & False Security

One-offer vs. evolution:
- Abagail compares the security of a consistent offer to the necessity of change for solo entrepreneurs and very small teams:
  
  “We get this false sense of security around what worked before, but that can quietly become a cage.” ([06:13])
- She cautions against letting past investment in a business direction prevent logical pivots.

3. Practical Signs It’s Time to Experiment

Five clear signals:
1. Feeling uninspired:
  - “You start dreading doing what you used to love. Red flag, number one.” ([07:14])
2. Hitting a plateau:
  - “Your growth, financially especially, has stalled out—even though your effort hasn’t.” ([07:28])
  - Shrinking (not just stagnating) is an even bigger red flag.
3. Audience evolution:
  - Classic examples discussed: Blockbuster and PalmPilot failing to adapt to a changing market ([08:10], [09:16]).
  - “Is this even what people want anymore? Or has technology changed so much that what I’m offering is no longer relevant?” ([09:31])
4. Craving alignment:
  - When what excited you starts to feel like an obligation ([13:51]).
5. Curiosity or jealousy:
  - “If you’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… you have a quiet desire to explore something new and it is tugging at you.” ([13:57])

4. The Value of “Micro Experiments” vs. Overhauls

Small-scale testing:
- Abagail advises starting with small experiments—tweaking one thing at a time, like messaging or pricing, rather than an all-in pivot:
  
  “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:
- Record both results and how it felt to launch or experiment:
  
  “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])

5. Rest vs. Reinvention

Distinguishing exhaustion from the need to pivot:
- Don’t mistake the need for rest for the need for change—and vice versa ([20:54]).
- “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. Are you sure you don’t need rest first?” ([21:18])

6. Reflection and Debriefing

Regular check-ins:
- Abagail recommends debriefs after experiments: focus not just on numbers, but on what you learned and how you felt ([19:16]).
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])

Notable Quotes & Memorable Moments

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])

Key Timestamps

[01:00] – Distinction between business “seasons” and the need for experimentation.
[04:47] – Innovation as discomfort.
[06:13] – False security, sunk cost fallacy.
[07:14-09:31] – Five signs it’s time for experimentation; classic examples (Blockbuster, PalmPilot).
[13:51-13:57] – Audience evolution and the quiet desire for change.
[15:10] – Small-scale “micro experiments” instead of massive pivot.
[19:16] – Debriefing: measuring not just results, but also energy and enjoyment.
[20:54-21:18] – Importance of distinguishing between the need for rest vs. true reinvention.
[22:13] – Invitation to take a small step and reflect.

Closing Thoughts

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.)

Transcript

A (0:00)

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.

B (0:19)

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.

A (0:28)

I don't believe in one right way to build a business.

B (0:31)

I'm here to help you build business your way. One that supports not only the life.

A (0:35)

You have, but the life you want.

B (0:37)

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.

A (0:50)

You'Re creating your first digital product, growing.

B (0:52)

An email list, or scaling an already profitable business. Settle in. It's time to talk strategy.

A (1:00)

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.