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.)