How to Know When It’s Time for Experimentation & Reinvention

Update: 2025-10-28

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Episode 996: Show Notes

Sometimes the business that got you here can’t take you where you want to go! Today, we are talking about when it’s time for experimentation and reinvention. This is not so much about how much energy you have to give and more about when you know that change is vital. Yes, it’s scary to make changes, but sometimes leaning into that discomfort helps you reinvent yourself and your business. It’s easy to get a false sense of security around what worked before, but that can quietly become a cage that prevents you from considering other options. I’m curious, what are you maintaining because it feels safer, not because it’s still working?

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Signs That It’s Time to Experiment

These signs are actually pretty recognizable and have some practical cues as well! The first sign sounds kind of obvious, but we often try to ‘band-aid’ this; you’re uninspired. Red flag number one is when you start dreading doing what you used to love. Another sign it’s time to experiment is if you’ve hit a plateau or if you’re even starting to go backwards. You may already be kind of aware that something has to change, but you may not know what needs to change yet. The final sign that it’s time to experiment is that you might be feeling a little jealous or a little curious. This feels like a quiet desire to explore something new that’s tugging at you.

Reinventing Strategically

I’ll be honest, sometimes you may think that walking away is the easiest thing to do. But I want you to be strategic and not chaotic. I don’t want you to make decisions from a place of emotional dysregulation. You can start with micro-experiments, so it feels less crazy! Start to think of this more like testing than pivoting. Reinvention is going to come after clarity, so collecting data is essential to becoming clear on things! Try something new, track results, make adjustments, and trust what the data and energy are telling you. It’s really that simple! One successful experiment can become the blueprint for your next chapter.

The Power of Debriefs

I want you to learn the difference between knowing when you need rest and when you’re excited and ready for something new. These things are not the same, and if you do the opposite of what you need, it won’t help the way you want it to. I find that debriefs really help me gauge whether I’m making the right choice in the right season by learning from my experiments. Change can be scary, but it isn’t punishment! It’s an invitation and opportunity to move in a new direction. I just want you to take one small step, and then tell me about the results of that experiment. Every business will hit this point, and the ones that thrive will be brave enough to reinvent!