This isn’t really a question of “can we get the fun back?” Because that early chapter has passed. It’s more about asking: “how can we create fun now?”

What does that look like for you at this stage - in how you work together, how your days are structured, and how you connect? Fun isn’t just an outcome; it’s an approach. So instead of trying to recreate what was, think about how you can build a business and partnership that feels fun now, in this stage of your partnership.

It’s also worth noting what this highlights: how far you’ve come. It’s a pattern I see often - the early days are chaotic and unpredictable, but the newness and adventure of it all makes it feel exciting. That phase naturally evolves. The fact that it now feels more structured, more like “a job,” is a sign of maturity - that you’ve built something stable.

And yet, that doesn’t mean fun can’t exist now, it will just look different. Maybe it’s through creativity, shared wins, small experiments, or a lighter energy in how you communicate and make decisions together. It’s about intentionally designing for fun rather than just expecting it to happen (yes, I appreciate how “un-fun” that might sound, but trust me…)

From my own experience as a co-founder, I also know how easy it is to look back on the early chaos with rose-tinted glasses. That initial stress can feel fun in hindsight because you know it worked out - you got here and made it through that period. Does that resonate at all?

Before you talk to your co-founder about this, take a moment to think through:

• What does “fun” actually mean to me now?

• What would make this stage of the business more fun?

• What part can I play in creating that energy day-to-day?

Then open the conversation with your business partner: share what’s come up for you, ask how they experience fun in the business, and explore what might help bring more of it back. Approach this conversation with curiosity and positivity - you’re creating the next version of fun in your partnership. And that’s a pretty cool thing to do, right?