When you make a big life change, it sparks conversations with people who are wrestling with the same questions you once were. I recently caught up with an old friend who asked the question that stops most people in their tracks: 'Can I even do this?' The truth is that mini-retirements aren't a one-size-fits-all solution. Whether you need a short sabbatical to reset or a long-term bridge to entrepreneurship, the path only becomes clear once you define your 'why.' Here is the framework I use to determine the duration, the financial impact, and the level of risk for a season of intentional exploration.

For a long time, I thought of my first business as just a 'silly card game' (a bit of a defense mechanism against the fear that a simple idea couldn't have true value). But after the high-stakes world of business acquisition fell through, my perspective on risk underwent a massive shift. I realized that without a massive loan draining our cash, the runway we’ve built is much longer than I thought. It turns out that 'silly' idea might actually be the most sustainable path forward, and I'm finally ready to stop calling it a side hustle and start calling it a business.

There is a lot of buzz out there about buying a business (thanks to the social media influencers who make it look like a weekend hobby), but I’m here to tell you it isn't all it’s cracked up to be. From the grueling timelines and the 'cash drain' of the search phase to the legal minefields of asset vs. stock sales, the acquisition journey is a mountain of work before you even get the keys. If you aren't prepared to build a team of experts or handle the anxiety of a deal falling through, you might want to stick to the W2 life.