Building a start-up requires you to always be searching for more, faster, and bigger. Everything.

But how do you set goals and stretch your team to achieve what are often considered “unattainable goals,” especially when you feel limited by the obstacles in front of you.

What if you started with a different mindset? What if, instead of focusing on the challenges, you allowed yourself to dream big and imagine the best possible scenarios? This is the essence of the "Wouldn't It Be Great If..." exercise — a method I use to help leaders set aggressive goals without being held back by perceived or real limitations.

But before you can dream big, it’s crucial to Start with the Truth. Ground yourself in the facts of your current situation. Understand where you are, what your resources are, and what your challenges truly are. Once you have that foundation, you’re ready to move on to the exciting part—imagining what could be.

When you ask yourself, "Wouldn't it be great if…," you’re giving yourself permission to think beyond the constraints of today. You’re allowing yourself to envision a future where the barriers you see now no longer exist. This isn’t about ignoring reality; it’s about freeing yourself from the mental blocks that prevent you from pursuing your most ambitious goals.

I use this all the time, both in my personal life and in business.

Years ago, my wife and I did this exercise together. I said, "Wouldn’t it be great if I didn’t have to ever ride NJ Transit again?" and “I could attend every lacrosse game.?” At the time, it seemed like a far-fetched idea. Commuting was a necessary evil, or so I thought. But instead of dismissing it as impossible, we started thinking about other ways to make it happen. Could we move closer to work? Could I find a job that allowed for remote work? Could we restructure our lives to eliminate the need for that daily grind?

By not getting stuck on the immediate obstacles, we opened up possibilities that we hadn’t considered before. And eventually, we made it happen. I no longer have to deal with NJ Transit, and I don’t miss it a bit, other than maybe a piping hot slice at Don Pepi’s. IYKYK.

The same approach works in business. I once worked with a leadership team that was hesitant to set aggressive growth goals because they were too focused on the challenges—limited resources, a competitive market, and internal constraints. But we flipped the script. We started with "Wouldn’t it be great if we doubled our revenue in the next year?"

At first, there was pushback. It seemed too aggressive, too out of reach. But once we allowed ourselves to imagine it, we began to see ways it could be done. By working backwards from that goal, we built a plan that can make the impossible possible.

The "Wouldn't It Be Great If..." tool is about more than just dreaming—it's about turning those dreams into reality. Once you’ve imagined the best possible scenario, it’s time to work backwards to create a plan. This plan will be rooted in the truth of your current situation but driven by the vision of what could be.

So, next time you’re setting goals—whether in your personal life or in business—ask yourself, "Wouldn't it be great if…?" and let your imagination lead the way. You might be surprised at what you can achieve when you’re not restricted by the obstacles in front of you.

Start with the Truth, then think big. You certainly won’t get there if you don’t try.