Wouldn’t It Be Great if…
Building a start-up is a never-ending sprint for growth. Everything has to be bigger, faster, greater….Everything. Being a CEO means you have to be an eternal optimist.
But realities get in the way. All….the…time.
I want to share one of my favorite frameworks for setting goals and breaking through internal log jams. “Wouldn’t it be great if….”
Let’s give an example that you may have encountered.
It’s budget season and your investors are pushing for faster growth; your team is asking for more resources, and you’re stuck trying to balance your big dreams and the realties of your day-to-day.
Often these are at odds. Your investors are pushing you to grow faster. Your team is likely being conservative and asking for more resources if they have to grow.
And you are trying to balance your desire to build an amazing company and you probably don’t want to miss yet another annual plan..
So, how do you break through and get to something meaningful and innovative?
Try starting by finishing this sentence:
“Wouldn’t it be great if…”
Share your vision of what great is and what you really want and ignore the constraints or the realities of the current situation.
For example, let’s say you grew 30% this year and your whole leadership team is telling you that 35% is the right goal for next year. But you know that the best companies are growing much faster than that.
“Wouldn’t it be great if we could grow at 50% or better next year?”
Your team may scoff or not believe it, but you’re not done yet.
You need to work backwards. “Now, what would need to be true for that to happen?”
Your sales leader might say, “we need 10 more reps.”
Your product leader might say “we need to triple engagement.”
Your success leader might say “we need to improve our NRR to 115%.”
This is where you now drill down into each of these and continue to work together to understand the possible.
Can you really add 10 more reps? Maybe not. But can you improve ACV by 15% by adding an upsell motion? How would you do that? You can give that goal to your sales leader as part of planning
Same with all parts of your leadership team. If you need to grow 50% next year and each team needs to have stretch goals to get there. Ask each of them to ask themselves the same questions..
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 immediate barriers, 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.
So, next time you’re setting goals—whether in your personal life or in business—try asking, “Wouldn’t it be great if…?” You’re not ignoring reality; you’re giving yourself permission to see beyond the limits of today’s constraints. When you start with this mindset, you open up space for innovation, clarity, and purpose, aligning your team (or family) toward a vision that’s bigger than the immediate obstacles.
After all, the most rewarding outcomes often come from goals that once seemed impossible—until you dared to imagine otherwise.
