"Twenty years from now, you will be more disappointed by the things you didn't do than by the ones you did." — Mark Twain
I got a call last week from a friend whom I hadn't spoken to in a few months. He said, "Scott, I need to chat with you about how to start taking some leaps. It's time I make some bold moves because so far to date, I've been too conservative."
I love these phone calls because someone is giving me a pass to be honest, and more importantly, to help someone dream big.
I find we just don't dream big enough, and eventually we look back and wish we had taken those big leaps and those bold decisions that we thought so much about and just didn't make happen.
What was interesting about our conversation wasn't that he didn't have ideas, because he had plenty of them. It was that every single one of them came with a built-in exit ramp. A reason to wait. A reason to delay. A reason to keep things exactly as they are for just a little bit longer. It sounded logical on the surface, responsible even, but underneath it all was the same thing I've seen a thousand times: fear dressed up as strategy.
So I asked him a simple question: What does your life actually look like if you don't change a damn thing? The same job, the same routines, the same conversations, the same frustration that shows up on Sunday night when you start thinking about Monday morning. Because that's the part people don't want to sit with. It's easier to imagine a big future than it is to confront a stagnant present.
Then we flipped it. If everything worked out, if you actually went for it, what's the upside? Not the safe version — the real version. The one where you lean all the way in. The one where people might question you, where things might get uncomfortable, where you don't have all the answers figured out yet. Because that's where the gap lives — between the life you're currently tolerating and the one you keep thinking about when things get quiet.
Here's the truth most people avoid. The cost of staying the same is almost always greater than the cost of taking the risk. It just doesn't show up immediately, so we ignore it. It shows up slowly, over years, in missed opportunities, in smaller paychecks, in conversations you never had, in ideas that never left your head. It shows up when you realize you played it safe and still didn't get the outcome you wanted.
So if you're sitting there thinking about making a move, stop waiting for the perfect setup. It doesn't exist. There is no clean moment where everything lines up, and suddenly it feels easy.
There's just a decision. A messy, uncomfortable, slightly irrational decision to go do something that might actually change your life. The question isn't whether it will work out. The question is whether you're willing to find out.