The Sentences We Tell Ourselves
I’m slammed right now. Let’s talk next quarter.
When we hit $10 million, then I’ll be ready.
Once I clear my desk, I’ll finally get to the big stuff.
I hear some version of these lines from CEOs and business owners almost every week. I’ve said a few of them myself. They sound reasonable, even responsible. Nobody argues with a leader who’s just trying to get through the current crunch before tackling the next big thing.
But listen closely and you’ll hear what’s really being said. Each one is a bet on a future that never comes: a day when the desk is clear, the inbox is empty, the business runs itself, and all is right in the universe. That’s when, finally, there will be time for what really matters. That day never shows up. And the promise quietly rolls forward, month after month, quarter after quarter, until someday becomes a place we live.
I call it the Someday Trap. It’s comfortable, it’s crowded, and almost everyone I know has spent time in it.
The Right Time Is a Myth
Here’s the uncomfortable truth. The conditions we’re waiting for almost never arrive on their own. More time doesn’t appear; it gets taken. More money doesn’t free itself up; it gets reallocated. Less work isn’t coming, because successful people attract more of it. The busier you are, the more someone wants a piece of you.
The project you’re finishing will be replaced by another project. The quarter you’re waiting out will be followed by another one, just as full. And here’s the part almost nobody wants to hear: as the business grows, you don’t get more time. You get less. More customers, more employees, more complexity, more decisions that only you can make. The $10 million company doesn’t have a calmer CEO than the $5 million company. It has a busier one.
I learned this the hard way. On November 12, 2015, my boys’ mother moved 2,500 miles away and I became a full-time single dad. I had one week to plan. Nobody asked whether it was a convenient time. Nobody waited until my calendar cleared. Life simply showed up and said, now.
And here’s what surprised me: I figured it out. Not perfectly, but I did. When there was no option to wait, I made the time, found the resources, and reorganized my priorities in days. The capacity had been there all along. What had been missing was the decision. More specifically the will to make a decision.
That’s the trap in a nutshell. Someday isn’t a scheduling problem. It’s a decision we keep postponing, dressed up as patience.
Why Do We Keep Believing Someday Will Be Better?
Here’s what fascinates me. These are smart, experienced people. Every one of them can look back over the last five years and see that next quarter was never lighter than this one. Yet they keep betting that it will be. Why?
Part of it is how we see the future. Today’s calendar is packed with real, specific demands. Next quarter’s calendar looks wide open, because the fires haven’t started yet. We mistake an empty calendar for free time, when it’s really just time we haven’t spent yet.
Part of it is that busy feels productive. Answering the email, fixing the quote, jumping on the customer call, approving the expense report. Each one delivers a small, satisfying win. Meanwhile the work only the CEO can do, the strategy, the key hire, the hard conversation, the hour spent thinking about where the business is headed, sits untouched because it doesn’t scream.
And part of it is plain old habit. Many owners got where they are by doing everything themselves. It worked at a million dollars. It doesn’t work at ten. But it’s comfortable, and it lets them dodge the harder question.
That question isn’t “When will I have more time?” It’s “What am I spending my time on that someone else should be doing?” In my experience, CEOs and owners aren’t short on time nearly as often as they’re working on the wrong things. Their hours are the most precious resource in the company, and they get frittered away on tasks someone else could do, often better and almost always cheaper.
Someday won’t fix that. Only a decision will.
What the Best Leaders Do Differently
I spend more than 500 hours a year sitting with CEOs and business owners here in San Diego. The most effective ones aren’t less busy than everyone else. Many of them carry more weight than anyone in the room. What sets them apart is that they’ve stopped waiting for permission from their calendar.
They treat their own growth the way they’d treat a critical customer commitment. It goes on the schedule first, not in whatever scraps are left over. They don’t say, “I’ll work on the business once things settle down.” They say, “Friday mornings are for strategy, and my door is closed,” and then they protect that time as fiercely as a board meeting.
They also understand something most of us forget: the investment is usually what creates the capacity. The leader who finally hires the operations manager gets back twenty hours a week. The owner who joins a peer group stops making the same expensive mistakes alone. The executive who starts sleeping and eating well suddenly has the energy to handle the chaos that once flattened them. The thing we’re waiting to afford is often the very thing that would make everything else affordable.
In the Navy we had a saying that the sea doesn’t care about your schedule. You don’t wait for perfect weather to get underway. You prepare, you commit, and you sail in the conditions you’ve got.
Make Someday a Tuesday
So here’s my challenge. Pick one someday. Just one. The key hire, the strategy session, the peer group, the hard conversation, the vacation you keep promising your family. Then give it a date and a time this week, put it on the calendar, and tell someone who will hold you to it.
It won’t feel like the right time. It never will. Do it anyway.
Because the real cost of the Someday Trap isn’t the thing we postpone. It’s the person we could have become while we were busy waiting.
Someday isn’t on the calendar. Tuesday is.