There's Never A Good Time (Only the Right Time)

Borrowed

"We only have a choice about the decision we are about to make, not the consequences."

From "The Road Less Stupid" by Keith J. Cunningham [Book]

Learned

We kicked off this quarter with some decisions we’d already made weeks prior, so a lot of it has been announcements, sequencing, and the conversations that follow. Through it all, one question I’ve been sitting with is: what would this look like if we’d acted sooner?

I’m not suggesting we got it wrong. But the real work happens after you take action on a decision, and now that I’m in that part, it’s an interesting exercise to sit with whether we could have gotten here faster.

What makes it worth doing is that it cuts both ways. There are things you only find out once you’ve made the change, and some of what we’re working through now would have surfaced earlier and given us a head start. But the other side is just as true. Pieces that are now central to where we’re headed weren’t in place yet, and I’m not sure the earlier version of this is the better one.

So I can argue it either way, which is usually a sign the more useful question is underneath. If we did move slower than we needed to, what were we waiting for? Because the truth is, there’s rarely a good time to make big changes, only the right time.

A good time is made up of conditions we don’t control.

When I try to picture what a good time actually looks like, it’s a list of things that are out of our control. No upcoming launches, no client delays, the team perfectly resourced, knowing which prospect will sign, and nobody caught off guard by any of it. Each one is reasonable on its own, but together they’d all have to line up at once. So if that’s the bar, I’m not really waiting on a decision. I’m waiting for circumstances to give me permission, and they never will.

A right time is made up of conditions we do control.

The other list is a lot shorter, and all of it is ours. We know what needs to happen, and we understand what it’s going to cost. That’s the whole list. And when I look back at what we’ve moved on, both were true well before we took action.

The reasons to wait are usually real.

Say you know someone isn’t working out. You also have two launches next week and a client who’s unhappy with a recent presentation. Both are true at the same time, so the move becomes “after we get through these launches.” Completely reasonable, except that by the time they’re done, there’s something else. Worse yet, one of those launches gets delayed. From the inside, sequencing and stalling look the same, and I’m not sure there’s a reliable way to tell which one you’re in while you’re in it.

Waiting is also a decision.

Whether we act or not, time keeps moving, and things keep developing. So the choice was never between doing something and nothing happening. It’s between changes we’re directing and changes that happen on their own. When we act, we own what comes next, good or bad. When we wait, the situation unfolds anyway. People fill the quiet with their own read on what’s going on. Small confusions settle in until they start to feel like process. None of that gets logged anywhere as a choice with risk, but we feel the cost eventually.

The right time is about what we’re willing to carry.

Ready is not the same thing as certain. Of course we want to see how something lands before committing to it, but all we have is conviction. Cunningham’s line puts it well: you get a say in the decision, not in the consequences. So the preparation that actually matters is deciding up front that whatever comes with it, we’ll take it.

Things do tend to fall into place once you take action, in ways you couldn’t have planned for, and looking back, it’s hard not to feel like it went the way it was supposed to. I believe that. Yet, I don’t want to lean on it so much that I stop asking what I’d gain by acting now, and what it would cost.

Thought

Where am I waiting for a good time when I know it's the right time?