I remember creating my first online giving form back in 1999. It was a simple, unsecured page on my church’s website for a building campaign. My boss looked at me and said, “This is a waste of time. No one is going to put their personal information on a website.”

He was certain. But he was also wrong. That little form received five donations—one of them for $12,000.

At the time, his thinking wasn’t unusual. In 1999, trusting a website with your credit card number felt dangerous. But what felt “unsafe” then has since made old methods of giving nearly obsolete. Most churches and nonprofits today couldn’t survive without digital donations.

Here’s the leadership lesson: what feels risky today will soon make yesterday’s playbook obsolete.

I’m watching the same pattern play out right now with AI, digital funnels, and new donor/client acquisition systems. Leaders who cling to “the way it’s always been” will soon find themselves sidelined by those willing to experiment before the rest of the world is ready.

If you want to grow, you can’t afford to only play by proven rules—because by the time something is universally proven, it’s already outdated.

So let me ask you:

• What part of your strategy is at risk of becoming obsolete?

• What new opportunity feels a little uncomfortable but could change the game for your organization?

Because the future doesn’t wait for anyone’s comfort zone.