Do People Really Fail to Plan- or Do They Fail to Execute?

Steve Freeman
Jan 14
2 min read

People Don’t Fail to Plan — They Fail to Execute

One of my first real professional jobs was selling insurance for a captive insurance company, Bankers Life and Casualty. I was 23 years old and, truthfully, had no idea what I was doing.

The job was hard. But I was full of energy, ambition, and had a healthy fear of failure—so I worked hard to succeed.

As part of our training program, we had to memorize an opening script from a Financial Needs Analysis training manual. One phrase from that training has stuck with me ever since (and I’ve heard it many times over the years):

“People don’t plan to fail, they fail to plan.”

We used that line as part of our sales process to help people make a decision and move forward.

Over the years, however, I’ve come to realize something important.

Many people are actually very good at planning—but not so great at execution.

And the truth is, a great plan without execution is just a document.

I’ve seen it time and time again. A person, a company, or an organization creates a thoughtful, well-designed plan… and then it just sits there. Little to no action. No traction. No results.

And if I’m being honest, I’ve been guilty of this myself.

Over the years, I’ve gotten really good at planning—but I’ve sometimes struggled with execution. Why? A few reasons stand out:

The plan is too complicated. It looks great on paper but feels overwhelming to implement.
Fear of failure. After putting so much work into a plan, the question creeps in: What if it doesn’t work? As long as you stay in “planning mode,” the plan can’t really fail.
It’s not a plan you truly believe in. Sometimes peer pressure gets the best of us. We attend a meeting or conference, hear a great speaker, and create a plan simply so we can say we did—without real conviction behind it.