How I Stopped Planning and Started Improvising Everything

Published: 3/9/2026

Benjamin Franklin said: “Failure to prepare is preparing to fail.” And he’s right. I say, stop writing, planning, and preparing everything you’re presenting. Also, I’m right. Let me explain.

Big days with a presentation, an interview, or a meeting demand preparation. They often cost us a few hours of sleep in the process. But what if I told you there was a way to work smarter, not harder?

Just Wing It

Ha. Kidding. Don’t we all wish! But the joke is actually 50% true. You are more ready than you give yourself credit for. And I found this out by, one day, just winging it. It went so well, it permanently changed my approach.

Long ago I signed up to do a Toastmasters speech. I knew I wouldn’t have much time to perfect it, but I welcomed the challenge. Fast forward to the day of the speech and I had only written about 20% of it.

So that morning, I threw up my hands and happily spent an hour forgetting all about it before heading to the club. I knew my key message and the flow of the stories, so I left the exact words to appear in the moment.

They Can’t Tell How Much You Prepared

Of course, I didn’t tell anyone I was improvising. I took the stage just like any other speech, hit all of my points, and left with no one the wiser. Then I gave a TEDx talk with mostly flow and minimal memorization. I even started improvising spoken word poetry, which gave me some of my best performances. Once I started in one area, it snowballed into every creative, technical, and performance facet of my life.

You can do the same with your speaking. Think about topics or stories that you can tell from memory, off the top of your head, with zero planning. That’s because, in a sense, you’ve been preparing your whole life to talk about those. Presentations, interviews, and meetings are just like that, with some tweaks to the format and audience.

It starts with your expertise. Whether that’s design, or software, or finance, or basket weaving, the core content will always be the same. You just massage 10-20% of it to fit the context – 30 second interview response, 5 minute presentation, 1 hour keynote, 3 hour group workshop. So focus less on the what, and more on the how.

Structure Over Script

You know your core ideas. This is the 80% that’s usually already done before you ever get the assignment. The next step is to condense them into memorable, actionable snippets that you can recall and repeat on command. Have an idea of examples and explanations you’ll use to illustrate your points without trying to memorize every word.

Now order your key points and fit them into an intro-body-conclusion structure (full guide on speech structure here). Or practice some answers to interview questions with P.E.E.L. responses (full guide to interviews here). Or try some questions on a test audience to see how you might engage listeners in your real talk or workshop. This is the 20% that fits your existing expertise into the appropriate format for the occasion.

Act Natural

Think of a friend or family member who tells the same (good) joke or story every so often. You’ve probably heard it enough times to repeat it yourself. But what is it about them that makes the same story resonate on each retelling?

It’s not verbatim repetition. Watch how they read the room, lean into the audience, and time the punchline just right for different people or in different places. Did they need to rehearse every day for three weeks to pull that off? Of course not. Your stories, expertise, and message should be totally natural and easy for you to launch into at a moment’s notice.

Preparation Done Right

Forcing ourselves to adhere to a script often pleases the control freak in our brains. We think that if we can just say every word exactly as we wrote it, execute our stage choreography, and flash every slide at the perfect moment, we can guarantee the outcome. That is an illusion of control and a setup for a weak performance.

Instead, lean on your foundational stories, insights, and takeaways. Use the ones that are already part of who you are, or if you have to use something new, tell it like you would a story from your life.

Don't sweat the small stuff. Let the exact words find you in the moment. That way, you lead the talk, and everything else falls into place.