written by LOU BLASER

A version of this essay first appeared in Midlife Cues, a weekly newsletter about intentional living in our middle years. Get it in your inbox; you're going to love it.


Sure. Coming up with a plan is a good thing.

Consider #allthethings you’re going to learn about that thing you want to do as you’re fleshing out the details.

Plus, it feels… shall we say, safe?

Even though no one can really guarantee anything, having a plan in our back pocket feels like we’re a little bit in control. 😊

Here’s the thing, though.

  1. Any plan naturally comes with assumptions. (See “Building on This” segment below for more on this.) But we forget these are assumptions that need to be proven right or wrong.
  2. You know that saying that a plan often falls apart as soon as it meets with reality? Yep.
  3. And some of us use “I’m coming up with a plan” as legit reason for delaying action. Procrastination is sneaky.

I’m not a fly-by-the-seat-of-your-pants kinda gal. Quite the opposite.

But as I got older, I learned how to depend less and less on a fully-baked plan.

I discovered the beauty of a (deliberately) rough outline. And I learned how to have fun experimenting and testing the waters to see what happens.

As much of a planner as I was, this was not easy.

But I managed to cross to the other side. And the experience from over here is so much better.

Lemme just say there’s something to be said for holding plans loosely… and for allowing serendipity to step in and show us something we’ve never even considered possible.


Let’s not hide behind our plans — or more specifically, the process of planning.

No more hiding. No more waiting to be ready. You’re ready now.

(Also, if not now, when exactly?)


  • Part of the challenge with planning for a “desired future” is that we’re naturally biased to think about what our present self wants/needs/might find preferable in the future. The problem is there’s a very good chance our future self won’t be in agreement with that. There’s something called “temporal discounting”, a battle between present and future self that we have to consider.
  • One thing planning does is it calms the part of us that likes to worry. In moving toward a more relaxed, less rigid planning style that makes space for experimentation and serendipity, I had to learn how to manage Ms. Worrywart. Here are some solid tips on how to stop worrying.
  • Speaking of serendipity, what even IS it? Why does it feel like it’s happening to others and not to us?! Is it that we’re not noticing it? And how do we take advantage of it, in the off chance that we actually recognize it? 🤭 What is Serendipity?


“Serendipity is nice, but hoping for luck and the magic of happenstance shouldn’t be an excuse for a lack of proactivity. I had to learn for myself that waiting isn’t a life plan.”
— Karen Finerman, businesswoman and CNBC Fast Money panelist


These days, “directionally” is a favorite word.

As long as I’m heading in that direction, I’m good. 😊

What’s your planning style? Where are you on the scale between “Let’s plan every detail of this sucker” and “Huh? What plan?”

Cool Beans,
Lou Blaser


A former management consultant and IT leader, Lou Blaser is the editor of Midlife Cues and the host of the Second Breaks podcast. She is also the author of Break Free: The Courage to Reinvent Yourself and Your career. Lou’s work is focused on exploring how to navigate, thrive, and turn midlife into the best phase in our life.