Art of Starting Over: Know the Difference Between Planning vs Preparing

You’ve heard the saying “when luck meets preparation?” That’s what’s been happening to me in Dubai. I’ll explain in just a second, but let me ask you a question. Have you ever felt like the only reason you got through something was because you were prepared?

Last week’s blog took a turn none of us expected. If you missed it, you might want to go back and read it because the experience shaped this week’s lesson. You can read it here.

I am still in Dubai, but I have a flight booked for March 15th and the government called me and asked if I was still here and if I needed help. I said yes, so hopefully either way, I’ll be out soon. If you want details, read the full story. But the short version is…

I was in Dubai meeting with prospects and networking. I got here January 31st and I stayed because I kept getting more opportunities. I was in the middle of one of the retreats I was able to host when the calm I had been writing about the week before suddenly changed. Just days earlier I had written about how safe the UAE felt and how that safety had helped my nervous system relax during this starting over journey. 

Then, in what felt like a movie scene, the sound of explosions reminded me that the world can change in a moment. What mattered most in that moment was not the fear. It was the decisions. I had to make some decisions that felt like I could be harmed if I made the wrong decision.

I had to decide whether to shelter in place or move. I had to decide what was essential enough to put in one backpack. I had to decide whether I wanted to sit alone in a hotel room or be with people I trusted. I prayed, I meditated, and I even “thinkitated.” Then I chose safety in numbers and ran across the resort property to a friend’s house. A hotel worker insisted on walking with me so I would not go alone. That moment reminded me that while danger can appear anywhere, kindness can too.

That night wasn’t about politics or strategy. It was about preparation. And that’s the part that connects to starting over.

Before all of that happened, I had planned my trip to Dubai carefully. I came here with the intention of building my work internationally and hosting retreats. As opportunities appeared, I did more planning. While I was here I booked four retreats. Each one required its own planning, logistics, and coordination. Because of that planning, I was able to execute all four successfully.

But there was also a moment where planning failed me.

The biggest prospect I had while in Dubai led me to believe we had a sure thing. I expected that opportunity to move forward, so I focused my attention there. When they decided not to proceed, I realized I didn’t have a backup plan for that specific situation.

Thankfully, it turned out to be fine. The four retreats I was able to secure needed my full attention anyway. But the moment reminded me of something important about starting over.

Planning and preparing are not the same thing.

Planning is for the things you know about or can reasonably predict. It might rain. The flight could get delayed. The car could break down. These are the kinds of things we plan for because they happen often enough that we expect them.

Preparing is different.

Preparing is for the things that come out of the blue.

There’s a flood because a random pipe bursts. The person standing in line ahead of you suddenly has a heart attack. You’re going through peri-menopause but you get pregnant.

You cannot predict those things, so you cannot plan for them in the traditional sense. What you can do is prepare yourself mentally and emotionally for the unexpected. Starting over doesn’t come with a manual, but you can still plan and prepare.

Planning helps you move forward with structure. Preparation helps you stay steady when life changes direction.

In my case, planning brought me to Dubai and allowed me to host the retreats. Preparation helped me handle the things I never expected, like the sudden war and even the disappointment when a promising opportunity did not move forward.

One keeps your journey moving. The other keeps you grounded when the path changes.

Starting over requires both. You can plan the steps you want to take. You can plan the opportunities and even cultivate them. But you also have to prepare yourself for the parts of the journey you cannot control, predict, or even imagine.

I try to remind myself and my clients often to 

Expect the best.
Plan for the worst.
Prepare for the unimaginable.

Because if you are willing to do all three, starting over stops feeling like chaos and starts feeling like growth.

And sometimes, when preparation meets opportunity, it even feels like luck.

It’s like we say in Chicago, stay ready - you ain’t gotta get ready!