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In my 20s, I was a night owl. Okay, more accurately, I liked to party. I lived in New York and had some great friends. We spent a lot of late nights together, always just “one more round” before the bars closed at 4am. Maybe we’d even go to a club after. I loved it.
But I also loved to sleep. Every night (or early am) I set the alarm with big plans: up early, work-out before work. And then the morning came, and I hit snooze five, six times. I was world-class at it. I made it to work on time, of course...but many times just barely.
Work was fine. I liked learning and growing, and the challenge it provided. But my friends were the main event. And work helped me pay for it all.
I was enjoying my youth, and I have no regrets. But looking back 25 years later, something was clearly missing.
I didn’t have a vision.
I knew that I loved my people. But I had no idea what I wanted to be when I grew up.
So I wandered. I kept rising in my career and taking on more responsibility. I liked it. It just never quite fit.
And then, in 2024, I took a course on Life Planning. For the first time, I built my own Living Vision (a picture, in my own words, of what I truly want). It included this line: “I will use my talents to empower millions of people to live with purpose and passion.” I said it out loud to my instructor, who listened deeply, like nothing else in the world mattered. And hearing those words come out of my mouth changed something in me.
Granted, I’m a late-in-life convert. But having that vision, and seeing the path it’s taking, drives me in a way that I didn’t know was possible. I’ve learned that obstacles will always show up. But when your vision is strong enough, they just stop becoming reasons to quit.
That same year, a friend told me that he and his wife take a weekend every December to plan their next year. He said they’ve done it for decades. He likened it to strategic planning. I’ve sat through more corporate strategy offsites than I can count -- but it never occurred to me to do one for my life.
So every year since, instead of a simple New Year’s resolution, I do my own life planning: I design a vision and a plan for my year.
And yes, you need a plan: where you’re going, what’s in the way, how you’ll get around it. And the plan will probably be wrong within weeks, because it always is. Eisenhower said plans are worthless but planning is everything. Most people get stuck when reality stops matching the plan, and they fight reality instead of adjusting.
My longer-term vision doesn’t move, but how I get there does. New ideas get incorporated. So does whatever the past year threw at me that I didn’t see coming.
And it isn’t just for my work. It’s for all of my life. How do I want to improve my relationship with my kids this year? How can I deepen my relationship with my wife? Where and how can I inject more fun into life? What kinds of things will I do that light me up?
Get clear on what deserves your time and what doesn’t. Then protect it. Without a plan for how you’ll do that every year, you’ll wake up one day and think, “How did I end up here?”
Now the alarm goes off at 5:30 and I’m up. No snooze. Starting the day doesn’t feel heavy anymore.
Because I’ve already decided what this year, this week, and this day are for. And what they’re not for.
The weekend my friend described stuck with me. So much so that my wife and I decided to imitate it. We do our own weekend life planning session each year. And I decided to invite others along too.
On January 9-10, I am hosting a retreat at Lake Austin Spa Resort where we will do this very thing over a weekend. I call it Best. Year. Ever. We build a vision. We build a plan. We have fun doing it. And we get honest with each other about where we are and where we want to go.
It’s a community where we cheer each other on and hold each other accountable. And if you’re serious about not leaving your life to chance, we’d love to have you there.
Reply to this email or leave a comment and I’d be happy to send you more details.
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