On Planning
Or, how to move ahead in life.
Lately, I’ve been thinking about plans.
About direction.
About the paths we take—and those we leave behind.
And one thing seems clear: without the right plans, we can end up in places we never intended to go.
There’s certainly value in openness and change.
Flexibility matters.
But too much change—without structure—often leads to reaction rather than purposeful action.
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Discovering Your Own Path
Recently, I’ve had the opportunity to reflect on the kind of life I want to live—by observing the lives of others.
This past weekend, I met a fascinating couple who travel the world to participate in Parkrun events.
They have nearly 500 combined events between the two of them, having run along the Snake River in Idaho, across the deserts of Namibia, and even atop the ancient walls surrounding Lucca, Italy.
If you’re unfamiliar, Parkrun is a global network of free, weekly 5K run/walk events, held in over 91 U.S. locations and hundreds more worldwide. Sponsored by Brooks, the mission is to build a positive, inclusive community—“no time limit, and no one finishes last.”
What struck me is this:
It takes real planning to live this way.
Intentional planning.
One which affords for variables to co-exist withn those plans.
All to travel the country in a van—adorned with enough stickers to make any overlanding enthusiast jealous—and simply enjoy life.
One footstep after another.
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Planning and Positioning
Shane Parrish, author of Clear Thinking and founder of Farnam Street, writes:
“Over the long term, the average person who constantly puts themselves in a good position beats the genius who finds themselves in a poor position.”
The challenge for us, of course, is figuring out how to get into that good position.
I would argue, as would many others, that a good position is the result of good choices.
Epictetus, writing in the first century, said:
“If your choices are beautiful, so too will you be.”
If we desire a good life—one that may still be marked by challenges beyond our control—then the quality of our choices must reflect the quality of life we hope to build.
Save a little money today, and you build the nest egg for tomorrow.
Exercise today, and your body becomes more resilient to the stressors of tomorrow.
Read more quality books—and consume less on-demand media—and you train your mind to think critically rather than just go along with the mob.
Not all solutions will fit everyone.
But there is a solution for each of us.
How we spend our time determines the nature and quality of our lives.
And that choice, thankfully, is still ours.
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The Wisdom of Autonomy
At a midpoint in my professional career, I came across a quote from Ryan Holiday that has quietly shaped my perspective:
“My definition of success is autonomy.”
The older I get, the more I see the deep wisdom in that.
True success isn’t defined by what you own, or how many zeros sit in your bank account.
True success is the daily freedom to pursue what matters—to you, and you alone.
For the couple I met over the weekend, success looks like thousands of steps taken in breathtaking places most of us only dream about.
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Dare to Dream
We have just under five months left in 2025.
Tempus fugit, right?
So, ask yourself: What do I want the rest of this year to look like?
Maybe it’s paying down debt to create more financial freedom.
Maybe it’s taking on some debt to finally take that trip you’ve always dreamed of.
Maybe it’s as simple as reading more—or spending more time around the dinner table with loved ones.
Or maybe, just maybe, it’s taking more steps.
Figuratively.
Literally.
For yourself.
Because as Shane Parrish reminds us:
“Time is the friend of someone who is properly positioned and the enemy of someone poorly positioned. When you are well positioned, there are many paths to victory. If you are poorly positioned, there may be only one.”
Let’s hope for many paths to victory.
Let’s plan for them, too.