How Long-Distance Destinations Influence The Way We Plan
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I’ve driven back and forth across the United States 4 times now.
The first time I did it it seemed almost impossible. Driving 3000 miles by myself, stringing together Hampton Inns and interstates with unfamiliar numbers, was pretty far out of my comfort zone.
After all, I thought driving from my hometown to my college campus was a haul—and it was 22-minutes from door to door. I grew up in a place where anything you could want was about 5 minutes away. We drove farther by choice—not necessity.
As I got older, my horizons broadened.
I road-tripped with my college roommate through West Virginia and Kentucky and Massachusetts. I learned what it was like to have—shocker—a 45-minute commute.
But even still, driving across the country is a whole different beast.
There are long stretches with no stores or lunch stops that look familiar. The landscape quickly becomes foreign. The accents change.
That first time, I knew that it was possible to drive across the country. I even knew I could do it—that I would do it. But there were also so many variables that I had no way of predicting until I was in them.
Now I know that I can wait to book a hotel until the mood of the day has been assessed and a destination has been chosen. I know I can plan route and make a change at the last minute. And I know that I can eat trail mix for 3 days straight and it will be okay!
So the uncertainty is a little more familiar—but I can never eliminate the uncertainty. It’s part of the experience.
Now, I can tell you what kind of trip has almost no uncertainty: the route I’ve walked or run almost every morning for the last 2 years. I know each crack in the pavement, where each mile ticks up, and even who I’m going to pass along the way.
Depending on how I’m feeling and the amount of time I have, I can turn that route into a 3-mile run, a 5-mile walk, or even a half marathon if I’m training. I just go a little farther and push a little harder to make it happen.
There’s nothing wrong with that predictability, of course.
I get a lot out of it: a more meditative running experience, more focus on the podcast I’m listening to, fewer variables to interrupt my flow.
When I’m just going a little farther or pushing a little harder, though, I don’t have to get creative with my route. I don’t have to problem solve or choose between equally good options. That’s good for my morning routine.
But driving across the country doesn’t work like that. I’m regularly checking in with the route to see if I want to go a different way. I’m prioritizing stops and problem-solving lunch ideas. I’m taking into account the needs of the people who are in the car with me and making adjustments.
The farther I’m going, the more margin for error and opportunities to make creative choices I have.
When I’m sticking close to home, there are few options for how to get where I’m going.
The same is true in how a business develops.
In my business, I like to make a distinction 3 goal-adjacent things: vision, strategic priorities, and projects.
Vision is the long-distance destination. It might be 5 years out, 10 years out, or even farther.
Strategic priorities are the choices you make along the way to get to your destination in a way that works best for you and your company.
Projects are the different stops of the journey—rest stops, hotels, cities, parks.
Planning for your vision is distinctly different than planning for a project.
Projects tend to be pretty linear. You have a really good idea of what you’re going to encounter along the way. You know basically what order you need to do things in, too. And they have a distinct end point—with some sort of immediate payoff.
On the other hand, when you’re planning toward your vision, you’ve got be open to calibrating & recalibrating. Orienting and reorienting. Identifying mistakes or failed experiments and charting a new course.
Strategic priorities are those calibrations and recalibrations. At any given time, we can choose between 5 or more different ways to get where we ultimately want to go.
When we choose to go in a particular direction first, we’ve chosen our first strategic priority. We create projects that help us navigate based on that strategy. Once we’re satisfied with our progress in that direction, we can reorient and choose to go a new way, with new projects—all in service of our destination.
Now, the mistake I see business owners make is that they substitute project-planning methods for long-term planning.
And because it feels impossible—like a cross-country road trip—to linearly plan for a long-term goal, the long-term planning doesn’t actually ever happen.
Instead, business owners substitute shorter-term goals for vision so that they can apply that more linear, predictable planning approach. And this leaves them setting “realistic goals.”
Just like with my predictable morning route, there is a time and a place for realistic goals. And that time and place is with projects!
Realistic goals just don’t do us much good when we’re looking at longer-term planning.
Instead, destinations that seem unrealistic from your current vantage point create room to think creatively, identify your options, and recalibrate when things don’t work out the way you thought they would.
They give you more margin for “error” and more room to experiment.
Your long-distance destination doesn’t have to be measured in time. You can measure it in audience size, hiring goals, or product development.
It also doesn’t have to be measured in financial terms. You can measure it in the time you spend working, the activities you do on a daily basis, or the business model you operate in.
Where do you want to go?
What’s the far-off destination that edges into your daydreams?
What’s the most obvious way to get there?
How else could you make it happen? What are all the plausible and seeming implausible options for your journey?
Teasing out all the different options can be a bit overwhelming—no doubt. More options can easily cause analysis paralysis and decision fatigue.
But the goal in having more choices isn’t to make it more complicated to find the “right” way forward, of course.
The goal is to inspire your creativity.
When I’m driving cross-country, I might be inspired to only stay at a certain brand of hotels, or to pull over for any “largest _____ in the world” tourist trap, or to nab any National Park Service passport stamps I can (and by “I,” I mean Sean).
Maybe I want to see what it’s like to take the most northerly route without adding more than 2 hours to my arrival time.
Maybe I want to hit as many states as I can that I’ve never been to (looking at you, Iowa!).
When you let the distance between where your business is at now and what you’re setting your sights on next, you can get creative about your priorities, desires, and constraints for that “trip.” You know there is no “right” way to get there—so you can let go of that motivation and embrace something more purposeful & unique.
And finally, you don’t have to know how to get from Point A to a distant Point B all at once. Sure, having a general game plan is nice. But you really can take it one day at a time.
In past years, I’ve mapped out the route that I thought we should take. But I’ve never booked more than 1-night’s stay in advance. Because what if we learn something new about a potential stop? What if we have a change of heart and decide to go south instead of north? What if, as happened in 2019, Lola is over it and just wants to put in a 12-hour day from Theodore Roosevelt National Park in North Dakota all the way to Kalispell, Montana?
That kid is a trooper.
I really only fill in the details of my plan one leg of the trip at a time.
That way, when unexpected things inevitably happen, I don’t feel like my effort has gone to waste or that I’m somehow “not sticking” to the plan.
I use the information I have at the moment to plan my next step—even if it’s an unexpected one.
Again, when we choose a business goal that’s relatively close to where we’re at right now, it’s easy to try to fill in all the details. We figure out not only how to get from Point A to Point B, but all the pit stops we’ll make along the way. And if we learn something new and make a change? We berate ourselves for not sticking to the plan.
Planning—just like road tripping—is about progress, not perfection. It’s about learning, not rigid execution.
And to do that? I serious I need distance between me and my goal.
I’m passionate about planning differently. I love finding ways to get creative with my plans and take an unconventional approach to my goals.
That’s why I developed The Commitment Blueprint, an unconventional approach to planning, goal-setting, and execution. It’s a written program that guides you through identifying your long-distance destination and creating a flexible plan for getting there—without rigidity or all-or-nothing thinking. Plus, it includes The Leadership Dashboard, a tool for incorporate your plans into your daily work and project management.
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