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One of my favorite trainings that I received— and gave— as a community organizer was strategic planning. I enjoyed thinking about what intermediate steps an activist group could take to get from their Point A (their current reality) to their Point B (their ultimate goal). One of the things I learned from that training was to put these steps on a timeline, and to make them specific, measurable and doable. I continue to use that training as a coach when I support my clients in designing action plans to make the lives they want for themselves into the lives they have.

So, it was ironic that I did not think to apply these lessons when I first began my cross-country road trip with Maradog.

Some background: in case you didn’t know, my family and I moved last month from Seattle to Hudson, NY (about two and a half hours north of New York City). For several reasons, I ended up driving from Seattle to New York with our dog, Mara. Since Mara is still waiting on her license— apparently having your own facebook page doesn’t qualify as sufficient proof of human identity (who knew?)— I had to drive solo. And we only had seven days to make the 2,945-mile trek: I made a commitment to myself (and to my wife) to be at the Albany airport to pick up my family when they arrived— which would be six days after the movers finished loading our stuff onto the moving truck.

Thinking about driving 2,945 miles wasn’t daunting to me, so much as it was unfathomable. But as it got closer to my departure date, I started to wrap my brain around what that meant.

Thinking of myself as a good strategic planner, I made a few decisions.

One was that trying to drive the journey straight through with little or no sleep was not an option for me in my forties. That decision was made even easier for me when I considered the fact that I would have an aging dog along for the ride who had had a recent bout of bladder issues. On a similar note, I decided to try to be realistic in pacing myself for this trip, in terms of how many hours I would drive every day—since 2,945 miles is a marathon, not a sprint. So that meant that I would have to stay in hotels and motels.

At the same time, though, I was aware that I had a timeline to keep. I also was aware that it would be less straightforward than usual for me to find dog-friendly accommodations. Bearing those facts in mind, I decided to chart out a place or two where I might stay each night— depending on how far I got each day. So, on the day I left, I had a few possible rough itineraries in mind.

I didn’t get on the road until after 7:30 p.m. on the first day, though, after getting delayed by dealing with the movers and other final moving details. Between my late start and encountering a huge rain storm in the Cascades, I hadn’t gotten very far by the time I stopped for the night at 12:30 a.m. I wasn’t even 100 miles from Spokane— my fall-back option for where I’d stay the first night.

That meant that in order to get back on track with the one itinerary I’d worked out that still that remained an option, I would have to drive 525 miles the next day— and a good chunk of that would have to be through the Rockies. I didn’t have much choice— I needed to get to at least Bismarck by the 3rd night if I wanted to have any realistic chance of making it to Albany on time, and if I didn’t catch up in Montana on the 2nd day, that wouldn’t happen.

It felt pretty daunting to me to think about driving 525 miles in one day, as I thought about it at breakfast that morning. I was in Central Eastern Washington, and I was going to have to get to Central Montana that night. It felt even more daunting once I started driving on I-90 again. My GPS suggested it was going to take over 10 hours, and the miles felt like they were going by slowly.

But I had learned a lesson from the previous day.

That first night, I had no idea what the benchmarks (the landmarks, cities and towns) were on the way to Spokane; the only thing I could see was how far away Spokane continued to be. On the second day though, I had familiarized myself, beforehand, with the benchmarks on the way to where I was going— Spokane, Coeur d’Alene, Missoula, Butte, Bozeman.

To me, 525 miles was unbelievably far. But 137 miles to Coeur d’Alene for lunch… not so much; 165 miles to Missoula for gas, a walk with Mara, and a snack… that seemed manageable.

Although I knew that I needed to get to my destination that night in Central Montana— even more so after I put the room on my credit card around the time I was driving through Missoula— by staying focused on the benchmarks (the intermediate goals), I was able to make the trip feel doable for me. My error the previous night had been to not break down the intermediate steps of my cross-country trip (i.e., the 7-day itinerary) into even smaller intermediate steps for each day (i.e., cities and landmarks that would be signposts of my progress).

In spite of the exaggerations of my GPS, I did get to my destination that night in good time, even after taking several breaks for Mara and myself.

So, how can you take what I learned and apply it to your own life?

I’ll give you a clue: I’m not thinking you’re going to read this, hastily pack a suitcase, and then walk out to your car to take off on a cross-country road trip.

Instead, ask yourself: what is it that I am working on now that feels like the end is far off in the distant future, or what is it that I have given up on? Maybe it’s an idea for a new career. Maybe it’s a book you’re writing. Maybe it’s a script you haven’t started or a movie you need to finish editing. Maybe it’s a new consulting business, or a move to the other side of the world.

And now ask yourself something else: how can I break these projects down into even smaller intermediate steps than I already have? Perhaps instead of ‘updating your resume,’ you need to write the new entry for your current job first— or even gather the bullet points for it. Perhaps instead of ‘writing the next chapter,’ you need to get as far as writing part of a specific scene. Perhaps you need to contact the embassy first of the country where you want to move instead of just fully ‘educating yourself on the legal requirements’ of moving there.

You get the idea.

Now try this: try accomplishing your first benchmark tonight. I’m serious. Try it. You don’t have to finish it (though that would be ideal). But just try making it a reality.

You might be surprised: it might just be more doable than you think.

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