During the summer after I graduated from college a sinking feeling began to creep up on me. While I'd readily said "goodbye" to school for good, now I was looking at a seemingly-endless expanse of time ahead of me with no new semesters, long breaks, advancements or graduations to look forward to... just work and whatever I made of it. I like work and making my own path through it, but something about this horizon of unstructured sameness unsettled me enough that I got very close to signing up for more school.

Over the following decade, I got used to the never-ending stretch of time, and we began to build Pathwright as a never-ending series of projects. (Software is never "done".) We'd start and finish projects and then pick up the next. We hit (and missed) plenty of launch dates in no particular rhythm. We tried out many project management tools and methods from kanban boards to project management software to sticky notes and saw marginal improvements.

In other words, we worked pretty much the same way as every other company. But no matter how hard we tried, we couldn't get away from the feeling that we were running on a treadmill that we couldn't switch off or slow down. As the product and team grew and projects stacked up, we ran into frequent periods of intense work and subsequent burnout. After a particularly rough stretch of time leading up to launching Pathwright 2, we knew we had to get off the treadmill. That's when we stumbled across this article about how Basecamp works in six week cycles. We've learned a lot from Basecamp over the years and had nothing to lose by giving this method a try in the new year of 2017.

Most new ideas we try on for size work to a degree, and we adapt them a bit for marginal overall improvement. But this idea was not like that: It worked immediately. It worked amazingly. And it's still working.

Five Benefits

Now, it's hard for us to imagine not working in six-week cycles that we refer to as "Trails." In addition to recovering the more natural rhythm of work and rest we humans are wired for, here are five benefits we can't do without:

1. Time-boxing projects into six-weeks helps us plan smaller & smarter.

It's notoriously impossible to predict accurate timelines or costs for software projects (and that's true of any multifaceted, creative project). Humans are simply no good at predicting the future. Once we finally accepted our finite planning powers, we gained a tremendous amount of mental clarity and focus from simply limiting our time horizon for projects to "what can we realistically accomplish in just six weeks?"

As for how many projects we plan during one trail, we followed Basecamp's lead and commit to:

• ⛰ Expeditions: A few bigger projects that will take four to six weeks.

• 🏞 Hikes: Seven to ten smaller projects that take anywhere from a couple of days to a couple of weeks.

After the first few trails of taking on quite a bit too much, we added a "Notch Day" smack in the middle of the six weeks that acts as a checkpoint to review project progress, share feedback, and help each other edit down projects to even smaller sizes when we can.

2. We get to hit the reset button every six weeks.

While we try to keep projects within the six weeks, we don't stress out if we don't quite make it. Instead, we hit the "reset" button during the two weeks in-between trails.

We call these two in-between weeks 🏕 "Camp weeks" which are a break from focused projects to focus instead on review, exploration, and planning at a slower pace.

Any projects not finished in the previous trail are reframed and reshaped as a new project for the next trail or put on a waiting list for a future trail.

3. There's time to look back, think, and plan.

Our 🏕Camp Weeks in-between each Trail are a welcome respite. We take a slower pace, re-orient ourselves towards our goals and mission, and begin to map out the next six-weeks of work.

Camp weeks not only provide us with a nice break, but also help us zoom out from periods of detailed focus to reflect on our mission, strategy, and goals. This big picture review every six weeks helps us avoid the common pitfall of prioritizing the urgent over long term impact.

4. We have a rhyme and reason for saying "later."

Before we worked in trails, it was more difficult to tell team members and partners with a great idea or pressing need that we'd have to get to it "later." While later is necessary 93% of the time, it could come across as subjective and arbitrary when our only framework for planning was whatever we decided was next in line. Additionally, we spent a lot of time and energy attempting to synthesize all this new feedback with current plans as it came in (which was all the time).

Now that we work in Trails, we can simply share that we'll consider the idea during an upcoming Camp Week and get back with them — and then forget about it until then. While we still have to say "later" to most requests, at least there's a rhyme and reason behind it and our team and customers have all generally found knowing the rhythm of our work reassuring.

5. We get to share more of what we've accomplished.

🏕 Camp Weeks carve out enough time to share what we accomplished in the previous trail with our team and customers every seven weeks. We call this 👩🏼‍🏫 "Show & Tell" and it's become a something we look forward to. It's a bit like a mini-graduation we get to experience together six times a year. We're twelve trails in now, and I'm still amazed by how much our team accomplishes in just six weeks.

If you feel like you're running on a treadmill, experiencing bouts of "sprints" and burnout, then it's time for you to try something new as well. We unequivocally recommend giving some form of this work & rest rhythm a try and would love to hear how it works for you.

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