From Thinksgiving to Strategic New Year Planning

The fun thing about owning your own company is that every now and then you get to institutionalize ideas that inspire and excite you. Back when I owned a digital analytics agency, I instituted the practice of encouraging employees to spend the week of Thanksgiving engaged in big picture thinking, for themselves and the company. At the beginning of the week following, we’d all meet and review and if there were ideas we could try implementing to improve the company, we put them in place.

Someone — maybe it was me, maybe an employee — called it “Thinksgiving” and the name stuck.

Several years later and running a different company, I still practice Thinksgiving, only now at some level I carry it all the way through the end of the year. What starts during Thinksgiving incubates during December as I wind down my other work, and then luxuriate in spending the last week of the year immersed in deep strategic planning and big picture thinking for the next year. It feels decadent and liberating, and it really inspires me to enter the new year strong.

Let’s call it “Thinksgiving+.” I’ll tell you about it in case it inspires you to do your own version.

What’s different about Thinksgiving+ from traditional New Year’s resolution-making is that so often resolutions stem from arbitrary pressures we put on ourselves to be a more idealized version of ourselves. This process, instead, is intentionally about what will fulfill me, my business ambitions, and my personal ambitions, so the goals originate from aligning my intentions and efforts, and it becomes much easier to follow through on them. In practice, it might be the difference between an arbitrary resolution to do more exercise, versus observing that I always enjoy bike-riding and also want a little more exercise, so I’m going to try to remember to use bike share for short trips more often instead of, say, taking the bus.

Also, although the process overlaps with goal-setting for the year, as opposed to making resolutions, these aren’t necessarily commitments I’m trying to make with myself; they’re more like saying what I want out loud, so I can hear myself say it. It’s not at all about putting pressure on myself and trying to motivate myself to stick with it; it’s about being clear and honest with myself about what I want to see happen, and what kind of work I’ll need to do to get there. It’s a subtlety but it matters immensely in practice.

The other piece that makes a big difference is that once I have my plan and goals outlined, I rename and reconstruct the taxonomies of my life so that they align: my notebooks in Evernote, my lists in Remember the Milk, and my folders in Gmail, to name a few. I try to ensure that they reflect the verbiage and the spirit of the goals and the focus, so that I have contextual reminders of my big-picture direction.

Not everyone has the luxury to take the week between Christmas and New Year’s Day and invest it in planning, and perhaps not everyone would want to. But even if you only spend a few hours this week thinking about how you want 2016 to look and feel and sound and smell, even if you only write down a few thoughts about what you want in your heart of hearts, I’m betting it’ll be easier to make it happen. Good luck.