Triannual Planning: Thinking Thrice About Quarterly Business Strategy

During the last couple of weeks in August, I found myself thinking heavily on quarterly planning, end-of-year goals, and aspirations for 2026. I’ve developed quite a love/hate relationship with goal setting over my 43 years of existence—having much to do with how much wasted time and effort goes into setting goals that are nowhere near achievable given the time constraints—but I still must admit that I am much too giddy in the face of a potential planning session than is necessary or normal.

In true contrarian fashion, I began ruminating on the possibility of operating outside of the normal four slices of the year to which we’re all so accustomed: the quarter. There isn’t necessarily anything wrong with the quarter, mind you; I like the number four, as some of you may know if you’ve read my blog about the 90-90-30-30 daily productivity block schedule I utilize fairly regularly, and a year can be divided cleanly into four blocks. That checks out, according to my obsessive-compulsive tendencies.

But, as I began throwing together some high-level goals to take on during the remainder of the year, I realized there was a bit of a problem. As I mentioned earlier, what I hate most about planning is the tendency for most goals to derail—or perhaps never even take flight to begin with—due to our human tendency to overestimate what can be accomplished in the limited timeframe of three months. I’ve always come away from quarterly planning meetings in the past with between 4-6 big goals to complete by quarter’s end—in addition to all of the work that falls within the scope of my primary job duties—and I can count on one hand how many times I’ve actually accomplished the feat over the course of the last 20 years of my professional existence.

The problem was this: I had the utilitarian vision of planning just one goal to strive towards each month of the quarter, but that means I’d be organizing three tasks per period instead of four unless I doubled-up one month. Admittedly, this is a somewhat trivial issue (unless you really like the number 4, like me), but wouldn’t it be superb if I could plan four synergistic, company-focused goals in keeping with the convention I’d developed and to which I'd now grown accustomed?

I give you Triannual planning. I now divide up my year into three periods of four months, which not only extends a normal “quarter” by 30 days, but also allows for four highly focused goals, one per month. I needed a way to track these four-month periods over the course of the year, so I designed a triannual planning track to facilitate this need.

The idea is straightforward, and borrows a bit from what already works well in other planning methods: you begin planning for the triannual period ahead by analyzing the one behind you (with a few twists, of course).

Most of us are familiar with the obligatory “wins and losses” section of every review meeting; this has always left a very sour taste in my mouth, as the language is quite stigmatizing. What a terrible way to motivate yourself for the next three or four months ahead! Instead of confusing our self-worth with our work, we can choose to use less demeaning language and go into our session with a clear conscience. 

For instance, I’ve chosen to head this section with the words “did” and “didn’t” to avoid getting my own panties in a twist from the get-go. We all do and don’t do things over the course of a three- or four-month period; this is where I get to choose four things I did that directly impacted my business in some way, and conversely, four things I didn’t do that I either planned to or would have liked to do given more time, money, etc. They can be goals I specified during the previous period or not; the important point here is to clearly define the four things that were done and the four things that were not done, devoid of any unproductive and misplaced remorse.

Once those eight items are listed, we move on to the “will” category for the coming triannual period. These 4 tasks become the goals that we will then divide among the next four months; they can be informed by the tasks we did or didn’t do in the previous period or not—that’s completely up to us, the direction we’re heading or would like to head, and the importance we attach to each of those tasks.

Now that we have four goals we’ve decided we will work towards over the next four months, we can apply our per diem method of attack: the 90-90-30-30. These can be sprinkled into any number of slots to tackle over the course of four weeks. However, since we’ve decided that these goals are important to us and the business—and since we are only planning one per month instead of 1.5-2 like we were under our previous three-month quarters—we’ll double the effort, which leaves us with two sessions of 90-90-30-30. That’s eight hours of focused effort per month on operations-oriented work, or 32 hours per triannual period. For me, that’s in the ballpark of a $5,000 investment into my own business if billed as client work—or $15,000 per year.

What I love most about this is the flexibility. Some days I may only have time for 30 minutes of research toward a monthly goal, and another day, 90 minutes of focus time. No problem—I just schedule those blocks for myself and check them off on my triannual planning track once completed so I know how much time I’ve spent so far. Personally, I pack up and head to the library with just an iPad and a notebook when I have 90 or 30 minutes on the list since most of my operational goals do not require my design desktop setup. That removes the possibility of being tempted to perform any of my normal technical work and facilitates the focus time I will dedicate to monthly goals.

It's time to stop jamming up our time with goals just to keep up the appearance of busyness and momentum (which oftentimes results in utter failure and disappointment once we come face-to-face with that “wins and losses” section); our efforts are best spent on the focused work we can reasonably accomplish within finite periods of time. Just like our work, our goals should be high quality—not high quantity.

Another point to remember: the best way to manage tasks is not to create them in the first place! However, I've found that there is always something I can choose to focus on apart from client-facing projects in a given month—even if it's writing blogs or putting together a music video for inspirational purposes. Eight hours a month is definitely achievable, especially when you stop to consider how much time we waste on social media platforms and doom scrolling throughout the day.

Take back your time, attention, and effort for yourself or for your business. It's what is known as the "new gold" in big-tech circles (i.e., your data, which is composed of your time, attention, and effort); reinvest as much of that value back into your life and profession as possible. If you're interested in giving triannual planning a whirl, you can download my triannual planning track to assist you.