Annual Planning, Part 2

Strategic planning, the radically moderate way

Reassuring Disclosure: I link to a bunch of products like these wall calendars in this post and I don’t receive anything at all for doing so. These are just things I’ve used that I like and I’m way too distracted to set up some kind of affiliation thing where I would get kickbacks, so rest assured I don’t benefit from you buying anything here in any way. I probably should, but I don’t.

Why Make Plans?

If you haven’t read Part 1 of this annual planning series, you might find it helpful. But this post also stands alone for those who don’t have time.

Around 13 years ago I was finishing up my first book and expecting my first child. I had seemingly unlimited time, wrote a lot, but still felt stressed.

I was a classic binge writer; I would engage in increasingly creative avoidance tactics until a deadline loomed, and then I would sit down and write for hours straight. This “strategy” (if you want to call it that) got me through college and grad school, so why not keep it up?

Unfortunately, this genius strategy stopped working as quickly as a bug hitting a windshield when the first kid arrived. Suddenly my time exploded into tiny half hour increments, my brain fragmented into a million different hormonally-directed pieces, and I found myself navigating the reality of pumping in Starbucks bathrooms while trying to write in tiny haphazard chunks of time between childcare duties and teaching.

It was clear the situation was unsustainable. I was irritable with my husband (irritable might be an understatement…), distracted with my firstborn, and felt like I was constantly dropping balls without even being fully aware of what those balls were. I missed deadlines but still kept committing to things because I didn’t have a sense of what I was already committed to and had no idea where my time was going or how I was using it. Everything felt kind of awful and out of control.

Part of the problem was my total lack of a workflow, but the other part was the effect of having kids on my brain. I often compare new parenting to the Vonnegut story Harrison Bergeron because doing creative or academic work around an infant feels a lot like trying to do work while someone blows a bear horn in your ear at random intervals. It’s stressful and it sucks.

I knew I needed a system, and ideally a system where I could draw hard boundaries between my creative/academic work and parenting. Having relied on unlimited time and binge-writing for years, I had no idea where to start. Fortunately, my university was an institutional member of the National Center for Faculty Development and Diversity (NCFDD) and it was in their Faculty Success Bootcamp that I finally learned the art of time management at the tender age of 31.

The Faculty Success Bootcamp teaches a very simple time-scaffolding approach that involves semester/quarterly planning, weekly planning, and then daily planning. I eventually went on to coach in their program for many years and fell in love with the structure and sense of control that planning gave my pinball brain. (Sidebar: I highly recommend this program for all academics at any stage. What I offer below is a very quick summary of some of what’s covered in the program, but they add in coaching support and accountability and additional skills. It’s 100% worth it, especially if your university supports the program cost like mine did).

The result of finally learning how to manage my time is that in the last 13 years I’ve published two academic books, many articles, written another manuscript, a random unpublished novel (don’t ask), got tenure, made full professor, had two more kids, stayed married (so far!), and (mostly) didn’t lose my mind or health in the process.

The *only* thing I’ve done consistently right that entire time has been sticking more or less to my time management practices, the way a drowning person clings to a water logged flotation device. Sometimes it wasn’t pretty and plans often fell apart midway through, but it still helped a lot.

Plans Protect Your Goals and Values

The reality of human life is that we all move around our shared landscape, but which direction we take has a good chance of being dictated by other people unless we really work to make it otherwise.

One of the biggest misconceptions about planning is that you do it so you can be a better cog in the wheel of capitalism or bow down to your productivity overlords. That’s a complete perversion of the goal of planning.

The goal of planning is to help you identify your goals and priorities and then make space for them in your life.

Unless we own our goals and by extension our time we’ll end up somewhere we don’t want to be. And we’ll have no clear idea how we got there. We’ll get to the end of our lives and realize we spent most of our precious lives working for someone else’s goals.

As Mary Oliver asks so simply and yet profoundly, “Tell me, what is it you plan to do with your one wild and precious life?”

Because I’m a good Bootcamp graduate, I do quarterly planning, which is the best kind of planning (fight me on this one). It’s good to have big picture goals for the full year, but you should not approach your planning with the full year in mind.

There are lots of reasons for this, but here are a few:

A full year is too overwhelming, looking that far out is demotivating, and so many things change across the entire year that you end up giving up because suddenly the plan you made is totally irrelevant to where you’re standing now. Yearly planning also makes it really hard to course correct, which you will almost definitely need to do.

How I Plan

Instead of planning a full year at a time, I start with a few big picture goals for the year, things like projects I’d like to have finished, vacations I’d like to have planned, and experiences I’d like to share with the kids, and I keep those somewhere (usually in my paper planner).

I also take into account data from my annual review.

What worked well last year? What didn’t? What do I need to change for this year?

Looking over my annual review, there are a few clear areas I want to address:

1. Putting my phone away in the evenings and doing more intentional quality time with the kids.

2. Weekly finance checks with my husband, because finances got away from us a bit toward the last half of the year.

3. More intentional home organization and upkeep to keep home feeling a little more calm and a little less chaotic. In 2024 we definitely leaned into the chaotic more than a little and I really felt it.

So this is step one: figuring out how you’re feeling about life and what you’d like to keep or change. Here’s mine:

Next, I do a brain dump of other things I’d like to accomplish for the year. Since I’ve been doing this for a while, I typically have a few buckets that are important to me that don’t change much from year to year. These include leadership goals (associate dean work), writing goals, family goals, personal health goals, spiritual goals, and finance goals. Yours will likely be different. I’m focusing below on home, writing, and personal for the purposes of this post.

Once I have these written down, I do a second round of breaking these goals into constituent parts. Some people do this in a super scientific way and break goals into projects and then projects into tasks. I have minimal patience for that kind of planning , so I mostly eyeball it and go from there.

As you see above, the Home/Personal bucket does a lot of work, and as I mentioned in my Annual Review post, sometimes things like finances and spiritual growth get lost. For finances, at least, I try to set up systems that are “set it and forget it”, like auto deposits into a savings account I can’t easily see. That’s worked pretty well, all things considered. The more you can automate or create systems for goals, the more focus you have for other things that require hands-on work.

Notice too that planning can be as simple or as complex as you want. If you’re brand new to planning, start with one or two big goals and let everything else go. If you’re a spreadsheet maven and just love data and planning, run wild.

Step three involves breaking these big goals from step 2 into how you’ll actually get them done. This is where pesky SMART goals are useful. You want to make sure it’s very clear how a particular goal is going to get done. Seeing “be a guest on podcast” on your list for the day is going to set up all kinds of mental alarm bells and lead to lots of avoidant behavior (ask me how I know). But if you see something like “create list of 10 target podcasts including contact information” that’s both more tangible and less likely to create mental chaos.

Here’s what that looks like (more or less) in my annual plan:

It’s worth keeping in mind the difference between process goals and outcome goals. Saying something like “lose 10 pounds” (outcome goal) is not only vague, but leaves you feeling defeated when you don’t hit it. Something like “track macros and workout 3 days per week” are process goals that you can accomplish even if the pounds don’t magically float off. For other goals, the outcome is the whole point (like my goal to find a d*mn agent/publisher for this book) and a process goal would sort of miss the mark. For that outcome goal to happen though, I have to focus on process goals. For almost all of your goals, both process and outcomes will matter and you’ll want to keep a rough eye on both.

Once I have this list, I figure out which tasks need to be in what quarter. Since I have a fellowship salon scheduled for May, I need to work the salon-based tasks backward from May to make sure there’s time to do all the various things I need to do. Given the vicissitudes of podcasting schedules, I also need to front load the podcast requests so I can get on people’s schedules early in the year. Those two projects therefore end up in my first quarter.

For stuff with less external accountability, like writing, workouts, and QT with family, I have to create visibility and accountability. These goals roll across all my quarters, so I usually just copy them from quarter-to-quarter.

We then move to step four, which is when you actually create your actual quarterly plan. After I have these goals laid out and a rough sense of what needs to happen to accomplish them, I split the year into quarters: January through March, April through June, July through September, and October through December.

In each quarter, I fill in the “boulders.” These are things like vacations, big holidays, really busy times at work or in my kids’ school or my husband’s coaching. I know not to schedule big deadlines or goal-setting around these boulders because stuff just won’t get done.

Once I have the skeleton of each quarter more or less filled out, I take a look at my goals and map them roughly onto each quarter. Some goals extend across all quarters, like finance stuff, while others like articles may only exist in a single quarter (but I do expect them to boomerang back at some point, so keep boomerang projects in mind as you plan).

Above is my plan for the first quarter, broken out by week. The colors just represent the different months so it’s easier for me to see what’s going on. (I couldn’t get Substack to cooperate on editing the image, so please excuse amateur-hour over here in the design department.)

For whatever it’s worth, I worry less about projects that have built-in accountability, as most of my administrative work does. That stuff gets more or less taken care of by my Outlook calendar and my weekly planning process. I don’t schedule it (much) on my bigger plan unless it’s a large multi-part project I’m responsible for. I know the projects exist and that’s all I need to know. If you’re feeling really overwhelmed, it might be best to get all your big goals onto paper so you can see them.

This year I’ve added a new (totally optional) step, which is mapping my plans onto these fun wall calendars I started this post with. This means I can see my plan any time I look up from my computer. I do this just for work goals, leaving my office space more focused on that area.

Why all the visual redundancy? I have the kind of brain that forgets things exist if they’re not in front of me. Just having goals written down isn’t enough. I have to bash myself over the head with these goals repeatedly. You’ll find I have copies of my quarterly plans hanging all over the place, tucked into my planner, and existing in various forms throughout my office and house. Seeing goals daily (and not having to hunt for them) helps me stay focused, prevents the overwhelm of knowing I need to be doing things but not knowing what, and most importantly, prevents me from having to spend valuable family time catching up on work projects I lost sight of.

The last step of quarterly planning is the most crucial and often where things fall apart: you have to actually use the plan.

Each week, usually on Friday afternoon, I look at my quarterly plan, add whatever tasks are on there to my week, and find time for them in my Outlook calendar. Over the years as my goals became more predictable, I started blocking out time for big picture or “deep work” on Outlook so people couldn’t schedule over it. That makes my weekly planning even easier, since I already have a structure in place for when that work gets done. I just have to sit down and do it. (That doesn’t always follow, of course, but it makes it more likely). Weekly planning meetings should not take longer than 30 minutes to an hour. Don’t let planning become an avoidance activity of its own. Set a timer each week mif you find yourself spending too much time on planning and not enough time actually doing the work.

Planning Reality Check(s)

Now, all this looks fancy and makes me look like an extremely organized person, so it’s a good time for a reality check.

Will all this get done? Nope.

I can guarantee that at least one of these weeks I will get sick and then another week one of my kids will get sick. The car will break down or the dog will eat an extension cord or our septic will break (again).

I write all this down and map it out not to guarantee that everything will get done in the week that it’s assigned or even get done at all. I write all it down because if I don’t write it down I’ll be pushed and pulled away from my own goals and priorities by whoever is at the top of my inbox or screaming the loudest.

Let me repeat this: the goal of a quarterly plan is NOT to be held hostage to the plan or shroud yourself in a cloak of shame when the plan goes awry. And it’s definitely not to compare your plan to other people’s plans. Some people’s plans eat mine for breakfast and that’s fine. We’re living different lives and have different goals. So take a deep breath and remember:

The goal of a quarterly plan is to ensure your priorities and goals stay front and center.

If you don’t have a plan there’s a good chance that you’ll end up somewhere you don’t want to be and you’ll have no idea how you got there.

It’s also important to give yourself grace. Now that I’ve gotten better at strategic planning, I have fewer overall goals, I build in more white space to account for screw ups and general life-happenings, and I give myself more grace to adjust things if I need to move something around.

This is a quarterly plan, not a blood contract. Plans change all the time and for good reason. If you have a plan you’re much more likely to end up near-ish where you’d like to end up than if you don’t.

But it’s really important (especially for my type A readers) to remember that the plan isn’t the point. Living your values and accomplishing your goals is the point. Don’t mistake the mechanism for the ultimate goal.

What You Don’t See

There are some things that aren’t included on my annual plan. Some aren’t included by design, others aren't included because there’s no way to plan for them, and some aren’t included because I’ve already worked on them and they’re established habits.

1. You might notice some extracurriculars are missing. I don’t volunteer at my kids’ school. I don’t do (much) community service. I don’t belong to a chorus or a climbing gym. I could do these things and at some point I’d like to, but right now they just don’t fit. And I have to be ok with that. All of us have things we *could* be doing that are valuable and meaningful that just don’t fit because of whatever season we’re in or whatever part of our landscape we’re traveling on. There are far too many things in life that are worth doing to do all of them. Choose carefully, guard your time, and make those hard choices in a way that’s compatible with your goals and values. Having clear goals helps you justify those choices, even when they’re not easy.

2. This plan also doesn’t show the daily stressors that every human life entails whether you have a plan or not. Having a plan doesn’t mean I don’t yell at my kids when they’re taking 15 years to put on a pair of socks and it doesn’t mean I don’t have to clean the dog puke out of the carpet when I’m late for work. Life happens whether you have a plan or not. Plans don’t eliminate stress. They do, however, reduce the chances that you’ll drop balls and they make many kinds of unavoidable stress more predictable or more manageable.

3. This also plan doesn’t include the habits like daily acts of self-care that I already have locked in because I’ve been doing this for years. I read for pleasure daily, I get 8 hours of sleep (almost) every night, I don’t work (most) nights and weekends, I read to my kids most nights before bed, and I listen to guilty pleasure murder podcasts on my commute. There were some years when those habits were on my quarterly plan as goals because I wasn’t doing them consistently. I can now drop them from my plan because they’re part of my daily routine. Over time, goal-setting and planning make your life better. And that’s a great thing.

This leads me to one of the unsung benefits of planning. Quarterly plans (or any plans at all) help you say “no” to the things that don’t fit your plan. If someone comes to you with a potential project, you can take a look at your quarterly plan and let them know that you’re booked until after March. Or, if the project is an amazing opportunity, you’ll realize that you need to move (or dump) another project for a new one and you’d better prepare accordingly.

Having a plan helps you recognize the tradeoffs you’ll be making in terms of time and energy. And you’ll have a clearer picture of what you’re giving up in order to take it on. If the thing you’re giving up is time with people you love or energy you could spend on activities that are deeply meaningful, hopefully your plan can help you think twice about what sacrifices you’re really willing to make.

Your Turn

All this sounds super complicated, but most years it takes me about two hours (max), another hour each quarter to plan that quarter, and then 30 minutes each week to swap tasks onto my Outlook. I easily waste more time than that every year reading celebrity gossip (see one of my goals above).

Remember, it’s just five simple steps:

1. Assess how you felt about the last year or how you’re feeling in general. Get some data points if you can.

2. List your goals and priorities for the year (it’s ok to be wrong! That’s good information to have).

3. Make a list of what needs to get done for those things to happen.

4. Map that list onto your calendar, whether you want to do it by month or by quarter (strongly suggest not mapping farther out than a quarter)

5. Work the plan weekly by reviewing it weekly and making sure those tasks get onto your calendar or daily list or whatever else you use.

That’s it!

If you want to geek out further, here are some other annual planning and productivity resources I’ve found helpful over the years (just don’t use them to avoid doing your annual planning):

1. Cal Newport’s work, particularly Deep Work, has been really helpful in how I structure my weeks.

2. The book The 12 Week Year goes into all this in much more detail if you want a full guide to quarterly planning.

3. Laura Vanderkam has a ton of books I’ve really liked, but her classic on time management is 168 Hours: You Have More Time Than You Think.

4. The podcast The Productivity Show is a resource for all things productivity, including annual and quarterly planning. They also have a blog, trainings and coaching products and while I’ve never tried any of those, I’ve heard good things.

As always, let me know what you think! Do you find these kinds of posts helpful? Is there any area you struggle with in planning that you could use help with? Do you have an amazing tip to share? Let me know in the comments! I’d love to hear from you.