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Melissa Shanahan

#238: Annual Calendaring: Optimizing What Matters Most to You

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What does the landscape of your life and business look like over the course of a year? How do you line yourself up with where you want to go and the person you want to become? And how can you use your calendar to tee yourself up for success in 2024?

As a law firm owner, you may be prone to getting mired in day-to-day legal work, keeping to-do’s in your head, reacting to unforeseen obstacles, or shuffling things around on your calendar. If you’re ready to give real thought and care to your business, feel more organized than ever, and stay on course with the goals you’ve set, the practice of annual calendaring is non-negotiable.

Join Melissa this week as she shows you why annual calendaring is your secret to having a more stress-free and ease-filled 2024. You’ll learn why carving out the time to practice annual calendaring matters, examples of what you might consider putting on your calendar, and her top tips for creating a calendar that works for your life and business.

If you’re a law firm owner, Mastery Group is the way for you to work with Melissa. This program consists of quarterly strategic planning facilitated with guidance and community every step of the way. Enrollment will be opening soon, so join the waitlist right now to grab one of the limited seats!

Show Notes:

What You’ll Discover:

• Why the practice of annual calendaring matters.

• Examples of different task and achievement categories to consider putting on your calendar.

• Why Melissa recommends practicing calendaring ahead of time twice a year.

• What CEO time means, and why it’s important to include on your calendar.

• Melissa’s top tips for creating your annual calendar.

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Jon Acuff’s Neu Year Calendar 

At-A-Glance Monthly Calendar

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Full Episode Transcript:

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I’m Melissa Shanahan, and this is The Law Firm Owner Podcast Episode #238.

Welcome to The Law Firm Owner Podcast, powered by Velocity Work, for owners who want to grow a firm that gives them the life they want. Get crystal clear on where you're going, take planning seriously, and honor your plan like a pro. This is the work that creates Velocity.

Everyone, welcome to this week's episode. As we are about to enter a brand-new year, at least as I'm recording this we are, today it felt completely appropriate to do an episode on annual calendaring.

This is something, calendaring, thinking forward on your calendar, and getting things set to the best of your ability is something that will tee you up for a more successful year. It will prevent you from having to be reactive in moments, not realizing that something is coming up, and then when you do realize it, you put it on the calendar and it's a hassle, because you then have to move other things to make room for it and then rearrange some things because you didn't realize how close it was.

There are so many little things like that, and also bigger things that we have in our head, and we know we want to do, but we don't put it on the calendar. And so, it gets pushed out or creates some stress.

Annual calendaring is a practice I like to do twice a year. I always look 12 months out every time I do it. I like to do mine in July and in December. So, every July, I calendar forward 12 months. I review what's very near term, because the work that I've set up with the previous calendaring workshop for myself has taken care of that space. But I always look ahead 12 months.

So, in July, I look through to the next July. And in December, I look through to the next December. I find that that cadence works really well. Let's talk a little bit about why this is important. I did mention a bit ago one reason why it's important, it helps you to not be reactive in the middle of the year.

But I'm going to mention a couple more things, just to make sure we're all on the same page on the reasons for spending time to do this. The most important thing that you can do as a business owner is to make decisions ahead of time and follow through on those decisions.

This goes for every area of your business; within the finances of the business, around people in the business, around your offerings, and how you're going to be structuring the delivery of services, making decisions ahead of time about the revenue that you're going to generate for the firm, and about the profit margins that you want to see, and making decisions to line yourself up with those profit margins.

There are all kinds of things to consider, and the more that you can make decisions ahead of time, the more straightforward it is to take the right actions that will give you the results that you said you wanted to create. That actually brings the results to life that you have stated that you're going to do.

So, making decisions ahead of time really brings those decisions to life, those end results to life. That is why we do this. Now, when it comes to calendaring, this is really about… It's not about time management. It's much different than that because we're not talking about week to week, day to day.

What we're talking about is the landscape over the course of the year, and are the things in your calendar, that line you up with where it is you say you want to go, who it is that you say you want to be, and with all of the results that you want to create?

There are different categories of things to consider when you are putting things on your calendar ahead of time. We're going to go into those more in just a moment. But I really want to establish why this is a good practice. There's zero downside. This practice of calendaring ahead of time your year, and carving out space for things that you say matter, allows you to be much more organized as you walk into your next 12 months.

And the more organized you are, the more you understand the landscape month to month, and quarter to quarter, of how things are going to look, the easier it is for you to operate day to day fully present and fully dropped into whatever it is you want to focus on.

Because you know these other things have been taken care of. You know that you've done the work to carve out space for the things that matter. This is also why I like to do this twice a year, because as you move through the year, things crop up that you hadn't considered before, or there's opportunities that come your way that you didn't have when you were doing this four or five months ago. So, it is good to do this more than once a year.

But doing it for 12 months, looking out every time you do this, is very important for your business and for your life. Before I do this, there are certain categories of things that I think through before I go to town, so to speak, on calendaring. I do some thinking prior so it makes calendaring easier, and it makes that activity a little bit smoother.

I think through the categories that I need to consider when I'm blocking off space for things. So, certainly, even if you only had personal life, and business life or firm life, if you just had those two broad categories, you could make a list of things that you can think of you know you need to put on the calendar right now, because it's a priority.

For example, in personal life, I will put down the days or weeks that my kid is out of school. I can't have a normal work schedule that week, most likely, unless I want to have a normal work schedule when my child is out of school, but then I'm going to have to line up resources. So, that stuff needs to be on the calendar.

Quite frankly, where I am with this, I don't want to work normally when my kid is out of school. I would rather have lighter days and/or find fun things to do with my family. So, I block on the calendar, the school calendar, I make sure that those days are blocked off for me. So, there's never going to be anything scheduled there for me, it's not going to be a conflict.

The bulleted list is school schedule, doctor's appointments, dentist appointments, vacations, or trips. Maybe it's not like a full vacation, but trips that we want to take. Even if I don't know where they're going in the calendar, I want these things to be placed on the calendar. So, if I have any specific trips, I will list those out.

I list any athletic events that I want to take part in; if I'm training for a half marathon, or something bigger or something new. If there's anything that I want to do adventure related or health and exercise related that is a milestone to get to, I make sure that that's going on the calendar. I make sure my wedding anniversary is on the calendar, and maybe a little space around that in case we decide to do something.

Birthdays of those that I care about the most. Holidays: I carve out and protect certain spans of time I know I want to be present with family around the holidays. Every year, we have a Christmas cookie baking extravaganza and there's a lot of prep that goes into that. And so, that's protected; just a little bit of padding around that day so that it gives me space to prepare in the ways that I would like to prepare.

Also, any events related to your health and wellness. Is there anything you want to train for? Put that on the calendar. Maybe it's a 10k, maybe it's a marathon, maybe it's something entirely different. But what do you want to train for or prepare for, and line yourself up with being able to do? Put that stuff on the calendar.

Okay, so basically, right now I'm saying put that stuff on the calendar, but you're just making your list. You're making lists of all the things that need to be placed on the calendar.

Then I want you to make a list underneath the firm side of things. So, there are certain things that you would want to be prepared for, or have your time reserved for. What are those things? For instance, members and clients always have strategic planning once a quarter, that we host for them. It is on their calendar. So, once a quarter, they have a strategic planning session for their firm, and that goes on their calendar as they're planning ahead.

Also, any team rollouts or team retreats that you want to have. We can write that down as a bullet on your list that's going to be calendared. Any deadlines for your business that you know you have coming up. So, really thinking through for your firm, what makes sense to put on the calendar so that we can plan for it, make sure it's reserved, and we're good to go.

Now, in addition to everything that you just put on the list, that's going to be going on the calendar, I want you to add CEO Time. What I mean by this, you can call it whatever you want, but I'm going to refer to it here as CEO Time.

There are chunks of days or weeks that you should plan on taking to give yourself space to think about your firm, the health of your firm, and the issues that have come up in the firm. And solving for those, with your thinking time, the direction, the vision, evaluating the finances… deeper than a typical evaluation.

Really looking at the profit margin, really looking at levers that you could pull in order to optimize for the things that matter most to you.

Some of this is done in strategic planning, but strategic planning is one day; there is some prep for it that we help people through. But it's one day and it's very focused on coming out of that day with: You need goals for the business, revenue goals, cases open/closed, sometimes profit margin, sometimes conversion rate.

But there's really specific goals that if they are hit, it means that the firm is growing in a way that feels really healthy to you as the owner. And so, that's one thing that comes out of it. And the second thing comes out of it, is key quarterly priorities, that you're going to get done that quarter, in an effort to be able to hit the goals.

So, as you do that planning, it's very important work, but it's different than the CEO Time that I'm talking about, where you just take space, you read some materials that you've been wanting to read, you do maybe some consumption of information that feels important to you, you do a lot of creation, not just consumption.

So, writing, output, not just having inputs. You will write in your journal about your firm and the direction it's headed, and the current state of it. Really get clear. No one else does this for this business, it's you. That's you. So, if you don't do it, no one's doing it.

And what happens with that is you start running, running, running, running, running, and even though it may be a fine trajectory, you don't know what it could have been had you taken space. You don't know what it could have been had you allowed yourself to listen and think deeply about your firm.

So, I highly recommend putting in CEO Time. I do, some days it's three days in a week, some days it's a full week, but I try to take it every couple of months. To take space to think, use my brain, get in tune with the business in a way that I haven't been because I've been busy within it, in a good way, like productive and busy.

But stepping out of that to just be with and think for your business, it's a game changer. I will use that time. I can use that at my discretion. So, there's times where I'll use it to develop content. I will use it to develop a new addition to one of the programs we have, because it's the right thing to do, but I just need some space to think through it.

Sometimes I will dig into the finances and evaluate deeply. Sometimes I will reach out and have coffee or meetings with colleagues in the space, and just learn about what they're up to and how they're thinking about their businesses. And then it gives me some space to think through it. Sometimes it's rereading a few chapters in a book that I have really found useful in the past and I want to revisit.

I can use that space any way I want to. And the only way this gets to happen is if it's carved out well in advance. If I don't carve it out well in advance, it will literally never happen. So, I want to encourage you to do this for yourself. And you decide your cadence, maybe it's once a quarter, maybe it's one day a month. But make a choice about what you would like.

This is progress, not perfection. You don't have to take a week at a time right away. Take what you think you can give that's not going to stress the business or hurt the business or stress the firm out in any way. If it's planned for in advance, what can you take from the firm? But it's really what can you give to the firm? Your brain being utilized in this way, really is giving to the firm. So, how do you line yourself up with that?

If you take the space, you will be giving your firm an advantage that it wouldn't otherwise have. And you will be able to get your firm further faster in a way that you just can't, unless you take space and give thought and care to this business without being mired in the legal work and in the day to day.

Okay, so now you have your lists of things that need to be put on the calendar in advance. And when it comes to calendars, there's a few things I really love to have on hand and use. Of course, I like a digital calendar. But I do not start there when I'm doing annual planning with my calendar. I use paper calendars because I use pencil. Once it's all in and it feels like it's going to work, then I have an assistant put it into the digital calendar.

So, let me talk about the paper calendars for a second. The paper calendars that I love. Well, they're not all paper, there's two. One is, a big one that you could put on your wall that has the whole year at a glance, and the kind that allows you to write in the days of the month. So, it has to be big enough for that.

It can't just be the numbers. I don't know if you know what I mean. But there's wall calendars that just show the numbers, the dates all the way through the year. I want the date and then a box that I can write something in. So, that's what I'm looking for.

You can look up “calendars.” There is calendar that Jon Acuff makes called The New Year Calendar; I'm pretty sure. I will link it up here. Also, I think at the top it's says “Focused,” so maybe it's The Focused Calendar now; I don't know, maybe the name has changed. But I will link that here.

The other calendar that I love to use for this is a monthly at-a-glance calendar. Now, when I say this, you probably think, “Oh, I know what she's talking about.” You probably don't, because somebody turned me on to this several years ago and it is not one that you can find I find in the stores very easily. It's very specific. I will also put this in the show notes. And if it tickles your fancy, you can get it too.

It's inexpensive, it's super thin, and it has, when you open it up, when it shows the month, the month is spread across two pages. So, across both pages, and it has enough room for you to write in something per day. That's it. There are 30 squares on this page and you can write stuff in. On the next page is the next month; 30 squares or however many days in the month there are.

But it is helpful, because it does let you flip through the year really fast. It's not one of those calendars that's on a spiral that you have to go one over and the next, like a traditional calendar. It's more of a planner style, but it's only the month at a glance. That is very helpful for planning.

Again, with that paper planner, the monthly at-a-glance, I use a pencil. Once I feel like things are pretty sorted there, then I will use a dry erase marker with the calendar that's going on the wall. You can decide where you put that.

I like having that close to me so I can see a bigger perspective about where things are headed, where I am, what's coming up, and all of that. But of course, I have the more granular stuff in front of me if I need it. Those are the two things that I love, love, love. I will put those in the show notes.

You can begin calendaring now; the first part is thinking through it and then you're going to calendar it. However, I would argue there are things that you need to think through more before you start putting things on the calendar. I can't know if that's true for you, but I would imagine there's a few things you're going to have to get on the same page with someone else about, in terms of dates and timing in the year.

If you don't have to check in with anybody about anything, you could just make all the calls, then you're good to go. You can sit down and start calendaring your list. If you do need to talk to someone else, so that you can make some decisions about dates, then you're going to have to do that before you sit down for the calendaring session.

What you can do, no matter what, is go ahead and calendar the things that are nonnegotiable. Like the school schedule, if that's a thing in your world. A school schedule is not something you can change, you don't have say over, so go ahead and calendar that. If there's anything else you don't have control over, go ahead and calendar those dates in so you know it's taken care of off the bat.

The next step, if this applies to you, is to have some conversations with the people you need to have conversations with, around dates for some of the other things that are on your list. You can make a note of the results that came from those conversations, and the dates that were chosen or agreed upon, or guidelines that were agreed upon.

And once you have all the information, then you're ready to start really calendaring everything. After you do all the nonnegotiable stuff, and you put that in the calendar for yourself, I would prioritize the list that you have. It's all going to go in the calendar, but I would start with the most important things and get those on the calendar first, and then move down the list in terms of order of priority.

Pencil things in, and once you're all done with personal then go to the firm side of things. Pencil things in, and then have a look and make sure nothing's overlapping. I mean, you'll see this as you're doing it. It'll unfold if there's an overlap. You'll see it as you're doing it.

In terms of the amount of time you give yourself to actually calendar all of the stuff, I would give space. Because you're going to have to coordinate some things, you're going to have to prevent some overlap, and you're going to have to take some things into consideration that you didn't foresee at the beginning. So, I would give a couple of hours to really calendar everything.

You can try to do it shorter than that, maybe you can, it just depends on the complexity of your life and how many things you have on your list that you need to get into the calendar. Once you have everything penciled in, and it feels like a thumbs up, this is good, all the protections are in place, then you can put, with a dry erase marker, all of those events on a wall calendar; if you’d like to have a wall calendar of any kind.

Then, I send a snapshot of either the wall calendar… It depends, it doesn't feel like it stays the same for me every time I do this… sometimes I'll send snapshots of the paper calendar to an EA and they will take care of it. Sometimes I'll just take one big picture of the year on the wall calendar, and I'll send that over; whatever floats your boat.

But once you have it documented, you can pass it along for it to be put into a digital calendar of your choice. Making sure that whatever needs to cross over into the firm's calendar, so that people can't schedule where you have these events. Just making sure all of that is taken care of so everything really is protected.

This exercise will help you feel so organized about your year coming up. Even if you've done a version of it before, there's always a way to learn from the way you've done it previously, and see if you want to tweak or improve anything about your process for doing this. So, hopefully this gave some good ideas.

I will say, that every month moving forward, after I do one of these bigger calendaring workshops, every month I have a recurring event on my calendar to look ahead a full three months ahead. Just to make sure that everything is looking good, lining up, and if I see any flags, I can nip them as early as possible.

But remember, I also do Monday Map/Friday Wrap. Every week, I sit down and I look at the next week, and I fix the calendar so that the calendar tells me what I need to do. My job is to follow my calendar. My job is to honor my calendar. And in that I catch things, too.

Sometimes I'll look ahead beyond the week, but I'm really in tune with my calendar, and the more in tune with my calendar I am, the easier it is in your monthly sessions, where you're looking ahead. It doesn't take me that long, it takes me like 20 minutes, max, to look ahead three months and make sure it's all shaping up the way that I want it to be shaping up.

That's really it. That's the extent of it. I do some deeper planning when it comes to the event types that are typically on my calendar. I think through those. Maybe someday I'll do a podcast episode on it. I do work with members in this way, and I'm continuing to evolve how I teach that and how I facilitate that.

But there is a way to really tee yourself up so that you're making sure to, week to week and month to month, ensure that your activities are lining up with the goals that you have, etc. So, I'm always learning new and better ways to teach that.

But in terms of annual calendaring, in terms of the high-level stuff, if you can do this, what I've mapped out here, you will set yourself up in a great way to enter into 2024. Then you could do it again at some point you decide ahead of time. Maybe that's even something you put on the calendar, right? The annual calendar.

You decide again when you're going to do this for 12 months; maybe in the middle of the year. This cadence will help keep you feeling more in control over all the things that need to be managed, and all the things you want to have done. All right, everybody, have fun with this. Happy New Year. Bye-bye.

Hey, you may not know this, but there's a free guide for a process I teach called Monday Map/ Friday Wrap. If you go to, it's all yours. It's about how to plan your time and honor your plans. So, that week over week, more work that moves the needle is getting done in less time. Go to to get your free copy.

Thank you for listening to The Law Firm Owner Podcast. If you're ready to get clearer on your vision, data, and mindset, then head over to where you can plug in to Quarterly Strategic Planning, with accountability and coaching in between. This is the work that creates Velocity.

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