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The Top Calendar Mistakes That Are Holding You Back

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Before I get started I wanted to share a free resource with you all.  If you’re like most accountants, you’ve probably said a few of the following: I don’t have enough time, There aren’t enough hours in the day, I wish I had more time, There are too many things on my to-do list, and  Time just seems to get away from me.

Well, as we all know, accounting is hard but your time management shouldn’t make it harder.

Since time is something we could all use more of, I created a Guide titled “3 Simple Steps To Create More Time.”  This guide will teach you some simple steps for managing your time so that you can have plenty of it.

You can download it at https://thesmarteraccountant.com/3-steps/

Have you ever looked at your calendar and thought, “There’s no way I can get all this done”? I’m going to bet most of you listening to this episode are nodding your head..Most accountants I talk to have a calendar full of meetings, reminders, and tasks. But somehow, they still feel behind.

It’s a strange thing, isn’t it? You plan your week, you try to be organized, and yet your days still feel rushed and messy.

The truth is, it’s not just about what’s on your calendar. It’s also about how you’re using it.

Your calendar might look full, but that doesn’t always mean it’s working for you. Sometimes it’s just a list of things you hope you’ll get to, like a big wish list.

The problem is that a lot of us were never taught how to really use a calendar. We just pick a system and hope for the best.

But if your calendar is stressing you out or making you feel overwhelmed, it might be time to look at it a little differently. Not to blame yourself—but to start noticing what’s not working.

There’s no one-size-fits-all way to plan your day. What works for someone else might not work for you at all.

Still, there are certain things many of us fall into without realizing it. Habits that seem helpful at first but actually make things harder.

And when your calendar stops helping and starts hurting, it can leave you feeling stuck. Like you’re trying really hard but still not getting ahead.

For example, have you ever finished a long day and wondered where your time went? That’s usually a sign that something’s off—not with you, but with how your time is being planned.

The good news is, small shifts can make a big difference. You don’t have to toss out your whole system to start seeing changes.

Sometimes, it’s just about paying closer attention to the little things you’ve been doing for so long you don’t even notice them anymore. That’s where the magic often happens.

This isn’t about being perfect or planning every second. It’s about finding a better way to use your time—one that actually works for you.

If your calendar is starting to feel more like a source of stress than a tool for support, you’re definitely not the only one. And you’re not doing anything wrong.

So what if the way you’re using your calendar is the real issue—not how much you have to do?

Let’s talk about it.

Why a Full Calendar Doesn’t Mean You’re Getting More Done

For a lot of accountants, having a full calendar feels like a sign of success. If every hour is filled with tasks, meetings, or deadlines, it seems like you’re being productive.

But here’s the problem—just because your calendar is full doesn’t mean it’s helping you. In fact, it might be part of what’s holding you back.

A packed calendar can give you the illusion of progress, even if you’re spinning your wheels. It looks organized on the outside, but it might be hiding the fact that nothing is really getting finished.

Many accountants fall into the trap of thinking busy equals effective. But being busy all day without feeling accomplished usually points to a bigger issue.

Your calendar isn’t just about your time—it’s also a mirror for how you think. In other words, how you plan your week says a lot about what you believe is important and how much you trust yourself to follow through.

When you fill your calendar without prioritizing, or when you keep moving things around because you don’t feel like doing them, it creates a loop of frustration. You start to doubt your own planning, and over time, your calendar becomes something you ignore or avoid.

As you may already be experiencing, this can lead to a lot of stress and pressure. You might be working more hours, but still feel like you’re falling behind.

That’s why a full calendar can sometimes make things worse, not better. It can hide problems like poor prioritizing, overcommitting, and not leaving space to think or recover.

The bottom line is, if you’re constantly feeling overwhelmed, your calendar might be part of the reason—not because you’re doing something wrong, but because it’s not set up to actually support you.

So what’s really going on here?

Let’s take a closer look at why this is such a problem.

The Hidden Cost of Common Calendar Mistakes

When your calendar isn’t working for you, it doesn’t just lead to a missed appointment or a late deadline. It creates a cycle that’s hard to break.

You put too much on your calendar, thinking you can power through. But when you can’t keep up, you start skipping tasks or pushing them to the next day.

After a while, this becomes your routine—plan too much, don’t follow through, and feel behind. You start to feel like you’re always playing catch-up.

Unfortunately, this often leads to frustration and self-doubt. You might even start blaming yourself, wondering why you can’t stick to your own schedule.

And once you lose trust in your calendar, it loses its power to help you. It becomes a list of wishful thinking instead of a clear plan you can rely on.

But here’s the bigger issue—it’s not just a scheduling problem. It’s a thinking problem.

These habits don’t come from laziness or poor discipline. They come from what your brain believes about time, effort, and expectations.

If you’re not aware of how your thoughts are shaping your calendar, you’ll keep falling into the same traps. And without intention, those traps quietly shape your day-to-day life.

To really understand why these mistakes happen, we need to take a closer look at what’s going on in your brain.

The Brain-Based Reasons Your Calendar Isn’t Working

If your calendar feels like it’s not helping you, it’s probably not just a planning problem. It’s a brain problem—and once you understand how your brain works, you’ll start to see why so many of these mistakes happen in the first place.

Let’s walk through the 6 most common calendar mistakes and how your brain plays a role in each one:

Mistake #1: Overscheduling

Filling every hour with tasks, meetings, and deadlines might seem like a good way to stay on top of things. But when there’s no breathing room, your brain doesn’t get the space it needs to think clearly.

The prefrontal cortex—the part of your brain responsible for planning and decision-making that i refer to as The Supervising Parent—gets overloaded. And when that happens, your lower Toddler brain takes over, trying to keep you safe by pushing you toward easier, more comfortable tasks. That’s when procrastination, avoidance, or burnout start creeping in.

Example: You block every hour from 8 to 6 with client work, emails, meetings, and calls. But by mid-morning, you’re already behind. By the end of the day, you feel drained and discouraged, even though you barely took a break.

Mistake #2: Not Prioritizing Properly

When everything feels equally important, it’s hard to know what to focus on first. Most accountants end up reacting to whatever seems urgent—even if it’s not actually important.

This happens because of what I’ve mentioned before on the podcast – the Mere Urgency Effect. Your brain gives more attention to things that feel urgent, even if they don’t matter much. That’s how you can spend hours answering emails and checking off small tasks but still feel like nothing meaningful got done.

Example: You start your day cleaning up your inbox and taking care of a few quick tasks. By the time you sit down to work on a big client file that’s due tomorrow, your energy is gone—and the pressure is building.

Mistake #3: Not Following Through

You make a plan, but when the time comes to do it, you don’t feel like it. So you move it to another day. And then another.

This happens because your brain wants to avoid discomfort. It doesn’t care that you planned to write the report or call the client—it just wants to feel better right now. Without emotional awareness, you’ll keep putting things off and slowly stop trusting your own calendar.

Example: You scheduled a time block Tuesday afternoon to review a tax plan. But when 2 p.m. hits, you just don’t feel like it—so you move it to Wednesday. Then Thursday. By Friday, it’s urgent and stressful, and you’re mad at yourself for not doing it sooner.

Mistake #4: Skipping Reflection and Review

Planning the week ahead is helpful. But if you never pause to reflect on what worked and what didn’t, you’ll keep making the same mistakes.

The Zeigarnik Effect explains why this matters: your brain holds on to unfinished or unreviewed tasks. Without closure, your mind keeps circling around what’s incomplete—even when you’re trying to focus on something else.

Example: You plan your week every Sunday, but never look back at how the previous week went. You don’t notice that Thursdays are always a crunch or that certain meetings never run on time—so you keep repeating the same problems.

Mistake #5: Using Your Calendar Like a Task List

If you treat your calendar like a giant to-do list, it loses its power. You plug things in at random without thinking about time, energy, or what matters most.

A calendar should be a decision-making tool. It’s where you make choices in advance about how you’ll spend your time. If it’s just a long list of hopes, your brain won’t take it seriously—and neither will you.

Example: Monday morning, you plug in things like “follow up with client,” “update spreadsheet,” and “finish report.” But you don’t block time or estimate how long anything will take. By lunch, you’re already behind—and the day feels off track.

Mistake #6: Not Including How You Need to Feel to Follow Through

Most calendars only answer two questions: What are you doing? and When are you doing it? But they leave out a crucial third question: How do you need to feel to do it?

It’s important to understand that your feelings drive your actions. If you plan something hard without deciding how you want to feel—like focused, calm, or confident—your lower brain will jump in and try to escape the discomfort. That’s when you skip the task and push it to later (again).

Example: You schedule a time block to call a tough client, but you forget to plan how you want to feel in that moment. When the time comes, you feel nervous and uncertain, so you skip it. You tell yourself you’ll do it later, but later never feels better.

The bottom line is that these mistakes aren’t about being lazy or disorganized—they’re just what happens when your brain is trying to protect you from discomfort, uncertainty, or too much pressure. But the good news is: once you understand what’s really going on, you can start using your calendar in a much smarter way.

Let’s look at how this all plays out with a real coaching client example—and what happened when they started thinking about their calendar differently.

Becoming a Smarter Accountant: Stopping The Calendar Mistakes

One of my coaching clients came to me completely overwhelmed. His calendar was packed every single day, from the moment he woke up to the moment he went to bed. On the outside, it looked like he was organized and on top of everything—but inside, he was exhausted and always felt behind.

He said, “I don’t understand. I plan everything, but I still feel like I’m barely keeping up.”

We took a closer look at how he was using his calendar, and it didn’t take long to spot the problem.

He was overscheduling himself with no breathing room. His days were so full there was no time to think, reset, or deal with anything unexpected. The most important work often got pushed to the end of the day when his energy was already drained.

He was also treating every task as equally important. There was no clear prioritization, so he ended up reacting to whatever felt urgent—even if it wasn’t. That left little time for the things that actually improved his productivity.

And like a lot of accountants, he wasn’t following through on the calendar he had created. Tasks would get moved from day to day, and each time that happened, his trust in the calendar—and in himself—went down.

What we uncovered was that his calendar wasn’t broken—his brain was just overwhelmed and trying to avoid discomfort. It was pushing him toward what felt easy in the moment and away from what required real focus.

So we made a few simple changes.

He started creating space between tasks. He blocked his most important work during the time of day when he had the most focus. He began reviewing what worked and what didn’t each week. But the biggest shift came when he started asking, “How do I need to feel to follow through on this?”

Once he started planning how he wanted to feel—whether that was confident, determined, or focused—his entire approach changed.

He stopped dreading his calendar. It stopped feeling like a burden and started feeling like a tool that was actually helping him.

And even though he wasn’t working more hours, he was getting more done. He felt calmer, more in control, and more trusting of himself.

If your calendar isn’t working for you, it doesn’t mean you’re doing it wrong. It might just mean your brain needs a better plan.

Let’s wrap up with a few key takeaways.

Key Takeaway and Action Item

Your calendar isn’t just a tool for tracking time—it’s a reflection of how you think, what you believe about your responsibilities, and how much trust you have in yourself to follow through.

When it’s filled with too much, or when it’s used like a giant to-do list, it stops being helpful. Instead of guiding your day, it starts adding to the noise and pressure.

Smarter Accountants understand that the goal isn’t to cram more into the calendar. The goal is to make better decisions in advance—and to create a calendar they can actually follow.

They schedule with intention, not pressure. They plan their energy, not just their time. And they learn to include the one thing most calendars ignore: how they want to feel when it’s time to take action.

This shift isn’t about working harder. It’s about thinking smarter.

So if your calendar has been stressing you out or making you feel behind, it’s worth asking:

“Is my calendar helping me feel focused and in control—or is it just helping me stay busy?”

That one question can open the door to some really honest answers—and some really powerful changes.

Okay, as I finish up, let me pull back the curtain and share a personal story of how I can relate to this topic.

Pulling Back the Curtain

Now let me pull back the curtain…

A while back, I remember looking at my own calendar and realizing it was packed with so many things I thought I should be doing. Every time block felt tight. I’d move things around constantly, try to squeeze in more than I had time for, and then feel frustrated when the day didn’t go as planned.

One day, I looked at my calendar and thought, “This feels like a punishment.” Not because the work was hard—but because I was using my calendar like a checklist for proving my worth. If I finished it all, great. If not, I felt horrible guilt.

What finally shifted everything for me wasn’t a new app or system. It was learning how my brain works. Once I started planning with my brain instead of against it, things got easier.

I stopped overscheduling. I gave myself breathing room. I started picking feelings on purpose—like calm or committed—before I stepped into harder tasks. That alone changed everything.

Now, I use my calendar as a support system, not a scoreboard. And that’s what I help my coaching clients do too.

If this episode spoke to you and you’re ready to make your calendar work for you, not against you, there are two easy next steps:

First, take The Smarter Accountant Quiz at www.thesmarteraccountant.com to see where you might be underusing your accountant brain.

Then, if you’re ready for more personalized support, schedule a free 30-minute call with me at www.thesmarteraccountant.com/calendar. We’ll look at what’s not working and talk through smarter, brain-friendly solutions.

And as always, if you found this episode helpful, share it with another accountant. You never know who needs to hear this.

The truth is, you’re already smart. But this podcast will show you how to be smarter.

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