“I Keep Underestimating How Long Things Will Take”
Show notes
Before we get into today’s episode, I just want to share something real with you.
My health hasn’t been so great lately. And when that happens, it has a way of affecting everything — your energy, your focus, your patience.
It’s made me slow down a little more than I’m used to. And it’s also reminded me how important it is to be a little more understanding with yourself when you’re not feeling your best.
I know a lot of accountants push through no matter what. You keep going, even when you’re tired or run down.
But sometimes, giving yourself a little space and a little grace is exactly what you need.
I’ve decided to do a little less until I feel better and I’m happy with my choice. Just think about it for yourself – are there somethings you’re used to doing that you could cut out when you’re not feeling good.
Maybe this week is the time to consider that. Maybe this week is the perfect time to adjust your priorities.
Let’s get started with this week’s episode…
This is a topic that matters because so many accountants walk through their day feeling behind, even when they start with a clear plan. It can quietly shape how you feel about your work, your time, and yourself.
You might begin the morning feeling calm and ready. By the end of the day, that calm is gone and you’re wondering what happened.
Nothing terrible had to go wrong. The day just didn’t go the way you thought it would.
Most accountants don’t talk about this out loud. They simply keep going and hope tomorrow feels different.
I’ve worked with accountants for many years, and I hear this again and again. It’s not about ability, effort, or care.
You are smart. You are capable. You are someone who takes your work seriously.
That’s why this experience can feel confusing. You know how to think things through, yet time can still feel slippery.
You might notice yourself feeling rushed even when you planned ahead. Or you might look at the clock and feel surprised by how fast the day moved.
Sometimes it shows up as staying later than you meant to. Other times it shows up as carrying work in your mind long after the day ends.
It’s easy to make this mean something about you. Many accountants quietly wonder if they should be handling things better.
I want you to know this is more common than you think. You are far from alone in feeling this way.
In fact, this topic touches something deeper than schedules or tasks. It connects to how we see our work and how we see ourselves doing it.
It can affect how confident you feel when planning your day. It can affect how much control you feel you have over your time.
And when those feelings shift, everything else can feel heavier. Even simple moments at work can carry more pressure than they need to.
I’ve seen accountants shrug this off as just part of the job. They accept it without stopping to look at it more closely.
But when something keeps showing up in your life, it deserves your attention. Ignoring it rarely makes it fade away.
There’s also something very human about this experience. It speaks to how we think, how we hope, and how we picture the day ahead.
You may have noticed this pattern more than once. You may even catch yourself expecting a different outcome next time.
That hope says something important. It shows you care about how your day unfolds.
And caring about that matters. Your time is part of your life, not just part of your work.
So let me ask you this. Have you ever ended a day feeling surprised by how little space it seemed to hold?
And what might change if you began looking at this experience with curiosity instead of judgment?
That’s where I want us to begin today. Not with fixing or solving, but with simply noticing.
Because when you pause long enough to notice, you give yourself room to understand. And understanding is always a powerful first step forward.
We’re going to gently walk into this conversation together. Just you and me, looking at something that touches many accountants more than they realize.
I’m really glad you’re here for it.
Why Accountants Keep Underestimating How Long Work Takes
Let’s talk about what this problem really looks like in everyday life. It often shows up as thinking something will take less time than it actually does, and noticing that pattern happening again and again.
You sit down to plan your day and the schedule looks reasonable. Nothing seems extreme or unrealistic when you first look at it.
But as the hours pass, things begin to shift. Tasks stretch longer than expected and the space you thought you had starts to disappear.
Before long, the calendar feels crowded. There’s little room to breathe between one thing and the next.
You may find yourself moving faster just to keep up. That pressure to rush can become part of the rhythm of the day.
Breaks start to feel optional. Stepping away can seem like something you’ll do later, even when later never comes.
Work that didn’t fit into the day quietly travels with you. It shows up at night or over the weekend, asking for more of your time.
Many accountants then turn toward planners, apps, or systems hoping something will click. When those don’t seem to help, frustration can grow.
It’s easy to wonder why nothing sticks. It can start to feel like you’re missing something everyone else understands.
That feeling can be discouraging. Especially when you care deeply about doing your work well.
Over time, small doubts may begin to form. You might question your ability to manage your time the way you want to.
And when those thoughts settle in, they don’t stay limited to planning your day. They can shape how you see yourself as a professional.
This is why naming the problem matters. Seeing it clearly allows us to step back and look at it with fresh eyes.
Because once we recognize what’s happening on the surface, we can begin to look underneath it. And that’s exactly where we’re headed next.
The Real Cost of Getting Time Estimates Wrong
Now let’s look at why this matters so much. This isn’t just about a schedule running off track now and then.
When time keeps slipping past expectations, it touches many parts of your work. The effects often show up quietly before they become obvious.
You may find yourself missing internal targets you meant to hit. Even small delays can create pressure that follows you into the next task.
Expectations with coworkers or clients can begin to feel tight. You might sense tension even when no one says anything directly.
There can also be moments when the quality of your work feels harder to protect. Stress has a way of crowding out focus.
And stress rarely stays contained to one task. It tends to linger and shape how the rest of the day feels.
Outside of work, the impact can grow as well. Hours stretch longer than you planned.
You might stay late or bring work home in ways you didn’t intend. Over time, that can chip away at the sense of balance you want.
Your schedule may start to feel like something happening to you instead of something you guide. That loss of control can feel heavy.
When that heaviness stays around, overwhelm can settle in. It becomes part of the background rather than a rare moment.
There’s also a deeper layer that many accountants feel but don’t always name. Accuracy is something you value and take pride in.
So when time doesn’t line up with what you expected, it can feel personal. It can feel like you missed something you should have seen.
That feeling can shape how you judge yourself. And self-judgment rarely creates the calm or confidence you deserve.
This is why the conversation is bigger than calendars or lists. The surface issue points toward something happening beneath it.
Because struggles with time are often connected to patterns in how the mind works. And understanding that connection opens the door to a completely different way of looking at the experience.
That’s what we’re going to explore next.
What Accountants Need to Understand About Time Estimation
Now let’s look at something important to know about this experience. There are reasons this happens that have very little to do with effort or intelligence.
The human mind has natural habits when it comes to thinking about time. One of those habits is something called the planning fallacy.
The planning fallacy simply means we tend to believe tasks will take less time than they actually do. Even when we have past proof that they often take longer.
When you picture getting work done, your mind often sees the smooth path. It imagines things going according to plan without delays or surprises.
It doesn’t mean you’re careless. It means your mind prefers the hopeful version of the story.
Another habit is leaning toward the best possible outcome. We assume things will move along without bumps.
The mind also has a way of remembering the good moments more clearly than the hard ones. It holds onto the times things went well and softens the times they didn’t.
Because of that, past experience can appear simpler than it really was. That shapes what we expect next time.
There’s also the simple truth that many real-life factors go unnoticed when planning. Interruptions, shifting attention, and tiredness rarely show up in our early picture of the day.
All of this is human. It’s part of how people think, not a flaw in how you work.
Then we add the accounting layer on top of that. The nature of the work brings its own challenges.
Some tasks are straightforward while others grow in depth as you move through them. The difference is not always clear at the start.
Many steps remain unseen until you’re already in the middle of the work. Those hidden moments quietly add time.
There are also requests from coworkers or clients that arrive during the day. Each one shifts attention and energy.
And mental energy itself is not constant. When your mind is tired, progress naturally slows.
This is where a Smarter Accountant perspective becomes powerful. Estimating time is not something you are born good or bad at.
It’s something that develops through awareness and experience. Like any other professional ability, it can grow.
The more you understand your thinking patterns, the more clearly you can approach planning. Managing your mind shapes how you relate to time.
This is why time management isn’t something you either have or don’t have. It’s something learned and refined over time.
And seeing that opens up a new way of viewing this experience. Next, we’ll look at a real story that brings this into everyday life.
Becoming a Smarter Accountant: Getting Better At Estimating
I want to share a story that may sound familiar. It’s about a client who came to me feeling frustrated with her days.
She planned carefully and showed up ready to work. Yet she always felt behind before the afternoon arrived.
Her calendar was packed from start to finish. Every hour had something assigned to it.
By evening, she often felt drained. There were still things left undone.
She told me she believed she was simply bad at planning. That label had followed her for years.
It shaped how she spoke to herself. It shaped how she judged her work habits.
There was embarrassment in her voice when she talked about it. She thought she should have figured it out by now.
As we explored her day together, something began to stand out. Her plans were built on a picture that left parts of reality out.
She wasn’t noticing the pauses between tasks. She wasn’t seeing the small moments that naturally take time.
She didn’t include the human parts of the day. Conversations, questions, and shifting focus were missing from the picture.
When she saw this clearly, something softened. The blame she carried started to loosen.
Instead of labeling herself, she grew curious. She began looking at her habits with new eyes.
That curiosity changed how she felt about the situation. It replaced frustration with understanding.
And understanding gave her space to breathe. She no longer saw herself as the problem.
This is why stories like this matter. They remind us how shared this experience really is.
Many accountants walk into coaching with the same belief. They assume something about them needs fixing.
But often, what they need is a different way of seeing. A chance to step back and observe without judgment.
That shift alone can feel freeing. It opens the door to growth in a gentle way.
And once that door opens, new possibilities begin to appear. Which brings us to a few key ideas worth taking with you as we wrap up this conversation.
Key Takeaway and Action Item
Let’s take a moment to gather what we explored today. We talked about a pattern many accountants quietly experience — thinking something will take less time than it actually does.
We looked at how this shows up in daily work. Full calendars, rushed moments, and work stretching beyond the hours you planned.
We also talked about why this matters. It can shape your stress, your confidence, and the way you see yourself as a professional.
Then we stepped into something deeper. This pattern isn’t about intelligence or discipline.
It’s connected to how the human mind naturally thinks about time. It’s human, and it’s shared.
We explored how accounting work adds its own layer. Complexity, hidden steps, interruptions, and energy levels all play a role.
And through a coaching story, we saw something powerful. When judgment softens and curiosity grows, understanding begins.
Understanding doesn’t solve everything overnight. But it changes how you stand in the experience.
Before we close, I want to offer you a question to sit with. Not to fix anything, just to notice.
Here it is:
Where in your day do you assume things will move faster than they usually do?
This question matters because awareness is where change begins. When you notice patterns instead of labeling yourself, you create space to respond differently.
It shifts the focus away from self-criticism. It brings your attention toward observation and learning.
And that small shift can reshape how you relate to your time. Not through force, but through understanding.
Next, I want to pull back the curtain and share a personal moment when I had to make this exact shift myself.
Pulling Back the Curtain
Pulling back the curtain…
I want to share something more recent before we wrap up. This topic isn’t just something I teach — it still shows up in my own life.
Not long ago, I caught myself planning a full day of work that looked completely reasonable at first glance. I felt confident about what I had laid out.
By mid-afternoon, I noticed the familiar squeeze. Things were taking longer than I had pictured.
Nothing dramatic happened. It was simply a series of small realities I hadn’t fully accounted for.
A conversation ran longer than expected. A task needed more attention than I thought.
Energy shifted as the day went on. Focus wasn’t as steady as it had been that morning.
Years ago, I would have made that mean something about me. I would have told myself I should know better by now.
But this time was different. I paused and noticed what was happening instead of judging it.
That pause came from the work I’ve done managing my mind. It helped me stay curious instead of critical.
I adjusted my expectations without frustration. I let the day unfold in a more honest way.
Moments like that remind me why I teach what I teach. Even after decades in public accounting, these patterns are human patterns.
They don’t disappear because you have experience. They become easier to see when you understand how your thinking shapes your planning.
That understanding is what led me to develop Container Calendaring and the time practices I share today. They grew out of real moments, not theory.
Learning to guide my thinking before guiding my schedule changed how I approach my time. It brought more calm into my planning and more compassion into my reflection.
And that’s exactly why I continue sharing this work. I want other accountants to feel that same shift.
If this episode resonated with you, I’d love to invite you to take the next step. A great place to begin is by taking The Smarter Accountant Quiz at www.thesmarteraccountant.com.
It’s a simple way to learn more about how your mind approaches work and time. Many accountants tell me it helps them see themselves differently right away.
You can also schedule a free 30-minute call with me at www.thesmarteraccountant.com/calendar. It’s a chance for us to talk about what’s going on in your world and see what support might look like.
And if you know another accountant who might benefit from this episode, please share it with them. These conversations reach more people when you pass them along.
Thank you for spending this time with me today. I’m always glad we get to learn and grow together.
As I end each episode, the truth is that you’re already smart. But this podcast, I promise, will show you how to be smarter.