Too often, I see people come to me when they’re already deep in the struggle—when they’ve reached a point of exhaustion, frustration, or regret.
They say things like:
“I wish I had realised sooner that I was taking on too much at work. I thought I could manage, but now I’m completely burnt out.”
“I wish I had spoken up when I was given the workload of two people, instead of assuming I could handle it. Now I’m resentful, exhausted, and stuck.”
“I wish I had started managing my time better when my son was three, instead of waiting until he’s 13 and realising I haven’t spent enough time with him.”
These stories break my heart because they’re avoidable. No one sets out to be overwhelmed, overworked, or regretful. But, like the boiling frog theory, small choices—like overloading our schedule, underestimating how long things take, or assuming we’ll “find the time later”—build up over time until suddenly, we’re in crisis mode.
Dean Daskalou, a client of mine, put it perfectly:
“If you’re struggling with your working habits, ask yourself—what are you waiting for to make a change? Are you waiting for everything to fall apart, to hit rock bottom, or for someone else to tell you it’s time? It could be your employer, a client, or even a colleague pointing out that things aren’t working. But deep down, you already know. My advice? Don’t wait for that moment. Don’t wait until you’ve let someone down and realise you could have done better. Take ownership now—because it’s not about anyone else; it’s about you. Be proactive, make the change before you’re forced to, and set yourself up for success.”
🕒 Find this quote in Dean and my YouTube chat at [29:15].
And one of the best ways to take control now is by getting better at estimating how long things actually take. Because when you know what you’re working with, you can plan smarter, stress less, and finally feel in control of your time.
Why We Miscalculate Time
Most of us fall into the trap of optimistic scheduling—assuming we can get more done in a day than we actually can. There are a few reasons why:
- Wishful Thinking – We hope for ideal conditions: no distractions, perfect energy levels, and everything running smoothly. But reality rarely works this way.
- Fear of Reality – We avoid estimating time accurately because we don’t want to admit we won’t have enough hours to do it all.
- Lack of Awareness – We simply don’t track how long things actually take, leading us to repeat the same scheduling mistakes.
The Two Types of Time Miscalculators
Most people fall into one of these two categories:
1. The Overestimator
Overestimators assume tasks will take longer than they actually do. This can lead to procrastination and avoidance because a task seems daunting. They wait for the “perfect” time to tackle it, which never comes.
2. The Underestimator
Underestimators, on the other hand, assume they can finish everything quickly. This leads to overcommitment and last-minute scrambling, often resulting in stress, rushed work, and missed deadlines.
Neither approach is ideal. The key is to find a realistic middle ground that allows you to plan effectively and work efficiently.
How to Accurately Estimate Task Time
1. Start Asking the Right Question
Instead of only asking, “What do I need to do?”, start asking, “How long will this take?” These two questions go hand in hand. Planning is incomplete without considering the time required for each task.
2. Track Your Time for Two Weeks
To build awareness, spend two weeks tracking how long tasks actually take you. You may be surprised at the difference between your estimates and reality!
- Before starting a task, write down how long you think it will take.
- Time yourself while completing it.
- Record the actual duration.
- Repeat for various tasks and note any patterns.
Once you have this data, you can begin making more accurate predictions for the future.
3. Use the “Three-Times Rule”
If you’re doing a task for the first time, assume it will take three times longer than you expect. Why? Because new tasks require more mental energy, problem-solving, and adjustments.
For example, if you think setting up a new project will take an hour, give yourself three hours just in case. Over time, as you become more familiar with the task, you’ll be able to adjust your estimate.
4. Learn from Past Experiences
If you’ve done similar tasks before, use that information!
A client of mine once struggled with preparing presentations. She repeatedly underestimated how much time they took, leading to stressful, last-minute cramming. When we reviewed her previous presentations, we discovered each one took around 20 hours from start to finish.
Once she acknowledged this, she was able to schedule 20 hours in advance for her next presentation—resulting in better preparation, reduced stress, and improved performance.
5. Be Honest About Your Energy Levels
Not all hours are equal. A task that takes 30 minutes when you’re energised could take double the time when you’re tired.
Consider:
- Your peak productivity hours – When do you work fastest and most efficiently?
- Your natural energy dips – When do you struggle to focus?
Plan challenging tasks during high-energy periods and easier tasks when your energy is lower.
6. Break Down Large Tasks
Big tasks can feel overwhelming and lead to avoidance. Instead of estimating a vague “huge project,” break it down into smaller, trackable steps.
For example, instead of writing “Work on report” in your planner, break it down like this:
- Research: 2 hours
- Outline: 1 hour
- Draft: 3 hours
- Edit & proofread: 2 hours
Now, instead of a daunting, unmanageable task, you have clear, actionable steps with accurate time estimates.
7. Use Time Blocks & Buffers
Once you have an accurate estimate, protect that time in your schedule. But don’t pack your day back-to-back with tasks—leave buffer time for interruptions, breaks, and unexpected delays.
A good rule of thumb:
- Short tasks (under 30 min): Add 5-10 min buffer
- Medium tasks (30-90 min): Add 15-20 min buffer
- Large tasks (2+ hours): Add 30+ min buffer
This way, if something runs long, your entire day won’t be derailed.
The Power of Acting Now
If you keep telling yourself, “I’ll figure out my schedule later,” or “I’ll get my time under control when things calm down,” you might be walking the same slow path to burnout, stress, or regret.
There is no “perfect” time to start managing your time better—except right now.
Your Next Steps
- Start tracking your time today – Choose a few daily tasks and estimate how long they’ll take. Then, track actual time spent and compare.
- Identify your miscalculating pattern – Are you an overestimator or an underestimator?
- Adjust your planning accordingly – Use past data, time blocks, and buffer time to create a more realistic schedule.
Because three years from now, you don’t want to be saying, “I wish I had started sooner.”
Ready to Master Time Estimating?
If you’re ready to take your time management skills to the next level, join Right on Time: A Practical Challenge. This hands-on challenge will guide you through exercises to refine your estimating abilities, helping you create a schedule that actually works.
You’ve got this!
