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Why do I always underestimate how long things will take?

Casey Schmalacker

Written by

Casey Schmalacker

4 min read

⏳ “I thought this would take 10 minutes… it’s been an hour! Why am I so bad at estimating time?”
If you constantly underestimate how long things take, you’re not alone. Whether it’s finishing a project at work, getting ready in the morning, or running errands, many people struggle with time estimation—only to feel frustrated when things take far longer than expected.

This isn’t just a bad habit—it’s a well-documented cognitive bias called the planning fallacy. It causes people to assume tasks will take less time than they actually do, often leading to stress, missed deadlines, and last-minute rushing.

The good news? Once you understand why this happens, you can use strategies to improve your time estimation and plan more realistically.

🧠 Why Do We Consistently Underestimate Time?

Underestimating time is a common executive function challenge, influenced by several key factors:

📌 The Planning Fallacy

Psychologists Daniel Kahneman and Amos Tversky coined the term planning fallacy, which describes our tendency to predict best-case scenarios while ignoring potential obstacles.

⏳ Poor Time Awareness

Some people struggle with time blindness, making it hard to sense how much time is passing or gauge how long tasks will take.

🔄 Task Switching Delays

Shifting between tasks takes time, but our brains often don’t factor in these hidden transition costs.

🚀 Optimism Bias

We tend to believe we can complete tasks faster than we actually can, especially if we’ve done them before.

😰 Forgetting the “Unexpected”

Interruptions, distractions, and technical difficulties are common—but we rarely account for them in our planning.

🔍 Lack of Self-Monitoring

Without regularly tracking how long things actually take, we don’t adjust our expectations for the future.

🚨 The Consequences of Poor Time Estimation

When you underestimate how long things take, it can lead to:

  • 📅 Constantly running late for meetings and appointments
  • ⏳ Missing deadlines or rushing to finish projects
  • ⚡ Increased stress from last-minute scrambling
  • 🔄 Overloading your schedule and feeling overwhelmed
  • 📉 Reduced productivity from switching between unfinished tasks

Breaking free from the planning fallacy starts with **awareness and strategy**.

🎯 Strategies to Improve Time Estimation

Here are some simple ways to develop a more accurate sense of time:

⏳ Track How Long Tasks Actually Take

Before making future estimates, track how long common tasks really take. Use timers or apps to measure your work.

📊 Use the “Double It” Rule

When estimating time, double your initial guess—this accounts for interruptions and unforeseen delays.

⏲️ Try Time Blocking

Assign specific time slots for tasks instead of assuming you’ll “find time” to do them.

🚦 Build in Buffer Time

Add extra minutes between tasks to avoid back-to-back scheduling failures.

🔄 Review Past Mistakes

Look at when you’ve underestimated time in the past—what went wrong? What can you change?

📅 Plan for the Unexpected

Account for potential roadblocks, like needing extra time to transition between tasks.

🎮 Gamify Time Awareness

Test yourself by guessing how long a task will take, then time it. The more you practice, the better you’ll get.

🚀 Prioritize Tasks Realistically

If your to-do list is always too long, cut it down to what’s actually achievable in your available time.

🧠 How Executive Function Coaching Can Help

If you underestimate how long things take, executive function coaching can provide targeted strategies to improve your time awareness and planning skills.

With coaching, you can learn how to:

  • 📅 Improve time estimation with proven techniques
  • ⏳ Develop better scheduling and planning habits
  • 🚦 Reduce last-minute stress by anticipating obstacles
  • 🎯 Strengthen self-monitoring to adjust expectations over time

Time estimation isn’t about guessing—it’s a skill that can be developed. With the right strategies, you can break free from the planning fallacy and start managing your time with confidence.

Need help improving your time management? Contact us for executive function coaching today!

 

Casey Schmalacker

Casey Schmalacker

Casey Schmalacker, Vice President at New Frontiers, is a seasoned leader in marketing, sales, and business development. With a dual degree in Government and Law and Economics from Lafayette College, he has spent the past 10 years coaching students, adults, and organizations to improve executive functions, soft skills, and workplace performance. Casey's approach is rooted in strategic development and a passion for personalized coaching, emphasizing a culture of continuous improvement.