How to set boundaries
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Ever tried time blocking and absolutely hated it? You’re not alone.
In this episode of It’s About Time, I share why time blocking doesn’t always work, how your personality shapes the way you manage your time, and three practical steps you can take to find strategies that actually fit you.
By the end, you’ll stop blaming yourself when a system doesn’t stick, and instead start building time management strategies that work with your personality — not against it.
Time Blocking: My First Attempt (and Why It Flopped)
About 10 years ago, I had just walked away from a decade in crisis communications and was in that in-between space of figuring out what was next. Excited and nervous all at once, I dove headfirst into books about goal setting, starting a business, productivity, planning, and habits — basically anything I could get my hands on.
And in one of those books, I first came across the idea of time blocking.
If you’re new to time blocking, here’s the gist: instead of working from a never-ending to-do list, you assign every task a spot on your calendar. Your day is divided into blocks of time, each dedicated to a specific task or category of work. Sounds smart, right?
So, being the achiever I am, I decided to give it a try. And not just a little try — I went all in. I blocked everything: sleep, my morning routine, brushing my teeth, driving to the gym, working out, making lunch, eating lunch… everything.
And you know what? I hated it.
Looking at my perfectly planned calendar made me feel boxed in, trapped, suffocated. Even though the blocks were full of good things I wanted to do, I wanted to rebel against my own schedule. Within days, I was convinced that time blocking just didn’t work for me — or maybe I just didn’t work for time blocking.
The Personality Connection
Not too long after that failed experiment, I signed up for training to become a certified Myers-Briggs practitioner. Now, I’d taken the Myers-Briggs before, but this was the first time I truly dug into it.
That’s when the lightbulb clicked on.
As an ENTJ, I naturally think in terms of big-picture outcomes and possibilities. I like flexibility, options, and seeing the forest instead of counting every tree. Of course I felt suffocated by a minute-by-minute schedule! It wasn’t about laziness or lack of discipline. It was about personality.
And here’s the truth: personality plays a huge role in the way we approach time.
If you’ve ever taken something like the Enneagram, CliftonStrengths, or the Myers-Briggs — or even a silly BuzzFeed quiz about your ideal fall workout routine based on your favorite pasta shape — you’ve seen how we all have different ways of thinking, deciding, and living. Those tendencies show up in how we manage our calendars, to-do lists, and energy throughout the day.
For some people, structure feels like freedom. They thrive when every hour has a purpose. For others, structure feels like a cage. They want flexibility and the ability to pivot when life shifts.
Neither is right or wrong. They’re just different.
And this is where so many time management strategies fall flat. Most productivity books and systems are written by someone who built a method that worked for them. They shared their playbook, but it wasn’t designed with you in mind.
And here’s another layer worth mentioning: more than 90% of time management books are written by men, who studies show don’t carry the same invisible mental load that women do — remembering birthdays, meal planning, permission slips, scheduling the dentist appointment. That’s a whole episode in itself, but the bottom line? No wonder some of these systems don’t work for us.
Trying Again (and Finding What Worked for Me)
Once I understood the role personality plays, I gave time blocking another try — but I did it differently.
Instead of cramming every tiny detail into my calendar, I blocked out bigger chunks of time around themes or projects. Things like “creative work,” “admin catch-up,” or “client calls.” That gave me structure, but also the flexibility to decide what those blocks would look like once I got there.
And this time, it worked.
Today, time blocking is one of my go-to strategies. It’s one of the “OG, back-to-basics” tools I use personally and teach in workshops. The only reason it works for me now is because I adapted it to fit my personality — not the other way around.
Time Management Is Like Shopping for Pants
Here’s the best way I can describe it: managing your time is like shopping for pants.
If you try on a pair and they don’t fit, you don’t storm out of the store saying, “Welp, guess I’m never wearing pants again.”
No. You try a different cut, a different size, or a different brand until you find what fits.
Time blocking — and time management in general — works the same way. Just because one system doesn’t work for you doesn’t mean you’re broken. It just means you haven’t found your fit yet.
That’s why I created the HEART Method. HEART gives you a flow to follow, but it’s flexible. It’s a perspective shift, not a rigid system. Each letter stands for Habits, Energy, Attention, Resources, and Time. It’s designed to help you create a schedule that works for your personality, your season of life, and your unique priorities.
Action Steps: How to Make Time Blocking Work for You
Step 1: Learn about yourself.
Get curious about your personality. Explore the Enneagram, CliftonStrengths, or Myers-Briggs. And here’s the key: even a basic understanding can give you powerful insight into why some strategies fit you better than others.
Step 2: Pay attention to what feels easy — and what feels hard.
Sometimes things feel hard because they’re new, and that’s normal. Other times, they feel hard because they’re not a match for how your brain naturally works. If you’re not sure which one it is, try asking yourself:
- Is this hard because it’s unfamiliar, and I just need a little more practice?
- How could I make this feel easier?
- Is it the activity that feels hard, or the method I’m using to do it?
- Does this feel like resistance I can push through, or is it the kind of friction that drains me every single time?
Step 3: Take the quiz.
Want an easy first step? Take my free “What’s Holding You Back?” Quiz. In about five minutes, you’ll find out whether you’re an Optimist, a Firecracker, an Architect, or a Mover & Shaker — and what that means for how you approach time. You’ll also get resources tailored to your personality type, so you can start building strategies that fit you.
Final Thoughts
If you’ve ever walked away from time blocking — or any other time management strategy — feeling like you failed, I want you to hear me: you are not the problem.
You don’t need to force yourself into someone else’s system. You just need to find the strategies that fit you.
Managing your time doesn’t have to feel like a constant uphill battle. With a little self-awareness and the right tools, you can create a system that feels natural, doable, and sustainable — one that actually works with your personality, not against it.
Resources Mentioned:
- Take the free What’s Holding You Back Quiz
- The Myers-Briggs Type Indicator
- CliftonStrengths
- The Enneagram Institute
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