Managing To-Do's

How does time blocking work & 7 mistakes people make when doing it

July 1, 2020

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Two weeks ago, a prospective client asked,

“I’ve tried time-blocking before, and it didn’t work. How is your method different?”

Man oh man, do I get it.

It took me a LONG time to figure out how to make time-blocking work for me and now my clients. I almost gave up, too.

How does time blocking work?

Time-blocking, in short, is putting an entry in your calendar for when you’ll do an activity or task. Basically, you don’t just use your calendar for events with other people – you use it to figure out when you’ll do your tasks and activities. People time-block varying amounts of activities, from some just time-blocking the occasional call to a pediatrician they need to make to others that time-block everything they do.

Sounds simple enough, but, yikes, can it get unwieldy fast.

Without guidance and support, it can become:

  • overwhelming (hi, way more cluttered calendar),
  • defeating (“ugh, I didn’t realize how long XYZ took, so I didn’t block enough time…”), and
  • frustrating (you have to move all the blocks of time around when a curveball hits).

When I first started, I felt all of that. I stuck with it because I could catch glimmers of its value, but it was a process.

I eventually figured out a way that time-blocking, within the right system and with the right approach, delivers. When done right, it provides incredible clarity and freedom and helps you go to bed feeling proud of today and calm about tomorrow (which feels pretty different from the days when I relied on to-do lists to get things done).

So, let’s dig into the common hangups that derail time-blocking efforts and explain why you should give it another chance – this time within the right system.

It’s worth it. As one of my clients recently stated:

“I didn’t realize how much I carried [a to-do list] with me, but knowing it’s on the calendar and [I have] time for it… indescribable peace.”

Let’s get you there, too.

Time-Blocking Mistake #1: Giving up when you inevitably underestimate how long things take

One thing every person quickly realizes when they start time-blocking:

Things take longer than we realize.

And that’s frustrating! You plan out this awesome day, but then you can’t keep up with it because half the stuff is taking longer than you thought.

While there are strategies I teach to help alleviate the pain of this stumbling block, here’s the important thing I want you to hear today:

Time-blocking is likely the first time you’re tying a task to the amount of time it takes in a concrete way.

Just like anything else, don’t be surprised when you’re not an all-star at it when you start off. As with any skill, you will get better at it over time.

Most importantly – DON’T GIVE UP. Giving up deprives you of time-blocking’s magical results.

Giving up is essentially saying, “I’m not great at knowing how long things take OR… I don’t LIKE knowing how long things take, so I’m just going to go back to living in denial.”

(Which likely explains the prior frustration and defeat we felt when, most days, we never made it through as much of the to-do list as we expected.)

Instead, if you stick with it, you’ll hone your skill and create realistic game plans in the process.

And that will allow you to end the day feeling accomplished and confident about tomorrow.

And that makes you feel better about yourself and WAY less stressed out.

So, play through the discomfort and learn from experience.

And, I’ve gotta say, working through this with other women going through the same experience is incredibly freeing and supportive. One of my favorite parts of my group program is watching the women truly get that they’re not alone in feeling the ways we feel about our to-do lists – and also swap ways that they overcame time management challenges.

Time-Blocking Mistake #2: You start out by calendaring your to-do list

This one is SO common and makes total sense.

We hear about time-blocking, and think, “okay! Let’s do this!”

We break out our calendars and start filling in the time with our tasks.

And then we try to play it out – and it’s a disaster. Nothing goes to plan. You don’t get to half of the things.

You feel even more defeated than you did by your to-do list because at least then you didn’t have that heightened level of hope.

But here’s the thing:

Your totally-understandable approach just didn’t account for all the things you have to do that AREN’T on your to-do list.

Making meals. Answering email. The drive to that event. The drive home. Taking your dog out. Putting the kids to bed. Relaxing with your partner.

Those are all things that take our time (and, sometimes, a lot of it). If they’re not represented in your plan, your plan isn’t going to work (bonus perk of this approach: your calendar starts to help you manage all those things, so it’s not up to your brain to juggle it all! Hello and welcome, lighter mental load.).

Before you time-block your to-do list, you first have to determine what time you can give to your to-do’s. Only then can you find homes for them in your calendar that’ll actually play out.

Make sense?

And while that’s a lot of information that now lives in your calendar, my method walks you step-by-step through how to do this in a non-overwhelming way.

Time-Blocking Mistake #3: Not blocking time for the fun stuff

The goal of time-blocking is to block time in your calendar for all of your activities.

But our brains immediately go to the work stuff. The kids’ stuff. Life logistics.

So, we fill our days, even our weeks, with “productive” stuff.

And at first we feel like we’re getting a ton done, which feels amazing because it’s kind of a new feeling…

But then we start to get tired.

We’ve scheduled out our full days and haven’t protected time for the fun things that refuel us.

And, to be clear, I don’t mean “leave white space” (though – don’t get me wrong, I love white space).

I mean – block time for specific fun activities, even if it’s just “watch Netflix with [your partner]” or “Read [xyz book that I’ve been meaning to read for two months but keep forgetting to pick up when I’m tired and instead scroll Instagram for 45 minutes… and walk away thinking I have no free time].”

Getting specific (instead of leaving it as just white space) helps tired Future You remember to do the thing that’ll refuel her and light her back up, instead of filling that time up with work or life logistic-y work.

And a bonus tip: Use your weekly planning session to block time proactively for the fun stuff (this is included in the step-by-step agenda I give my clients for their planning session).

Don’t just get to the fun stuff during your leftover nooks and crannies of time once everyone else has taken what they need from your schedule.

Block it ahead of time, and protect it.

Time-Blocking Mistake #4: Believing you must follow your time-blocks rigidly for it to work

Some people won’t even try out time-blocking because they think it’ll make life feel too rigid. Sterile. Less spontaneous.

I get where that thought comes from. But nope.

After doing it for years, I actually find it gives me MORE FREEDOM to be spontaneous or take a day off and ENJOY IT MORE.

Here’s why:

Because I time-block, I have a visual game plan of how I’ll get everything done in my personal, family and professional life over time – at least for the next few weeks and, when it comes to big goals, months.

When a curveball hits or if I even wake up one morning not in the mood to attack that project or I just want the night off, I move whatever blocks of time are in the upcoming space to a new time.

So long as I can find another home in my calendar for something I don’t want to do and that home still allow me to hit my deadline, done!

And here’s the thing: This is how you were likely doing it before.

Rearranging. Calculating when you could do it if it’s not today and still hits the deadline…

But you were doing it all in your head. Rearranging to-do lists and mental time-blocks around in your mind. Not totally sure it’ll all come together because it’s only in your head.

Using my method, it’s visual. It’s written down. It’s like a little puzzle you rearrange – and then DON’T HAVE TO MEMORIZE to play out.

Make sense?

PLUS, because I have everything on my plate game-planned-out over time, I know my new plan works – both for the project itself and the other parts of my life.

I’m not just guessing and hoping I can get it all done over time. I know I can. Even when I decide to move the blocks of time around.

And that lets me enjoy my downtime more. There’s no guilt or unease.

The takeaway: time-blocking doesn’t have to be rigid. It can be flexible. It actually provides more freedom in your mind and allows you to enjoy time off more (planned or spontaneous).

It frees up your mind for the good stuff.


Time Blocking Mistake #5: Trying to time-block in a paper calendar

Now, I LOVE paper. I process by writing pen to paper, and paper planners got me through college and law school.

But when it comes to managing your time as a modern working woman trying to juggle all your roles, well… here’s the thing:

To get all of the magical results of time-blocking, you need to account for where all of your time is going.

To do that, you have to block time for alllll of your activities, including those that don’t show up on your to-do list (working out and showers, getting kids ready, making meals) – see Mistake #2.

That’d be a lot of info to write out every week. Especially if you’re someone who writes and re-writes until it looks pretty (cough*me*cough).

Plus, time-blocked paper calendars get overwhelmingly cluttered real fast because you can’t filter what you see (i.e., you’re stuck looking at whatever you put in there all the time – you can’t click parts of your schedule on and off like you can in a digital calendar).

AND you can’t calendar out weekly, monthly or every-two-week things with the same speed and accuracy like you can in a digital calendar, where you just repeat events and – ta-dah! –you’re done.

At the end of the day, time-blocking in a paper calendar is just, candidly, too much work and takes too much time.

Long story short: effective, powerful time-blocking (and it really is powerful) requires a digital calendar if it’s going to stick for the long haul.

That might mean it’s not for you. Or it may mean you may want to switch it up.

And if my paper-loving mom who used a paper planner for 40+ years can become a Google Calendar convert and whiz, so can you.

(For all the reasons I think paper planner users should switch it up to a digital calendar, read this article.)

Time-Blocking Mistake #6: You’re too broad with your time-blocks

We’re going to tap into my lawyer days for this one.

Let’s say I have to draft a brief. I think, “meh, it’ll take me 10 hours.” I pick five 2-hour windows and title them, “Draft XYZ brief.”

Done! I’ve time-blocked, right?


It’s definitely better than putting “Draft XYZ brief” on your to-do list. At least you have some hours protected for it.

But this approach likely will still end up in a last-minute scramble and a lot of stress – exactly what we’re trying to avoid.

Right now, when Future You sits down to work on her brief, she’s not really sure what to do. She’ll spend 5-10 minutes every time trying to figure out what to do to chip away at that project.

If instead she knew exactly what to do, she could make the most of the protected time when it rolls around – ESPECIALLY right now during COVID times when you more often have to work in the nooks and crannies.

Additionally, I hate to break it to you, but because Past You didn’t break down all the steps and then estimate how long each bite-size step takes, your general guess at how long the overall project will take likely WAY underestimates how long it actually takes (see Mistake #1).

This prevents you from creating a truly realistic game plan and will likely still end in that last-minute scramble. Because you know this on some level, you don’t get the peace of mind that a true game plan provides (our main goal).

We’ve got to get you more specific so you can reap the benefits.

I walk my clients through a 6-step process to back out deadlines/projects, and I give them more examples than they probably want of how to do it in real life (from backing out legal brief deadlines to prepping for major meetings to the small, miscellaneous tasks that we have to do on the home front).

As one woman who just wrapped up my program said, “The systematic approach to stepping out larger projects/preps/etc. has been enormously helpful…For the first time, I feel truly able to quantify my workload and needs to the people in my world who can help, from my boss to my husband!”


Time-Blocking Mistake #7 (THE FINAL ONE!): Time-blocking without a larger system

Time-blocking is great. But it can leave you with:

an overwhelming mess of a calendar,

a living-in-the-weeds feeling (i.e., you’re hitting all these little tasks you blocked time for but you’re not sure if you’re moving the ball forward on your big projects), and

the potential to blow by an entry and let a task fall through the cracks.

To avoid that…

  • You’ve got to set up your calendar in a way that allows you to load it up with alllll the information – and then filter what you view so you can have clarity, not overwhelm.
  • You must have built-in protected time to look up and ahead to figure out how to spend your time in the next few weeks to get you where you want to go. Also, bonus perk: this allows you to avoid decision-fatigue every day because you already have a game plan for the day (one you can easily move around if a curveball hits).
  • You must get intentional with your calendar, protecting focus time from meetings, email and other interruptions so you can immerse yourself in projects and get in the flow.

My method hits all these points.

In addition to helping you figure out exactly what to time-block in your personal, family and career lives in a way that fits you and your life, my programs show you:

  • How to set up your calendar so you can have ALL your time-related information in one spot when you plan – and also simplify what you see to get clarity when living your day-to-day life;
  • How to think through carving out and protecting focus time during your weeks so that you get the real work done during work hours (not nights and weekends);
  • How to make sure things don’t fall through the cracks so you can feel confident you’re on top of it all; and
  • How to plan each week (with a specific agenda you can personalize). To time-block successfully in a way that truly helps you design out and spend your time the way you want, you can’t skip the designing part. This will let you strut into your weekend with the peace of mind that you have a game plan to get everything done.

If you’re sick of feeling scattered and the last-minute scrambles & are ready to experience the magical benefits of time-blocking while skipping making the above mistakes, let’s get you there.

I help women like you trade in that stressed out, putting-in-180%-and-showing-up-at-a-60% feeling for getting things done with calm clarity.

As one client, Brenda Lomeli, said, “I’m no longer overwhelmed, so I can enjoy each part of my day…” In addition to my programs being effective, you’ll be surprised at how weirdly fun they are, too.

Interested? Learn more about my time management for professional working women here. And don’t hesitate to reach out with any questions!

Click here to learn more about my time management program for professional working women

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