Overwhelmed by your to do list? 5D's to the rescue!

Does it ever feel like your to do list is a many-headed hydra; as soon as you cross something off, two more grow in its place? Or perhaps you feel like a juggler on a stage with countless balls in the air, and hecklers on the sidelines?


I’ve been serving many people who feel exhausted and overwhelmed by their to do lists. The truth is, many items on your list don’t actually need to be there. Really. And those that really are your responsibility can be scheduled or done in a way that enhances your energy rather than drains it. The 5D’s can help you regain control.

The Story

When I eagerly accepted the role as school superintendent/administrator at a K-8 charter school, I knew that the first two years would be exceedingly busy for me. I was coming into school leadership from University administration where I had been teaching teachers for seven years, not the traditional pathway of teaching credential → teacher → administrative credential → principal. Here in California, you don’t need an administrative credential to lead a charter school, so I would have to learn on the job. It was going to be a steep learning curve for me, and I knew it.

And I had a first grader and toddler at home... What could possibly go wrong?

Initially, I was working 60+ hours per week, but I was in love with what I was learning and doing every day. My brain was growing by leaps and bounds. I was deeply involved in my son’s school. I got paid to do things that filled me with purpose and joy: build a trusting team, grow exceptional teachers, help kids learn from mistakes, and even go river rafting with the school.

I call this special feeling: Shiny New Object Overwhelm. I’ve experienced it several times in my life -- first year of college, first year teaching, and now in my first year leadership coaching. One of my clients is in the midst of Shiny New Object Overwhelm now as her business enters a period of exponential growth with new clients, new employees, and a new office. Like a kid in a candy store, you’re super busy but surrounded by tantalizing Shiny New Objects. It’s a short period of time to really invest in something meaningful to you. You learn to delegate and say "no" when possible. Then, you suck it up and dive into the deep end, knowing that eventually you’ll settle into a more steady, sustainable pattern.

But for me, as time passed, the workload never lessened. This was a new type of overwhelm, what Bill Burnett and Dave Evans call Hydra Overwhelm. They say:


“You may have Hydra Overwhelm if:

  • You have too many different responsibilities.

  • You are reporting to too many managers (more than one) at the same time or are running too many client projects or side hustles concurrently.

  • You are consolidating important data from too many different sources.

  • You have to deliver status information and/or reports to too many people.

  • You regularly use legacy systems that are cumbersome and poorly designed.

  • You lack control or are micromanage.

  • You are working in isolation.”

Sound familiar? For me, I enlisted the help of another superintendent who taught me two things:

  1. Stop “shoulding” on yourself. Not every to do list item belongs on your list. Many of the items on my list were actually things that I felt like I “should” do, but didn’t really have to, like pick up the phone when the receptionist was out, responding to every email or call by the end of the day, etc. Other items honestly belonged to other people. I had to facilitate some fierce conversations and created a decision tree a la Susan Scott to get clear with my team what each of our responsibilities actually was.

  2. Time blocking. I was constantly running around reacting to things instead of moving with intention through my day. A new text or email pops up → respond immediately. A 5 minute gap between meetings → do the simplest thing from my to do list. A question from a staff member → might as well handle it now. Instead, I regained control by scheduling time to do the things that were true priorities. The hardest part was sticking to it except in true emergencies.

Wow, what a difference that made. Suddenly, I had control over my day instead of feeling like I was putting out fires all the time. And the things that were on my list actually belonged there because they really had to be done, by me, that day, and felt meaningful or even joyful to do.

I started blocking time for emails at the start and end of the day. I did “rounds” before and after recess to check on the playground and pop my head in every classroom to take the pulse of the school. Next, there was a fairly quiet time in the office, so that’s when I set aside time to write reports or analyze data. All my meetings and phone calls went in the afternoons when I was least fresh, but the social connection could keep me energized. And at 5:15 an alarm rang to say “Irene go home”.

Manage Your Energy

The final tip that I learned when COVID hit last March and my to do list exploded once again was this: manage your energy, not your time. You only have 24 hours in a day. You can’t get more of it. However, you can control how much energy you have.

Imagine that you have an internal gas tank that fuels your activity through the day. After a good night’s rest, it’s full. From the moment you wake up, everything you do either refuels or drains your gas tank. Things you love refuel you. Things you dread drain you.

For me, there’s lots of things personally and professionally that refuel me: time with family and friends, writing, reading, learning, teaching, art, walks, time outside, making and eating delicious food, etc. And there are many things that drain me: dishes, doomscrolling, hoop-jumping reports that nobody will read, taxes, cleaning the bathroom, broken sprinklers, micromanaging/being micromanaged, etc. A new ritual for me this year to ensure my energy gas tank is completely full to start my day is what I call “morning joy”. The very first thing I do when I wake up must be something that refuels me, and conversely, can not be picking up my phone to read emails, news and Facebook.

If you redefine or reframe an energy drain well, it can at least become neutral or perhaps even a positive. For instance, I’ve started to do dishes when singing and dancing to music that makes me happy. My son caught me belting out Defying Gravity from Wicked yesterday in the kitchen. Another idea is to connect annoying bureaucratic tasks with something truly meaningful. For example, “complete and submit CCEIS Implementation Plan” (an accountability measure imposed by the Department of Education) became “support Catherine and Sara with CCEIS” (a mission I care deeply about). Or perhaps give yourself a reward like sushi and a cocktail for cleaning the garage. Yum.

The 5D’s

Whether you are in Shiny New Object Overwhelm or Hydra Overwhelm, the 5D’s can help you manage your to do list. They stand for: Dump, Delegate, Date, Do, and re-Define. I’ve organized them into a handy flow chart that you can download, alongside a handy worksheet where you can write down all your to do list items, at home and at work, and 5D each and every one. The basic premise is that for each item on your list, from “clean the garage” to “submit CCEIS plan”, go through each of the questions on the list below.


What if I didn’t? That is, if it didn’t get done, how bad would it actually be? Question everything. Never “should” on yourself.

  • DUMP — Cross it off your list.

Does it have to be me? Is it really your responsibility? Is there anyone better suited or who likes it? Could you trade? What about a committee?

  • DELEGATE — It might require a difficult conversation or training, but it’s better to teach someone to fish than give them a fish over and over.

Does it have to be now? If it’s not essential to do today, then schedule it.

  • DATE — Actually block time off on your calendar. Then treat that scheduled time as sacred unless there’s a real emergency “Sorry, I have a meeting with this report.” Avoid time confetti by bunching the little stuff, like get through all your email at a specific time each day.

Does it enhance or drain your energy? Read your energy meter.

  • DO — If it enhances your energy, do it!

  • re-DEFINE — If it drains you, re-DEFINE it, then DO it. For instance:

  • What makes me think it has to be this way?

  • What else is possible? Get creative. Get strategic.

  • Can I link it to a mission or goal that’s really important to me?

  • Can I make myself want to or need to? (e.g. Do it with a friend. Give yourself a reward afterwards. Pair it with something you love. Etc.)

Tip: Be very cautious about dumping or delaying self-care and rest. The answer to "What if I didn't?" for those types of items is burnout — stress-induced physical and emotional exhaustion that may result in fatigue, insomnia, alcohol abuse, heart disease, diabetes, ulcers, illness, and loss of personal identity. Don't go there.


Someday Maybe

Sometimes it’s hard to DUMP, DELEGATE or DATE. I found it helpful to create a “someday maybe” list for those things that I’m not quite ready to fully let go of, but also don’t really have to, want to, or have the capacity to do now. It’s like a parking lot full of ideas and projects I can take for a test drive when I have the time, energy, and capacity later on.


Read More

Here's that Handout with a Flowchart and Worksheet where you can 5D your to do list.


This is a fabulous article about time blocking by ToDoist. Note: ToDoist is a for profit company that builds beautiful, user-friendly to do lists. I use ToDoist personally for my to do list and consider it my external brain. And no, they aren’t paying me to promote them. I truly love this company.


This article by Tony Schwartz and Catherine McCarthy about managing your energy, not your time, is excellent.


Going Further


If you’re looking for someone to help you personalize the 5D's to combat your own special version of Shiny New Object or Hydra Overwhelm, I’d love to help, especially if your overwhelm is getting in the way of you bringing a vision worth fighting for into reality. It’s my way of paying forward what that other superintendent did for me! Sign up for a Resilience Session on my calendar.


If you’re an educator and struggling with overwhelm (and honestly, what educator isn’t struggling this year?) I’m assembling an intimate mastermind team of eight passionate teacher / school leaders to create work-life synergy, resilience, and career sustainability. 5D your to do list with a powerful group of professionals. Create a self care routine over the summer that actually sticks with you into the school year. Most importantly, rediscover why you fell in love with education to begin with and thrive. Find out more on my website. Or let’s set aside an hour to discuss.

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