Nonprofit Summer Exercise 2: The Cup List


This is the second exercise in the Nonprofit Summer series… you can read more about the concept here, and catch up on the first exercise here. 

So yesterday we kicked things off with a bit of reflection. Today we’re looking forward to the next ten weeks.

Chances are you’ve got the list. It likely started as a sticky note on your desk around January, became a series of randomly stuck pieces of paper by mid March, and now is potentially a tabloid-sized poster you look at every time you get up to refill your coffee.

The Summer Bucket List.

All that stuff you don’t really have time for in the regular day to day but tell yourself the summer is a great time. Likely, to match your workplace list, you’ve got a personal one, too. If you’re anything like me, your list may include everything from simple things like “research webinar software” to more complex projects like “redesign general brochure” to ridiculously grandiose shots in the dark like “read this list of 12 books.”

The Summer Bucket List is a lovely sentiment… but one that causes us unnecessary stress. Lofty goals are sweet, but too many lofty goals will make you freak the geek out.

You seriously think you can single-handedly redesign the website in two months? REALLY?

You haven’t had time for Professional Development all year long and you think you’re going to knock off taking a series of 12 webinars on planned giving that you’ve had saved since last November? MMMKAY.

All this PLUS walking 5 miles a day, eating healthier, learning to make willow furniture, refinishing your bathroom, getting your kids to and from seventy gazillion summer activities, taking a Coursera on the American Civil War, AND drinking 8 glasses of water a day.


This isn’t encouragement to set the bar low. This is encouragement to set the bar reasonably. Or you will continue to drive yourself snake. Challenges are wonderful, and we all need them to continue to thrive and better ourselves. But we can’t do everything. Certainly not in 10 weeks.

Exercise 2: The Cup List

A Bucket List is fine if you’ve got the time or you’re Morgan Freeman. But a bucket is just too big a vessel for our short summers. The solution? A Cup List.


Start with your work lists… all those sticky notes that you’ve left aside until July 1. 

Divide them into two lists.

  1. A list of things that you and you alone can accomplish – without the help of any team members, without your ED, etc.
  2. A list of the things that you need to collaborate on somehow – whether it’s working with a team member, getting approvals, having to work with multiple individuals on multiple moving pieces.

How long is each list? Is one significantly longer than the other, or are they about the same? What is the magnitude of each item? Is it just one task, or actually a series of complex tasks?

Set aside the list of things you need help with for now. We’ll come back to them another time.

For now, focus on that list of things that you alone can tackle.

Imagine yourself at the edge of a pool of possibilities. With the Bucket List, we get a lot more than we can handle.

What if you were to cup your hands and dip them into the pool of possibilities? What would you want to catch? If given the chance to seize a limited number of opportunities, what would you choose?

I can’t tell you how many is appropriate or reasonable. I just encourage you to be honest with yourself.

Some of you will go for the fat goldfish that you’ll need to grip with both hands. Others will choose several tiny stones from the bottom. The point of this is to realize that there is no way to do everything from the pool of possibilities… you need to choose your top few priorities and file the rest in the laterbase. Your choice will likely be difficult.

What did you choose? Why did you choose it? In future posts, we’ll look at some ways to approach knocking these out of the park.

What about what got left out? All that stuff you didn’t choose… how does it make you feel to say “I can’t do this right now” ? Is it really painful? Or freeing? Are you choosing things you really want to get done, or choosing based on external pressures?

After you’ve made your choice(s), take the time to write out both why you chose what you did, why you didn’t choose other things, and a bit around the process you used to make your choices. Of course, we can’t always do exactly what we want in the order we want to, but sometimes we may notice certain habits in how we prioritize the work we do.

When I did this, I discovered so many things that simply weren’t necessary, but that I was keeping on sticky notes or as calendar entries that only stressed me out. There were a lot of things that weren’t getting done for a good reason: they simply weren’t important. Many other things I realized I could quickly get off the list and make room for the things I REALLY want and need to accomplish.

My cup is not half full, half empty, or runnething over… my cup is just right, and I’m confident it will quench my thirst.

Do you have a Summer Bucket List? How do you normally track and choose? What would your Cup List look like? Let me know what you think!


The Cup List works well for summer networking and meetings too. It’s nearly impossible to meet up with people during this time, given scattered schedules.

Make a list of the three people you simply need to spend some time with this summer… maybe they were on your networking reflection list from yesterday, or maybe a new connection that you’d like to solidify before the fall.

f you have questions about this exercise or anything else, please don’t hesitate to connect with me! And if you’re game, tweet your progress and insights as you go along!