Don’t be a Nonprofit Sisyphus Successful Nonprofits: Don’t be a Nonprofit Sisyphus

Don’t be a Nonprofit Sisyphus

by Ro

Don’t be a Nonprofit Sisyphus

by Ro

by Ro

Many nonprofit executives come to me for coaching after months of feeling like they – or their organizations – are not moving forward.

They will share the sense that every day and every week and every month blurs together. It’s a series of repetitive tasks (weekly staff supervision meetings, monthly Board and committee meetings, regular invoice reviews followed by signing check after check, the daily onslaught of email, etc). While not representative of all my coaching clients, executives often say, “Every day just feels like a grind.” 

Suffering from the Sisyphus syndrome. 

A quick level-set for people who, unlike me, didn’t spend their teenage years reading mythology and playing Dungeons & Dragons: The ancient Greek gods condemned the powerful and cunning ruler Sisyphus to eternal punishment in Hades. Moments after his death, Sisyphus found himself at the foot of a hill and quickly learned his fate: pushing a large rock to the top.  At this point, you probably remember the story, but just in case here’s a refresher: as Sisyphus reaches the hill’s peak, the rock rolls back down to the bottom. Sisyphus must then trudge back down to the rock and begin pushing again. 

This Greek myth holds many lessons for executive directors. 

Most important, every version of this story has Sisyphus pushing a rock up a hill. Not up a mountain. Not up a cliff. A mundane, gentle sloping hill! Additionally, the gods sentenced Sisyphus to push a weight that a normal human being could actually get up the hilltop at least once and probably a few times.  Finally, Sisyphus never does anything different. He no longer has the freedom or free will to rethink or strategize a better way to keep the rock at the top of the hill — or even the ability to question the point of moving it to the top all together. 

You can imagine Sisyphus’ first moment in Hades, when a demon tells him to start pushing. He probably laughs to himself, “Easy-peasy lemon-squeasy! I’ll finish this in just a couple minutes!” Within the hour, his body sweats and heaves. By the end of the first day, he’s shaking, exhausted, worn out, and feeling genuine panic about his fate. 

This describes the state of so many executive directors. After years – maybe decades – of hard work and career achievements, they are finally in the CEO role. During the first few months, newly appointed executive directors are excited and enthusiastic about these ongoing tasks; they feel new and appropriately challenged. But, over time, as a chief executive masters the skills necessary to succeed, those daily, monthly, and even annually recurring tasks start to sap energy, creativity, and even enthusiasm for the mission. 

But Sisyphus Syndrome is not inevitable! 

Here’s what you can do to stop the endless wash-rinse-repeat cycle in your work life:

1. Evaluate your ongoing tasks

Conduct a time audit for the next week or two by tracking your work-related activities in 15-minute increments. At the end of your evaluation period, ask yourself four questions about each of the 15-minute increments:

        • Did I enjoy doing this task?
        • Is this task essential for our organization?
        • Does this task help our organization achieve its strategic goals?
        • Can I delegate this task to someone else? 

(Note: You aren’t asking if there’s someone currently on your team who can do this work. You’re asking if you are the only person in the universe who can complete this particular task).

Delete and diminish

In the afterlife, Sisyphus lacked the ability to say, “No. Pushing this rock up the hill remains pointless, and I refuse to do it any longer!” In this life, we have that freedom. 

My coaching clients are often surprised to learn they complete several ongoing unnecessary tasks. When deleting one of these from your task list, no one notices or cares. And ignoring the task doesn’t impact your organization’s capacity to achieve its strategic goals. 

I once worked with an executive director who spent 10 minutes every morning to create an email auto responder informing senders of his availability that day. This automated message essentially told all senders the best time to interrupt his day – not just clients, colleagues, and partners, but also lots of sales people.  Unsurprisingly, he had a hard time getting work done between meetings because people knew when to call or stop by his office and ask, “You have 5 minutes?” When he stopped creating a daily auto responder, he gained an extra 10 minutes each morning and the ability to achieve more between each meeting. 

Just that ten-minute savings accounted for an additional week of work each year! (10 minutes x 5 days = 50 minutes; 50 minutes per week x 48 weeks = 2,400 minutes; 2,400 minutes = 40 hours). Imagine being able to recapture a full week of work by changing just one habit. Oh, the things we could accomplish!


When people first began telling the story of Sisyphus, humanity existed in a very different world. If you wanted a boulder at the top of a hill, you and a group of people had to push it to the top. Thousands of years later, we have smart technology that can do many of the pointless, mind-numbing tasks for us.

Whether through email rules or artificial intelligence, I often use automation to get time back in my day. And I’ve helped coaching clients automate in ways that are authentic to them. A few quick examples:

            • After checking my email’s junk mailbox daily for years, I created an auto responder for any items hitting my junk folder. The response lets senders know that my email system flagged their message as spam and will auto-delete it soon. I encourage senders to call me, but the automated email reply doesn’t provide a phone number because (a) my clients and colleagues have my phone number and (b) anyone can easily find my phone number on the website. This saves me 5 minutes a day, 25 minutes a week, almost 2 hours every month, and 20 hours (or half-a-week!) each year.
            • When I started my consulting practice, I also opened a business credit card account (I charge any business expense that I can and use the points for fabulous trips. This month my husband and I are going to Hawaii for the week entirely on points). Since most of my business expenses, are transacted to my credit card, the receipts flow into my email. For years, I would spend 3 to 4 hours a month saving PDF copies of email receipts for 40 to 60 transactions and hunting down those receipts that had slipped through the cracks of my cumbersome all-manual system. If you asked me a few years ago, I would have boasted that the time enabled me to justify over $50,000 of consulting-related travel expenses in an IRS audit.  I produced a receipt for every transaction – even $2.50 subway fare – and the IRS couldn’t deny a single item deducted. While I felt sweet victory with the IRS, I spent more than a full work week each year just tracking credit card expenses (4 hours per month x 12 months = 48 hours per year)! 

A few years ago, I discovered Microsoft Power Automate, which Microsoft includes in Office 365 subscriptions at no extra cost. I created Power Automate flows to identify email receipts and convert/save them as PDFs on my computer. I now spend about 45-mintues each month on the credit card statement – – – and regained almost a week of my work life back!

        • Recently, I began experimenting with a chat bot  that schedules meetings for me. The chat bot has full access to my work calendar, knows when I’m in a different time zone, and interacts with meeting attendees in a human-like way (though I always acknowledge it’s an AI chat bot when scheduling a meeting). This AI bot has enabled me to stop scheduling meetings, which has freed up a significant amount of time and emotional energy in my week.  Last week, the chat bot scheduled a dozen meetings for me, and some of these meetings had multiple participants. It likely saves me two-hours per week, which frees up 100 hours – or 2 ½ weeks – each year! 


Imagine if Sisyphus had a team at the bottom of the hill who he delegated tasks to. He might say to the team, “Let’s take turns pushing the rock while everyone else brainstorms and experiments with new ways to finally keep the rock at the top of the hill.” 

If you can’t ignore or automate a task, consider delegating it to someone on your team, to a contractor, or even to a new employee. 

Since most of us became managers as a result of being very successful individual contributors, delegation doesn’t come naturally and can even feel uncomfortable. But an inability to delegate often becomes the single biggest obstacle holding you back. 

I once had a coaching client who clung tightly to every possible task because “no one could do this as well as me.” This sentiment signifies a die-hard individual contributor, and in our work together she learned to become more of a coach, a leader, a mentor, and – at times – a touch up artist to make that grant proposal, funder report, or email newsletter perfect. In the process she gained a couple dozen hours each week. 

2. Prioritize Strategic Tasks

Now that you’ve slashed 5, 10 or maybe even 20 hours of soul-sucking work, I want you to think about how you make the most of your new-found time. 

If, like many of us, you’re working 55 or 60 hours per week, then consider cutting back to working just 40 to 45 hours instead. You’ll become more relaxed and refreshed in all areas of your life, and you’ll approach work in a more strategic and focused manner as a result. 

But if you still have extra hours in your day, think about the ways you can use this additional time to grow your organization and impact your mission. Here are a few examples:

            • Schedule half-a-day each week to focus solely on implementation of those tactics in your strategic plan. While 4 hours a week might not seem like much, these hours will add up over the course of a year. And you can make a surprising amount of progress in 200 hours (4 hours per week x 50 weeks per year).  
            • Spend more time mentoring and coaching your direct reports. Help them become the best leaders, managers, and do-ers your organization has seen. 
            • Strengthen organizational partnerships and build new relationships that will help your nonprofit achieve its goals. 
            • Commit time to cultivating “big asks” of funders, donors, Board members, and partners. It’s nice to get the $1,000 gift, but that gift doesn’t have a serious impact on your mission. The $100,000 gift probably will. 

Just remember – you aren’t Sisyphus, and no one has sentenced you to an eternity of endless grant reports, expense reimbursements, unread emails, or horrible meetings. You can choose to stop pushing that rock, focus on ways to change the game, and achieve new levels of success for yourself and your organization. 

Why I’m writing about this:

Almost since the start of Successful Nonprofits® in 2014, nonprofit executive directors, founders, and development directors have sought me out for executive coaching. Through these coaching engagements, I have a big impact on the trajectory of a nonprofit leader and the organization they lead. And that describes the drive behind my professional work as a consultant.  

Additionally, check out the following Successful Nonprofits® resources if this post was helpful:

Blog: Categorize and Triage Your Fires

Blog: Stop Feeling Overwhelmed By Your Email

Podcast: Coaching for Nonprofit Leaders with Deb Stallings

Podcast: Insider Tips from an Executive Assistant with Jeremy Burrows


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