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How to succeed when Sisyphus failed

Do you ever feel like you’re Sisyphus – cursed by Hades, God of the Underworld, to push a boulder uphill for all eternity. After hours/days/months/years of backbreaking effort, just as you are inches from the top, the boulder slips out of your grasp. You watch helplessly as it rolls away from you. With exhausted steps, you stumble back to the bottom of the hill, brace yourself against the boulder, and push.

I’ve been feeling that way a lot lately.

I push many boulders. There’s really big boulders like reproductive rights, the safety of our children and teachers in their classrooms, climate change, and the very foundations of democracy. THEN there’s little, everyday boulders like the never ending stack of dishes, to dos, bills, laundry, emails, and yard work. PLUS there’s caring for the relationships that matter like marriage, our dearest friendships, our families, our colleagues, and (though I often neglect this one) our own self-care. That’s a lot of boulders.

It’s absolutely, 100% true that pushing boulders is exhausting. That’s true whether you are a child building a sand castle watching a wave roll in, a parent doing dishes for the seventh time in a single day, a veterinarian at 6 pm staring at the stack of charts that still need to be filled out before you can go home, a reproductive rights activist watching in horror as Roe v Wade is overturned, or a CEO with yet another employee resignation on her desk.

But it’s also, absolutely, 100% true that you have control over this Sisyphean situation in a way Sisyphis did not. And no, I don’t mean shouting “F*%# this,” burning down the house and moving to New Zealand. (Though goodness knows my husband and I have thought about it.)

  1. You can choose which boulders to push.

  2. You can push with others.

  3. You can change your mindset around boulder pushing.

  4. You can take in the view from the top of the hill, where it’s possible to see that “the arc of the universe is long, but it bends toward justice.”

Choosing your boulders

You only have so much energy capacity. Think of every boulder as a living thing, a precious living being that requires a constant stream of food, shelter and love to sustain. You wouldn't invite every single stray animal into your home. So choose your boulders carefully. Having a clear sense of your purpose and values helps tremendously to choose where to expend your limited energy.

Personally, I choose just three boulders each day to push. Today, Sunday, that’s writing this piece, doing an errand run to get ready for the busy week ahead, and spending precious weekend time with my kids and husband. (These are associated with core aspects of my purpose and values: my purpose of encouraging the light, self-care, and family respectively.) If I choose these boulders as my priority today, I'm accepting that the little rocks and pebbles (those to do list things that aren’t critically linked to my purpose and values like dishes, laundry, and washing the car) might not get done, but progress will be made on the three, and that matters more. And some of the little things might still get done. In the breaks and little snatches of time between working on my big three boulders, the little pebbles will naturally fill in the gaps. My job is to keep pushing the big boulders and let the little things go.

Make this method of choosing three boulders your own. One client chooses three boulders across the week rather than by the day. Another who struggles with self-care follows time management guru Laura Vanderkam’s excellent advice: limit yourself to only one boulder for career-related things. The others are labeled in permanent marker: “self-care” and “cultivating the relationships that matter most.”

Push with others

The research is clear that going it alone is bad for your health, productivity, and success, while being surrounded by a community of support is good for you. As Chris Peterson, one of the 100 most cited psychologists in the world said, “I can sum up positive psychology in just three words – Other People Matter. Period. Anything that builds relationships between and among people is going to make you happy.”

The guilt I feel for not doing it all is alleviated by the certainty that I’m not fighting that fight alone. Kathryn Kolbert who argued Planned Parenthood v. Casey before the Supreme Court said, “coalition is queen. We've got to find allies and work with them.” I have and will continue to add my voice and resources to the fight in a way that leverages my impact to the greatest benefit. I don’t have to attend every march or knock on every door. There are millions of us. All of us are moving this boulder together, leveraging each of our own efforts to our greatest ability. This is a team effort, not a solo sport.

Change your mindset

Poor Sisyphus had to push his boulder alone, in the dark, in Hades. We however, have a choice. Instead of despair and defeat, we can find purpose, passion, and even pleasure in the labor ahead. There are friends and fellowship to be found in the coalition. There is fiery, angry, warrior passion to provide rocket fuel for our labors. And there’s pleasure to be found in good, meaningful work that fulfills our purpose.

“Forces beyond your control can take away everything you possess except one thing, your freedom to choose how you will respond to the situation. You cannot control what happens to you in life, but you can always control what you will feel and do about what happens to you.” ~ Viktor Frankl, Man’s Search for Meaning

Changing your mindset also means monitoring your energy and taking breaks when you need it. This is a marathon, not a sprint. If you are having trouble finding pleasure in the work itself, when pushing boulders becomes exhausting, take a break to rest and restore. Seek comfort in the present moment. Your soul needs breaks like the ones I’ve taken in the past 24 hours: making pancakes with my daughter, doing a centering practice, singing Journey at the top of my lungs, sharing a glass of prosecco with a friend, watching Mark Rober YouTube videos, watching the birds, and savoring the smell of a cup of chai tea. Sisyphus couldn’t take breaks, but you can.

“The arc of the universe is long, but it bends towards justice.”

These wise words belong to Theodore Parker and were quoted by icons like Dr. Martin Luther King Jr. and Barak Obama. It’s true. Unlike Sisyphus who never makes progress, climbing the same damn hill every day, pushing the same exact rock every day, if you look at the long game, there has been a great deal of progress because enough people are staying engaged and taking action on the things that matter. Sometimes the actions are really big and garner national attention. I personally prefer the small, intimate actions that directly impact people that I’m on a first name basis with. Big or small doesn’t matter. What matters is that with enough people pushing the same boulder in the same direction over the long haul, real, measurable progress is made.

If you step back and take in the long view at the level of generations, not days or months, you can clearly see the bend towards justice. Perhaps the boulder is a little lighter. Perhaps the hill is a little less steep. Perhaps you get closer and closer to the top each time. Perhaps there’s more of us pushing with you. No matter what, if you stop and take a moment to notice the view you'll see that there’s progress. There’s hope.

“Hope is often misunderstood. People tend to think that it is simply passive wishful thinking: I hope something will happen but I’m not going to do anything about it. This is indeed the opposite of real hope, which requires action and engagement… Hope is a human survival trait, and without it we perish.”~ Jane Goodall, The Book of Hope: A Survival Guide for Trying Times


Let me leave you with the wise words of Paul Krafel, a mentor of mine. He once said to me:

“Culture is like a castle, Irene. It’s like a sand castle on the beach. You spend all this time building a beautiful castle, with towers and bridges, and a moat. But the sun, waves, and wind – all the forces of entropy – will gradually erode the castle into nothing unless you continually put energy into rebuilding the castle.”

He was talking about school discipline and student behavior at the time (I’m sure all my fellow school leaders and most parents out there can relate), but I’ve returned again and again to this analogy hundreds of times. The things that matter most in the world don’t just happen by accident. Entropy will gradually erode even the most beautiful castle unless all of us continue to look for success, stay engaged, and take action.

  1. Choose your boulders: You can’t build 100 sandcastles by the water’s edge and expect them all to remain standing at the end of the day. Choose the three that are truly the most important and focus your energy there.

  2. Push with others: Building castles is a team sport. Do it with friends so that you don’t do it alone.

  3. Change your mindset: There’s pleasure to be found purely in the process of castle building. The sun is warm on your face. The sand feels good between your toes. The bubble of friendly conversation with your friends adds a lovely soundtrack.

  4. There’s progress and hope: And this is where the sandcastle analogy breaks down. No matter how many sand castles you build, it won’t fundamentally change the beach. But human history and social progress can and does change. There’s progress if you can step back and see it.

Read more

These two blog posts of mine offer more depth on understanding your purpose and values – two keys to choosing to push only the boulders that are truly most important to you.

If you are looking for a read to restore your hope or find comfort, I highly recommend The Comfort Book by Matt Haig (a recent pick by my book club) and The Book of Hope by Jane Goodall.

Going Further

If you are seeking others to push with you side by side, schedule a time to chat. The Collective Wisdom Mastermind is enrolling now. Our purpose: to make leadership less lonely by finding a flock to soar with. Receive the support and collective wisdom you need to “level up” your leadership and take action on your biggest challenges or wishes.

If you are longing for a private, safe haven where you are fully seen, valued, honored, and embraced as the inspirational leader and messy human you are, reach out ASAP. With all my individual leadership coaching clients, I am now using a Shift Positive 360 to recruit the people above, below, and beside them at the organization into allies. I only have the capacity to take on one new client at the end of summer. Might it be you?

If you love this article, consider sending it to someone you know that really needs this message now. And subscribe to my blog for a steady stream of insights and ahas. Not too often. No spam.

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