Escape the Sisyphean cycle: Create bite-size tasks and celebrate the wins
Small wins, steady progress, and the psychology of getting unstuck
In Greek mythology, Sisyphus is a cunning king who cheats death twice. As punishment, Hades condemns him to eternally roll a boulder up a hill. Each time Sisyphus nears the top, the boulder rolls back to the bottom. It’s a hopeless task where Sisyphus’ efforts are constantly erased, stuck in a perpetual state of frustration and exhaustion.
The Sisyphean cycle is an easy trap to fall into. In our ambition for productivity and growth, we often set unrealistic goals for four reasons:
We overestimate our abilities and underestimate our needs
We compare ourselves to others, trying to emulate someone else’s success
We succumb to external influence, chasing other people’s expectations
We seek instant gratification, overlooking the fulfillment that comes from gradual progress
Once we realize the futility of an overreaching goal, we lose motivation, procrastinate, burn out, and give up.
The key to breaking free from these never-ending loops is straightforward: make tasks small and achievable, celebrate small wins, and create a positive feedback loop in the process.
Positive Feedback Loops
Dopamine is the neurotransmitter of pleasure and reward. It’s released not only when we achieve something but also in anticipation of a reward. The anticipation and the feeling that we’re getting closer can be more motivating than the outcome itself.
Alex Korb, author of The Upward Spiral contrasts poorly defined goals with achievable goals:
A nebulous goal might be “Spend more time with my kids,” whereas “Play board games with my kids every Sunday” is a specific one. When goals are poorly defined, it becomes difficult for the brain to determine whether you’ve actually accomplished them or are even moving toward them. Not only does that mean less dopamine, but the lack of perceived progress can be demotivating. On top of that, not believing you can achieve your goals increases feelings of hopelessness.
When we break down a long-term goal into clear, measurable steps, we use our body’s reward system to create a positive feedback loop. Completing one bite-sized task results in a sense of satisfaction and motivation to continue working towards the long-term goal. So celebrate those wins—even the tiny ones. Each one is proof you’re moving the boulder a little higher up the hill.
Bite-Size Tasks in Practice
Recently, I committed to creating a marketing landing page that displayed pricing for a Wunderite partnership: a seemingly simple project that quickly grew into something sprawling.
My first mistake was defining the task as “Marketing website content updates.” Vague. Broad. Infinite. The perfect Sisyphean setup. In reality, I should have broken the project into smaller increments:
Familiarize myself with our WordPress theme and tooling
Set up realistic-looking dummy data in our app
Update three product videos
Capture two high-quality screenshots
Prototype a pricing layout
Design a custom page header and footer
Record a Loom walkthrough for review
Incorporate team feedback
Instead, I dove straight in: overestimating my ability, comparing my design to others, feeling pressure from external expectations, and craving instant results. Each day became another round of pushing the boulder uphill.
After four days of frustration, I reframed the project:
I accepted the time commitment and adjusted my expectations
I stopped comparing my work to other designs
I defined a clear end goal and communicated it to stakeholders
I took joy in gradual progress, not perfection
Once I shifted my mindset, progress started to feel possible again.
To make sure I didn’t repeat the mistake, I created a project tracking spreadsheet in Airtable and broke future marketing tasks into half-day increments. Then I set clear boundaries with our Sales Manager:
I can commit 10–20% of my time to this project. Each week I can address one task. Please prioritize by marking them as Highest, High, Medium, or Low.
That clarity was liberating. What felt like an endless hill became a series of manageable steps: each one achievable, each one a small win.
The Power of Tiny Wins
When you’re facing a monumental project, break it down into ridiculously small and specific tasks.
I followed this same principle to write this article. My goal was to finish the draft, but on days when I couldn’t find the motivation, I’d give myself one simple target: write a single sentence. One sentence became two, then a paragraph, and eventually a complete draft.
Feeling stuck or hopeless isn’t failure. It’s a sign to simplify the goal and make progress possible again.
The journey of a thousand miles begins with a single step.
It takes awareness to remember that slow progress still counts. Sisyphus was doomed because his effort never accumulated. The boulder always rolled back down. But your boulder doesn’t have to. Every small task you complete, every moment of celebration, pushes it a little further uphill. And unlike Sisyphus, you get to keep what you’ve built.
That’s the quiet victory of bite-size progress: it compounds. Each small effort builds on the last until progress starts to feel inevitable. Over time, you look back and realize the mountain isn’t quite so steep anymore.
The next time you feel stuck or overwhelmed, don’t curse the hill. Just pick one small rock, move it forward, and celebrate that win. Because the difference between futility and fulfillment isn’t the size of the task, it’s whether you let yourself feel the reward along the way.