The Sisyphus Portfolio – Are You Rolling the Same Rock Up the Hill Every Market Cycle?

In Greek mythology, Sisyphus is condemned by the gods to push a heavy boulder up a hill for eternity, only for it to roll back down every time he nears the top. It’s a story of repetition, frustration, and endless effort… but also resilience, meaning, and persistence.

We save, we rebalance, we rebuild after bear markets, only to watch the cycle repeat. The market falls. You climb again. Or is the grind itself the point? And whether we like it or not, investing often feels the same. You climb. But does that make the effort meaningless?

Drawdowns: When the Rock Rolls Back Down

Every investor eventually faces the moment where the portfolio (the rock) comes tumbling down the hill:

• A market crash
• A tightening cycle
• A geopolitical shock
• A bad earnings season

Months or years of progress compress into weeks of losses. You’re left staring at the metaphorical stone, wondering if you have the energy to push again. But here’s the philosophical twist:

The market doesn’t punish you for the fall, it tests you on whether you choose to start pushing again.

Rebalancing as the Eternal Push 

Rebalancing always feels like work:

• Selling winners

• Buying losers

• Resisting the temptation to chase hype

• Reinforcing discipline even when it hurts

It’s a quiet, repetitive act, very unglamorous, very Sisyphean. And yet, over decades, rebalancing is one of the key drivers of risk control, return smoothing, and long-term survival. You’re not pushing the rock because it's fun. You're pushing it because it keeps your portfolio alive.

Why We Resist the Grind

Investors crave finality, the moment where we say:

I’ve built it. I’m done.

But markets don’t work like that.

There is no done. There is only maintenance, adjustment, humility, and another step...

The Sisypus Portfolio reminds us that:

• Markets will always cycle

• Drawdowns will always return

• Rebalancing will never stop

• Discipline is an unending practice

This is not failure, it’s the nature of the game.

The Camus Interpretation — Finding Meaning in the Push

Albert Camus famously reframed the myth:

One must imagine Sisyphus happy.

Why? Because meaning doesn’t come from being finished, it comes from showing up. Investors, too, must find meaning in the repetition:

• The discipline of saving

• The routine of rebalancing

• The courage to rebuild after losses

• The patience to endure cycles

The grind is not a punishment, it is the cost of compounding. And compounding pays extraordinarily well.

The Wisdom of the Sisyphus Portfolio

Instead of asking:

When will this get easier?

Ask:

How can I get better at pushing the rock?

Every push moves you a little higher than the last cycle. Discipline beats prediction. Persistence beats timing. Because here’s the hidden truth:

Even if it doesn’t feel like it. Even if the rock rolls back. Over long time horizons, investors who embrace the grind outlast those who search for shortcuts. Consistency beats brilliance.

Final Takeaway

If market cycles make you feel like Sisyphus, good. That means you're experiencing investing honestly. The goal is to master it, accept it, and build wealth through it.

But only some have the resilience to keep pushing. The goal is not to escape the grind. Because the rock rolls back for everyone.

Stay up to date by subscribing to my Newsletter.