Practice: Audit Your Striving

THE PROBLEM

Are you too busy? Are you working too hard to be productive with every minute of your time? In today’s episode I want to talk about the perils of over-optimizing your life, and what the Stoics had to say about managing your time.

“So, concerning the things we pursue, and for which we vigorously exert ourselves, we owe this consideration – either there is nothing useful in them, or most aren't useful. Some of them are superfluous, while others aren't worth that much. But we don't discern this and see them as free, when they cost us dearly.” — Seneca

Here's a question I want you to think about for a moment: When was the last time you did nothing? And I don’t mean meditation with a timer. Not a "recovery walk" you logged on your fitness app. Not a vacation you planned three months in advance and packed with activities. I mean genuinely, unscheduled, purposeless nothing.

If that question makes you a little uncomfortable — good. Stay with that discomfort. It's worth paying attention to.

We live in a culture that has turned busyness into a virtue. Hustle culture doesn't just govern how we work, it's taken over how we live. We optimize our mornings and time-block our evenings. We have productivity systems for our productivity systems. And somewhere along the way, the pressure to be efficient with every minute stopped being about work and started being about everything.

We feel guilty resting, like we're falling behind if we're not growing, improving, achieving. We half-listen to our kids because our brains are already solving tomorrow's problem. We treat our relationships like line items — something to maintain, to check in on, to be efficient with.

And the really insidious part? We've gotten very, very good at it. By every external measure, many of us are crushing it. The career is moving. The goals are being achieved. The metrics are trending up.

And yet, quietly, underneath all of it, something feels off. Like you're running hard but not sure where you're going. Like you're winning a game you didn't consciously choose to play.

That feeling, that discomfort? That's wisdom trying to get your attention.

Today I want to talk about what the Stoics, and specifically Seneca, had to say about this. Because he diagnosed this problem two thousand years ago with surgical precision. And his answer isn't what you might expect.

THE PHILOSOPHY

Seneca was a wealthy, powerful man. Advisor to an emperor. One of the most successful people in Rome. He knew ambition from the inside. And late in his life, he wrote a short essay called De Brevitate Vitae (On the Shortness of Life) that I think is one of the most important things ever written about how we spend our time.

He opens without pulling any punches:

"It is not that we have a short time to live, but that we waste a great deal of it."

Read that again. He's not saying life is short. He's saying we make it short — by squandering it on things that don't deserve it.

And here's what's critical: Seneca isn't targeting the lazy. He's targeting the ambitious. The strivers. The people who are busy every minute of every day, and still somehow missing their lives.

He writes:

"People are frugal in guarding their personal property; but as soon as it comes to squandering time they are most wasteful of the one thing in which it is right to be stingy."

Think about that. We password-protect our phones. We lock our cars. We negotiate our salaries. But time, the only resource we cannot earn back, cannot borrow, cannot buy, we hand it over to anyone who asks. We let hustle culture tell us exactly what to do with it.

Now here's where Stoic philosophy gets really sharp. The Stoics made a distinction that completely collapses hustle culture. They separated preferred indifferents — things like wealth, status, achievement, success — from the actual good. The actual good, for a Stoic, is virtue: living with wisdom, justice, courage, and temperance.

Preferred indifferents aren't bad. It's fine to pursue success. But they are not the point. They are not where meaning lives. Hustle culture has convinced us otherwise, that the scoreboard is the point of the game. And so we optimize furiously for things that, when we finally get them, leave us standing in the end zone wondering why we don't feel the way we thought we would.

Marcus Aurelius asked himself a question I think we should all have tattooed somewhere: "Ask yourself at every moment: is this necessary?"

Not "is this productive?" Not "is this optimizing my outcome?" Is it necessary? Does it serve the life I actually want to live? Because far too often, we’re chasing things that others have told us are important, not necessarily what really make a good life. Maybe it’s the job we hate but want for the prestige. The expensive car to make others jealous. Or even the fancy house that we don’t get to enjoy because we’re too busy being productive.

And Seneca is pretty clear about this. He calls out those that are busy building fortunes with no time to enjoy them. Those that ingratiate themselves to others for promotion. Others who are driven by greed traveling here and there for wealth.

And this is where temperance, one of the four cardinal Stoic virtues, comes in. We tend to think of temperance as moderation, as holding back. But temperance, for the Stoics, is discernment. It's the wisdom to know what deserves your energy and what doesn't. It means the appropriate action, with the appropriate amount of energy, at the appropriate time. It's the discipline to say no to the noise so you can say yes to what actually matters.

Busyness

Here's the harder truth Seneca is pointing at: busyness is a choice. Not always a conscious one, but a choice nonetheless.

But why do we choose to get stuck in being busy?

I think for many people busyness, striving, and achievement are how they gain their sense of worth. It’s like they have to prove that they have value, rather than recognizing that they are valuable because of who they are, not what they achieve. External success is a substitute for internal character.

A secondary reason for busyness is that it pushes off time being alone with yourself. Because if you're always busy, you never have to sit with the harder questions. You never have to ask whether the life you're building is the life you actually want. Busyness is armor. It keeps the big questions at bay.

But Seneca reminds us that it truly is the inner life that matters, not externals:

“A man thus grounded must, whether he wills or not, necessarily be attended by constant cheerfulness and a joy that is deep and issues from deep within, since he finds delight in his own resources, and desires no joys greater than his inner joys.” — Seneca

Busyness is a way to feel productive, but ignoring what really matters—building character and connection with others.

What is it all for?

I think the most important thing to remember is that life is about living and experiencing. We strive because being useful and creating is important. It give us purpose and a sense of accomplishment. There’s nothing wrong with striving. But when we go so caught up in striving and being productive in all areas then we miss out on the happy accidents of life. We don’t leave idle time for creativity and just thinking about things. When our minds are bored then we have space to connect things that we might not have ever thought of. This is why we have shower thoughts. This is why walking away from a problem and allowing our minds to wander often brings the eureka moments that help us break through resistance.

It opens us up to chance encounters. One of the things that I noticed when I was living in Amsterdam is that when I first got there I would regularly chat with people on the metro or on buses. I often had great conversations with people that I otherwise wouldn’t have met. But I was kind of an outlier. Most people were staring at their phones or had their headphones on. Over time adopted this behavior as well and missed those unique encounters.

The point of this whole episode is make sure that we leave time for enjoying life, that we allow our minds time to relax, for connection, and being open to chance.

THE PRACTICE

So what does this actually look like? I'm not here to tell you to quit your job or spend three hours a day in contemplation. The Stoics were practical. They were active in the world. What they asked was simply that you live in it deliberately.

Here are three practices I think are worth sitting with.

Audit Your Striving

This is the core Seneca practice. Regularly, maybe once a week, maybe once a month, ask yourself: What am I actually working toward? Is it creating joy, or just getting more?

Write it down. Don't just think it. Write it. Because writing forces honesty in a way that thinking doesn't. You may find that what you're grinding toward is something you genuinely care about. Great. Keep going with clarity. But you may also find that you've been chasing something because it's expected of you, because it's what people like you are supposed to want. And that discovery, uncomfortable as it is, is worth everything.

Seneca writes:

“There is nothing the busy man is less busied with than living: there is nothing that is harder to learn.”

Is what your busying yourself, worth your time?

Protect unstructured time (and defend it like it matters).

Not as a reward. Not after you've earned it. As a non-negotiable part of a well-lived life.

This is where real thinking happens. Where creative ideas surface. Where you remember who you are outside of your output. Where your relationships get space to actually breathe. If you need to schedule it to protect it, schedule it. But stop treating it as empty space to be filled. It is not empty. It is where your life is.

Be present with the people in front of you.

This one might be the hardest, and it might also be the most important. The most insidious cost of over-optimization isn't burnout. It's the slow erosion of connection. When you're always half-present — body in the room, mind three steps ahead — you are not actually with the people you love. You're near them. There's a difference.

In her book Daring Greatly, Brené Brown wrote:

 “Connection is why we're here; it is what gives purpose and meaning to our lives.”

The Stoics would agree, framing it through their idea of cosmopolitanism — that we are all members of one human community, and our obligations to each other are important. You cannot fulfill those obligations on autopilot.

Full presence isn't soft. It's not a nice-to-have. It is, Seneca would argue, the whole point.

Conclusion

Let me bring this back to where we started.

The problem isn't that you're not productive enough. The problem isn't that you need a better system, a sharper routine, or a more optimized morning.

The problem is that we've confused the map for the territory. We've gotten so good at the how of living that we've stopped asking the why.

Seneca saw this in Rome. The ambitious people surrounding him — running from one obligation to the next, accumulating, achieving, never pausing — and dying, he said, without ever having truly lived. Not because their lives were short. But because they were never fully present in them.

He wrote: “He who is everywhere is nowhere.”

You can be everywhere — every meeting, every commitment, every optimized hour — and still be nowhere that actually matters.

The Stoic invitation isn't to do less. It's to choose more deliberately. To ask, regularly and honestly: Is what I'm striving for really worth it? Am I creating joy, or just getting more?

That question takes courage. It is easier to stay busy. It is easier to keep the calendar full and the metrics moving and never stop long enough to look up and ask if this is the direction you’ve actually chosen.

But you have that courage. The fact that you're here, listening, asking these questions — that's evidence of it.

So this week, I want to leave you with one thing. Not a task. Not an optimization. Just a question to carry with you:

Am I living deliberately enough?

Not perfectly. Not without ambition. Just deliberately. With your eyes open. Knowing what you value, and letting that — not the culture around you, not the scoreboard — be what guides how you spend the one thing that is truly, only, yours—your time.

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Thanks again for listening!

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My book Stoicism 101 is available! Order here!

Find out more at https://stoic.coffee

Watch episodes on YouTube!

Find me on linkedIn, instagram, or threads.

Thanks again for listening!

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