Using the Idea of a Work-Rest Fractal to Find Balanced Success

How one the most successful tech entrepreneurs in history came to rethink his approach to work-life-balance and what we can learn from it.

“It is with deep sadness that I observe the current culture of intensity in the tech industry. […] These companies are both destroying the personal lives of their employees and getting nothing in return.”

— Dustin Moskovitz

Whether through personal experience, depictions in movies or shows like The Social Network and Silicon Valley, or through stories from friends and family, probably almost everyone has a clear image of the (stereo)typical tech startup culture.

We might picture a bunch of hacker kids straight out of college who believe their company is going to change the world (even if their entire business is based on sharing two-second cat videos online), hunched over their computers day and night, only getting up to grab some takeout pizza or decompress with a drinking spree.

Or we might think of a fancy office where every desire of a worker is satisfied, with perks ranging from massages, napping pods, and meditation rooms, all the way to free food being served several times a day (and night), and fancy office parties every other Friday.

To many, either of these scenarios might sound like a dream come true: the energy and momentum behind a young startup driven by a band of passionate and youthful founders. Or the high salaries and seemingly unlimited perks of an established tech giant.

But are we over-glorifying the positive aspects of this and completely ignoring the downsides? Are the crazy hours put in at early-stage startups maybe just a way to feel more valuable and accomplished — visible busyness at a corporate level? And are the perks of big companies just golden handcuffs that ensure workers spend as many hours at the office as possible?

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Dustin Moskovitz is maybe in a better position to answer this than almost anyone else in the world. He has seen it all from the inside. And more than just passively experiencing it, he and his close friends helped shape this culture.

During his days at Harvard University, he shared his room with a guy called Mark Zuckerberg. Together, back in 2004, they tinkered on a little website called Thefacebook, which allowed Harvard students to find out who is in their classes and how they are connected with them. This little experiment later turned into facebook.com. And the rest is history.

During his time at Facebook, first as the company’s first CTO, and later as its Vice President of Engineering, Moskovitz lived up to the stereotype outlined above (and maybe even contributed to creating it in the first place).

His team worked crazy hours, with 14 to 16-hour days being the norm, pushing new changes to the site almost every day, which would often break things and force them to work through the night to fix it, just to repeat the same cycle the next day.

As Max Kelly, Facebook’s first cyber-security officer described it:

“Around 1 am, we’d know either we’re fucked or we’re good. If we were good, everyone would be like ‘whoopee’ and might be able to sleep for a little while. If we were fucked, then we were like, ‘OK, now we’ve got to try and claw this thing back or fix it.’ If 4 am rolled around, and we couldn’t fix it, I’d be like, ‘We’re going to try and revert it.’ Which meant basically my team would be up till 6 am So, go to bed somewhere between 4 and 6, and then repeat every day for like nine months. It was crazy.”

While this clearly doesn’t sound ideal from a work-life balance point of view, many would argue that it’s precisely this kind of work ethic and sacrifice that allows companies like Facebook to grow as rapidly as they do. And you might think Moskovitz, who through all of this became the youngest self-made billionaire in history, also believes this temporary sacrifice was more than worth it.

But he doesn’t.

In his own words:

“I wish I had slept more hours and exercised regularly. I wish I had made better decisions about what to eat or drink — at times, I consumed more soda and energy drinks than water. I wish I had made more time for other experiences that helped me grow incredibly quickly once I gave them a chance. You might think: but if you had prioritized those things, wouldn’t your contributions have been reduced? Would Facebook have been less successful? Actually, I believe I would have been more effective: a better leader and a more focused employee. I would have had fewer panic attacks, and acute health problems — like throwing out my back regularly in my early 20s. I would have picked fewer petty fights with my peers in the organization because I would have been generally more centered and self-reflective. I would have been less frustrated and resentful when things went wrong and required me to put in even more hours to deal with a local crisis. In short, I would have had more energy and spent it in smarter ways… AND I would have been happier. That’s why this is a true regret for me: I don’t feel like I chose between two worthy outcomes. No, I made a foolish sacrifice on both sides.”

Moskovitz is entirely disillusioned by the prevalent Silicon Valley culture.

“I […] hear young developers frequently brag about ’48 hours’ coding sprints. This kind of attitude not only hurts young workers who are willing to ‘step up’ to the expectation but facilitates ageism and sexism by indirectly discriminating against people who cannot maintain that kind of schedule.”

He has become a firm believer that overwork does much more harm than good and is particularly concerned about sustaining overwork over the long term. “We have also demonstrated that though you can get more output for a few weeks during ‘crunch time,’ you still ultimately pay for it later when people inevitably need to recover,” he says, adding, “If you try to sustain crunch time for longer than that, you are merely creating the illusion of increased velocity.”

Crunch time can be useful and productive if used sparingly and deliberately, but making it a habit isn’t a great idea.

Not only is it detrimental in terms of productivity and health, ultimately leaving everyone involved burned out, at the same time it tricks you into believing that you are getting a lot of stuff done and that doing less would just slow down progress.

It’s the glorification of visible busyness, and it creates a vicious cycle.

Until the inevitable breakdown.

To stay productive in the long term, you have to use a different approach. Just like in a marathon, you have to pace yourself.

Moskovitz has become a true proponent and evangelist of a different approach to work.

“Rest matters. […] As an industry, we are falling short of our potential. We could be accomplishing more, and we could be providing a better life for all of the people who work in technology. If you’re going to devote the best years of your life to work, do so intentionally. You can do great things AND live your life well. You can have it all, and science says you should.”


In 2008, together with engineering lead Justin Rosenstein, Moskovitz left Facebook to start a new company called Asana, creating the project management software of the same name.

Asana was from the start built with these newfound believes in mind, and he and his co-founders have “worked hard to build a culture at Asana where people don’t work too hard.”

They provide free training in mindfulness to all their employees. And they track how much people work. Not to tell them off if they don’t work enough, but to check in with them if they put in too many hours and encourage them to take some time off.

Asana believes that a great working environment should be in service of optimal productivity, and not littered with golden handcuffs that keep people in the office. When you’re done with your work, you should go home.

“If you’re keeping people till 8 or 9 that’s actually shooting yourself in the foot. Those hours just aren’t as productive as the ones at the beginning of the day.”

And worse than that, they might also hurt productivity at the beginning of the next day.


Moskovitz and his team are also deliberately trying to use this to combat the prevalent ageism problem. Kids right out of college might have no problem working in the typical tech culture. But people later in their career or life, with family, kids, and other obligations, either can’t or don’t want to live the kind of lifestyle that most startups require.

As a result, many companies are missing out on a lot of good potential talent, especially talent with experience, something rare to come by in the first place. By encouraging a healthy approach to work-life balance, Asana can attract everyone.

Given the cultural (mis)perception of what it takes to grow rapidly, some young and eager candidates are actually a bit worried by this lack of overwork, but Moskovitz clarifies that this is not a sacrifice or tradeoff. This is a deliberate business choice to improve results.

“We sometimes have candidates tell us they are worried that means we don’t move fast enough or have enough urgency. I’m not sure what I would do if I thought these values were actually in conflict, but fortunately, they are not. We get to encourage a healthy work-life balance in the cold, hard pursuit of profit. We are maximizing our velocity and our happiness at the same time.”


Asana is trying to encourage this approach not only in their own employees but also their large user-base. In August 2019, they added a new feature called “Workload.”

In a blog post announcing the feature they proclaim that “in a recent study of workplace trends among over 6,000 knowledge workers conducted by Asana & 4Media, 82% of respondents say they’ve experienced being overworked and 42% believe staff morale is low because of too much work.”

Asana developed Workload as a solution to this problem, making sure that, among other things, managers can easily spot if one of their team members is overworked and enabling them to take action to ease the time pressure.


Moskovitz’s own approach to time off is now deeply embedded in his lifestyle, on every timescale from the hours to the years. He calls this the “work-rest fractal”:

“Work-life balance is fractal — it’s important to consider at every level. […] We all take lunch breaks during the day, and the government even mandates that hourly workers are given a short break every four hours. People take a day or two off each week and several weeks off each year. A longer sabbatical every few years is similarly restorative on an even longer arc (though not available to everyone). Real work-life balance is best achieved when you take into account these time frames, and you trade between them, whether or not you’re aware of that. If you don’t take those breaks after each focused period, you’ll probably start getting distracted more and lose speed. If you skip a weekend, you’ll probably need to take more breaks during each workday. If you don’t take vacations, you’ll start taking even more breaks or working shorter days. If you don’t compensate at all, you’ll burn out. Maybe not today, maybe not tomorrow, but someday and until you take a real vacation (in proportion to how burnt out you are).”

Rest and time off happen at many different levels, from the micro (like a single deep breath or a coffee break) to the macro (an extended vacation or even a sabbatical).

Each of these scales is important and deserves our attention. Part of building a better rest ethic is becoming aware of this, and making and defending the space for downtime at each level.


Action: Consider your work-rest fractal.

Within a single work session, are you taking enough breaks? If not, consider, for example, the Pomodoro technique.

Within a day, are you using long lunch breaks and walks to replenish your energy, and do you treat yourself to a good night’s sleep every day?

Within a given project, are you using weekends and short vacations to reset and recover?

Within your career, are you treating yourself to more extended vacations and sabbaticals to disconnect and gain perspective?

If the answer to any of these questions is no, try to make the change! Time off is something that can, and should, be incorporated into your life on every single level.


This article was part of an early draft of our bestselling book Time Off: A Practical Guide to Building Your Rest Ethic and Finding Success Without the Stress by John Fitch and Max Frenzel, with illustrations by Mariya Suzuki, but did not make it through the final editing process. If you enjoyed this article, we are sure you’ll love the book as well.