Your work and its meaning

💌 The Roundup // 015

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Look at your calendar from last week. Does the way you spent your time reflect how you derive meaning from life? What about in the last month? Scanning my own calendar, it would be easy for someone to conclude that my career is the primary way I find fulfillment in my life. And I suspect I’m not the only one. 

While many people (including me) get genuine fulfillment from work, that doesn’t mean it’s the ideal environment for all of us to pursue meaning. Yet, for many, the idea of deprioritizing work can feel like a betrayal– like we are reducing our capacity for finding meaning. Where does this feeling come from? Should we pay attention to it, or do we need to find a way to move past it to build lives that are truly worth living?

Part I: Stop me if you’ve heard this one

It starts in a Silicon Valley garage, where a couple of college dropouts are tinkering with a new piece of technology. Before they know it, they’ve disrupted an industry and spawned one of the most valuable companies on the NYSE. Or, there’s the one about the determined young woman who overcomes the sexism of her old-school law firm, to land a corner office and a Partner title. Stories like these are vehicles for meaning that are capable of influencing the decisions we make about our careers.

Stories shape our career choices by embedding themselves into our identities. While some of these stories originate from the backstories of specific aspirational figures like Steve Jobs, Michael Jordan, or Ruth Bader Ginsburg, over time the individuals get abstracted into archetypes, giving us room to substitute ourselves into their shoes. When we emotionally resonate with a hero’s struggle, we often subconsciously attempt to weave their narrative into our identity. 

There are plenty of rewards available to those who can influence our decision-making. As a result, storytellers are continually competing to craft narratives to drive our behavior. Companies tell stories to convince us to buy their products. Political parties tell stories to inspire us to vote for their candidates. Nations tell stories to convince us to sacrifice in service of the country. 

Stories that influence our career decisions are particularly valuable. Picture a talented engineer working at an early stage startup. Given the value she creates, her company can’t afford to lose her. To prevent her from taking a higher-paying job at Google, her manager needs to convince her that the time and money she’s sacrificing working at the startup represents a worthwhile tradeoff.

This reliance on the persuasive power of stories extends beyond a manager’s relationships with his direct reports. The manager’s labor benefits the CEO, who enriches the investors, who all hunt for deals to help their limited partners. No matter where you sit in the economy, you stand to benefit from the narratives that drive the work of others.

To keep everyone productive requires great storytelling at multiple levels. The company must articulate a vision of how its products will make the world a better place. Industry leaders need to direct the efforts of organizations with calls to greatness. And national economies need to tie their citizens’ labor decisions to group-level heroic struggles. As these narratives drive our choices, they fuse into our identities and become increasingly challenging to resist.

Part II: Accept no substitutes

Of course, there’s nothing inherently wrong with taking inspiration from these stories as long as they serve your goals. If our startup engineer loves the impact she creates in her job and gets to spend enough time with her kids, then the narratives she associates with are serving her well.

The problem comes when stories hijack your brain, compelling you to pursue outcomes that aren’t aligned with your long-term goals. While an investor may want to inspire the founder of his portfolio company with stories of entrepreneurs who risked it all to build massive businesses, that doesn’t mean it’s in the founder’s best interest to internalize those narratives. 

But these stories can be hard to resist. Shaping your life and career to follow in the footsteps of a hero can feel meaningful. But, the sense of meaning you get simulating someone else’s journey can erode easily.

Imagine that your identity is a house. Building a sturdy one requires a strong foundation. If you use only external narratives to construct your foundation you may be able to put a roof over your head, but the first hurricane that comes along will topple the whole thing over. To build a strong identity requires authentic experience– the kind that can only be gained overcoming obstacles in the pursuit of worthwhile goals.

Part III: Aligning your career with your pursuit of meaning

Work may or may not be the right environment to facilitate your pursuit of meaning. A startup founder may find that work is the ideal context to make an impact on employees and customers. Meanwhile, a parent may simply want a job that pays enough to allow her to raise a happy and healthy family. Whatever gives your life meaning, it’s essential that your career choices facilitate, rather than limit, your ability to pursue those goals.

In my experience, work typically plays one of three roles in the pursuit of a meaningful life:

1. Work as a source of meaning

It’s hard to create meaning without facing challenging obstacles and achieving worthwhile goals. For many of us, work is the easiest place to find those things. Whether it’s investing the hours in mastering a craft or getting a life-changing product into the hands of millions of customers, work can be a tremendously fulfilling endeavor.

That said, it’s easy to get lured away from meaningful work by empty rewards. The modern workplace is designed to deliver rewards that seem valuable but are in fact quite empty. Winning status through promotions and raises may feel good in the short term, but rarely creates a sense of lasting meaning. 

Be cautious when choosing which people and organizations to affiliate with. Your dedication will make you a desirable teammate, and potential partners will want to fill your head with visions of the accomplishments and impact you can have by working with them. Find your own north star and aim to work with those who can help you pursue it.

To retain your motivation, immerse yourself in stories of people who used their work to accomplish great things. Surround yourself with peers who are driven to do the same. If you can keep going when the going gets tough, the real rewards will come.

2. Work as an enabler of meaning

For most of history, people did not see their work as meaningful. Instead, they saw activities like raising children and caring for relatives as the stuff that made life worth living. Work simply supplied the resources to make those things possible.

However, as work has gained more prominence in our modern lives, personal pursuits can easily get overshadowed by the professional sphere. Part of work’s power comes from the incentives it offers. Earning higher salaries and promotions often provides more immediate rewards than the longer-term joys of child-rearing. Our modern society also gives people more status for their work milestones than what they accomplish outside of work. These rewards will make it tempting to surrender your time to work or turn your extracurricular activities into economic pursuits. Keep in mind what matters to you so you don’t allow it to become subservient to work’s powerful draw.

3. Work as part of your portfolio of meaning

This is both the most common strategy and also the hardest to pull off. If you allow it, work will overtake everything else in your life. There is always more money to be earned. Always more status to be gained. Some days you’ll feel like you are competing with those who derive all their meaning from work and falling short. On other days you will be jealous of people who find their meaning from activities outside of work. However, just like when investing your money, a portfolio strategy is likely your best option.

To prevent work from taking over, find ways to get incremental goal fulfillment from your extracurricular activities. I found that the best way to prioritize writing was to commit to publishing this newsletter every month. Watching the follower count tick up gives me an incentive that rivals the rewards of work. Take this strategy with whatever you care about. Set goals for your health, your family, or your craft and reward yourself for accomplishing them.

Be diligent about setting boundaries. When you’re pursuing important activities outside of work, put your laptop away, and turn Slack notifications off. Just because you get offered a job with more responsibility and a fancier title doesn’t mean it’s a good idea to take it. While juggling multiple meaningful activities may be challenging, your life will ultimately be much more robust if your eggs are in multiple baskets.


It’s okay if you don’t know which strategy makes sense. I’ve changed mine more than once. And, while a portfolio strategy seems right for the time being, that could change when Ash and I start a family.

I’m also far from perfect at living up to my ideals. I consistently fail at prioritizing the things and people that matter to me. Particularly over the past few months, it’s been nearly impossible for me to keep work from seeping into every free block of time.

But what’s important isn’t perfection. It’s making an effort to be deliberate about what gives your life meaning and prioritizing it. While it’s easy to assume that the narratives in your head are guiding you in the right direction, don’t be so certain. To find what truly matters you may need to reexamine your own story to understand your best path forward.

Perhaps you’ll be lucky enough to find work that aligns with what gives your life meaning. Or maybe you’ll decide to merely work in the service of your passion. But no matter what road you pick, make sure you’re writing your own story.

Thanks to Ash, Justin, Liz, and Sachin for sharing feedback on early drafts of this.


If work dominated your every moment would life be worth living?

(5-minute read by Andrew Taggart)

What if the distinction between work and life doesn’t exist? Maybe we don’t need to choose, because there is no life– it’s all just work. This concept called “total work” comes from German philosopher Josef Pieper who, in 1948, theorized that work might eventually take-over all human activity.

How, in this world of total work, would people think and sound and act? Everywhere they looked, they would see the pre-employed, employed, post-employed, underemployed and unemployed, and there would be no one uncounted in this census. Everywhere they would laud and love work, wishing each other the very best for a productive day, opening their eyes to tasks and closing them only to sleep. […]

In this world, eating, excreting, resting, having sex, exercising, meditating and commuting – closely monitored and ever-optimised – would all be conducive to good health, which would, in turn, be put in the service of being more and more productive.

If work is all there is– what are we to do? Can we resist by carving out some activity that is completely unspoiled by the vestiges of work? Or, do we rebel through the subversive activity of finding holiness in our output?

🎨 How art-ification became a lucrative corporate strategy

(5-minute read by Ana Andjelic)

Visit the online shop of any successful artist and you’ll notice something interesting. While the artist may command tens of thousands of dollars for a painting, everything in her online store tends to have a relatively low price point. To some extent, this demonstrates the difference between products and art. While products tend to be purchased at a reasonable markup, art is often bought for many multiples of what it cost to produce. In part, this difference is driven by consumer perceptions around scarcity as well as the mythology of the creator.

Companies that create products would ideally love to be able to change the markup of an artist while retaining the benefits of scalable product production. To pull this off, a company must be able to elevate the creator of its products to the status of an artist. While this is common practice in the fashion world, it has also been successfully pulled off in tech by none other than Apple. Both Steve Jobs and lead designer Jony Ive achieved mythic status as creators, allowing their creations to command a much higher margin. What other companies should boost their margin by building a mythology around the creators of their products?

⚙️ Leverage Points: Places to Intervene in a System

(41-minute read by Donella Meadows)

The death of George Floyd has inspired a renewed wave of interest in fixing America’s broken criminal justice system. Many well-meaning reformers have vocalized support for popular solutions like defunding, or in some cases, abolishing the police. While these proposals have shades of nuance, it does not take much research to understand how they could backfire and lead to even greater loss of Black lives.

Fixing complex systems is hard work. Reforms that seem beneficial often create adverse second and third-order effects that show up elsewhere. Meanwhile, interventions that improve people’s lives can have little alignment with popular sentiment.

For those committed to doing the work, one great tool-kit to pick up is systems thinking. While this is a broad topic, a great place to start is this article from Donella Meadows, which shares the most effective places to exert leverage in a system. These ideas can help reformers see reality more clearly and intervene in ways that bring about genuine positive change.

On Anti-Racism

(1 hour and 36-minute listen by Coleman Hughes, Glenn Loury, John McWhorter, Kmele Foster, and Thomas Chatterton Williams)

In 2015 I picked up a book called The New Jim Crow: Mass Incarceration in the Age of Colorblindness. Reading it felt like an intellectual earthquake. It woke me up to horrors in American history that I missed in my education and helped me comprehend the pain residing in America’s Black community that continues to be perpetuated by inequalities through our criminal justice system. If you’re trying to understand the frustration and rage that has spread through our streets, I highly recommend you read it. I’d also suggest that you don’t stop there.

If you spend too much time on social media, it’s easy to get the impression that the only way to be an ally against racism is to proclaim support for rioting and tearing down statues of George Washington. In reality, there is plenty of worthwhile debate taking place among sensible people about the best way to build the kind of multi-racial society that most Americans want to live in.

I was lucky enough to encounter many of the thinkers on this podcast over the past few years. Their ideas equipped me with the right frameworks and arguments to process our current conversation regarding race in America. If you’ve been experiencing your own intellectual earthquake lately, and feel motivated to make personal and societal changes, I’d recommend you tune in to what they have to say.

🚪Stop Firing the Innocent

(11-minute read by Yascha Mounk)

Does cancel culture exist? Some argue that what free-speech advocates refer to as “cancel culture” is simply just the type of healthy debate that these advocates claim to support. While there may be some truth to this, I believe the power of social media mobs to ruin the lives of innocent people requires a new set of norms. In particular, I put the onus on American corporations to stop sacrificing innocent employees to appeal to the demands of social media mobs.

Of course, there are plenty of instances where people express vile opinions that should disqualify them from their jobs. However, in reading this piece, you’ll find there are also lots of cases where employees inadvertently trigger cultural trip-wires that they weren’t aware of. Given the high reputational cost of being fired for this kind of behavior, companies owe it to their workers to presume innocence and conduct thorough investigations.

One of the core tenets of liberal democracy is that people should not be punished for accusations against them that are unsubstantiated, for actions that are perfectly reasonable, or for offenses that were committed by others. No matter how worthy the cause they invoke, you should not trust anyone who seeks to abandon these fundamental principles.

Without draconian measures, it’s hard to see how society will be able to curb the trend of people calling on companies to fire their employees. That means it’s up to businesses to preserve the norm of due process and protect their workers from unfair accusations. If corporate America fails to uphold this responsibility, we risk making the price of free expression too costly for regular people and turning it into a luxury for the very rich.

🇺🇸 Shouting Into the Institutional Void

(10-minute read by George Packer)

Is America capable of manifesting the kind of reforms protesters are demanding? I’m not referring to our will to change– I’m talking about the capability of our institutions to respond to the demands of the people. Taking stock of our institutional arsenal, the answer seems to be a resounding no.

We have a president who is incapable of calming the nation, a Congress that no longer has the will to solve problems, and a press that has become too partisan to retain public trust. Even our public health officials have lost the confidence of the American public.

As I’ve mentioned before in this newsletter, many of America’s institutions are no longer capable of serving our needs. To build a better future, our generation can no longer depend on appealing to authority to solve our problems. We must instead get to the hard work of institutional overhaul across every domain of American life.



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*Header Image Credit: Evan M. Cohen