Be Happy: Work on Problems that Matter

I got my first job at 14 sacking groceries because I wanted a $250 BMX bike that my dad wouldn’t buy for me. I got the bike not long after I started my job, but I ended up spending a lot more time working at that grocery store than I did riding BMX. I really disliked my job. I would slowly unload groceries into customer trunks, and then get every last cart from the corrals before pushing them back to the entrance—all to delay returning to the checkout lane to bag more groceries. Shifts were only 3 or 4 hours, but every time I looked at the clock above the entryway, only 15 minutes had passed.

High school wasn’t much different for me. Classes were mostly unengaging and I didn’t have a sense of personal purpose when solving stoichiometry problems. I enrolled in advanced placement courses freshman and sophomore year because I wanted to be in the same classes as the cool and smart kids, but by junior year I was pretty disillusioned about how the coursework related to my personal life and hopes for the future. I began stuffing my schedule with periods for newspaper, yearbook, and ceramics. I even took a lower-level algebra 2 course that gave me three years math credit even though I’d already taken advanced algebra 2 the year before. Overall, high school failed to help me envision an exciting and purposeful future for myself.

The summer before senior year, I was on my annual flight to North Carolina to visit my grandparents. Sitting next to me was a balding-and-mustached middle-aged man in a navy business suit and burgundy tie. He was friendly, conversational, and took an interest in how I spent my time and what I had planned for the future. Something he said made an impression on me:

Some people work to support their passion, and some people’s work is their passion.

— Sage advice from a random guy on an airplane

What kind of person was I? The answer was immediately clear: I’m a person who wants to love my job. If I’m going to spend the majority of my waking hours for the rest of my life at work, then I want to love what I do.

I remember those first waking moments on Saturday mornings before work at the grocery store, and how dreadful it felt realizing I had to spend yet another day sacking groceries. What a drag. The thought of feeling that way every single day of the week for the rest of my life was terrifying. I didn’t yet know what I wanted to do with my life, but whatever it would be, it had to matter and not just be a job to pay the bills. I wanted to feel a sense of purpose in how I spent my days because that personal freedom made me feel happy. Having ownership over my day-to-day decisions, without the burden of obligation, was my life-long aspiration.

I never intended to go to college, but years later found myself taking a graduate seminar on content management systems and found my professional passion in making websites. There’s a nexus of disciplines in the making of a website—it’s sort of a renaissance medium. There’s the traditional art of layout, and I found pleasure in choosing fonts and colors, mostly because I understood that I could elicit delight through my aesthetic decisions. There was art even in the structuring of the hypertext markup and the semantics of stylesheets. There was eloquence evident in the word choices of header and navigation titles. The social dynamic implicit in uploading my website over FTP was exhilarating—I put my own work before the world and suddenly I could interact with people from Finland and Japan. There was adventure and potential in the web and it was a way for me to define my own sense of purpose and to take charge of my own happiness.

How to identify “problems that matter”

During my early career as a designer I took a couple jobs at mission-driven companies. Both were disasters that left me questioning my self-worth, intelligence, and talent. At the same time, I was skeptical my burden of responsiblity because nobody seemed to know what we were working toward. Product rarely shipped and teammates were often frustrated with their own positions. In retrospect, both of those companies had the same problems most technology companies have in the startup space. Both had issues with viability—how to make money at scale—and also sustainability—how they would evolve their business models to work long-term. Not having clarity around both of these issues resulted in social dynamics and management practices that left me feeling unsupported and incapable of doing my best work.

It turned out that pursuing work with a mission-driven company wasn’t enough to find professional happiness and over the past year I’ve been trying to grapple with how to define problems that are worth working on and how I can be successful when I’ve found a mission I want to invest myself in.

I’ve found that evaluating companies based on four key principles—utilitarianism, morality, viability, and sustainability—leads to finding work that’s purposeful and impactful.

Problems that matter are utilitarian.

While I was in college I elected a philosophy course and was introduced to the concept of utilitarianism, which is a doctrine that states that an action is right insofar as it promotes happiness, and that the greatest happiness of the greatest number should be the guiding principle of conduct. This was probably my earliest guiding principle for identifying problems worth solving. Designing for the web is, by nature, designing for scale, and if you’re going to work on the web, it’s my belief that you should focus on doing the greatest good for the greatest number of people possible.

The best minds of my generation are thinking about how to make people click ads. That sucks.

— Jeff Hammerbacher, This Tech Bubble Is Different

There’s a moral flaw in utilitarianism, though. My professor posed an ethical scenario to illustrate the moral quandaries you can face if you adhere to pure utilitarianism:

Imagine you’re offered a position researching chemical and biological warfare. It’s against your principles, but you’ve had poor health, no other job prospects, and your family is suffering without financial support. If you don’t take the job, a peer who revels in the work will accept the position.

It’s a tough position to be in. If I take the job, I would be going against my own moral principles and contributing to a field that will likely result in the deaths of thousands, perhaps millions, of human lives. On the other hand, there’s no guarantee that my research will be put to use, and even if it is, am I culpable for the actions of military leaders? Without any ethical guidance, the most utilitarian decision is to accept the job because there is no guarantee for other offers of work or that my work will directly result in the loss of human life.

Problems that matter should adhere to your personal morality.

utilitarianism needs to be offset by considerations for the minority, for the individual, for the humane and the just, which leads me to my second principle for evaluating whether a problem is worth working on: it has to adhere to your personal morality. Principles of right and wrong can be quite subjective and malleable, but I believe that trusting an individual to honor their conscience is the best counterbalance we have to the faults of utilitarianism.

. . .design isn’t just about problem solving; it’s about creating a more humane future.

— Dan Saffer, The End of Design As We Know It

If solving a problem is not in line with my personal moral principles, then I shouldn’t spend my all my waking hours working toward a solution. When I took a job at an energy startup several years ago, I did so because energy efficiency is not only utilitarian, but because I believe solving for it is morally correct—I felt compelled to make a positive impact against climate change.

Producing meaningful work requires viable solutions.

There was a problem at that energy startup, though, which prevented many employees from being successful in their work. That problem was viability—how to determine product/market fit for a solution—and it’s my third criterion for determining problems that are worth working on.

At that startup, the mission, business models, and products were not aligned. That resulted in a lot of smart people spinning their wheels on projects that would never launch or that would close down shortly after launching. We didn’t have a process in place for hypothesizing and evaluating product/market fit, and so we couldn’t design and build products that had customer value. I couldn’t have known this would be an issue when I accepted the job offer, but then again, it isn’t easy to determine viability at a company like that, which experienced tremendous growth and tens of millions in revenue year over year, and went on to IPO. However, for every startup with revenue, there are thousands more without a business model, and those are quite easy to spot.

Effective startups should have a business model from day one.

There’s a strong chance you’ve used Slack or have at least heard of it. Remind is like Slack for K–12 teachers, allowing them to connect with students and parents outside the classroom, as well as with their colleagues. The problem they’re solving—significantly better communication between teachers, students, and parents—is one we can probably all agree is utilitarian and morally upright. As of this year, over 35% of teachers in the U.S. and 1.5 million teachers globally use Remind.

I admire what Remind is doing, but the reality is that you can’t run a business on free. This brings me to my fourth criterion for evaluating whether a problem is worth working on: sustainability. In other words, how can a company generate revenues and then increase them toward profitability?

Longevity is not a goal in itself; it is a bi-product of taking on a big problem.

— Khaihan Krippendorff, Great Companies Solve Problems That Matter

For every venture-backed mission-driven startup, there are thousands more that are questionably utilitarian or morally upright (not to mention viable) and play the VC game to raise millions without any revenue strategy. I’m a firm believer that any sound business model will generate revenue from goods and services on day one, just like any brick and mortar; think how absurd it would be to open a restaurant, retail space, or beauty spa and just give everything away. Capitalism, at its best, allows an entrepreneur to sell valued goods and services at a premium and then pay a little back into the system that allowed them to achieve their success, so that others might have the same opportunity. The financial institutions and multinational companies that are propped up with government subsidies and bailouts would cease to exist without that support and cannot truly be called capitalist enterprises. Similarly, startup endeavors that subsist purely on venture investment are not sustainable.

Working on problems that matter improves your quality of life

There you have it—if you want to work on something that matters, if you want to determine whether a problem is worth working on, something that will bring you purpose and joy, you can apply the principles of utilitarianism, personal morality, viability, and sustainability.

When I think of companies that meet this criteria, household names come to mind: Google, Airbnb, Uber, Wikipedia. You might question these companies based on a lot of PR issues they’ve faced in recent years—Google for privacy, Uber for its aggressive business strategy and its flaunting of market regulations, and Airbnb for its number of guest horror stories. But each of these companies has undeniably redefined our day-to-day experiences and our thinking about what’s possible.

More often than not, if you find a company solving problems that are utilitarian, morally upright, viable and sustainable, you will find purpose in improving not only the quality of life for hundreds of thousands—as in the case of companies like Omada Health and charity:water—but your own quality of life. You will wake up excited to go to work each day, with teammates you love, challenges that stimulate you, great opportunities for professional growth, and a portfolio to set yourself up for success wherever your next adventure may be.

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