Creating a Laboratory for Work 🧪

reframing work as a job to a series of experiments

Why do we expect to get promoted, but don’t anticipate career pivots? Our default is to keep marching forward along a pre-determined trajectory rather than rest, wander, or even turn back around. As a society, we know how to celebrate predictable advances up the corporate ladder, but we lack the language, process, and institutions to welcome transitions in work. By transitions, I don’t mean simply going from one company to another, I mean a larger transformation from one line of work to a completely different one. I believe part of this disconnect can be explained by the stories that we tell ourselves.

Three stories

We devour stories of successful individuals. We watch their interviews, read their biographies, and buy their products. We study their childhoods, daily routines, and big decisions. We even map their habits, diets, and idiosyncrasies to our own.

The problem is most popular stories fall under one of two types.

The first story is about early commitment. A young boy or girl discovers their calling and with the help of parents, coaches, and mentors, they achieve mastery. Mozart composed his first piece of music when he was five. Serena and Venus Williams started playing tennis under the coaching and (home-schooling) by their dad at age four. Tiger Woods started golfing at age two under ruthless regiments prescribed by his father Earl. In the case of Mark Zuckerburg, his story usually starts when he was at Harvard and launched The Facebook, but he too showed early signs of genius. Zuck started tinkering with computers when he was 10 and his parents nurtured his curiosity by hiring a private programming tutor. Before starting college, he had built a personalized music website and even turned down an offer of $1M to buy it.

The second story is of the late bloomer. Like the first story, it shares a similar theme of dedication, but the characters don’t achieve notable success until later in life. In this story, the individual also discovers their craft at an early age, but they slowly chug along for decades until the world one day discovers them. Morgan Freeman started performing in plays when he was nine, but didn’t get his first break for another four decades. JK Rowling didn’t start writing the Harry Potter books until she was 32, but from a young age, her role models were always authors. Samuel L. Jackson didn’t get his hit role in Pulp Fiction until he was 46, but back in college, he switched majors from marine biology to acting and didn’t look back. As a little girl, Estée Lauder as fascinated with her mother’s skincare routine and studied her uncle’s work as a chemist, but didn’t start her company until she was 40.

I’m past the age of qualifying as a child prodigy, and I also don’t possess any outlier abilities, so the first story doesn’t resonate with me that much. While it’s possible I eventually fall under the second story, I have some reservations. I don’t feel like I’ve found the one thing that I obsess over, and if I’m being honest, I don’t want to wait until my 40s to know.

Fortunately, I think there is a third story. One that has more sharp turns and abrupt detours than the first two. The third story shows that despite years of uncertainty and multiple career changes, it is possible to achieve mastery. Jimmy Chin lived in his car for seven years as a climbing bum before his first documentary came out. Ed Thorp went from academia to counting cards in casinos to starting the first ever quantitative hedge fund. Steven Pressfield worked as a copywriter, schoolteacher, tractor driver, bartender, apple picker, and attendant in a mental hospital all before he published his first book at age 52.

The third story resonates with me given my trajectory thus far. I may have achieved some level of micro-success by getting into a good college and landing my first job as a PM, but I also realized that it’s not for me. It feels like a first world problem to have a well-paying, desirable job that you also no longer want. I didn’t just walk away from prestige and paychecks. I also shut the door on one of my few known paths to success.

Blank canvas

I thought that quitting my job would fill the void of meaningful work, but now I see that it was merely preparing the proper environment. Any form of removal, whether it’s quitting your job or ending a relationship, makes space for something new, but it isn’t the actual thing. I gave myself a blank canvas, but I didn’t immediately know what to create. I made space for something new, but… space is just space. You ultimately have to fill it with something.

For the first year, “being on sabbatical” felt accurate. In this second year, it doesn’t feel as right. I’m not traveling the world and I no longer have any lingering symptoms of burnout to recover from. Rather than continuing to be on sabbatical, “experimenting with work” sounds more accurate. Last year, when someone asked me “So what do you do?” I said “I used to be a PM and now I’m on sabbatical.” But now, if I responded with “I’m experimenting with work.” I think they would either be confused or mistake me for a wannabe startup founder. With this newfound framing, I’ve been musing on the general theme of experimentation with work and wondering why is it not more common. I’ve been asking myself why did I have to quit my job and live off of savings just to experiment with work. I’ve explored the limitations of existing methods of experimentation and envisioned new possibilities. I’ve come to believe that creating the conditions for each of us to explore and find what type of work makes us come alive is paramount for a flourishing society. I’m all for taking a break, going on sabbatical, and traveling the world. But while leisure and work can certainly overlap, they are not the same thing. And there is no amount of relaxation, hobbies, or even therapy that can replace the fulfillment brought by meaningful work.

Deciding what to do

As a society, we place a tremendous amount of pressure on young people to decide what they want to do. I had to decide my college major when I was still in high school. In my application to UC Berkeley, without knowing what it entailed, I chose mechanical engineering. Before my first semester was over, I realized how much I disliked physics and decided to switch my major to electrical engineering & computer science without ever writing a single line of code. Through a combination of coursework and internships, I gave the software engineering path an honest try, but I found it too focused on minute details. I’m lucky that I was able to adjust my trajectory within the safe walls of college and landed on product management before I graduated.

For others, particularly those in the pre-professional paths like law or medicine, it can feel like your fate is sealed before taking your first step on campus. At the age of 18, incoming pre-med students commit to 12 years of school and training (and debt) before any tangible, lived experience of what it’s like to be a doctor. With virtually zero years of “adulting”, incoming freshmen are demanded to know what they want to do for the rest of their lives, without a chance to try out different types of work. With a high amount of uncertainty, the odds are stacked against the emerging adult. We ask them to place a bet without knowing their hand or even what game they’re playing. School doesn’t prepare you to like your job. It only prepares you to get a job and even then, it doesn’t prepare you to do your job. It takes direct experience to know if a certain type of work is fulfilling.

College does provide some buffer to take different courses and meet other students, but the current instantiation of education falls short of reviving the Renaissance. Liberal arts institutions fail to provide a foundation of writing, history, philosophy, and psychology prior to students exploring potential career paths. On the other hand, pre-professional universities (like UC Berkeley) lean more vocational and less scholarly and rarely show students what the actual job is like. Instead of holding recruiting events and career fairs, if colleges simply sent every pre-business student a 12 hour long vlog of a day-in-the-life of an investment banker, then there wouldn’t be nearly as many college freshmen chasing that path.

Sometimes the allure of money and prestige leads people to pursue a job for the wrong reasons. For example, after winning millions as a professional poker player, my former coworker bagged groceries for a year. The over-fixation on monetary outcomes eventually led him to take a minimum wage job just to un-numb himself.

No amount of compensation reports, podcast interviews, or google searches will replace on-the-job discovering. This is backed by the 70-20-10 Model which states that ”individuals obtain 70% of their knowledge from job-related experiences, 20% from interactions with others, and 10% from formal educational events.”

If the majority of learning comes from direct experience, then how can we make it easier for people to try new jobs?

Experiment

To find meaningful work, we must experiment. The problem today is that it’s too difficult to experiment. Once you graduate and no longer qualify for internships, it’s hard to test out new jobs. With long recruitment cycles, equity vesting cliffs, and the stigma of quitting early, it feels too risky to leave a job before the one year mark. As a result, you end up sticking with your current job. Even if it sucks.

Modern work moulds people into thinking they should stay in their current career path because exploring alternatives would be too risky, expensive, or time-consuming. Since most people have a full-time job, the time to experiment is limited. With only evenings and weekends to spare, there’s only so much energy left for side hustles, passion projects, and creative pursuits. While it’s certainly possible for a side hustle to turn into a main hustle, it’s difficult to experiment and explore with most of your attention directed to your job. True experimentation acknowledges that finding your next thing may require the intentionality of full-time reflecting, wandering, and curiosity chasing.

Existing experimentation methods

I think we need a lot more ways to experiment with work, but that doesn’t mean there aren’t any existing options. However, just like a self-guided sabbatical, they don’t come without tradeoffs.

Rotational Programs
My first job out of college was at Uber where I was an associate product manager (APM). For those unaware, APM roles are highly sought after and have a lower acceptance rate than the most selective universities. My program accepted ten new grads per year and was structured as three 6-month rotations before you’d become a “real” product manager. As an EECS major who was terrible at coding but still wanted to work in tech, this was my dream job. Although I only lasted ten months before getting laid off in May 2020, I learned so much. The rotational aspect combined with the tight-knit APM community exposed me to far more than if I was just a normal employee. Not only did I have my own experience of working on two contrasting teams, where one was engineering dominant and the other was sales driven, I also absorbed what everyone else was doing. Every day, my cohort would eat lunch together and gossip about our respective work. This allowed me to piece together a mental model of which orgs, teams, and leaders were the best. We also had guest speakers, field trips, and shared our work with each other. If I had a normal job, I’d have only one perspective, but with ten others across two rotations, I became aware of twenty unique experiences, each one varying significantly across manager, product, coworkers, and org culture. While my experience in a rotational program was largely positive and prepared me well for my next job, I wish more of them existed. Unfortunately rotational programs seem to only exist for graduating students.

Employer-offered Sabbatical
Some companies offer tenured employees a paid sabbatical. Uber offered one and I think it was structured similarly to Automattic’s program which is a paid three month sabbatical for every five years. Although it’s better than nothing, I think it falls short of what’s needed. Since it’s only three months and funded by the employer, my assumption is that employees would rarely use the time to experiment with new types of work. Instead, they’re more likely to relax, travel, and play.

Externships
The top three consulting firms, Bain, BCG, and McKinsey all offer their own version of an externship. Instead of moving to the next client, consultants are embedded at other companies (often clients of the firm) for a few months. In theory, I’m a fan of externships because they’re the closest thing to post-college internships. But in practice, they’re more like a downshift from traveling and working 60-80 hours a week to a more humane schedule. I have a few consulting friends who have done externships and in each case, the primary reason to pursue it was to take a break from the intensity of consulting rather than to experiment with work. I can’t help but wonder if this is mostly just a way for overworked consultants to get closer to baseline.

MBA
The most popular option today is to get an MBA. While none of these options guarantee that you’ll find your next calling, at the very least, an MBA will get you the stamp of approval that most employers still value. I’m sure that being surrounded by a few hundred other high-achieving hoop-jumpers for two years can be a rewarding experience, but the question is at what cost? Getting an MBA is way more expensive than I thought. According to a current Stanford GSB student, all-in costs are around $150K a year, or 5x what I spent in my first year on sabbatical.

Fortunately, there’s a workaround for the high price tag. Many consulting firms offer to cover tuition in exchange for two more years after the two years of B-school. But there’s a conundrum with this loaded four-year contract. The type of consultant who would leave their firm for an MBA is also the exact same person who would not want to work there for another two years. If anything, the two year delay probably makes it worse.

If you want to get an MBA and can afford it, then it’s probably still a good option. My main gripe with this path is how much clout is associated with paying $300K to sit in a classroom, party, and travel for two years. People in search of a career transition end up taking student loans instead of exploring the less prestigious, but also less expensive options.

Others
I left out a few. Vocational (trade) schools seem promising, but if I’m being honest, they don’t appeal to the same crowd. The Entrepreneur-In-Residence (EIR) role within venture firms does fit the theme of experimentation, but there’s so few of them and there is also the upfront constraint of only venture-scale startup ideas, which is just one type of work. There’s also cohort-based programs, which I find promising because they can be delivered online and configured to be shorter and less expensive, and are accessible in both directions - meaning the course instructor could be anyone teaching anything and the students could also be anyone living anywhere around the world. Lastly, there’s a method that’s reserved for a special crowd. A few years ago at a VC firm’s holiday party, I was starstruck by the presence of a just-retired NBA player. When I asked him what he was doing here, he told me he was interning at the firm.

But even with all these existing methods, there’s still much to be desired.

Emerging experimentation methods

Apprenticeships
What’s old is new again. The origins of apprenticeships go way back to the Middle Ages when craft guilds were still a thing and your last name indicated your occupation (Baker, Smith, Miller, Taylor, Fisher, Potter, etc.) Under the guidance of a master craftsman, a typically younger, less experienced person would train alongside them in a workshop. Instead of a student in a classroom, which can only simulate, an apprentice in a workshop is exposed to the actual tools, process, and problems that the master craftsman must work with.

Apprenticeships are distinct for a few key reasons. The apprentice closely follows a similar path of development as the mentor. Compared to the modern manager-to-direct-report pairing, the apprentice-mentor pairing has a tighter alignment in career trajectory. A senior software engineer reporting to an engineering manager doesn’t necessarily want to become their boss who is a people manager and no longer codes. An apprentice wants to do what the mentor is already doing.

An apprenticeship views who the mentor is as the most important factor, whereas other forms of work don’t. When you apply to a normal job, you don’t even know who the hiring manager is. All you know is the job title, the company, and maybe a bit about what the team does. I’ve never heard anyone ever say that their manager was the #1 factor for them joining. But in an apprenticeship, choosing the right mentor is crucial. Although the actual responsibilities are likely to change over time, if the apprenticeship is a good match, then the apprentice will naturally be intrigued by the tasks.

New tools and platforms are making it easier for individuals to start their own businesses and share their ideas with the world. With the rise of solopreneurs and creators, alongside the erosion of trust in large educational institutions, I predict there will be a revival in apprenticeships. It may not always be called an “apprenticeship”, but I believe that this people-first orientation coupled with on-the-job training will become an appealing option to those seeking alternatives to student loans and corporate bureaucracy.

Permission-less Help
With the internet, it has never been easier to access information. With how connected we are, it’s become easier to reach people. In the old days, you had to know someone’s phone number to reach them. In the even older days, you had to know someone’s address and rely on physical postage for your letter to reach the recipient. Now, you can easily find anyone’s email or slide into their DMs. Even without direct access, it’s easier to get noticed. If you want to work for a creator, create some sample short-form videos of their content, post it, and tag them. If you want to talk to an author, write an in-depth review of their book and email them some follow-up questions. With how quickly information moves, it’s now possible to interview for a job that doesn’t even exist. Simply do the work first and then see if there’s an opportunity. It’s never been easier for fans to become collaborators.

Work Trials
More and more companies are incorporating an upfront trial period to their interview process. The best way to see how a candidate will perform on the job is to actually have them work on real tasks with real coworkers. I actually did a one-week long work trial in 2021 for a startup in LA. While I didn’t end up getting the job, the experience was illuminating. After a week of commuting to the office everyday, dealing with lackluster lunch options in the industrial district, and sitting in traffic every evening, I realized that although the work would be incredibly meaningful, the rest of my life would suffer. Hypothetically, if there was no work trial and I got an offer, it’s likely that I would’ve taken the job. I wouldn’t have experienced the real day-to-day and the shiny offer to work at an early stage startup may have overridden my hesitations around moving to LA and commuting to the office everyday.

Work trials today are viewed as the last critical step in the interview process, but as they become more mainstream, we may see them stand on their own. Right now work trials seem to serve employers as a better interview filter. In the future, the dynamic may become more balanced where job seekers will evaluate their prospective employers with just as much rigor.

Visiting Leader
Just like universities have visiting professors, companies could offer the “visiting leader” role. It’s always a big deal whenever an executive leaves or joins a company. Especially at large public companies, a change in executives requires weeks of PR and HR coordination to try and craft the right narrative. The stakes could be lowered with the visiting leader role. Imagine a CFO of a well-known company steps down. Instead of having secret interviews for their next big move, they could take on a much lighter, more exploratory role. The visiting leader would still get paid and sit in on important meetings, but they wouldn’t necessarily have to make any big decisions or produce tangible outcomes. Just like the other experimentation methods, they are there to learn and observe. In return, the CEO and other executives would benefit from the wealth of knowledge that they bring. After some time, it’d make sense to move towards a more concrete role or part ways. The elegance of the visiting leader is that the temporary nature of the role is assumed from the start.

Rotational Programs for Experienced Professionals
I think the same underlying principles behind new grad rotational programs could work for mid-level professionals. Imagine a software engineer who has been on the same team for three years and wants to explore new work, but also genuinely cherishes his or her coworkers. If given the option to transition to adjacent roles like product manager, data scientist, or product designer, I suspect the individual would accept the offer, even if it came with a big pay cut. A software engineer making $400K a year in total compensation is pretty common and with a 50% pay cut, they would still be making $200K.

Currently, the proper mechanics don’t exist because there’s still a stigma around wanting to change your job and also because compensation is rigid. Implementing some version of a rotational pathway for senior folks would allow companies to retain talent, but also retain knowledge. In the example, the software engineer has three years of team-specific knowledge. Even if they were to transition to a different role (and be mediocre at it for the first few months), the fact that they stay on the same team would be worth the temporary growing pains.

If I made an academy for experimenting with work

I envision a space where members arrive to heal themselves from burnout, take off their identity masks, but also do real work.

It would be different from retreat centers because even though there would be introspection, self-discovery, and cleansing, the focus would still be on each individual discovering what work they find meaningful.

It would be different from YC and other startup accelerators because the goal would be the exact opposite. Instead of narrowing in on an MVP by demo day, participants would go through multiple rounds of open-ended experiments. Instead of building one product for the external world, we would try to learn as much as possible about ourselves.

Most of the time would be spent on experimenting with work. An initial exploration scan would have members reaching far back to the depths of their childhood memories and ignored intuitions around what calls to them. Everything is fair game, regardless of required skills and projected pay. On your list, you could have quant trader and gardener right next to each other. Next, you would pick one to start. There are no wrong answers. From there, we identify the atomic unit of work. The action-oriented program would guide members through tight, fast loops of iteration with built-in reflection along the way.

• Accountability between peers would lack a sense of rivalry or competition just like how a professional swimmer might check in with an NBA player to see if they worked out, but wouldn’t ask to compare 100 meter free times.

• With each member going through a similar, yet different transition, there be a sense of community.

• But there would also be plenty of solitude to protect the state in which good ideas are born.

• Based on internal and external signals, you could move up and down a given track or switch.

• Unlike other schools, there are no grades.

• Quitting is not only welcomed, but is celebrated. Knowing what you don’t like is just as important as knowing what you like.

• As the program approaches its end, the finale would culminate in a grown-up version of show-and-tell. Bring your learnings and share them with the group.

• There wouldn’t even be a goal for immediate job placement. Members would be too busy experimenting with work to be applying for jobs.

I think this might be a great idea, but a terrible business. Typically, with a tuition-based model, you know what you’re getting. You go to college for four years so that you can slap a logo on your LinkedIn and name-drop your alma mater at networking events. But with something like this, the whole point is to enter the unknown. At the time you have to pay for this thing, you would have no idea what you would gain. Even with reviews or testimonials, they wouldn’t be very helpful because in this academy, each individual would navigate their own path rather than follow the same curriculum.

The other method is to take on some risk and bet on members’ outcomes through an income share agreement or partial ownership in future endeavors. However, it’s already hard enough to invest in companies. It’s even harder to invest in individuals. Investing in individuals who feel lost and are about to potentially start a new career sounds even harder to underwrite.

I’m not convinced there is any money to be made with this idea.

But that doesn’t mean it shouldn’t exist.

The closest thing that exists to this are fellowships. By giving out equity-free grants, programs like the Thiel Fellowship are able to provide the necessary capital for talented young people to drop out of college or never matriculate at all. But beyond the $100K check, what might count for even more than the money is the vote of confidence to dream big. Since the Thiel Fellowship has proven to be successful with its heavy-hitting track record, there have been other newcomer fellowships, but they all target young startup founders. What would it look like for others to be able to take a leap of faith and chase their curiosities?

Assuming that I had actual money to give away, there would be many possible configurations. High school graduates and college students are likely to move back home so they would only need $25K a year, but would also need more time and resources. Early to mid-career folks would need a bit more financial support because they’re likely living in a big city, but would already have basic professional skills and a sense of direction to head towards. Executive level folks wouldn’t need financial support, but assuming they’re older, they would need more encouragement to try new things, peer support to avoid feeling like the odd one out, and potentially help with kids. With the youngest group spread out across the suburbs wherever their parents live, a remote version makes the most sense. But with the older groups, I envision occasional in-person meetups because I find human connection a lot easier to form in real life.

Across the spectra of age, industry, role, and location, we need better ways to experiment with work. Whether you’ve just been laid off or have been experiencing burnout or simply feel stuck, there should be cheaper, more accessible ways to explore the unknown and find what makes you feel the most alive. I had to quit my job and live off of savings for over a year to experiment with work. My hope is not everyone has to do the same, because not everyone can do the same.