Category Archives: _Essay 📝

Everyone’s career sounds more impressive than yours

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This is something I’ve observed ever since I started working. Everyone else’s job always sounds way more interesting, technical, or impactful than mine.

For example, when I worked at Trail of Bits, I spent years working on a research project for automatically finding crashes in computer programs using a technique called symbolic execution. Sounds hard! Oh, and the technique is designed for programs where you don’t have source code (sounds extra hard!).

In many ways the job was cool, hard, and technical but what was really uninspiring was that 1. the tool wasn’t actually that effective and 2. we didn’t have any users (probably because of #1). As my colleague Yan once joked, it sometimes felt like we were working on a “Fisher-Price Symbolic Executor”. I often felt like an imposter “playing” software engineer/researcher.

When I visited my old colleagues at Drift, who were working on a web product with thousands of users, I felt inferior. It seemed like they were all working on such impactful and real-world problems. Maybe it wasn’t quite as “novel” as what I was doing but it sounded pretty technical and not easy to me!

However, the way they introduced me to other colleagues that didn’t know me was “This is Mark, he’s moved on and now works on the real hard stuff.” I can only speculate that they felt the same thing that I was feeling. From their perspective, I was working on a super hard, technical, sexy research problem — unlike their boring, run of the mill web app.

This has happened more times than I can count in all sorts of settings, especially conferences, where you’re meeting a lot of strangers who all seem to be smarter than you and do very impressive things at highly functional organizations. (Unlike stupid me, doing unimportant stuff at the dysfunctional dumpster fire of a company I work for!)

The point is familiarity breeds contempt. Being so close to your work dulls the good parts and makes the bad parts stand out sharply in relief. Chances are if you joined their team or organization you wouldn’t find it as rosy as you picture it now.

How to be happy

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Note to self:

  1. Remember: You are already enough just as you are, right here, right now. You don’t need to achieve or do anything. 1
  2. Remember: The only competition in life — if you must think of it that way — is to know yourself as fully as possible, and act with maximum authenticity towards that truth.
  3. Remember: All things considered, you have it good — many around the world would kill to switch places and inherit every single one of your problems.

“What could go wrong” considered harmful

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The retort “What could go wrong” is one of my big pet peeves.

It’s often used in response to a failure of a complex system or operation. Sometimes the system had clearly poor design, making it warranted. But more often these comments reek of hindsight bias and carry an arrogance — as if the speaker could have easily avoided the failure if they were the one in charge.

It’s possible to construct that kind of retort for almost anything if you try hard enough:

  • “Flying massive metal tubes around in the sky filled with hundreds of people, what could go wrong?”
  • “Cementing metal wires into the mouths of children, what could go wrong?”
  • “Shooting lasers into peoples’ eyes, what would go wrong?”

But if you did so, you’d actually be wrong a lot — because there are many complex systems that function correctly for most users, most of the time. They function because many people have poured blood, sweat, and human ingenuity into them to make them reliable. And it’s often not intuitive that they can work.

Even if sometimes people are truly negligent and deserve it, I don’t find the phrase of net benefit to the culture. I consider it harmful because it ups the consequences of failure — a necessity for innovation — in exchange for cheap virtue signaling from bystanders who often have no experience in the domain.

So rather than assuming incompetence, let’s all be a bit more charitable. The world is complex and less intuitive than it looks.

Core devs are not necessarily product experts

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A common misconception I long held is that core devs of a product must be the top product experts.

The reality is that, as a core dev

  • there isn’t enough time to be both a dev and a user
  • knowledge of the implementation taints you and can prevent you from seeing the product clearly
  • it’s extremely difficult to focus deep on the details, and also view the product from a high level, holistically

Yes, you will have the absolute expertise on certain product behaviors or possibilities. But almost certainly never for the whole product at once; just the part you’ve been working on lately, where the knowledge is most fresh.

This is why it’s so important to surround yourself with “power users” — those that are untainted and unburdened by the implementation, and can use their full mental power to absorb and innovate on the product simply as a product.

These are often the people that find the most interesting uses and abuses of systems, that the core devs weren’t even aware of.

This can happen for any kind of product, including and especially programming languages. Many of the interesting programming “patterns” are created not by the developers of the language, but by “power users”.[citation needed]

Why we get busier as we get older

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There are a few main reasons why we get busier as we get older:

Adulting

As you age, you increasingly lose free time towards dealing with “adulting” type of tasks: taxes, paying bills, taking your car to the shop, researching insurance alternatives.

Relationships

We as age, we accumulate relationships. And while they have numerous benefits and make life worth living, they don’t come for free. They require time and energy to maintain — and at the end of the day, can become tasks on our todo lists. Even something as innocuous as an old friend reaching to send a text or schedule a call can, at times, feel like burdensome tasks to accomplish.

When you’re a child or teenager, the only people you know are your family and your friends (your first generation of friends). Since you barely know anyone, you don’t really have to keep in touch with anyone. Thus, more free time.

Hobbies

We as age, we accumulate interests, hobbies, and pursuits. These also don’t come for free.

As an adult, you begin to explore the world — reading books, picking up rock climbing, learning to paint, planning & taking trips one or twice a year. Your old interests don’t exactly go away, and there are always worlds of new interests to discover. Part of you feels like you should maintain or get back to some of those old interests you cherished so much. Another part is excited to get into scuba diving.

When you’re a child or teenager, you might have just one or two pursuits that occupy your time outside school. That lack of all the historical hobbies from your past = more free time.

Aging

Aging implies that your body will start to perform worse and more slowly, likely even breaking in ways. You’ll spend more and more time going to doctor’s appointments, surgeries, tending to medical conditions. It will take more effort to maintain your body through fitness. This all takes time.

Like many problems in life, the frustration at your seemingly decreasing time as one ages can be helped by setting expectations properly. Instead of feeling cheated as you feel your allowance of time seems to shrink year by year, expect it. Expect that by all logic, given the adulting to do, relationships to maintain, pursuits to keep up with, and the natural course of aging, you should have no free time at all — which gives you more reason to celebrate and appreciate the rare free moment when it comes along.

WIP: Should everyone be a leader?

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I’ve been thinking about leadership lately.

Many children’s programs are designed to foster leadership skills. Why? Does this imply that everyone should have leadership skills? That everyone should be a leader?

This interests me because for the longest time, I never felt like a “Leader”. I didn’t have anything in common with “Leaders” I saw. It didn’t resonate.

But I’ve realized the answer is yes. Everyone should learn leadership skills.

Even if you have no aspirations to start a company or lead a nation, leadership is everywhere.

It’s obviously present on smaller scales — in local organizations, communities, and workplaces. And even if you don’t aspire to be at the top, in any non-trivial organization, it’s still leadership all the way down. Even if you explicitly reject managing people, you can still find yourself as a leader — for example, being a skilled individual specialist carries leadership in its own way.

But less obviously, as soon as you start any kind of project or endeavor of any kind — guess what, you’re now a leader. Any kind of pursuit creates an opening for a leader. By default, the creator fills the role.

Examples of endeavors:

  • Starting a family
  • Co-creating a relationship
  • Organizing a party
  • Planning a trip
  • A creative practice

Without leadership, you can only ever be a “leaf” node, at the end of the chain. Without leadership, you can only ever be a consumer, a viewer, an audience member.

Even if you never start any endeavor, at the very least, you are the leader of your own life. (Which, by the way, is a creative project.)

So, yes, everyone should have leadership skills — not because everyone “should” be a leader, but because everyone already is.

Location Capital

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Traditional forms of capital include money, relationships, and health. There’s another I’ve discovered but never heard mentioned before: location capital.

Location capital is how much experience you have with a physical place on Earth. For example, if you have a lot of New York City capital, you’re the one that knows all the cool restaurants and bars in NYC. Friends ask for recommendations for the perfect spot for their birthday.

Everyone has location capital of some kind. But no one can have all the location capital for every place, so everyone (even Jeff Bezos) needs to decide what places are most important for them to build capital in.

It’s useful to be aware of location capital because it can affect your decisions around where you spend time.

Let’s say you’re alone and deciding whether to eat out at a restaurant you’ve never been to. What’s the cost/benefit? In exchange for money, you get good food and save time & labor (from not cooking/cleaning/grocery shopping).

But that’s not all — because you’re going to a new restaurant, you also build location capital. This is a one-time “boost” you get from going to a new place. On further visits you’ll still get some, but less.

Your decision will ultimately depend on how much you value food, time, labor, money, and location capital.

Location capital can also act as a hedge against risk. If you’re planning a date, preferring a new place will help make sure your time isn’t totally wasted if the date goes poorly.

I wish I was aware of location capital sooner. I used to prefer staying in over eating out in order to save money. But now I realize those decisions came with opportunity cost. And as a result, I’ve built less capital for the cities I’ve previously “lived” in than I’d like.

In general, I think it’s a good policy to always be building capital (mostly the non-monetary kinds). Location capital is an interesting form of it and being aware of it can influence how you live your life.

Remote onboarding

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The biggest challenge when onboarding remotely was getting a feel for the culture. Without this, you have to play it safe and act conservatively (i.e. maximally professionally), however it can be draining to always be so buttoned-up.

The two things that helped me feel more comfortable were:

1. Seeing “micro unprofessionalisms” during zoom calls.

One colleague had a large drawing of “No Face” from Spirited Away on his wall.

Another’s cat jumped onto the desk, and then a baby ran into the room.

Another just had a mess in the background.

All of these show humanity and personality. They let the new team member know that the tone is relaxed and that there’s no need to stress over behaving perfectly “professionally”.

2. Getting hints from coworkers about work norms.

I have a coworker that’s brutally productive. But one day he said, “I’m going to be out for a few hours this afternoon to get my trombone fixed.”

It’s easy to overlook such a remark if you’re been on the team a while. But for a new joiner, even small comments like this provide valuable insight into what is and isn’t acceptable on their new team.

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To make your new team member’s remote onboarding experience more comfortable, be intentional about showing humanity — visibly display things that are unique to you (and un-blur your background). Also, remember that your team’s culture exists, must be learned, and can be proactively communicated.

What you should know before taking your gap year (and lessons from mine)

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or alternatively:

I took a year off from my tech career and now I won’t shut up about copywriting.

It was probably going to hurt my career. I was fine with that.

The plan was cliché: quit my job, sell my stuff, spend nine months in Southeast Asia. Produce electronic music, read, and maybe code a little. Then find another tech job and pick up where I left off.

Fast forward twelve months. I haven’t set foot on a plane, I created a software product for DJs, and I’ve developed an obsession with copywriting and digital marketing. What happened?

In this post, I’ll share how, despite all expectations, my gap year catapulted my career into a far more exciting trajectory. I’ll debunk two myths society tells us about gap years and share a framework you can use to generate your own life-changing insights, whether you can take a year or a week off. Lastly, I’ll share advice for taking a gap year of your own.

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How to pick a market that will make you money

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As a founder, picking your market is the most important decision you’ll make. It will impact every aspect of your journey, from product development to sales, and ultimately determine how profitable you’ll be. A good market compensates for poor execution on your part, while even the best execution will struggle with a bad one.

So what goes into a good market?

The key attributes are:

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