Unpacking is a way of re-inflating all the little particulars that had to be flattened so your imagination could produce a quick preview of the future, like turning a napkin sketch into a blueprint

When people have a hard time figuring out what to do with their lives, it’s often because they haven’t unpacked. For example, in grad school I worked with lots of undergrads who thought they wanted to be professors. Then I’d send ‘em to my advisor Dan, and he would unpack them in 10 seconds flat. “I do this,” he would say, miming typing on a keyboard, “And I do this,” he would add, gesturing to the student and himself. “I write research papers and I talk to students. Would you like to do those things?”

more likely, they weren’t picturing anything at all. They were just thinking the same thing over and over again: “Do I want to be a professor? Hmm, I’m not sure. Do I want to be a professor? Hmm, I’m not sure.” Why is it so hard to unpack, even a little bit? Well, you know how when you move to a new place and all of your unpacked boxes confront you every time you come home? And you know how, if you just leave them there for a few weeks, the boxes stop being boxes and start being furniture, just part of the layout of your apartment, almost impossible to perceive? That’s what it’s like in the mind. The assumptions, the nuances, the background research all get taped up and tucked away. That’s a good thing—if you didn’t keep most of your thoughts packed, trying to answer a question like “Do I want to be a professor?” would be like dumping everything you own into a giant pile and then trying to find your one lucky sock.

When you fully unpack any job, you’ll discover something astounding: only a crazy person should do it. Do you want to be a surgeon? = Do you want to do the same procedure 15 times a week for the next 35 years? Do you want to be an actor? = Do you want your career to depend on having the right cheekbones?

High-status professions are the hardest ones to unpack because the upsides are obvious and appealing, while the downsides are often deliberately hidden and tolerable only to a tiny minority.

When you come down from the 30,000-foot view that your imagination offers you by default, when you lay out all the minutiae of a possible future, when you think of your life not as an impressionistic blur, but as a series of discrete Tuesday afternoons full of individual moments that you will live in chronological order and without exception, only then do you realize that most futures make sense exclusively for a very specific kind of person. Dare I say, a crazy person.

We tend to overestimate the prevalence of our preferences, a phenomenon that psychologists call the “false consensus effect”3. This is probably because it’s really really hard to take other people’s perspectives, so unless we run directly into disconfirming evidence, we assume that all of our mental settings are, in fact, the defaults. Our idiosyncrasies may never even occur to us.

whenever you unpack somebody, you inevitably discover something extremely weird about them. Sometimes you don’t have to dig that far, like when your friend tells you that she likes “found” photographs—the abandoned snapshots that turn up at yard sales and charity shops—and then adds that she has collected 20,000 of them. But sometimes the craziness is buried deep, often because people don’t think it’s crazy at all, like when a friend I knew for years casually disclosed that she had dumped all of her previous boyfriends because they had been insufficiently “menacing”

This is why people get so brain-constipated when they try to choose a career, and why they often pick the wrong one: they don’t understand the craziness that they have to offer, nor the craziness that will be demanded of them, and so they spend their lives jamming their square-peg selves into round-hole jobs.

On the other hand, when people match their crazy to the right outlet, they become terrifyingly powerful. A friend from college recently reminded me of this guy I’ll call Danny, who was crazy in a way that was particularly useful for politics, namely, he was incapable of feeling humiliated.

Unpacking is easy and free, but almost no one ever does it because it feels weird and unnatural. It’s uncomfortable to confront your own illusion of explanatory depth, to admit that you really have no idea what’s going on, and to keep asking stupid questions until that changes.

Making matters worse, people are happy to talk about themselves and their jobs, but they do it at this unhelpful, abstract level where they say things like, “oh, I’m the liaison between development and sales”. So when you’re unpacking someone’s job, you really gotta push: what did you do this morning? What will you do after talking to me? Is that what you usually do? If you’re sitting at your computer all day, what’s on your computer? What programs are you using? Wow, that sounds really boring, do you like doing that, or do you endure it?

It’s no wonder that everyone struggles to figure what to do with their lives: we have not developed the cultural technology to deal with this problem because we never had to. We didn’t exactly evolve in an ancestral environment with a lot of career opportunities. And then, once we invented agriculture, almost everyone was a farmer the next 10,000 years. “What should I do with my life?” is really a post-1850 problem, which means, in the big scheme of things, we haven’t had any time to work on it.

While you might think turning a yellow spot into the sun is mainly about strong execution, it’s equally about inventiveness and vision. There are situations where I wouldn’t have been able to describe what the person ended up creating. I had a version of what “great” looked like in my mind—and they surpassed it in ways I wouldn’t have been able to articulate in advance.

Arielle because Balsamiq is a newsletter sponsor. She shared a story that’s an example of turning a yellow spot into the sun. Here’s what she said: “Something I did that completely changed my career in its early years: I kept a work journal. I noted down decisions I made as an IC and manager, decisions my managers made, the outcomes, the impact, and what I learned. I wrote down those "inside thoughts" we all have during meetings. I wrote down the advice I HATED and why, as well as the helpful stuff. I wrote down pivotal interactions with clients, peers, leaders, and direct reports. I wrote down specific phrases different leaders liked to use. It was almost scientific—I applied basic tactics I learned in science/psychology classes about field observation. I still reference that journal to this day.”

Most people in her shoes would have said, “I need a mentor. I need someone to teach me strategy. I need support. I need to ask execs to explain their decisions and get their feedback.” Not Arielle. Arielle took a little (i.e. the lived experiences she was getting on the job, like all her peers)—and she turned it into a lot.

There is no set of rules (beyond the first principles I cover here each week) to memorize. It’s the same foundational principles, like knowing your assets/levers/constraints, asking the question behind the question, thinking rigorously, etc.

Before you move on to the next shiny object, consider if you’ve really squeezed every last drop of juice from your current endeavor.

People celebrate the strategy at the beginning and the outcome at the end, but if you look more deeply, there was usually good decision-making and craft at each step, which layered up to greatness. That’s why turning a yellow spot into the sun isn’t only for dramatic projects. It’s equally about elevating stuff most folks think of as boring and small.

Keep an eye out for anything that makes you stop in your tracks, even small things. Note what makes it feel magical and add it to your mental swipe file.

Horrible advice: find a way to blend your work with your interests so that you no longer understand where your core work hours start and the obsessiveness begins. Do this for > 12 hours a day, every day, holidays included. Tell your loved ones that you're busy with work, and take small satisfaction that what you just said was half true. Develop an unhealthy addiction to liquid stimulants and spring out of bed every morning with a burning curiosity that wont abate until you've tripped over enough hurdles to crush your enthusiasm for a few hours. Rinse and repeat for a decade until you're no longer a jack of all trades, but a master of most. Try to convey your interests to those around you, and failing that, retreat to social media where you will attempt to spin these as career developing STAR moments. Accept the disappointment you will feel in knowing that no one will appreciate the efforts you went to in achieving this level of tedious mastery.

fully regretting that you didn't focus more on that thing, oh and the other thing plus you're certain life would have been better for everyone if you hadn't dont quite so much of...

I started trimming hobbies. To pacify myself, I told myself that I am not stopping FOREVER, but just for now. It worked. Most of them are gone, I continue with a few, and I occasionally dabble with one or two that I put away.

Start with a group of interests that has the most overlaps in terms of skills or resources needed - call these compounded projects. Out of the compounded projects, start with the one that interests you with 2 weeks of effort. If you can’t make a significant progress in that time frame, you either lack the skills, resource, or interests in them. Move onto the next compounded project.

After you finish with the list of compounded projects, review the original list and prioritize the interests based on your experience. Create compounded projects again and go at it. Repeat.

being elastic with your interest and skills while jumping from project to project is the right approach.

(1) Start by being clear with yourself what things you're interested in knowing about vs. what things you're interested in doing.

The more work in progress streams, the more time you waste context switching. Being intentional about the things you choose to do and the order in which you do them allows you to do more things in the same amount of time than if you tried to do all of them simultaneously.

I had a lot of interests: coding, playing musical instruments, cars, woodworking, embedded systems, audio/video engineering, etc, but I had to pare it down to just a few after having had several bouts of burnouts. I'd recommend trying 200 interests at a shallow level, and eventually you'll find some of them are more interesting than others