• Stepping stones can act as one of three things in your life: platforms to jump off, buoys to keep you afloat, or ropes that hold you back.
  • Sometimes, stagnation can happen because you're saying "no" to yourself—not because of outside influence.
  • Institutions can provide a good blend between risk-taking & stability; individuals you associate with will be impacted by your values, as will you be with theirs; whether stepping stones are necessary depends on your core beliefs
  • No matter what, your life's stepping stones will alter your values in some way: your goals will change. That's okay. What matters is your ability to use stepping stones to find some goal: the ones that you pick are a reflection of the things you truly care about

A lump of turmeric, a pair of pens, and a $20 bill.

For my family, picking between these three items forms a small but relevant part of one's life. It's a ritual called annaprasanna—literally, first feeding. Apparently, it's a fairly common activity for first-generation immigrants: for Koreans, it might be called doljanchi; for folks from China, it's zhuazhou. Wherever you might be from, I'm willing to bet you had something similar in your childhood: a series of items are laid out, usually around your first birthday, and your extended family watches as mini-you picks one of them.

Whatever you choose is supposed to represent the path that you pick in life: choose the money, and you'll become a businessperson; the turmeric, a chef; and the pen, an academic. I don't remember the thing that I picked, but I do remember the disappointed faces that stared back at me 16 years ago because of that choice.

In South Indian culture, your parents are responsible for making the largest choices in your life up until you're willing to make them yourself: the ritual is supposed to give them their first insight into the kind of life you will live—and hopefully, their choices will align with the type of person you would've wanted to be.


For the majority of it, your life is largely composed of a series of stepping stones: places to jump off in an attempt to get to someplace further. If the end goal is stability in your life, then how do you & your family work backwards to find your immediate next steps?

The obvious answer is simple: you find stability in the immediate vicinity of your life. You strive for excellence in your academics, maybe do a couple interesting things in your teenage years, and then hop off to a prestigious college. That's the life most people like me tend to live: the product of a strange conflation between ambitious autonomy and a familial culture of self-security.

The first stage of my life's coming to a close fairly soon: university application season's finished, scholarship interviews are complete, and high school graduation is lurking right around the corner. I find myself asking a simple question at least a few times a day: what's next?

I'm incredibly privileged to have found a little optionality in my career: I've got a side project that can let me live for a few months, some amazing friends to bounce ideas off of, and a roof over my head. I can choose to have a life that doesn't include the things I'm supposed to have been building up for the past 17 years: there are so many new communities, education systems, and people to find.

I have to jump into an entirely new ocean over the next few months. What do the stepping stones of that life look like—are they even necessary?

"Who's saying no?"

Highly recommend watching Big Hero 6: the core premise of the movie aligns well with this thought dump—the best ideas are staring you in the face. You are your own worst limiting reagent.

For most of my life, programming existed solely as an individualistic hobby. Every spare second I had was a chance to tinker around in Vim, even if there wasn't anyone to do it with. After 5 years of loneliness, I became somewhat fed up: I'd heard of a tiny conference called Hack the North, and even though I was a year under their age limit, I decided to send in my application anyways. 3 months later, when I found myself in the midst of 2 thousand other hackers—and realized that my love for programming was something that had to be shared—I couldn't help but ask myself: why didn't I try this earlier?

A good stepping stone unlocks a new part of your life—the best ones will show you parts that you never thought existed.

But in order for a stepping stone to be necessary to reach a new point, you first have to believe that you can't get there of your own accord.

The smarter you are, the easier it is to be stupid: you're far better at rationalizing new ideas to yourself, and your core beliefs drive the events of your life far more than they should. In other words, it's incredibly easy for you to hold yourself back.

It's easy to think of life as a series of permissibility errors: papers can't be published unless you have people backing you; your startup can't be funded unless you went to Stanford; you can't go to a hackathon if you're too young.

Obviously, that last one was proved wrong 5 years ago. Heading to Hack the North showed me, for the first time, that the default answer for most situations is not always "no": the thing holding me back from that turning point in my career was not anyone telling me I couldn't do it, it was my brain imposing an artificial restriction on me.

Stepping stones are only necessary if there is a dam that you cannot cross without some help. The point that I'm trying to make is that those dams may often be ones of your own creation. I encourage you to think about a situation you're holding yourself back from and really consider why you're not doing it.

Oftentimes, the only one saying, "no," is yourself. Stepping stones—intermediaries to large-scale goals—are only necessary if the goals themselves require someone more than you to achieve.

The Harbourfront

You're ready to jump into the lake: you make your way down to the end of the pier, and the water seems warm. Even if you recognize that stepping stones aren't always necessary to be able to swim, how do you navigate the murky waters of the goal you want to reach?

Skipping stepping stones can allow you to move at a rapid pace—but can also leave you without a support structure for the tougher currents in your journey.

This is where our definition of a stepping stone begins to split: they're not just platforms to jump off, but buoys that can keep you afloat. It's impossible to make it on your own, which is why choosing your stepping stones with care is important: it's the difference between going with the status quo—continuing values that might not be aligned with your ambitions—and fulfillment.

Brick and Mortar

Institutions are our first line of defense against instability: they function as collections of individual sources of knowledge. They provide jobs, a ladder to climb up, and an instant social network—and as a result, function as the least dynamic kinds of stepping stones.

When trying to find a good kind of buoy to save you from drowning, it's important to have one that's effective at what it does: the organizations you associate yourself with should follow that pattern. Universities and large companies provide an incredible amount of existing human capital: but working at them usually means giving up some semblance of risk-taking (whether that's in the form of peer pressure or contracts). Startups are volatile—they're not as effective as buoys—but they preserve values: your likelihood of crossing the river isn't just dependent on floating, it's dependent on how fast you can swim against the current.

However, the large volume of human capital that institutions possess also allow them to function as accelerators extremely easily: the value for you as an individual doesn't have to be the goal that the network is working for, but the network itself. No matter where you end up, every institution is capable of providing a pre-vetted set of individuals with values (and given that you've ended up there, likely fairly similar to yours).

Blue Conversations

In some sense, the individuals we associate with are just mini-institutions: founders, employees, directors, and everything in between all contribute to one larger cause—and individually, they have their own networks and sets of knowledge. The people we meet in life have a great effect on the values we pursue, depending on our relationship to them: if they're ambitious, you're more likely to be ambitious.

Preventing yourself from sinking means having people outside of yourself that can have values that resonate with your struggles; you can't speak to an institution, but you can to a close friend. There's a kind of osmosis that takes place within friend groups, a local extrema of belief systems that drive collective behaviour.

The value of individuals as stepping stones lies in dictating the size of the river: they're not buoys in the same way that institutions are—while they can provide opportunity, their real value is one of emotion. In having friends that resonate with the gap you're trying to cross, you'll be able to shorten the path to the other side.

Finding these friends is somewhat more difficult, but it's another good place where institutions can parallel your ambitions.

NOTE: This is not to make a statement about the "quality" of people. I think that's  incredibly stupid: do not choose your friends as stepping stones, that's a horrible way to go about life. The point I'm trying to make is that the friends you have & networks you find can act as a support structure far more effectively than institutional stepping stones.


Above everything else, the most important stepping stone to fall back on is yourself. The whole point of this exercise is to understand how to cross a metaphorical river: whether or not you want to cross it, to achieve some goal in your life, is dependent on the kinds of core beliefs you represent.

Operational stepping stones—the processes you run in your life to get to a specific goal—are the least likely to change your values, but are the ones most likely to change of their own accord. Sticking to your own guns means that you can't get perspective on whatever you do: in trying not to dilute the thesis that drives you, you're effectively making it worse. At the same time, actively trying to change your core beliefs of your own accord means being intentional about several parts of your life: your behaviours will have a massive impact on the events that play out, allowing you to have the ability to cross the river faster. The river might not change too much without outside input (at least, it isn't likely to; we're very stubborn as a species), but you can try to give yourself a leg up in your mission.

Fording the river

You've decided to take the plunge, and you now have enough buoys to keep you afloat—and after skipping as many stepping stones as possible, you : the only question left is how to get to the other side.

Make no mistake, you haven't actually done anything yet—just getting to this stage means that you're effectively at Chapter 0 of your goal. Crossing the river is your goal, not the preparation of trying to get there.

This is where the final definition of stepping stones can come in: they can also function as ropes that hold you back from the goal you try to reach.

Inverted qualia

If all the colours in the world changed—along with your memory of the previous colours—would there be any point in attempting to tell anyone of it?

We all perceive colour differently, but it's impossible to know how those interpretations differ. The people, institutions and operations we choose to go through and associate with as stepping stones will all have similarly individualized values—unidentified qualia that we will never be able to understand.

As you progress further down the river, inching forward in pursuit of a larger goal, the values that you've interpreted out of past stepping stones might become outdated—your next raise may look different from ones of decades prior; the way you conduct an event may need to differ based on new circumstances.

It's okay for the type of river you cross to change over time: that simply means that your stepping stones are working—they're giving you reason to refine your fundamental values.


When you recognize that your values are holding you back, it's important to start the process of finding stepping stones all over again. You don't have to shed your existing ones—as we discussed in the last section, having buoys every step of the way can be powerful for your ambitions! But it's important to understand the kinds of decision-making tools you lack.

These three definitions of stepping stones ultimately build up to a larger framework for trying to achieve things that are positively validating for you as a person:

  1. Recognize that you want to attempt to do something in pursuit of a goal (get yourself to shore)
  2. Realize that in some cases, the only reason you haven't achieved it yet is because you're holding yourself back (line yourself up with the pier)
  3. If the task seems insurmountable or risky, use stepping stones to give yourself some security—through institutions, individuals, and operations (put the buoys on & dive in)
  4. When things get too difficult, try to figure out what stepping stones are weighing you down/values you lack in your life & in pursuit of trying to cross the river

Further Reading

If you resonate with any part of this, there are a bunch of books that dive into these ideas somewhat more tangentially—I've found a lot of value in them (and if you're in Toronto, happy to lend you an annotated copy of any one of these)

  1. Educated, Tara Westover — showcases an alternate perspective on this thesis: how conventional education can be interpreted in different ways. Being different & following your own goals does not mean doing things operationally different, it means being set in your values.
  2. Washington Black, Esi Edugyan — honestly one of the most heartfelt books I've ever read; discusses the value of people in shaping your values & how accelerating the person you are (i.e. shortening the river) can be done entirely on your own.
  3. Finite & Infinite Games, James Carse — discusses these ideas within the lens of play: the river doesn't have to be one of your own creation. Your goal can be to find the place where you can pick from any one of a number of rivers.