#19: Explore vs. Exploit

figuring out how to figure it out 🧐

Tetons // back in August while I was Exploring, alternating between sleeping in a tent outside and in my car

I’ve been thinking about this topic of Explore vs. Exploit for quite some time now. When’s the right time to go broad and explore a bunch of different things versus committing to depth, putting the blinders on, and “giving it your all”? I planted the seed for this post a few months ago when I created a new record in my Notion table that I use to track all the swirling concepts in my mind that might one day turn into a more developed thought. Since then, whenever I’ve come across an interesting read, I’ve copy+pasted into this page that has since become a long bullet point list of URLs.

I spend so much time reading other people’s writing which reads like they took AP English in high school, majored in creative writing in college, and now they read poetry for fun. Meanwhile, I’m fully aware that my writing is more plain-English, easy-to-digest, and more of a straight road than a winding maze. Exactly what you might expect from a dude in tech who grew up being good at STEM subjects and always felt like English class was an obligation rather than a facilitator of curiosity. What I think I am good at though is being able to connect the dots across ideas, things, people. Like today I was walking around Chinatown in Manhattan and first I saw a young couple selling beef jerky and croissants at super cheap prices (3 beef jerkys for $5??) to old Chinese residents in a hush-hush way so I eventually came to the conclusion that it must’ve been stolen goods. Then I saw a truck for a lobster wholesale distributor outside a seafood restaurant. As I kept walking, I started to think about markets; what creates a buyer <> seller relationship and how the structure of a market (whether it’s stolen bread or lobbies 🦞) dictates how each actor behaves in this relationship. These two separate markets made me think about an idea that I’m currently pondering.

Recently, I’ve been doing more dot-connecting and there’s multiple layers of this at play. I’ve been noticing quite a few people in a similar background as me go through some version of figuring out what they want to do with their life (call it a quarter life crisis). It makes sense to me because up until now our life has followed this pre-defined structure of schooling. Then you need to give it 1-2 years in corporate America of learning how to work and chasing the corporate ladder before you actually start to lift your head up. The second layer of dot-connecting is much more granular. As I started to comb through the internet for existing thoughts on explore vs. exploit, I noticed some thematic patterns. I’ve searched far and wide and have collected a bunch of musings from folks who are far more eloquent than me. But before I drop this knowledge, I’d be remiss if I didn’t first define what the entire concept of explore vs. exploit means to me.

Deciding whether to go broad and explore a multitude of things vs. going deep on one thing is the ever-present dilemma that we all face on a daily basis. Do we travel the world and learn more about what it’s like to live in each location or stay put in one city and build deeper relationships with nearby friends? Do we try that new restaurant or go to our local favorite that we love? Do we spend time trying new hobbies or keep investing in ones that we know we already enjoy? Whether you notice it or not, every time you are faced with this type of decision, it is of the explore vs. exploit theme.

The Explore → Exploit sequence

Why is it ordered like this and not first Exploit and then Explore? Well, first you need to figure out what you actually want to focus on before you can take the plunge. And the only way to get to the starting point of Exploit is to explore. From an Atlantic article ‘Quit your job’: "People who switch jobs more frequently early in their careers tend to have higher wages and incomes in their prime-working years” - Henry Siu, professor at Vancouver’s School of Economics. It’s also not just a two-part process of first exploring and then exploiting. There’s actually a bunch of other decisions that need to be made like deciding when to start exploring and when to transition from Explore to Exploit.

First, you need to decide when to start exploring. This part is straightforward but hard. I think you should start exploring when you realize that your current path is not what you really want. It’s so simple, yet difficult because most people don’t want to admit that, for if they did, it would feel like they’re throwing everything away and having to run full-speed ahead into the fog of uncertainty.

Spending years doing something that you hate to eventually make enough money to do something that you like is just procrastination disguised as ambition.

- Young Money by Jack Raines

You can't do something you don't know, if you keep on doing what you know.

- Expanding Awareness by Michael Ashcroft

So let’s say you realize that you need to start exploring. That doesn’t necessarily mean quitting your job. In fact, none of this has to do necessarily be about career at all. I could apply this same logic to eating food or music or books or anything really. I won’t go too much into what to actually explore, but the gist of it is: do what you enjoy and follow your curiosity.

The Hard Part: when to transition from Explore to Exploit

When in Explore mode, it can often feel exciting to be constantly exposed to new experiences and novelty. The nature of being a beginner means you’ll also observe faster learning rates than someone who’s been doing the thing for a while which turns into fuel to keep exploring. It can be tantalizing to keep chasing one new hobby after the other, in a never-ending quest to collect all the labels. To have multiple labels next to your name is often perceived as a status symbol because the implication is that you have both the time and the money to do not just each thing individually, but to have enough leisure time to do them all together. This incentivizes people to try a bunch of things once and then claim that they have all these new hobbies like badges on a jacket. But after having the time to try new activities and realizing how much time you have to invest in a hobby for it to become your craft, now I’m always suspicious when anyone describes themselves with more than five-ish hobbies.

A few ski seasons ago, I didn’t think there was much more progress for me to make in skiing because I could already ski double black diamond runs in the resort. After spending more time in the mountains, skiing steeper terrain at bigger mountains like Jackson Hole and Alta with better skiers like this one guy Steve who grew up skiing 100 days per season on the Vail ski team, I’m more aware of my skill level in an appreciative sense and humbled to know there’s still a lot of room for improvement. I don’t think I would’ve came to this realization if I continued to ski in Explore mode, going a few times per year on weekend trips. It took months of living in mountain towns and skiing (Exploit mode) to realize this and now I have a much deeper relationship with the sport.

It’s only a matter of time before it’ll be time to commit… and that’s the hard part.

With infinite options on the table and your entire professional reputation and future prospects in your hands, you’re forced to ask yourself: what am I going to do with my time and how do I make sure I don’t mess this up?”

Mind Mud by Molly Mielke

If you haven’t gone through a solid period of Explore mode, then from the outside viewing in, it can be confusing why anyone who’s experimenting, maybe also nomad-ing (which is another layer of this and a more literal form of Explore mode) would ever want to leave that type of lifestyle. After two years of living semi-nomadically, I’ve learned: Nothing is without tradeoffs.

I’ve been a complete and total free bird for the last few months — no one I need or owe anything to in sight. And guess what? All I seem to be capable of doing with these wings is spiral in tight sequential circles. I’ve felt lost and confused, unable to wayfind anything that might provide me direction or a sense of purpose. I thought that with freedom’s high-level perspective I’d subsequently be able to spot where meaning was hiding somewhere within me, but so far I’m just not seeing it. - Mind Mud by Molly Mielke

This sorta answers the question of why it’s important to eventually switch modes, but still doesn’t touch on how to know when is the right time to go from Explore to Exploit. Perfect timing doesn’t exist. Life is full of turns, false starts, sneak peaks, teases, foreshadowings, and unexpected outcomes. You can’t plan exactly what’s going to happen for the next 10 years, let alone 1 year because so much changes over time. For myself, if my one year plan plays out exactly like it was concocted, then I played it too safe. If your one year plan goes completely as planned then what does that say about yourself through the lens of change?

Morning routines are important to have. It’s nice to wake up and go through a few minutes of the same actions to get ready for the day. But if my entire life was a routine, then I would just be on autopilot. I visualize a football coach yelling “You’re just going through the motions!” although I could be moving correctly and doing all the right techniques, but there’s no sense of game-time intensity or the desire of a championship because it’s just practice. I’ve realized that there is no framework, worksheet, pros and cons table, or coaching session that can make me figure out what is the next big move I need to take.

I see us as always having two distinct options: you either 1) consider all possible games  and then use your won influence wisely, or 2) design a custom game for you alone to play  that shamelessly follows the nose of your satisfaction. Don’t try to play both at the same time or you’re bound to feel frustrated by failing to achieve influence or satisfaction.

- Mind Mud by Molly Mielke

An alternate approach is a non-linear approach. It is premised on the idea that life is full of randomness punctuated by sudden moments – crises and opportunities – with vast potential for meaning making, when our skills and virtues shine.

Rather than struggle to discover a purpose or vocation, we become people who can recognize and exploit opportunities to create meaning as they arise – resourceful and audacious people who live adventurous lives.

This means not waiting to find your story arc, but rather recognizing that there are stories that pop up which you can opt into if you recognize them and have the right skills and virtues. It is about being prepared for the call to adventure, and cultivating the ability to recognize it, rather than believing we can direct our lives from the perspective of some knowable, ultimate mission. - Unverified Revelations

Liminal spaces: where you exist in transition

I’ve tried describing how I feel as being in limbo, but then I realized that it’s not the best word because limbo is more of a floating state without any sense of direction. Liminal seems more fitting:

Liminality (from the Latin word līmen, “threshold”) is the ambiguity that emerges in the middle of a fundamental transition. Liminality is the “in-between”, where the space and the participants no longer hold their past status, but have not yet fully transformed to their post-transition self… Liminality can be applied to a person standing at the threshold between their previous way and a new way of structuring their identity, their time, or their community. Think about a student who just submitted their last essay but has not graduated yet; an employee who’s being transferred soon but has not started their new role; a couple who’s engaged but not married… Whether it refers to people, places, or societies, liminality provides a playground for transformation, a game with no rules we’re all invited to join, a sandbox for liminal creativity… What happens in liminal spaces? Doubt, discomfort, unfamiliarity, anxiety. But also growth, change, and discovery. Liminal spaces offer all of the ingredients for creativity.

- Ness Labs by Anne-Laure Le Cunff

I’m using the current liminal space as a vehicle to contemplate. It feels like I’ve just boarded a plane and now I’m waiting for takeoff. I’m staring out the window and I’m not sure when the plane is going to leave the gate and start moving towards the runway. It feels like I’m sitting out in the ocean waiting for the next set to come.

Commitment creates purpose

One of the main reasons why I’ve been ruminating about Explore vs. Exploit so much is because I could see myself happy and successful across multiple paths and I also know that I can ultimately only choose one. There’s the opportunity cost of committing to one path and then constantly looking over your shoulder to see if those other paths were the ‘right’ one. The conventional pattern of thinking is that you start with the mission and then commit to it with all your energy. What if it’s more of a feedback loop and that we create meaning out of what we commit to? Everyone wants their journey to make sense and be received as rational so we end up just telling ourselves stories to make it make sense.

In the stable periods of history, meaning was supplied in the context of a coherent communities and traditionally prescribed patterns of culture. Today you can't count on any such heritage. You have to build meaning into your life, and you build it through your commitments -- whether to your religion, to an ethical order as you conceive it, to your life's work, to loved ones, to your fellow humans. Young people run around searching for identity, but it isn't handed out free any more -- not in this transient, rootless, pluralistic society. Your identity is what you've committed yourself to.

- Personal Renewal by John Gardner

I’m not trying to send you out “on the road” in search of Valhalla, but merely pointing out that it is not necessary to accept the choices handed down to you by life as you know it. There is more to it than that— no one HAS to do something he doesn’t want to do for the rest of his life. But then again, if that’s what you wind up doing, by all means convince yourself that you HAD to do it. You’ll have lots of company.
- Hunter S. Thompson

You can't connect the dots looking forward…

You can't connect the dots looking forward, you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something - your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.

- Steve Jobs

The hard part about all of this is that nothing ever makes sense when you’re in the actual act of doing. And then it all makes sense looking back. Even as I type this, I’m having to manage risk and uncertainty. There’s no amount of books, blogs, speeches, articles that can be consumed to remove this reality.

If you opt for satisfaction: realize that while the plot’s shape will likely only be revealed in retrospect, defining your game’s guiding principles might be a good place to start. In my case: “I solemnly swear I will not be boring.”

- Mind Mud by Molly Mielke

Some more thoughts

All from Unverified Revelations (emphasis mine):

Our creative powers do not flow smoothly and evenly like water from the tap to the drain, but chaotically like a babbling brook going from the mountains to the ocean – with different shoals, rapids, pools and speeds along the way. Believing that our efforts must flow from smooth, even and continuous effort rather than coming in uneven bursts leads to much unnecessary guilt and anxiety about “wasted” time.

When the world is full of possibilities for meaning, we adapt ourselves for resiliency, flexibility and maneuverability. Resiliency, because we must survive long enough to take advantage of these latent sources of meaning, and flexibility and maneuverability in order to act quickly and appropriately when they come up. Instead of looking for a cause to devote your life to, you might try to become someone who is useful and level-headed in a crisis, who is well connected and makes friends easily, or who regularly has good ideas.

Your heroes became what they were by breaking genuinely new ground - doing things that those before them thought were unthinkable or impossible. To be like them you must surf the void at the frontiers of meaning – and discover meaning where no one else thought it would be, transforming harsh barrens into lush gardens.

This requires a certain amount of faith – a willingness to trust your values and intuitions rather than the well-worn stories dictated to you by culture. Recognize that the heroes whose lives inspired you did what they did mostly by going out into the unknown and doing what others thought was impossible. This is not, incidentally, a guarantee that if you do so you will succeed – for the world we live in to be a meaningful one, there must be uncertainty and risk.

But the non-linear approach to meaning is about becoming a certain kind of person, the person who will, when given a chance, act effectively to realize their values in this world, even if those values are not articulable except as a felt sense of meaning. It requires us to become developed along multiple axes of development: capable of risking it all in a dangerous, uncertain and beautiful world full of hazard and opportunity.

The word “non-linear” stuck out to me. Instead of being rigid, predictable, and planned, be loose, opportunistic, flexible. The same word appeared to me this morning from another person in a different context:

Sometimes (often actually) in business, you do know where you’re going, and when you do, you can be efficient. Put in place a plan and execute. In contrast, wandering in business is not efficient … but it’s also not random. It’s guided – by hunch, gut, intuition, curiosity, and powered by a deep conviction that the prize for customers is big enough that it’s worth being a little messy and tangential to find our way there. Wandering is an essential counterbalance to efficiency. You need to employ both. The outsized discoveries – the “non-linear” ones – are highly likely to require wandering.

- Jeff Bezos

Closing Thoughts

Even from four days ago from when I started writing this to now, a lot has changed to the point where I’m questioning whether it’s time to go from Explore → Exploit. The trope “You’ll never know until you try” is ringing extra loud today. One thing I do know is that writing this out has brought clarity and is just another reminder that I am doing this (blog) for myself.