I recently saw an article in The Atlantic about how philosophers are suddenly getting a ton of jobs:

The degree we spent two decades joking about is now commanding real salaries because AI companies need people who have thought deeply about ethics, reasoning, and what it means to be a person. That article got me thinking about why so many of us seem to be collectively starting over.

The Lore (And Why It’s Not The Full Story)

The lore is that millennials were sold a lie by our parents: that the American dream would make us feel fulfilled and happy. It didn’t.

I think that’s true. I also don’t think it’s the full story. Stick with me here, because I’m going to talk about AI. I know, I know. But because of AI, we’re all being forced to ask ourselves: what does it mean to be human?

We haven’t seriously asked that question since the Socrates and Aristotle days, when philosophers sat on stoops contemplating existence. Or if we have, it hasn’t been at the forefront. Now it is. And once you ask what it means to be human, the personal version of the question follows fast: who am I, really? And what life does this person want to lead?

You know who’s already asking those questions? The people starting over.

That’s why I say you’re ahead of the curve. While everyone else waits for the question to come find them, you’re already sitting with it. Honestly, I’m optimistic about a future where being human is the whole point. Humans just wanting to be more human.

My Identity Startup

I think of starting over as an identity startup. That’s why I’ve branded this year my R&D (Research and Development) year. I’ve written about it before (the goals, the existential accounting that comes with it), but I haven’t really explained why the branding itself matters.

It started with the people in my life asking, “Sarah, what’s happening?” And I didn’t know how to answer that question honestly. Because the honest answer was: I don’t know.

“I’m doing my R&D year” lets me say I don’t know while also satisfying their curiosity. It makes it clear I’m intentionally trying to figure it out. That’s my answer. Most people can’t fathom leaping into the unknown without a plan.

I couldn’t either. I yeeted myself anyways.

Branding this year as R&D made me feel less insecure about not having answers. It reframed the angst of this year as curiosity about who I am. The whole point of the year becomes asking questions, learning, growing, researching, developing (*wink, wink*). Not having it figured out isn’t failure anymore. It’s literally the job description.

Honestly, I needed permission to f around and find out. Calling this my R&D year gave me that.

Companies do this all the time, by the way. They pour money into R&D with no guarantee of a product, because they know discovery doesn’t run on a schedule and requires space to create and iterate. We give businesses that grace constantly. We almost never give it to ourselves.

Say You’re Doing R&D

So if you’re starting over right now and you’re not really sure what your plan is, maybe just say you’re doing R&D.

You don’t need the business card version of your life ready for every dinner party. You need a container for the question. A frame that turns “I don’t know what I’m doing” into “I’m researching who I am.” Same reality. Completely different relationship to it.

So what do you think? Are we all starting over because we were sold a lie, because we’re searching for the truth, or both? Tell me in the comments. I read every one.

Our Search for Meaning

We are all born with a “life’s task” as Robert Greene calls it in his book Mastery - top 3 most impactful reads for me. It’s called a “personal legend” in The Alchemist, “micro-motivations” in Dark Horse, a purpose, colloquially, a “calling” in some spiritual traditions. Each of these get at the same thing: why you are put on this Earth. Personal legend has always felt most true - it goes beyond what we are meant to do and includes who we are meant to become and leave behind. But, for purposes of this article, I’m going to adopt Robert Greene’s “life’s task” to keep things clear.

This search for meaning underpins most of our society’s major institutions and systems. And it’s a quest some of history’s most famous (and infamous) masters shared that fueled their pursuit of mastery.

I recently read “You Might Be a Late Bloomer: The life secrets of those who flailed early but succeeded by old age” by David Brooks in The Atlantic (referenced as “The Atlantic article,” throughout). And I couldn’t help but see the parallels in the books and teachings I’ve consumed over the years in my own search for a life’s task. I’m starting to see not just a pattern but an Arc of Becoming, unique to your life’s task, your achievement archetype, and your time horizon.

The Arc of Becoming - Stage One: Remember

Robert Greene’s, Mastery covers widespread anecdotes of renowned and underground masters. Leonardo Da Vinci, Charles Darwin, Mozart, and my favorite story: Teresita Fernández who demonstrates the power of intrigue. Greene conducted years of painstaking research, as he does for all his books, into finding the shared traits of masters. I won’t summarize the book here, as I highly suggest the read; but, I’ll share a major takeaway that starts the arc:

We are all born with a life’s task and know that life’s task by way of the things we are interested in and our inclinations. Some of us stay true to it and pursue it from a young age, others of us, most of us, begin to ignore it in favor of fitting in to social structure and the expectations of our parents. But, the good news is, it’s always there for us to remember. All we have to do is go back and recall what we loved between the ages of 4 and 7. 

First stage of the Arc of Becoming: remember your life’s task. The second stage is the hardest and the one where most of us get stuck for the rest of our lives: the pursuit.

The Arc of Becoming - Stage Two: Pursue

I loved how Todd Rose and Ogi Ogas’ Dark Horse breaks down the traits of those who achieve success by pursuing fulfillment (a.k.a., their life’s task). The traits make up a mindset of four principles:

1. Know your micro-motivations

2. Know your choices

3. Know your strategies

4. Ignore the destination

In terms of your life’s task and this Arc of Becoming: recall your deep-seeded interests (signaled at an early age), look for opportunities that are a good fit with your micro-motivations, understand the particular ways you learn and grow best, and, finally, set your sights on the nearest, steepest climb, not the peak (i.e., enjoy the process).

The pursuit starts at: know your choices. Part of knowing your choices is tossing the options that aren’t a good fit. And that can be really hard, especially when those options are handed to us by people and systems we are taught to trust. I was stuck at number 2 until I was 33 years old. Only in the last year have I graduated to number 3 with using my strategies to make content and build a business. I am in the early stages of number 3, to be honest.

Stages 1 and 2 in the Arc of Becoming require self-awareness, courage to leave, and deep faith in that inner voice, your life’s task.

The third stage of the Arc of Becoming is arriving. Not “arrival,” but the act of it - arriving. And there are 3 types of arriving.

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I worked in Strategy at Google, and I spent half my time on the team responsible for making billion-dollar decisions. I learned a lot about how large corporations decide where to invest their resources. And, no surprise, most leaders rely on frameworks (a majority are ex-MBB - McKinsey, Bain, BCG - consultants). A lot of frameworks end up as decoration, something to put in a deck to legitimize a decision made in the elevator between 2 leaders.

But there are some frameworks that I, dare I say, like. The 2x2 is one of them. I’ll explain why, using my decision to quit Google as an example. If you’re a paid subscriber, I’ve included a template at the end plus an exercise to help you think through your own decision.

I wrote a few weeks ago about the 4 things well-made decisions have in common: beliefs, consideration, prioritization, commitment. This is the first deep-dive in that series.

What a 2x2 actually is

Two axes. Four boxes. That’s it. You pick the two dimensions that matter MOST for this decision, make each one an axis, and place your options in the grid.

The whole method lives or dies on one move that’s easy to skip: choosing the axes. The axes are your beliefs, turned into something you can measure your options against. For example, when I was deciding whether to leave Google, the axes were not “salary” and “title.” Instead, fulfillment and time freedom.

That’s why this is Method #1 in the series. It puts the beliefs conversation before the options conversation. Get the axes right and the grid does most of the deciding. Get them wrong and the grid will confirm what you’re biasing towards or against based on fear or uncertainty.

When to use a 2x2

The 2x2 isn’t the right tool for every decision, and knowing when to reach for it is half the skill.

If you have two or three options and one dimension/criterion that clearly matters most, you don’t need a 2x2. Rank them in a table and go. The 2x2 earns its place when the opposite is true:

• too many considerations to hold in your head at once

• options that resist direct comparison (a job offer, a move, a year off)

• and when the options carry different tradeoffs, so comparing them feels like comparing apples to oranges

The above is true for most big personal decisions. So, 2x2s are often a big help for life choices.

The other reason to use it is less about the decision and more about you. A list is easy to nudge with subconscious bias. You can reorder a pros-and-cons list all evening until it agrees with what you already wanted. A grid is harder to negotiate with. When you have to place every option against the same two axes, including the option you’re quietly rooting for, the wishful thinking becomes visible on the page.

A big decision I wish I used the 2x2 for

I once picked from a predetermined set of options. I had two offers out of business school: Google or Adobe. If I’d put that decision on a 2x2 with honest axes, fit would have been one of them, and the company that actually saw me for me (Adobe) would have been in the top-right box instead of the rejection pile. I didn’t run the 2x2. I picked the shiniest mold. It took me 4.5 years to work my way back from that one.

The trap to avoid

The most common mistake is two axes that are secretly measuring the same thing. Salary and prestige usually move together; that’s one axis, not two. The second most common is keeping a third dimension in your head while pretending the grid still works. If you’re doing that, the hidden dimension is probably one of your real axes. Redraw with it. An example of this is if a feeling matters to you, like wanting low stress, to feel inspired, freedom. A feeling can be an axis, but just make sure it’s measurable (can you actually rank an option as low, medium, or high inspiration?).

Once you’ve picked your axes, draw the grid, label your x and y axes with your criteria, then plot your options as low, medium, or high against each of those criteria. The top right box is usually your winner.

If you have more than two in the top right, you may need to plot those against another set of criteria. Or, you may use one of the next frameworks I’ll share: Risks and Opportunities (Rs & Os).

The template + walkthrough

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I love making decisions so much that I dedicated most of my 2 years at Booth to studying it, …

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The last 3 years have ROCKED me. I have felt grief I never knew existed, mourning my old life (to this day). Levels of joy I didn’t think were possible. I’ve been in depressions that have lasted weeks where getting out of bed is the best I can do. And many other emotions in between. It is a rollercoaster upheaving your life to rebuild from scratch. And it’s the most fulfilled I have felt.

I’m not here to glamorize starting over. It’s really hard, and I have no idea how much longer I have in this wormhole until I start seeing some light at the end of the tunnel. But, I’m learning to enjoy the process, slowly. By realizing that the one constant in a transition is time.

Transitions happen over time.

Time runs parallel to transition, I can’t get away from it. It will always be right next to me, passing. Only recently, have I realized that in order to enjoy the journey of becoming, I need to relate better to time, get along with it, befriend it.

That’s the premise of this whole Substack - finding my way to friendship with time.

I am exploring lots of ways to get to know time and to appreciate it. To build our relationship. Some of those ways are experiential (like sitting and watching melting ice for 14 min and 10 sec), intellectual (reading on physics and philosophy), and mere presence - sitting with time, letting it move around me.

In addition to documenting my life transition real-time, I’m documenting my relationship with time. They’re twins and can’t be separated. I’m hoping that by sharing my journey, I’ll reach people who are in a similar period of their lives or contemplating taking the first step to plot twist their life.

I felt very alone when I took the first step into burning down my old life. I still do sometimes. But, I’m finding that the more I share, the less alone I feel. Not only because I’m finding community around a shared experience, but also finding my way back to myself in the process. And if you love yourself, you’re always in great company.

If any of this resonates with you, I hope you’ll subscribe, reach out, comment with your experience wherever you’re at in your rebuild.

If you decide to give watching ice melt a try, please let me know what you experience. I’d love to gather more perspectives ✨.

photo: MoMA

These two clocks, touching, are the exact same make and model, and synchronized (set to the exact sam…

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A Thinking Walk is as simple as it sounds: it’s a walk where you do nothing but just let your mind (and body) roam and think. What differentiates it from just a walk is when you decide to do it: when you are doom scrolling your brain. You’re on a loop, and you can’t think about or focus on anything else.

Thinking Walks are dedicated to letting your brain think about those loops, which I know sounds counterintuitive. The ceremony of a Thinking Walk puts a start and end on your loop. It tells your brain, “go ahead and exhaust yourself silly on this walk running those loops.” The interesting part, and what makes these walks so effective, is the second you tell your mind it’s welcome to freely loop, uninterrupted, it doesn’t want to anymore. And even if at the start of the Thinking Walk it’s doom scrolling, it soon stops because of the distractions of exploring your way around, watching the birds, smelling flowers.

I took a Thinking Walk on Sunday because I was depressed and sinking lower into my couch by the minute. I felt my body go lifeless, exsanguinated of energy. It was a battle to get myself to leave the house, but the promise of transformation after just ten minutes of a Thinking Walk, got me out the door.

Sure enough, I was graced with an interesting idea. I had gotten lost on my way home (I knew generally where I was but not what street I was on or what turns I took). I found myself on a street that captivated me with its beautiful lawns and flowers and homes. I thought, “wow, this street is incredible, how have I never seen this?” Turns out, it was my street and I was two minutes from home. Why did my street look so different because I got “lost?”

I have a theory: when you’re safe to get lost, you get to explore instead of search. Not everyone has that safety; I had the luxury that day. When you have the freedom to take unpaved paths, you not only see more, you’re present for the experience. When you’re on a paved path, following a map, you’re looking straight ahead or down at the GPS. You rarely stop to look up.

This has me wondering how we can feel safe to get lost in other parts of our lives. Like finding our way back to ourselves. And, I’m thinking that feeling lost on your way to yourself is exactly the point. It’s what we are meant to do. If we knew our way back to ourselves, we’d be looking down the whole way at the path, the map. We’d never experience the exploration of ourselves.

I’m going to try to let myself get lost more. To let myself amble and try things, to look up and around, so that when I get home to myself, I’ve seen the world first-hand and not just a map of it.

Tip: When you get an influx of inspiration and ideas, try to opt for a voice recording versus typing on your phone to keep the flow open. Something about staring at a screen takes me out of the flow of the Thinking Walk.

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At 5 years old, the ocean sparkled, forest…

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When I dig into that anxious, unproductive feeling, I find a dimming self-confidence. A shaking little girl in a corner of a dark room with the spotlight on her to make the right choice. Not for her, but for some disembodied panel of judges that sit in the part of her brain concerned with worthiness: “what would the people who are better than you do?” Brutal betrayal by my mind.

You see, I feel anxious because I don’t trust that the choice I made to sit by the pool is the right one. I don’t trust my decision-making. I’m not confident in what I want and need — everything I decide is wrong.

They say anxiety comes from inaction. I think it comes from passive decision.

Next time you hear the voice say, “you could be doing something else,” ask yourself what your choices actually are. Then actively choose. And if the panel in your mind tells you it’s wrong, ask “who says?” If the answer is “you said,” then double-check your decision is aligned to what you value. If you’re met with silence, then make that decision with trust and confidence.

You have agency and you are an active participant in your relationship with time.

I share more thoughts in short-form on my Instagram @sarahovertime.

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