AI-powered Psychoanalysis: Journaling in Mem with author Tim Klein

Charting self-development, crystallizing the subconscious, and learning how to decide in Tim Klein's Mem journal project

DALL-E 2 prompt: “ A person lying on a couch in a futuristic-looking office with a psychoanalyst sat in a chair nearby taking notes, neon, digital art”

In January of this year, the writer Sheila Heti started a limited-run newsletter for the New York Times, made up of extracts from her personal diaries. Heti has been journaling for more than a decade, and amassed more than 500,000 words that document the events of her life, and her reactions to them. In the series for the NYT, Heti imported all of her diary entries into Excel and arranged each sentence in alphabetical order, in the hopes that it would "help [her] identify patterns and repetitions" across her life. "With the sentences untethered from narrative", she writes, "I started to see the self in a new way: as something quite solid, anchored by shockingly few characteristic preoccupations".

I was thinking about Heti's project as I spoke to Tim Klein, a teacher at Boston College and author, with Belle Liang, of How to Navigate Your Life, about how he has been using Mem to develop a curated journaling space that he hopes will help students to articulate their interests and values, and identify recurring patterns in their lives across time.

Klein, who also consults with high schools, colleges, and other organizations across the world, works in the science of purpose -- which he says "at a high level is like living a life that's personally meaningful, uses your strengths, and contributes to the world". If you've attached purpose to what you're doing in life then "all the research would show" you're probably more self-directed, have better relationships with your peers, are more engaged, and have a better mental buffer against the effects of stress. That's the thing, Klein says: stress can often be a motivating energy to achieve goals if you can see how those goals accord with your own sense of purpose in life. But "when you hit adversity, you're like, why am I doing this? And if you don't have a meaningful answer to that, then that leads to [a sense of] meaninglessness, which can [manifest as] depression, anxiety, all of those things", he tells me.

A sense of purpose is also a decision-making tool: a compass that can help keep you on track and aligned with your values when making important life choices. The challenge, of course, is knowing what is personally meaningful to you - the contribution you want to make to the world, and how to spot opportunities to make those contributions. So Klein wants to both encourage people - young people, especially - to reflect more on their lives ("the more you think about your life, the more likely you are to find purpose in it, right?"), and to put more institutional systems in place to encourage that self-reflection. "Right now", Klein explains, "we have a college and career navigation crisis on our hands, where more people are going to college, more people are in work, but no-one is successfully navigating school, work, vocation, and life". That's because "we've never taught people how to decide what to do with their lives. We tellthem what to do - get your grades, all of that stuff. But we've never taught them how to decide".

Klein thinks giving specific language to what "a sense of purpose" might look like to an individual is crucial. Without breaking down and analyzing why something feels meaningful to you, it's often hard to think about how you can pursue careers and hobbies that will provide you with that sense of meaningfulness. He and his research partner Belle Liang have isolated four elements of purpose, which are as follows:

• Using strengths that feel like a core part of your identity, to be able to show up as your best self for whatever you're doing

• Having the opportunity to refine and gain new skills that you are motivated to learn and master

• Making decisions that align with your core values

• Meeting needs in the world that you personally care about.

"So essentially purpose becomes using my strength and skills to make a positive impact that aligns with my core values. Again, the challenge is you have to know what your strengths are. You have to know the skills you want touse, you have to know the values, you have to know the impact. So our work is around equipping people with the language of strengths, skills, values, and impact, to help them identify those core elements and then when they think about doing something in the future, they can go, OK, is this an opportunity for me to use my strengths? Is there an opportunity to gain skills I care about? Does it align with my values? Can I meet a need in the world?"

To equip them with that language, Klein starts with four of what he calls "compass" questions, that reveal a person's basic values, talents, and drives and naturally lead to the elements of purpose discussed above.

"So, how do you want to be remembered?" he asks me.

My answer: ideally, as someone who was loving, and as someone whose writing made an impact on people.

"OK, so heart and mind", nods Klein. "And how do you want to grow as a person?"

I tell him that I'm always trying to get better at setting boundaries, and not absorbing so much of my identity in other people.

The next question is trickier: what do I want to stand for, and what am I willing to sacrifice in doing so? We discuss the binary of growth versus stability, and I decide that I probably value change and new experiences more than security, even when that change involves difficulty. (As a friend once wrote to me, “I know you have an ambivalent relationship with comfort”).

Finally, Klein asks, what impact do I want to make? What problems do I want to solve? Here, I suppose my answer is similar to that of the first question.

I’m no stranger to psychoanalyzing myself, but there’s something very helpful about thinking in terms of these questions, and verbalizing my answers to them. As Klein and I are talking, I’m already thinking about how illuminating this kind of introspection could be when combined with Mem’s AI. If you journaled in Mem consistently using Klein’s language of purpose, would our AI be able to - in essence - surface things from the subconscious over time, by identifying latent patterns in your writings about your behavior and values?

As it turns out, that’s exactly what Klein is hoping for. He shows me a Daily mem he has customized to include not only a schedule section and to-do list, but also five questions that encourage introspection, including: what would make today feel purposeful? what impact do I want to make? Each question links to another mem that provides a vocabulary and definitions for answering these questions.

“So”, Klein tells me, “they might have all this stuff to do, but here we're trying to provide them with a vocabulary for capturing what feels meaningful to them. One week it might be self-direction, the next it might be self-care; it might be recognition, or social ambition, or whatever. And then the idea is that they use this vocabulary to journal in here and the vision would be that they're using this language over time to talk about it, and that vocabulary becomes a framework for Mem’s algorithm”.

He’s hoping that as students journal in Mem each day and accrue more and more entries that verbalize their values, it might help them be more intentional when, say, applying for a job. “Imagine you’re looking at the values of this organization [you’re thinking about applying to], and they say, we prioritize integrity and discipline. Then the idea is, you’d be able to go to your Mem, search for “integrity”, and see every single time you’ve talked about that value, how you’ve applied it and where, and then you have this whole information set you can use to help you decide on whether this organization is a good fit for you”.

Klein also has another template that he wants to use for this project that is for capturing "moments that matter". “So if you experience a little formative moment during the day then you can capture who was involved, what happened, where, that sort of thing. But then we're asking you to think - what exactly was important about this? How did the moment make you feel? What strengths did you use here? What skills did you leverage? We're asking you questions based around those elements of purpose to get you to figure out what exactly made this moment meaningful, you know?"

What Klein also hopes his project will encourage students to do is "connect the dots between disparate experiences" in their lives. Being able to "tell the narrative of why we're doing what we're doing" is really important for a sense of coherence and meaning in our lives, he tells me. That tracks with me: I'm quite a nostalgic person, but I generally find it a source of strength and stability, because it helps me connect my current sense of identity with all the past "versions" of myself. Being able to see how past experiences have shaped the person I am now helps me perceive more meaning in my life, rather than considering the me of the past as a stranger whose actions I cannot comprehend. (So, more of a “continuer” than a “divider”, to borrow the terminology of Joshua Rothman’s recent New Yorker article).

In higher education, though, learning management systems like Canvas or Blackboard make it difficult for students to synthesize knowledge across classes, or record insights that they can take forward with them. “You take a class, you do this reflection, you write all these papers and all of that information lives in the class itself. It doesn’t stay with you as a person as you advance in life”. By asking his students to capture and collect all their learnings and experiences in one folderless digital space, Klein is hopeful that they’ll be better equipped to find coherence across their lives. “The easier it is to make a coherent jump between one thing you’re doing and then the next, the more purposeful your work’s going to feel; the harder it is, the more you’re going to question everything, you know?”

In the future, Klein “would love to take people through workshops where we go through the importance of these elements of purpose, help people to articulate these things. And then we set them up in a custom Mem workspace prepopulated with all the vocabulary and definitions and so on, and get them journaling in there.”

The last big problem Klein hopes Mem can solve is the “Blockbuster video”-style decision-making process in higher education. “If you go on a website, it’s all categorized in alphabetical order. But now we live in a Netflix world. I’ve always had this idea - and Mem is the closest thing to it - of [a digital space] where students can identify the values they care about, the skills they want to be learning, the impact they want to be having, and over time that turns into an algorithm that recommends classes, majors, extracurricular activities that other people with the same purposes have found meaningful”. Kind of like collaborative filtering but for identifying meaningful pursuits. The reason they can’t do it right now, Klein tells me, is because the psychometric inputs simply don’t exist yet; they don’t have enough data to curate this experience. But the more people use his Mem journaling space, and use it consistently, the closer this gets to feasibility.

“You’re always more unreal to yourself than other people are”, Marguerite Duras once said - meaning that the sense of a solid, consistent identity is only a function of external observation.  But maybe less so in the world of enhanced introspection that Klein envisions.