Pamela Hobart on the Existential Sandwich


Baiqu: Welcome to The Browser Interviews, today I'm very lucky to be sitting with Pamela Hobart, who is a philosopher turned philosophical life coach, aka "the life coach for smart people," and mother of three.

Welcome to The Browser.

Pamela: Hi Baiqu, glad to be here.

What is a philosophical life coach?

Baiqu: So we talked about this a little bit before the interview. Life coach I think we're all familiar with. A philosophical life coach and life coach for smart people, what does that mean exactly?

Pamela: My background is in academic philosophy. I dropped out of a PhD at Columbia in philosophy about 10 years ago. So what I saw was that there was kind of this hole in the market in between philosophical counsellors, who are like philosophers you can hire to sit with you and like talk about moral stuff. And a coach, who's more like goals, progress, and accountability. So I had this idea that maybe people needed some mix of that because their productivity problems tend to be all mixed up with philosophical problems around identity, and what kind of life to live. And so I just launched my practice, life coach for smart people is kind of tongue in cheek, and that was about two and a half years ago. Most of my clients find me on Twitter, and I just kind of took it from there.


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Baiqu: That's really interesting. And I mean, without breaking confidentiality, what sort of people come to you for coaching and what sort of questions, philosophical and practical do they have?

Pamela: So I would say my clients, the demographic is all over the place because what they have in common is this intellectual approach to life, or a very cognitive approach to life. Many of them have tried regular therapy and liked something about it; they like the space to talk out loud with someone who got to know them. But also didn't like something about it, for instance, it's common that therapists would sort of validate everything you say rather than pushing back a little bit. So within the coaching orientation, the client is assumed to be well enough that it's appropriate to argue a little when that's necessary.

A lot of people who work in tech, kind of "first-world" problems like "oh, I have this job that's really great in some sense, it pays a lot, I can work from home, but also I can't shake that it feels like I am not doing enough or I'm not doing the right things."

How to have a more "philosophical-coach" approach to life

Baiqu: So leading into my first question, what would you suggest if people wanted to have a more philosophical, coaching, orientated approach to their lives and work?

Pamela: Yeah when I was thinking about this question, my impulse was to go with standard critical thinking type fair like you might have in a college class. They teach you about fallacies of logic, ad hominem, and all these things. But weirdly, and I didn't necessarily anticipate this, but from working with the actual clients, I often end up doing more emotional work then straightforwardly philosophical stuff. Because the biggest barrier to thinking clearly is actually being too embroiled in our emotions.

So one thing that I ended up recommending to almost everyone, and then I'll share with you here today is this book called The Happiness Trap: How to Stop struggling and Start Living. It's basically the short statement of the philosophy behind a school of therapy that's called acceptance and commitment therapy. And to make a long story short, acceptance and commitment (ACT) is the idea that our goal is not really to get happy or to find ways to be happy, but it's to find ways to tolerate the emotional ups and downs of life, and do what we value despite that. To find a way to do what we value first, not after some time when we theoretically get happier. So I ended up recommending this to almost everyone because we do what we can with the cognitive stuff, we sharpen the arguments, you put all the considerations on the table, and usually it's not enough. It's sort of necessary, but not sufficient. So whatever's left, whatever anxiety or uncertainty is left, is the emotional tasks.

Baiqu: Yeah a kind of strange abstract pursuit of happiness as if it's a destination. I often find happiness is not a place where once you get there, it lasts forever. It's interesting being raised with a Buddhist background, the philosophy is very much around the idea that life is full of suffering and pain, and it's how we approach it and how we, like you said, tolerated it rather than leaving it behind, which I guess is just not really possible.

Pamela: It's not possible, no. And this is part of why what I do is like a little bit hard to sell at times. I'm not going to go on Instagram and say "I can offer you clarity, transformation, and happiness." It's more a case of we're gonna mess with all these grey area things and maybe you'll feel better, maybe you won't. Send me the money.

The type of people who I know, even just like socially, mostly agree with what you're saying here about happiness is not really a destination and we have less control over it than we'd like. But to know that theoretically, and to actually live with it on a day-by-day basis, there's a big gap. But those are tools you can learn, and the name for that set of tools is usually something like psychological flexibility. To be able to roll with the punches and not be so rigid that you have to feel a certain way, and things have to be in a certain way to do anything. And if any of that is not in place, then your life is on pause or ruined, which doesn't work out.

How to evaluate switching costs and failure baggage

Baiqu: No. I hope this isn't a sore spot, but just as you were saying that I was thinking, a PhD is quite a big commitment to make in the first place, and you say you dropped out of your PhD. How was that for you?

Pamela: Yeah, I've not regretted it. I think that like many people, I wanted academia to be something it maybe wasn't. When I got to New York, I realised that I really loved living in New York, but what people had to do to sacrifice to stay in New York and also stay in academia was very extreme. You know like teach at five community colleges on Long Island. So when I saw the reality of what academia was and that it was kind of a bad fit for my strengths, and that the job prospects were poor, I just thought I'll figure out something else. But now it's a little awkward because I know that people from my academic days see me crop up like a practicing philosopher. Sometimes I get some self-consciousness about, do they think I'm a sellout? Or I couldn't do the hard thing so now I do the easy thing. But they're really very different skills. The skills involved with listening to someone and giving them space to think more clearly and tolerate their emotions and grow in that way is totally different than are you careful at researching, and can you make a watertight argument in a one hundred page paper?

Baiqu: Definitely. I think it's a very different kind of approach. Isn't it? And I think it takes a lot of courage as well to walk away from something that you're like, okay maybe this isn't for me. Because it's not always easy to do that.

Pamela: You know I'd like to take credit for that. But it's long enough ago that it might've just been youthful over optimism. But one thing I do invite people to think about is there's such a heavy focus on goals and planning, and this top down what are your values and your preferences, construct this whole complicated life that you're now going to enact and force upon the world. And it's less clear, but just as valid to be like, I know academia isn't right for me, I don't know what's next, but it's okay to not have a plan. It's okay to not have this very heavily constructed rationalist thing. You can choose as a deliberate matter to let more path dependence in your life and more serendipity?

Baiqu: Yeah, because life never really goes to plan and I think the last year and a half has been a very in your face example of how things don't always go to plan. And that's funny because, everyone's like, oh like I wanted to do this, but then it didn't turn out this way, I feel like I don't know what the next steps are. But the thing is, I guess that's always the case, it's just sometimes it's more extreme and other times less.

Pamela: I agree. I think we're not taught this. We're taught what do you want to be when you grew up? Ok do the steps backwards, get this job, what are you doing next year, you should have something to say for yourself. So it makes people more self-conscious than they even should be and then when the plan goes awry, which is much more often than not, whether it's something big or something small, the switching costs are higher. Like you need a whole new narrative around it and you get all this failure baggage and some of that's avoidable.

What is an existential sandwich?

Baiqu: Yeah switching costs. That's very, very true. You were telling me about this really interesting article about this relationship between the practical stuff and the big moral philosophical stuff, and it being kind of like a sandwich. So in that vein, I'll ask you another question from my list, which is how do you cope with an existential crisis? Can you tell us a bit more about the existential sandwich?

Pamela: Yeah, the existential sandwich. People show up and they think they have a practical problem, like they procrastinate, and then it turns out that not only do they have regular challenges to doing the work, but they have questions about are they wasting their life? So you can tell them to download the productivity app, but that doesn't really touch the existential thing. So there's a bit of triage - maybe you have to do a productivity thing, but we're also going to talk about the existential thing. I mean, full disclosure, I don't think existential crises really get solved, and it's one expectation that I try to set with clients about what we're able to do. Like "what is the meaning of life?" - it's not answered. And it may even be an ill-formed question if the meaning of life is not something that is a sentence. If it's a feeling or an attitude that life is meaningful, then any sentence you offer, like the "meaning of life is love" or "family" or whatever, is going to fall short.

But there are two books that were really, really formative for me when I was going through what you could call an existential crisis a few years ago. My father was dying of brain cancer and this took about a year. So it was horrible because there was no real question about where this process was going, but it was also prolonged. I did a lot of reading during that time, which you could call bibliotherapy. And the two books that were most helpful to me, one is actually a kind of a Buddhist book, it's called The Five Invitations is a book about learning from death about how to live fully, which is of course like a cliche. But if you try to unpack what you learned from death about life, what is it? And so this author is very well placed to explain that because he is the founder of a hospice in San Francisco called Zen Hospice, and he's a Buddhist. So he has very many rich anecdotes about people dying and what he learned from that, and his own illness. So I had a good wallow when I was reading this and trying to make sense of death for myself. And it might be a different experience to read when someone you love is not dying, but I think it would be similarly useful.

The other book that I've recommended pretty frequently for existential crisis is called Seven Ways of Looking at Pointless Suffering. It's received less popular press than The Five Invitations, Five Invitations was like an airport bookstore kind of book for a minute there. So it's kind of an academic work by an academic philosopher, but what's really great about this one is that it's not an argument about suffering is actually good because XYZ, or suffering is actually terrible and life isn't worth living. Instead, the author Scott Samuelson, who's just like the most sensitive and well-read man, he takes the reader on a tour through many different perspectives on suffering that are historical, from Antebellum slavery, and jazz, to the Bible and Job. So it's a very rich sort of regular book and not a dry academic thing, even though it contains arguments within it. And the core insight of Seven Ways of Looking at Pointless Suffering is that humans have always faced a choice between either fixing the suffering or facing it, fix or face. Especially as technology has improved more and more, the urge is to fix. Like fix the disease, fix the poverty, get your coach, make it go away. And a lot of that's quite good, we wouldn't reject modern medicine whole cloth or anything, but the more we fix, the more atrophied the capacity to face the suffering becomes. Because they're totally different orientations. And this is some of what is gotten at in the Atul Gawande book that was really popular Being Mortal, that was about how a lot of these end of life treatments do not prolong life at a reasonable quality. They just sort of prolong your death. So it's something that we can cultivate deliberately - the ability to face some of this stuff and not be avoidant, not try to ignore the feelings or swish them down. But it is a task of a lifetime.

Baiqu: Yeah, it really is the task of a lifetime and I feel like I have so many questions, but people come to you, or go to a therapist when they are feeling inundated or overwhelmed by stressors in life. I think also, maybe we have a tendency to remember the pain more than we remember the joy. Do you work to guide people to experience the highs and to recognise the joys as well as facing the pain and the suffering?

Pamela: I think it's quite complicated and individual, because some people just naturally or genetically seem to be quite volatile emotionally, where they do get very big highs and low lows, not to a degree that you would call it bipolar, but just their space within the ordinary bell curve of some people are more fluctuated, and some people are more flat around their "happiness set point," which is a idea that we do have different baseline happiness levels. Happiness in the kind of momentary sense and that that's rather difficult to change. So I think as an individual, it helps to have the self knowledge are you ever going to be the even keel person or is it more like we're working with it in your kind of oscillations. And if you're an oscillator, there may be room to enjoy the highs more, even while realising that you can't hold onto it, you can't save it for later. It kind of passes.

And yes, the negativity bias is real. Especially since a lot of negative things are sort of momentary or like something happened, and a lot of the satisfactions of life are not specific. It's just like the satisfaction of sitting around your house with someone you love, or doing some work that was meaningful to you, but that was not particularly memorable. Another book I was going to mention today that helps to explain some of these things from sort of an evolutionary basis is, Good Reasons for Bad Feelings. So people joke about evolutionary psychology or evolutionary explanations being kind of armchair, but there are real ones, there are people who do this work. So this book is another book that straddles the academic and popular divide, where you could really not know much about academic psychology and read it, and get a much richer picture of why people might be the way they are with a negativity bias or different happiness set points and where it came from. That's not just speculative, that's empirical.

How to sound smart in a conversation?

Baiqu: Do you think having a background in philosophy helps you navigate life in general? And do you think that also helps you offer wisdom or come across as being smart in conversation with other people, by having some grounding in philosophy?

Pamela: I'm not sure if I would commit to the claim that literally every person needs to learn and be good at philosophy to live well. Sometimes people try to say stuff like oh, it's for everyone, or like the unexamined life is not worth living, where unexamined has a very particular meaning. But I do think that mental health and this emotional stuff are topics we run into online all the time. Like, oh, there's some study that says X, Y, Z makes you happier, do this, do that. So it's a very cluttered landscape that's very disjointed, and there are philosophical assumptions built into these things. Especially like cognitive behavioural therapy has been very popular for a while, and it has a particular view of what type of thing a human is. So the tools that you need to examine those kinds of built-in assumptions that are usually not surfaced, those are philosophical skills.

People when they're speaking and having a conversation with someone, especially maybe someone who's just an acquaintance or someone you've met. People behave most of the time on automatic mode, and this is cognitively easy. You know what you're going to say, you think you know what the other person's saying, you're not really listening fully. Sometimes people think that jumping in and responding quickly shows that you're ready, like you've thought of it all, and it is sort of an aggressive conversational stance. But what I find when I work with clients, part of why I can even have a business, is that good listening is just so rare. It's very rare to find anyone who's even like a B plus listener, but anyone who really wants to, can learn to be a better listener. So counter-intuitively, I come across as smart in the ways that my clients care about, not by running my mouth nervously and spitting out all these facts and ideas for their life. It's just by exercising care and then restating what they've said.

And I do a lot of thinking out loud. So sometimes there's this urge to not speak until you've decided what to say because you might say something that you don't really believe, or you might say something that they have an objection to. But it's a much better experience if you can take whoever you're speaking with, along for the ride. It offers more surface for connection rather than this shallow ping pong of the automatic conversation.

So it's completely opposite to the things I would have thought when I was back in grad school. In grad school, the way to look smart is you show up to someone's guest talk, you come up with an objection to what they're offering as quickly as possible, and then when the Q&A period opens, you throw your hand up like you're in third grade, and you dominate the floor and you ask this long convoluted question to score some points, and then play on your phone through the rest of it. It's the opposite of that in every way.

Best online purchase

Baiqu: I liked what you said about thinking out loud, because I've through this interview series met lots of interesting people and it's always been fascinating to me to get a glimpse into how someone thinks through their thoughts. And in a way that's almost more interesting to me than what they tell me in the end. Because everyone has a different process of thinking, right? Everyone has a different way of relating to something. And I think being able to have that touch point is really genuinely fascinating.

Now to take a bit of a sharp turn, I'm gonna ask you to recommend something that you bought online over the last like year and a half, that you would highly recommend.

Pamela: Yeah this is a good question. I buy a lot of stuff online because I have three little kids and it's very convenient. I can't give you just one, I could narrow it to two. They're both silly.

One is, there's this device it's called the Shark Vacuum Mop, and it's basically a Swiffer on steroids. You charge it up and it can vacuum, and the pad has a little bucket for the dirt. So when you're done with it, you just throw away the whole pad. This is like a humbling experience for me because my kids, every morning they wake up, eat a muffin or something and the floor is just a mess. I'm going to go speak with someone in like one hour about life and death, moral crisis, all this stuff, and you still have to clean your kids crumbs off the floor. Life is both. You know, it's not just being a talking head, it's also just attending to basic needs of yourself and your family. So I can't recommend the Shark Mop enough because without it I'm doomed. It will get the sticky stuff off. I really recommend it.

Baiqu: I see how it's contributed to your life.

Pamela: It really does. I think people are very quick to poo poo minor innovations. But some of these innovations means like you can not have ants and I can go do my work, and the spillover effect is that I can talk to someone about what's important to them, it allows me to be here today. You know, I think that reflexive "isn't it embarrassing that we have these things," is worth interrogating. And if someone said something like that to me in session like, "oh, I buy stupid things like X, Y, Z," I'd ask them do you really think that's stupid? Maybe some of them are, and some of them aren't. I don't know, this is my overthinking everything. I have a domain, I haven't done anything with it yet, is overthinking well.

Baiqu: Oh my God yeah. I would be the first jump on that

Pamela: The other purchase. So there's been this huge proliferation of wonderful at home manicure products because people stopped buying a salon. And I've been using a brand called Ohora. It's mostly sold at the site called Vanity Table. What they are is gel polish strips that are half cured in the light. So you stick them on your nails and then you cure it again. They don't shift, they last forever, they're really durable. I just love these things.

Baiqu: They look very professional.

Pamela: They're wonderful. I'm kind of an overthinking philosopher type, but I have many interests, also in vacuum mops and gel manicures.

Baiqu: I feel like I actually didn't realise how much I relied on other people for things like personal maintenance. And small gadget inventions do change lives. I had a chat with another guest and he was talking about a cooking thermometers, it changed his cooking life.

Pamela: You know, we can't rely on any, you know, you can't rely on the people in your life. You're not going to die or that you're going to be happy or anything, but like, can you have the thermometers so that you don't like food poison your kids? Yes. You can have it, buy it, good luck.

Favourite music, article, and daily habit

Baiqu: On to our last question, can you recommend a piece of music, an article that's stuck with you, and a daily habit that you practice?

Pamela: For music, I really like this band called Ratatat that makes funky electronic music, and the album that I listened to most of theirs is called LP4, is from 2010. I find this as really like an all-purpose album, you could like work to it, or you could be hanging out, or I go drive in my car. So this album, I never tire of it. So it's the best thing I could share with you guys today.

There are two online articles that I end up offering to people quite frequently. One is this article on Medium and I don't know the author, it's one that I found somehow and just has really stuck out to me, it's called The Deathbed Fallacy. And the argument in The Deathbed Fallacy is there was a very popular self-help book a few years back by a woman who was in healthcare, she had noticed that patients towards the end of their lives would frequently express the same regrets. Like not being true to myself, spending too much time at work and not enough time with my family, or not allowing myself to be happy, right? This happiness stuff is just it's fraught, like literally until the moment you die, people are now hung up on whether they were happy enough.

This is I think a good example of self help stuff that sounds completely like water tight. It's like, look, do you want to end up on your deathbed wishing that you'd been more true to yourself? No? You got to change something now. Regret proof yourself is sometimes how this is expressed, and I wanted to write about this myself, then I found this article, which was what I would have written, only actually probably better. And his argument was, the perspective you get on your death bed is retrospective, right? Like you know you're about to die. So it's only looking back, but we live our lives the other way, you have to make choices prospectively. And so it's not that being true to yourself or your family is bad, it's just that slice of perspective is not obviously more informative than the way you're already thinking. So this is an example of how thinking about things clearly, and philosophically, can put a check on common sense or shallower versions of advice.

The other article is by this guy who I would say he's like an learning expert, Scott Young, He blogs about learning and he has a course. He did a bunch of learning challenges where he taught himself how to program, math, all these things. And learning is very interesting because people are obsessed with education, right? What credentials you get or what your school is like. But they don't know anything about learning. They don't know what conditions are conducive to fostering motivation instead of damaging it, or sort of what ought we learn, and how do we think philosophically about what is even the right thing to be trying to learn in the first place? An obsession with education instead of learning. On that topic, I would read Ivan Illich Deschooling Society, but that's a tangent. So this article, The Neuroscience of Motivation is basically got this great metaphor that I share often about how motivation is kind of like water flowing down a hill. You don't have a giant tank of motivation that you just dispense on whatever task is in front of you. It's more of a natural phenomenon and if you wanted to make water move down a hill in a certain way, you'd dig a hole and make it easier, or you'd build a wall and make something harder. Those are the exact same tools we have available when you want to spend your time in a different way. Like, oh my life would go better if I spent less time in social media, more time reading, that's a philosophical question. And then how do you implement it? Is you make it easier to do the good things and you make it harder to do the bad things. That's all that's available. There are no magic tricks. So I invite people to remember this, you know, how are you making your water flow? Are you trying to push the water up the hill in your hands? It's not going to work.

Baiqu: And the final one is a daily habit. So apart from your Shark Mop in the morning with the muffin crumbs, is there a daily habit that you feel like is really good to practice?

Pamela: Yeah, this is a little mundane in comparison to all the philosophical fare in here, but if there were one habit that I try to do myself, and that I've recommend nearly across the board to everyone regardless of who they are, is really to choose what the main things you're going to do tomorrow, today.

This doesn't have to be complicated and it does not even have to be in writing. In fact, I have a small course on planning your time, it's called Anti Planning, it's for people that don't jive with regular productivity habits. So you don't even have to write it down, there's no app. But just morning, afternoon, evening, what are the main things you're going to do tomorrow? This means that when you wake up, you don't face those motivational barriers of I'm so behind I have too much to do, or I have 8 million things I want to do and I'm just going to think about it because it's not better to think about those 8 million things than to do one.

So choose the main points of what you're going to do tomorrow, today. It's actually sort of one of these existential partial-cures as well. We can't have overall clarity, but you can have this piece, wake up. What are you doing?

Baiqu: Yeah it's just a way of tunneling yourself right? So that when you wake up, you have this sense I know exactly what I'm doing.

Pamela: Absolutely. Every day, day in, day out. It's like the 80, 20 of time management.

Baiqu: Cool. Thank you so much for the chat. I'm going to try and think tonight about what I'm going to do tomorrow and I'll let you know how that goes.

Pamela: Good luck. Thank you so much.

Pamela Hobart

The Happiness Trap: How to Stop struggling and Start Living by Dr Russ Harris

The Five Invitations by Frank Ostaseski

Seven Ways of Looking at Pointless Suffering: What Philosophy Can Tell Us about the Hardest Mystery of All by Scott Samuelson

Being Mortal: Illness, Medicine and What Matters in the End by Atul Gawande

Good Reasons for Bad Feelings: Insights from the Frontier of Evolutionary Psychiatry by Randolph Nesse

Shark mop: https://www.sharkclean.com/

Ohora gel nail strips: https://vanity-table.com/pages/about-ohora

Ratatat LP4: https://open.spotify.com/album/72aBWaiTnk9GHNcuMuZwcJ

The Deathbed Fallacy: https://rikardhjort.medium.com/the-deathbed-fallacy-5e54d9639167

The Neuroscience of Motivation by Scott Young

Deschooling Society by Ivan Illich


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