Thank you to everyone who tuned into my conversation with Whitney Ladd Otto on Friday!
Whitney is a fellow executive coach to high performers, and a kindred spirit in many ways besides. Both of us draw on our backgrounds as mental health professionals, and as ambitious women who’ve taken circuitous paths to our fully-lived lives. Whitney thinks more in terms of managing energy, whereas I think more in terms of managing mindsets; but both of us fundamentally care about increasing our clients’ agency over the goals they pursue and the lives they build. And both of us are thinking a lot about how AI can be used to amplify (versus substitute for) that agency.
These intersections made for a wonderfully energizing exchange (aptly enough), which you’re welcome to watch above. Below are select excerpts from our conversation, with timestamps if you’d like to find them in the full recording.
Excerpts have been lightly edited for length and readability; ellipses mark larger cuts within a speaker’s turn.
The “builder’s mindset” origin story: who said we need ladders?
Whitney deftly drew out my biographical account of grappling with my own inner drill sergeant and Zen guru in graduate school. (0:01–7:27)
Whitney: The formula handed to a lot of high performers is faulty. And that formula is some version of: here, set these really lofty goals, get great education. Burn yourself into the ground going after those goals…
And when you reach those goals… magic will happen. There is a pot of gold at the end of that rainbow.
Gena: …Lofty but also kind of generic goals, right? Where you never actually spend too much time thinking about… what other paths are there and which ones might be better suited to me, given my temperament, given what else I want out of life, my strengths and weaknesses?
You’re on a ladder. And so now you just got to climb it….
Whitney: Right. Or you’re a sheep following the herd, and the pot of gold is on the other side of that hill. …I’ve been a very unhappy sheep at various times. Many of my clients are unhappy sheep. And so we’ve had to say: huh, I think there might be a different model or a different way to go about that.
And you and I have different vocabulary, but we were talking about a lot of the same things. I love your idea… about the builder mentality—not the drill sergeant, not the Zen master. So maybe you could speak a little bit about that, and then I’ll talk about how I talk about it?
Gena: Sure… for me, coming from the academic track, where my ladder was the PhD-to-tenure ladder that I was on for many, many years—my observations were very much around: wow, okay, so on the one hand, I can push myself to be more ambitious, but in this way that is really mean to myself.
Eventually I burn out and I rebel, and then I slack off and procrastinate, and then I push myself and yell at myself and tell myself I’m a failure again to get back on the horse. But the whole thing feels kind of slavish.
And a big part of what I noticed was that, in learning a bunch of the therapeutic tools that I learned in grad school—you know, it’s all “me-search,” right? We study psychology because we want to understand our psychologies. Certainly true for me—so I was picking up all these therapy tools that I could then use on myself. I got really good at doing acceptance and mindfulness practices and restructuring my negative cognitions, achieving a more balanced perspective, checking my perfectionism.
So I got very good at being okay with not getting the paper in on time… at being more accepting of the fact that this is hard and that nobody’s perfect.
But in the meantime, I also noticed that I wasn’t going for certain things, where what I really wanted to be studying was this kind of weird interdisciplinary thing that didn’t quite fit the mold of what the normal research project in my lab looks like.
And if I hustled a bit—in the sense of actually going to talk to a researcher on the other side of campus, and actually sending some emails, and making some bold moves to suggest a conference presentation, and despite feeling like an imposter, still making these strides to put together something kind of cool and unusual, and doing the hard lit-searching and fumbling around for words to articulate this pattern I’m seeing inbetween the fields—
There was this thing that I wanted, that a part of me was pulled to do, but I wasn’t doing, and I was making excuses.
And so I realized that, okay, sure, there’s this one terrible failure mode where I’m really hard on myself and I’m pushing myself toward whatever metric I have in my head as the one that leads to the pot of gold.
But there’s another failure mode where I’m opting out. I’m quiet quitting. I’m using these tools as an escape hatch to protect myself from some of the hard, scary, uncomfortable, messy work that my actual would-be goals would require….
And after working with clients and also seeing this come up for all of them, it’s like: wow, you’re also toggling between these two modes.
And I would even, with my clients: okay, so let’s not worry about the outcome. Let’s just focus on the process. Let’s just focus on your effort. And we’d be rating their effort, except the client would be like: okay, but part of the way that I measure effort is, is it actually resulting in something meaningful?
And if I’m ignoring whether I’m actually hitting the goals I want to hit—in some cases literally, because I was working with some student-athletes at the time—if I’m ignoring the fact that I don’t ever get to actually win a match, then we’ve lost the plot, because I love winning matches. That’s part of the point. [Part of] why I want to play this sport is because I really enjoy beating my opponent.
So I just realized: you know what? We need a third thing. Neither of these two is right.
They’re both assuming a low-agency framework where… the ladders are just part of the universe that we inherit. And our choice is: climb or stay on the ground.
But who said these are the only ladders? Who said we can’t build our own ladders? Who said we need ladders? Maybe we build a rocket ship instead.
And so that’s where the builder’s mindset came from. Very long answer to your question.
Whitney: …Yeah, a builder has agency. A builder decides what they care about and how they’re going to build it. And they’re friends with themselves in the process.
Be your own “chief energy officer”
We noticed some overlaps between my “builder” and Whitney’s “chief energy officer.” (7:27–13:12)
Whitney: For me, my builder is the chief energy officer. … I love the idea that we are all our own chief energy officer. We have to take on the role of the builder and say, I want to know what I’m building and I’m in charge of building. I’m in charge of this energy.
And I think, for me, the energy has particularly come into play because I work with a lot of women. And I think many women were trained: if you give your energy away, you’ll get the thing. It’ll come back.
Gena: Yeah, which is so backwards. Our energy is our most precious resource. But it’s so interesting, as I’m hearing you talk about this, our energy is also [a] self-perpetuating resource. If we’re energized by what we’re doing, that tends to generate more energy [and vice versa].
Whitney: …And as we’re stewarding, negotiating, doling out our energy, we’re tracking what’s happening. We’re tracking what’s happening to us and we’re tracking what’s happening outside of us.
Gena: We’re taking ownership of both. Just like we take ownership of our team, of our product.… This is something I say routinely to my founder clients. Your first customer, your first investor, your first founder, but also your first employee, your first product is you. And it’s the only one that you can’t fire.
Are you motivated? Are you energized? Are you aligned with what you’re building? Do you have fuel in the tank? If you’re not attending to that, you’re not being a good CEO, quite simply.
Budget energy for the hard things
We discussed how managing our energy includes budgeting our reserves so we have enough in the tank for whatever needs doing. (26:24–28:43)
Whitney: My days of working in addictions as a therapist really comes in handy, because in that world, you’re saying: okay, here’s this hard thing you’re going to have to do. Let’s organize your energy so that [you] can succeed at that hard thing…. we’re going to make sure that you have resources. We’re going to make sure you have a plan for and a plan after. We’re going to make sure you don’t exhaust yourself before you get there.
So it’s thinking about your own days that way. Because I think people think, oh, I’m just supposed to be able to grind all day long… We need to steward our energy. And part of stewarding things is understanding them. So if you are hot at 4 p.m. to be focused, you need to take advantage of that. If you can’t even speak full sentences at 9, you need to be aware of that…
Gena: …[Like] recognizing that actually it’s lower value for me to do whatever little half-assed bit of work I will do half asleep at 9 p.m., versus watching a movie or getting to bed early or somehow rejuvenating myself will lead to so much better work in the morning that actually, even if it’s just trying to do my best work, I’m so much better off taking this hour off.
Whitney: So emboldening people to take that seriously. I mean, one of my clients is like: oh, I’m distracted and I’m irritable. And I’m like: are you taking any breaks? Nope. Oh, right. Yeah.
There’s other things we work on now, but she started taking breaks. That cleared up a lot of those problems.
So a lot of it is just understanding our humanness…
Gena: Your brain and body use energy, and the energy runs out, and you need to replenish it somehow.
Curiosity as “one of the simplest energy retrievers”
We talked about energy as a depletable physical resource, but we also talked about how our access to that resource is heavily mediated by our mindsets and psychological states. (35:38–37:36)
Gena: So I guess this is still pushing at the edges of my own understanding of how we use energy. When is it literal, and when is it a metaphor?
How often do you see something that used to be depleting become energizing for someone? Or is that just not a thing? Is that just not really a useful lever?
Whitney: I think it’s a thing. Let’s take visibility. “Ah, I can’t be visible. Here’s why. I’m scared of visibility. Visibility is dangerous.” All my reasons.
Gena: I’ve got all these assumptions about it.
Whitney: Yeah. And then, if they want something that requires visibility, we will work towards it. And then it can be quite energizing.
Gena: It’s mediated by our beliefs and our implicit priors.
Whitney: So say that again, because I think that’s really important. That’s a great, simple principle of energy.
If I’m like, “Whitney, what were you thinking? That was such a dumb decision.” What do you think is going to happen to my energy?
Gena: But if you’re like, “Whitney, what were you thinking?” [said with an air of curiosity.] Even just your tone—literally even the words can be the same. “What was I thinking?” Where you actually really want to know, and it’s a curious thing to find out, right?
Whitney: I think curiosity is one of the simplest energy retrievers, gatherers, open-uppers there is.
Use AI to find paths you couldn’t see
As we turned to the question of how AI can amplify our agency, I brought up one of my favorite applications of LLMs: mining concrete examples to show what’s possible. (20:14–24:56)
Gena: One of the use cases that have been far and away the most impactful for me and, I would say, for my clients … is sourcing examples.
So whenever I’m talking to a client, or when situations come up, like: “I am never going to be able to hire for this role because I don’t have the network and because I’m such a late bloomer and because I have all of these inadequacies.” …I’ll go to [ChatGPT or Claude] and I’ll say, okay, can you give me ten examples of the following: founders who didn’t have a network, who hired great talent?
And it’ll give me ten people. And then I’ll go look them up and make sure it’s not hallucinated. And then I’ll share the best ones with my clients.
Whitney: What I love about that is it comes back to our original premise … to sort of break up the original model that we were handed that we don’t believe in. It says, only these people could do these things in this way.
Gena: Gena: And that’s BS. And ChatGPT can actually validate that…. Here’s not only that they could do it, but here’s how they did it.
Whitney: …You need the narrative.
Gena: [Yeah], having those stories and showing: this is how this person did it. And here are three crazy hacks they used.
[Like] the early days of Stripe, where they would go and literally install it on engineers’ computers at an event with a bunch of engineers at it. And that’s how they got their first users. They figured it out.
Whitney: I talk a lot about the experiments. As we’re trying to untrain old beliefs or untrain old mindsets, how do we run an experiment that’s counter to that? It’s in the direction that you want. And it’s small and it’s reversible.
Whitney: Yeah. But everybody was unsure and lacked confidence at some point, but they were willing to take action. Here’s the actions they took. And how are we going to get you to take action?
In my world, I talk a lot about the experiments. As we’re trying to untrain old beliefs or untrain old mindsets: how do we run an experiment that’s counter to that? It’s in the direction that you want. And it’s small and it’s reversible. It’s not high-stakes. It’s like: let’s just get out there.
Gena: Just like the MVP. Because I work with founders and I have to use tech-speak to connect, and now I’ve started using it even with everybody else I talk to because it’s actually so useful.
The MVP, the minimum viable product, has just become such a part of my vocabulary because it so helpfully operationalizes what we’re trying to do with an experiment.
It doesn’t need to be the full production. It doesn’t need to be: now you’re married. If you’re looking for love and you’re just trying to go and start asking people out, and you haven’t really had any dating [experience]—you don’t need to start out marrying someone. You start out chatting up a cute person of the sex that you’re interested in at a coffee shop. That’s the MVP. And then you go to the next thing.
Whitney: Well, I love that the MVP—the dual definitions are so connected, right? What you call the minimum viable product… and the most valuable player, right? They’re connected.
Gena: Oh yeah…
Whitney: Because in my world, it’s the most valuable player.
Gena: I hadn’t even thought of [connecting them]!
Whitney: It’s so funny how we’re in our little worlds. But you can’t become the most valuable player until you… You’ve got to start somewhere to get to the most valuable player. The path of the MVP is the MVP.
Make AI an amplifier of your best, not your worst
How AI is an amplifier of whatever energy we bring to it, for better or worse. (28:43–33:53)
Whitney: AI is an amplifier, right? It can amplify the speed of things, the capacity of things. But I think it’s so interesting that AI that’s added to cultures that are a little toxic and a little chaotic—
Gena: [Makes them] more toxic and more—
Whitney: chaotic. And it’s the same for our humanness, right? If we’re going to amplify and accentuate a system that doesn’t know how to steward its energy, doesn’t know how to lead itself, then… AI is not going to be as pretty in their hands...
AI can help us be better humans, right? Being able to embrace what makes us human: being a problem-solver, critical thinking, creative, innovative. But what energy needs to be running in our system for us to have access to that in ourselves? And what do we outsource?
Gena: Right… What do we need to be taking ownership of? What is the difference between outsourcing the mechanical parts of a thought process and multiplying our intellectual efforts, versus substituting [for them]?
Whitney: I like that question.
Gena: …In a way, we already had all of these problems before AI. It’s just, like you said, it’s such a massive amplifier.
Before, there was all kinds of parroting going on, and people would use jargony language to make it sound like they know what they’re talking about, but they would really just be regurgitating whatever they’ve heard somebody with high status in their field [say]…
But now we have a centralized repository of all the regurgitation that all of humankind has ever done. And it’s at our fingertips. And so, boy, can we regurgitate like crazy if we have a regurgitator on hand, you know what I mean?
…I feel like it’s a lot of what people are worried about in terms of slop taking over for human thought. That’s always been a risk. It’s just now the slop is that much more available and ample.
But the solution has always been the same, which is: yeah, you’ve got to learn to think and not skip that step.
Use AI as constructive critic
Where we realize we’ve both converged on a common tactic for amplifying our agency with AI. (1:01:35, and 1:04:59–1:09:52)
(1:01:35, and 1:04:59–1:09:52)
Gena: That’s probably one of the biggest use cases for me: just criticize this. Critique me. Tell me what my blind spots are. Tell me what I’m not seeing. What are the patterns here?
Whitney: I did something that was so cool…. This woman sent out a newsletter, and I was like—oh, there’s something I don’t like about that. And I put it in ChatGPT. I was like: why do you think I wouldn’t like this newsletter?
Gena: Nice.
Whitney: And I was like: do I do that? And ChatGPT was like: yes, you do.
Gena: Super valuable. Damn it. But it also gives you that as politely as you could ever ask for, right? But it tells you.
Whitney: Well, and it’s also nice because I’m asking and I don’t have an audience, right? So it feels like a safe way to get some feedback.
Gena: …Totally. And speaking of that, I actually just got an incredible use case yesterday talking to a colleague who published a book not long ago, and somebody wrote [a critical review with a lot of] cheap shots.
But she still wanted to get any insights she could actually use. So she put it into ChatGPT and she said: can you be the most thoughtful, measured, constructive reviewer and just tell me the takeaways from this review?
And it just did that for her.
Whitney: I love that. How brilliant. I’m going to keep coming back to this idea of agency. It gives us more agency. We can take these things from the world and filter them the way it’s most useful.
Gena: That’s right. And, crucially, we can understand its limitations and its biases, and we can correct those just like we do in ourselves, right?
We can say: don’t brown-nose me. We can say: give it to me straight. And then, of course, it’ll start [every sentence with] “So I’m going to give it to you straight”… But it will actually try to give it to us…
And then sometimes it’ll actually go a little bit overboard. So never take it as the word of God. It’s the word of the internet, averaged.
But still, how incredibly valuable, when you can retain that agency over how you’re using it.
If you enjoyed this conversation, be sure to tune in next Monday as fellow founder psychologist Keegan Walden and I discuss the question: “Do you have to understand your childhood to build a company?”
