Wrestling with AI

We are entering an era where someone might use a large language model to generate a document out of a bulleted list, and send it to a person who will use a large language model to condense that document into a bulleted list.
— Why A.I. Isn’t Going to Make Art (The New Yorker 🔒)

As I shared in my recent announcement that I’m looking for my next in-house product role, I have been wrestling with AI. Sometimes it feels empowering, sometimes frustrating, and occasionally dystopian.

I know I’m not the only one struggling with AI. Many of us are trying to make sense of what these tools mean for how we think, create, and contribute. They’re powerful, useful, even delightful. And like all technologies, they come with trade-offs and externalities. Jobs are shifting or disappearing. Spam and noise multiply. People lean on the tools instead of doing their own thinking. It’s hard to know who or what to trust.

As part of my grappling with this, I’ve sought out resources to understand AI in our world (and of course engaged AI in the process of helping me understand AI). I also embarked on having deep conversations with folks that have vastly different takes on this transition to a post-Generative AI world.

One conversation was with a successful musician collaborating with one of the most well-funded AI research labs, training algorithms to create tools for artists. Their view was that artists should be directly involved in shaping these tools so they serve us rather than replace us. In my other conversations with artists and art professors, the responses spanned the spectrum: from anger and avoidance, including a professor responsible for penalizing students who use AI; to curiosity and experimentation, weaving these tools into their creative process.

I’ve also spoken with members of the modern Luddite movement, who, contrary to the popular use of the term, are not anti-technology. They’re asking vital questions about who owns and controls our tools and challenging the ways technology is used to divide us, devalue us, and disconnect us.

And then there are the product managers and technologists who have learned to embrace AI because their jobs depend on it. Some wrestle with the ethical challenges these technologies raise, while others don’t see it as their role to ask those questions. I’ve been particularly concerned about the latter, like one product leader who proudly told me they’d replaced a full customer-support team with “better performing” AI bots (who, presumably, don’t mind the long hours because they don’t have children at home).

Throughout all these conversations, I’ve been pulling on a thread: in a world with AI everywhere, what is still left to for us to do as humans?

I’ve come to take my own view. These technologies are here to stay. We can and must use and understand them, and we can and must ask questions about how we use them and their impacts. They are already shaping us everywhere we look, whether that’s our Google search results, the emails and messages we receive, the expectations in our jobs. What would it mean to both engage AND ask critical questions? To see what we can create that would not be possible without AI tools, and also ask what capacities we lose when we outsource our own thinking to AI. To see what dull and challenging work can be taken on by AI, and ask who and what is harmed by the use of these tools (the “externalities” in economic speak).

Along this winding road of contemplation, I met up with my friend Cliff Flamer, a fellow coach and winner of the “World’s Best Resume Writer Award” (yes, it’s real, I checked). Unsurprisingly the subject turned to writing, something AI seems to be rapidly overtaking (and not just in professional contexts). We braved some existential questions about this work, but I left with some hope as well. What we came to was that writing well is about thinking clearly and bringing your own unique opinions, neither of which AI can do for you. I thought this conversation was worth sharing, so I ended up inviting Cliff to record an episode of the Livelihoods podcast…coming soon!

So I’d love to hear, what are you learning in your own wrestling with AI? What part of your humanness are you still holding onto in this age of AI automation?

To your livelihood,
Nat

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If you want to explore further, here are a few small experiments in co-creating with AI (mine and others’) that I think you’ll enjoy:

• Resonant Way (App): My client and sustainability product manager, Sondra Tosky, has been experimenting with AI “vibe coding” to create free privacy-respecting meditation and relaxation apps.

• The Thought Virus (Podcast): My friend Thomas Rudczynski created this short narrative podcast in collaborating with AI, to ask questions about how AI shapes how we think, or more specifically, how is AI shaping his thinking through the creation of this podcast.

• My own experiments: I’ve used AI for everything from making weird art for friends to writing manifestos on trust in the age of AI. One of my favorite projects was prototyping an AI-powered experience for Thrive Market, a playful attempt to get the hiring team’s attention that went mostly unnoticed, but was still deeply fun to build. And for the philosophy nerds: I co-authored a three-act play that brings two 19th-century Critical Theorists back to life to debate the meaning of creativity in the age of AI. And finally, I'll leave you with this...

AI Transparency Note

Given the topic of this newsletter, I want to practice what ethical use of AI might look like, and I think that includes transparency about its use. This newsletter was primarily written word-for-word by me, Nat Fassler. And, I have used ChatGPT to help me capture early thoughts that were incorporated into this newsletter, as well as to offer me support around clarity and concision.

Something is changing

The world we live in seems to be changing at an incredibly rapid pace. Our cultures, governments, technologies are almost unrecognizable from a decade ago. We can no longer trust that the norms that kept us comfortable and safe will exist tomorrow. And many of us are holding on even tighter to what’s bound to change, not trusting that what comes next will support us.

What a time to be alive.

When we can’t plan for the future, what we are left with is our capacity to sensemake. To notice what is possible in the present moment and make our own meaning from it. I’m not an optimist, but I’m also not a pessimist. Suffering is and always has been part of being a human, but so is joy, creation, connection — and I’m doing my best to be grateful for the later, and accepting of the former.

And with this coach-y introduction to set the tone, I’ll get to my point. After three years of working full-time as a coach, I’ve decided to search for a new in-house role in product management.

Coaching has filled me in so many ways. I’ve worked with so many incredible humans whose growth has inspired me, and built my capacity to show up with more courage and compassion. Supporting others in their creative work also reminded me how much I miss building alongside a team myself.

This summer I’ve been in the process of making this transition, taking on fewer coaching clients and exploring what’s next. I’ve been grappling with the current job market and economy, what I want and what it wants of me; and I’ve been wrestling with AI tools, their creative potential and their problematic implications.

In my best moments, I’ve been having a lot of fun with it. I have a fantastic community that is supporting me, including my peer job-searchers from Never Search Alone. And I’ve been “vibe coding” product prototypes and using ChatGPT to co-author a three-act play about the impact of AI on art (yes, very meta); I’m learning what is possible with these new tools and celebrating the unique ways my humanness is still essential. (This newsletter was drafted by me from scratch with AI helping me edit, and the m-dashes are my own!).

And in challenging moments, it’s been sobering. I’ve been grieving this beautiful chapter where I got to immerse myself in coaching, building a business, and running a podcast. And I’ve been looking out at a working world that seems in despair; as one person put it, “the grass is always browner” — a reminder that burnout is widespread, even for those with jobs.

And in all this, I’m making meaning and purpose for myself, knowing that I must choose what to do next without knowing where it will take me, and I’m okay with that.

So here’s my ask. Below is what I’m looking for in my next role. If you know anyone who works at an organization like this, and is hiring product managers now or in the future, I’d love your introduction.

I’m looking for a Principal or Director-level product role in a mission-driven, tech-enabled company with sustainable growth and strong culture, where I can build great products for humans and utilize my coaching capacities to strengthens teams and outcomes.

Here’s a bit more: I’m seeking a product leadership role (Staff, Principal, Group, or Director) where I can act as a player-coach: driving product craft and strategy, while mentoring others and staying close to the work. The right scope for me is leading small teams and owning a high-impact product area, where I can bring my blend of deep product craft and coaching capacity. I’m most energized by tech-enabled companies with sustainable growth and strong product culture. My sweet spot is building software products that empower people to create, collaborate, and connect in meaningful ways, backed by organizations that invest in people, value coaching, and build trust across teams. And I want somewhere where I can show up authentically as myself, specifically as a queer working parent (the companies I gravitate toward tend to be on “great places to work” lists, are certified B-corporations, and have maintained their DEI work).

Thank you for following my coaching journey; I can’t wait to share with you what’s next. I’ll continue to be sending newsletter emails about my transition and what I’m learning, as well as my continued work in coaching and on Livelihoods. Stay tuned.

To your livelihood,
Nat

Introducing Livelihoods, my new podcast

Since before I even launched my coaching practice, I’ve been dreaming of starting a podcast. Today, I’m extremely proud and excited to share the first episode of Livelihoods.

If it wasn’t obvious from my work as a coach, I am quite fond of having conversations with people about their work and their lives. I’m especially curious to understand how people find meaning and purpose in their work, something that has been central to my own career. My hope with Livelihoods is to share unique stories of how individuals have sought more fulfilling and sustaining work. These are not wild success stories, or playbooks for you to design your life after. Instead, I hope these conversations showcase the challenges and trade-offs along these paths with honesty and realness.

For this first episode, I interviewed my friend Pascal Carole who I met over a decade ago while working together in San Francisco tech. He’s come a long way since. We spoke as he was preparing for the harvest season on his vineyard in the Loire Valley of France, where he moved with his family and now works as a natural winemaker. I’ve been eager to hear more about his story and this transition, and I hope you appreciate Pascal's thoughtfulness and insight as much as I do.

In order for this podcast to be a success, I need your help:

• Listen to the first episode 

• Subscribe or follow on your favorite podcast platform

• Rate the podcast on Apple Podcasts or leave a comment on Spotify​

• Like and comment on my Instagram or LinkedIn post announcing the podcast

• Share it with a friend 

I hope you enjoy this first episode — I’ve already got another planned. Feel free to reply directly to this email to send me your thoughts and ideas.

To your livelihood,
Nat

You deserve to feel joy

Since the beginning of this year, a number of my clients have expressed guilt about their desire to feel joy. In the face of all the suffering they see in the world right now, what gives them the right to want joy in their lives?

You deserve to feel joy. You deserve to feel optimism about your future.

And no, I’m not talking about that “good vibes only” optimism that means having blinders on and ignoring suffering. I’m talking about your right as a human to yearn for a future that includes happiness, connection, love. You deserve those things.

But what about now? Shouldn’t I be taking care of those being targeted by hate? Yes, your care and mutual aid in support of immigrants, trans folks, and other marginalized communities is needed now more than ever. And also, it’s just as imperative that you practice self-care, self-love, and joy.

Your suffering does not make others suffer less. It’s a false belief that joy is a scarce resource, a belief perpetuated by extractive economics and political divisiveness. Joy is contagious, its abundance comes from you connecting to your own and sharing it with others. Especially those that are struggling.

You have my permission (which you don’t actually need): go find your joy.

And if you need support finding your joy during this disheartening and disorienting time, I have recently opened spaces in my coaching practice.

With joy and warmth,
Nat

Go deeper: Watch Pose on Hulu, a beautiful display of the healing power of joy in a marginalized community that faces so much suffering.

Authenticity is a practice, not a destination

authenticity (noun): The quality of being true to oneself, and the capacity to shape one’s own life from a deep knowledge of that self.

In our (dominant) culture, we tend to praise “authentic” people and want to emulate them. Our prized cultural icons—the artists, leaders, and culture creators—seem to have some special gift that allows them to live in the world authentically. So when we notice the ways we are masking our true selves, it’s not surprising that we want to live as boldly and with as much freedom as these exceptional humans. But something happens when we begin our own process of opening up, especially when we attempt to be our more authentic selves in our personal and professional relationships. Rather than feeling courageous, we often find ourselves feeling exposed and not greeted with the open arms that we expected to receive us.

The path towards authenticity has been a significant theme in my own personal development and in my work with clients. The hard truth is that this path is uncomfortable and even heart-breaking. My personal work in acknowledging the truth of my full experience and reality—first to myself, then to others—has been fraught with challenge. I’ve felt marginalized and othered. I’ve confronted shame about my identities. I’ve lost relationships and jobs. And yet, I would do it all over again if I had to. The path of turning towards what is true for me has lead me towards a life that feels more aligned and rich than I ever expected. In this process, I’ve learned that authenticity is a practice, not a destination. It takes lots of small steps. First, the endless process of learning about yourself. Then, slowly learning how to share yourself with the world with skill and discernment.

Earlier this year, I decided to seek out honest feedback about the coaching website I had recently launched. As a former product manager, I had the user research skills to run this process, yet this felt different. I wasn’t seeking feedback on a product sold by a corporation…this was much closer to home, this was getting feedback on me. I had put a website out into the world that I believed authentically told my story. So what if people hated it? While I didn’t encounter any haters, I did receive critical feedback from people who didn’t resonate with me and my offerings. At first I was reactive, and started brainstorming all the ways I could address this feedback. Yet as I sat with it more, I had a realization: by being more authentic about who I was in my coaching practice, I had to face the fact that some people would not like what I offered. Beyond that, I was exposing myself to a world where there are people who hate who I am. But this is not the whole story, because I also found that by telling my story more authentically, I was deeply resonating with people that I would most want to work with.

Fast forward to today. I just completed a process working with a wonderful designer on a new logo. When I first saw the three options she shared, I found myself drawn to a more playful logo, one that felt fun and exciting. Yet my fears came up. Would this make me seem less professional? So I retreated. I told myself that I would choose the simpler, cleaner option that would be more universally accepted. But I kept finding myself hesitating. I asked for another day to consider my choices. When that next day arrived, I caught myself. I listened to my gut and got out of my over-analytical head. I thought, “I want this one, it brings me joy and feels authentically me.” So here is my new logo for your enjoyment (or not!).

I’d love to hear what small steps you have been taking to practice living more authentically.

Go deeper:

Read: The Myth of Normal: Trauma, Illness, and Healing in a Toxic Culture by Gabor Maté. This compelling (and oft controversial) book calls into question the culture of “normal”, and how healing from this myth can lead us on a path towards meeting two of our core needs: attachment and authenticity. Note: the definition of ‘authenticity’ above was taken from this work.

Stuck

People often come to me when they feel stuck. Stuck in a career that no longer inspires them. Stuck in a job they don’t feel successful in. Stuck in patterns they want to break or habits they can’t seem to pick up.

Lately I’ve been feeling stuck. With all the busyness and stress of my work and life, my creative energy seemed to come to a full stop. The poetry and creative writing practice I had developed just didn’t flow. Nor did my nascent art practice. And the creativity I had for my coaching business dried up as well. This monthly newsletter took a pause. As did my Instagram. As did my project to refresh my website.

It wasn’t just that I was busy, although I surely have been. (Some of my most creative periods were also my busiest). This was different, I was in it. At the same time that my coaching business seemed to be getting its legs under it, I was navigating the swirl of life. There was a lot of challenge. I found myself supporting my family through various significant health challenges that impacted each of my parents, my kids, my partner, and myself. There was also lots of beauty, connective time with community, inspirational travel and art. Yet the density of everything I was up to left me in a feeling of scarcity.

My mind had been so hung up on the limits of my time that I neglected to focus on my energy. Old patterns reemerged. Rather than making space for self-care, I filled the gaps in my time with distractions. When my mind felt too busy to meditate, I turned to my email to check things off my list. When I couldn’t wind down before bed, a screen would keep me company. The things I was turning to in order to self-soothe were only reinforcing my stuck-ness.

I feel things starting to shift, and the fog of stuck-ness lifting. The density of my life has not decreased, but I’m once again making space to come home to myself. I’m choosing to meditate instead of checking my email; not every time, yet enough to remind myself that I have that choice. I’m choosing alone time to be in my thoughts and feelings, to journal and to rest, despite all the temptation of activity. I even took a candlelit bath.

Often when we feel stuck we try to do more. And in the cycle of scarcity it feels like we must do more. It can feel like we are in quicksand and must frantically try everything to prevent ourselves from being pulled under. Yet the trick to get out of quicksand is to move slowly. And the trick (if you can call it that) to get out of being stuck is to slow down. To take time to notice and not just act. To be rather than to do.

When was the last time you felt yourself stuck? What supported you to get un-stuck?
​

Go deeper:

• Read the classic HBR article, Manage Your Energy, Not Your Time​

• Or better yet, take a pause from reading the internet to make space for a few mindful breaths.

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Equanimity?

A few years into my career as a product manager, I received a performance review that left me scratching my head. In the review I was praised for my 'equanimity', a term I was barely familiar with prior to joining this company that included it as a core cultural value. Like most of this company's values, 'equanimity' had been appropriated from Buddhism, and was described as "a fundamental okayness with things as they are." Yet at the point when I received this praise in my review, I was the furthest from okay. I was struggling to feel alignment in my role, I was overwhelmed by the demands on me as full-time working parent of two young kids, and I was deep into work with a therapist and a coach to avoid heading into complete burnout. So what was I missing?

What I've learned in the following years is that what was mistaken for equanimity in my job was actually my ability to mask my emotional state. I was good, probably great, at appearing calm among the swirl and chaos of my role. Throw a complex product problem at me with extremely high expectations and few resources to solve it, no problem. Send me into a political environment with stakeholders that could never agree, I'll be building consensus with a smile on my face. Despite the increased challenge I faced as my leadership scope expanded, I somehow held it together at work. But the truth was, there was a cost to my masking. That cost was my mental and physical health.

In the last few months, a number of my clients have shared similar stories. They are great at holding it together during the storm. And they also are noticing the costs of doing so. What I have learned on my own journey, and what I have helped my clients learn, is that developing equanimity is not about suppressing our emotions. When we experience stress, uncertainty, doubt, frustration, we need a release valve for it. You don't have to yell at your boss or rage quit, but you might want to find a safe space to process your anger and set clear boundaries.

The path to equanimity requires us to feel our feelings, to fully experience them and make space to metabolize them. And only through that process can we begin to be okay. We begin to be okay when we see that our emotions are always in flux. We are okay when we are sad. We are okay when we are angry. We are okay with our emotions, not in spite of them. Are you okay?

Go deeper:

• Read about the Buddhist approach to equanimity here: Equanimity (Insight Meditation Center)

• This newsletter was partially inspired by conversations calling into question the idea of professionalism as a universal standard. Read: The Bias of ‘Professionalism’ Standards (Stanford Social Innovation Review).

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Play

What would it feel like to have more play in your life? This is a question I have been sitting in for myself and in my client conversations since the new year.

I have learned that play is not a thing. It is a feeling. Play is not dependent on having the time or capacity for "recreational activities". You don't need a pickle ball racquet or a bike for play, although those activities can certainly be playful. Play is accessible at almost any moment doing almost any activity with almost any other being (and certainly also when you are alone). Play feels like being open to any outcome. It feels like building something without regard for what it becomes, whether that's building a sand castle that will inevitably disintegrate or opening to the spark of a friendship with someone you may never see again. Play feels like imagining a beautiful future, a career where your heart is bursting with joy, a relationship where you safely walk toward your shame only to discovery a magical castle filled with delights.

Play is certainly not easy. When all day long you are confronted by threats to your safety: war, disease, layoffs, disaster. But in the midst of all this, there are children still creating carnivals out of couch cushions. So can you. In fact, I'd say that it's essential. That in spite of the pain and suffering in the world, we must be creating joy and passion and new possibilities for our futures. This has always been part of what it means to be alive. To be human. That despite everything, play is available to us right now.

Go deeper: Read Pleasure Activism: The Politics of Feeling Good by adrienne maree brown.

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I have a request

One of the most common challenges my clients face is asking for their needs to be met. This shows up at work, with unclear expectations of colleagues or stumbling through salary negotiation conversations. And it shows up in our personal lives, with ambiguous hopes for our romantic partners or unarticulated boundaries with family. It often leads to frustration and resentment.

Getting your needs met requires practice.

As a recovering people pleaser, I have spent a lot of time working to get better at clearly articulating my needs. And I still bumble it sometimes. My partner and I have started a practice of naming our needs by explicitly stating, "I have a request." It might be something simple such as, "I'd like you to wash the dishes after dinner." It could also be something more challenging that requires further conversation like, "I want you to spend more time with my family." It's often awkward to make these requests. And worse, sometimes the answer is not what we want to hear (saying "no" is a whole other newsletter topic). But the practice of getting better at asking for our own needs to be met has helped me and our relationship to grow and flourish.

So dear reader, in the spirit of getting better of asking for my needs to be met, I have a request for you. Please share my practice with one person that may benefit from coaching with me. Perhaps you know someone that's burnt out in their career or is looking to do work that feels more values-aligned. Perhaps someone you care about is in the middle of a major life or career transition. You can introduce them to me, or send them a link to book a free consultation conversation.

Go deeper:

Read: Nonviolent Communications by Marshall Rosenberg

Reflect: This reflection exercise is to support you in making successful requests for your needs to be met. Reflect once every day and ask yourself the following questions. Take brief notes so that you can begin to notice patterns.

1. What requests did I make today?

2. How successful were my requests (i.e. did what you requested happen)?

3. What requests did I avoid making?

4. What reason did I have for not making the request?

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