# Why I took a sabbatical, and what I learned Since I decided to take a sabbatical in Q4 of 2024 it's been a topic of conversation in almost every catch-up, coffee meet, interview, and pitch. I've seen just about every reaction to my decision from jealousy and apathy to genuine confusion. Through my conversations I've come to believe a few things. One, that the idea of a sabbatical, or even what it is, is not as well-understood as I thought it was. And two, that relaying my own story about deciding to take a break might help others navigate some sticky wickets of their own. >[!note] My idea of a sabbatical is primarily about reimagining your relationship to work > A sabbatical is an extended break from work—typically several weeks to a year—taken for rest, personal development, research, or creative pursuits. Unlike a vacation, a sabbatical is meant to be transformative: it's less about escaping work and more about reimagining your relationship to it. ## Research as leisure The most important place to start in my own decision to take a sabbatical is that it was rooted in the pursuit of "[[research as leisure activity - Clips|research as a leisure activity]]." A great truism of life is that our strengths and weaknesses are often opposing sides of the same coin—the things that make us uniquely great are often also our biggest liabilities. I do my best work on the edges of problem-solution spaces, which is another way of saying that when I take on a project, I go deep and then telescope out to make connections, synthesize, and build new ideas. (I talk about this as [[adjacent context]], which is also the [eponym of my newsletter](https://adjacentcontext.substack.com/)). In an early, emergent, or expansive moment of a project or business, this is a superpower. In moments of stasis, where the order of the day is to stay the course, it's a potential liability. This type of disposition feeds on novelty. If your primary creative fuel is solving problems, you will always find problems to solve. At a certain point, this becomes actively detrimental to a team or business. In my very specific case, it's obvious now when I look back that I had spotted this point approaching and started working ahead of my departure before I'd made the conscious decision. > [!quote] An excerpt from a management memo I wrote in 2024, captured in my periodic notes > We're getting close to the point where the most important and transformative work will be course corrections and optimizations on the path we've set here, and I know you guys are really well positioned to lead that work. Why "research as a leisure activity" matters in this context is because when Celine Nguyen gave me the working language in mid-2024 it was maybe the first time I was able to conceive of "weird little tangents" as a productive pursuit. I grew up in a midwestern environment firmly grounded in labor. There's always something to do on the farm or in the shop. Most of the time, these projects don't feel "strategic" or even connected, but they're tangible and have a beginning and an end, and so it's not a difficult exercise to convince yourself of a day spent meaningfully toiling when the product of your labor is there, staring you in the face. I can't remember a single instance of hand-wringing over spending a day repairing machinery instead of using it, but this is more or less how I'd allowed my relationship to knowledge work to develop. This was a pivotal moment for me when I both became aware that my relationship to work needed reimagined, and two, maybe it would be insightful to know how I'd spend my time when I had nothing I was "supposed" to do. ## Burnout, energy, honesty It was about this time that I also started to understand burnout. Viscerally, I mean, not academically. I think the same midwestern ideals of labor colored my definition of burnout. I would never have articulated it this way, but I started to become aware of my negative connotations—it was something bad, a manifestation of essential weakness. The reality is a lot more complicated and less acute. You can know the perfect definition of burnout and still not recognize it in yourself. It's almost never a single event, but the accumulation of years of lived experience, each subtly shaping your state of mind, relationships, and belief structures (this alone is a strong argument for [[embodied cognition]]). Working in any GTM role is challenging even in the best of times. Every day you wake up with a new challenge, and the half-life of your achievements rarely makes it out of the quarter where the goal line resets. For me, spending 15 years doing this mostly non-stop for equity-backed early and growth stage companies had the erosive effect of water and wind: slowly grinding down my rough edges to the point that I found myself wondering if I'd lost myself somewhere along the way. In situations like this it's not any one company job or person that "burned" you out. In [[Hyperobjects (2013)]] Morton describes Nature as "the featureless remainder at either end of the process of production" and sometimes I think about the human natural state and burnout in the same way. In an uncharitable view of late-stage Capitalism, you're either the exploitable stuff or the value-added stuff on either side of "work." Burnout is actually the day you wake up and realize you're not sure which one you are. Once you see it, you can't un-see it. So the second important feature of my decision to take a sabbatical was recognizing that the arc of my then current project, and an honest assessment of my energy and fit, were diverging. ## Externalities The third primary factor in my decision to take a sabbatical was, in a phrase, converging externalities. We've lived some big shifts in the world recently, between pandemics, political and social unrest, and paradigm shifting technologies. These are important to call out because one, working through this series of shifts is a big challenge for anyone, and two, they have big and very real implications on the future of knowledge work, SaaS and software development, and the conditions that govern how we market, buy, and sell things. ### On the "Profitable Efficient Growth" Firstly I'll say that calling the last five years a "shift" toward PEG is a rose-tinted assessment. Calling it a shift is giving a formless group of people much more credit than they deserve. The reality is that broad market compression (starting in 2020 with the pandemic) made zero interest rate policy untenable and forced investors to consider cash and business feasibility in a different way. The challenge with this, at least through my lived experience, is that the more speculative of our industries never really reckoned with this as a choice, and instead reacted to the emergent pattern half-heartedly. So rather than developing a new investment thesis, funds and investors simply paid lip-service to the importance of cash, marginally edited their SaaS metrics to center [Rule of 40](https://www.mckinsey.com/industries/technology-media-and-telecommunications/our-insights/saas-and-the-rule-of-40-keys-to-the-critical-value-creation-metric), and then went on demanding 3 year investment windows and 5x EBITDA multiples. This was broadly operationalized as "do more with less," which in practice meant that most companies cut spend and headcount across the organization while, paradoxically, expecting more from their teams. Without a playbook or a plan for reinvestment this has stretched into flatline purgatory for most companies, holding on or making marginal gains but incapable of earning buy-in for any big bets. You don't have to look very far to confirm what this means for operators now, "[[Pluralistic The Enshittification of Tech Jobs - Clips|a coder who picks up their fired colleague's work load by pulling 60-hour work-weeks isn't 'more productive,' they're more exploited]]." Or consider the findings from [[How Tech Workers Really Feel About Work Right Now - Clips|Lenny's Newsletter that 84% of tech workers report burnout now]], with nearly 45% reporting "significant" burnout. ### The Pandemic exposed our bad bets The great lie of the predictable revenue playbook is the assumption that revenue could ever be predictable. The entire framework is built on a foundation of over-reliance on [[computational thinking]]. In the years before 2020, the industry mostly tackled this in two ways: inventing new, more specialized functions and metrics to quantify GTM "effectiveness" or writing fluffy pieces on the importance and challenge of investing in "brand." When the pandemic took face-to-face sales off the table (and most business continued to succeed), teams had to reckon with how influence propagates in digital-first environments, and what that means for how the real world actually works. In hindsight, maybe the best large-scale A/B test to prove out the inconvenient untruths that the predictable era revenue was built on: that people are largely rational molecules flowing neatly through a linear series of gates that we (the providers) control. We now know that [[The 2023 6sense B2B Buyer Experience Report - Clips|84% of deals are won or lost before providers know they even exist]], that [[Report The Multiplier Effect - Clips|attribution-based measurement routinely overestimates channel contributions]], and that all GTM work, despite all the frameworks and terminology essentially boils down to [[How B2B Brands Grow|mental and physical availability]]. Or in other words, fundamentally no different than any other industry. We're in a very weird place at the moment where we know GTM work is probabilistic, relational, and emergent, but the predominant operating patterns are still maniacally obsessed with quantification, reduction, and control. ### The AI paradigm shift I've [written quite a bit](https://adjacentcontext.substack.com/p/you-keep-using-that-word-i-do-not) about artificial intelligence more recently, particularly in the [[what remains human|context of my research during and after my sabbatical]], so I won't belabor the point here. What I'll say here as it relates the externalities influencing my decision to take a sabbatical is that the period leading up to my decision was primarily defined by my attempt to grapple with generative AI on multiple levels. Firstly, in the way it was (and is) changing my essential relationship to technology—how I work, the tools I use, the world of possibility. Secondly, in the way it was changing the nature of my work as a GTM leader. Seemingly overnight, the product development *modus operandi* shifted to an AI-first mandate, completely upending the competitive landscape and established product portfolios. The knock-on effects of this to GTM, like how [[consumption-based pricing and changing value roadmaps|consumption and outcome-based pricing changes value roadmaps]] and how the [[Composability will define the next SaaS era|primitives of the software experience]] are intrinsically changing in hard to predict ways, combined with all the other externalities to create a very challenging period of [[cloudy thinking]]. In so far as I had hunches about where the industry and work was headed, I didn't have the confidence or moral grounding that I have now, and it did not seem likely that I would have time to develop it without stepping away. ## How to sabbatical All of these things—recognizing a period of evolution within my current project, a desire to rediscover some of myself and redefine my relationship to work, recognizing the accumulation of burnout and grappling with challenging externalities—was the cocktail that ultimately led me to take a step back. It wasn't a trivial choice for me, I don't think there was ever a moment where I saw all of these factors in totality. But at a certain point the weight of the decision became less about all of the things I wasn't happy with, and more about the opportunity I could unlock for both the team I was leaving and myself by stepping aside. From there, the conversation was internal, how to structure teams, how to manage our comms, and most importantly, how to actually do a sabbatical. When I started down that path, I realized that my academic understanding of a sabbatical was directional at best. *How long? What do I do? How do I know if it was successful? How will I continue to live and eat food and such?* ### The approach As it turns out, the most important thing I learned about sabbaticals is that they're slippery. My initial plan (which is maybe more indicative of my state of mind at the end of 2024) was to go outside until I felt like coming inside. In hindsight I think I modeled this approach on that of an inspirational leader I look up to, Jurgen Klopp (former manager of Liverpool FC), who tends to work really, really hard on a problem for about 5 years until [the energy runs out, then step away](https://www.nytimes.com/athletic/live-blogs/jurgen-klopp-leaves-liverpool-live-updates/4Nt372CGZthJ/Hl1qjQmvNcjv/) and wait form something to call him back. I thought I'd spend a few weeks away from the computer, working around the house and homesteads, knocking out the projects I'd been putting off until something pulled me back to the desk. That's not really how it worked out. I read a lot. I learned how to tuckpoint and reconditioned our fireplace. I took multiple day-trips to walk transect lines and look for seed plants for our meadow project. I laid pavers, worked gutters, walked my dogs, ran, and rode mile after mile. Through it, nothing called. There was no voice in the ether, no spark of inspiration, just a different kind of toil. These first few weeks eventually reminded me of the importance of structure and constraint. You can learn a lot about yourself when you examine who you are and how you spend your time when you strip away a lot of your obligations. What I learned about myself is that I'd happily plug just about any kind of labor into the hole labor left in me, without some conscious intervention. This realization led me to start thinking about how to apply some explicit structure to a sabbatical. I've always been very attracted to the ideas propagated by Stefan Sagmeister in his seminal TED talk, [The power of time off](https://www.ted.com/talks/stefan_sagmeister_the_power_of_time_off?subtitle=en). In it, Sagmeister argues for the importance of *productive time off,* shaved from your retirement years and sprinkled into your prime earning years. > [!quote] On the Sagmeister sabbatical > I thought it might be helpful to basically cut off five of those retirement years and intersperse them in between those working years. That's clearly enjoyable for myself. But probably even more important is that the work that comes out of these years flows back into the company and into society at large, rather than just benefiting a grandchild or two. Baked into that approach are some constraints: we're taking this much time off, we're going to this place, we're going to work on this project. Those weren't the perfect constraints for my situation, so I started to think a bit more about two lenses: who do I want to be (for myself and my community) and where is the opportunity? What I found was that this framing focused my thinking at the right scale. It was enough structure to anchor some deep inquiry in forward momentum, but also not so much structure that I felt compelled to define the shape of the outcomes. Slowly, some work started to coalesce. First, in some loosely-related work. I felt like I needed to develop a better, sharper point-of-view on the future of SaaS, and to examine what GTM looks like in the era of AI. This led me to finally take on a project to overhaul and re-factor my [[01 - readme|personal knowledge management]] system, and to start experimenting with some different "weird tangents," like how to embed structured knowledge in a locally-hosted LLM and effectively [[developing a knowledge agent|forking my brain]]. At the same time I started networking again. Talking with friends, co-workers, peers to get their perspective on where we are and where we're headed. I had some job conversations (mostly with PE-backed groups) and started to feel a lot more conviction about how misaligned products and markets are right now. I formalized these conversations as [[04 - questions|lines of inquiry]] and started digging deeper with the intention to "think in public." This work built upon itself until I [[developing a digital garden|developed this digital garden]], a project that turned out to be a larger labor of love than I anticipated. Slowly, my conversations turned toward more practical matters. I started taking on contracts that both interested me and furthered the essential pursuits of my sabbatical. ### Defining the edges Another way that sabbaticals are slippery is that unless you design them, they don't have clear edges. Eight months down the road (at time of writing) I'd still struggle to tell you where my sabbatical ends and the next phase of work begins. I could make a strong argument that I'm still on sabbatical, but that's probably a different post. At some point in January I decided to [[developing a practice|formalize my contracting work into a practice]], and I'm using this as the effective end of my sabbatical. It's a little squishy. To date, I've billed roughly $15K through [Greenhaus](https://www.greenhausgtm.com), by most accounts that's a respectable but unremarkable return on 8 months' work, but I'm thinking about the returns a little differently. But if I can pull from the scattered thinking, feelings, and beliefs that coalesced during my time away, one of the most important takeaways is just how valuable a skill [[reification]] is. The ability to make a hazy idea legible. To scaffold a gut instinct into something testable. To make a new way of thinking usable—not just by me, but by others. I have a hypothesis that in a world increasingly mediated by machines and optimized through computational thinking, the real premium lies in the thinking behind the tooling—the mental models, structures, and systems that shape how work gets done. It took me stepping away, zooming out, poking, and tilting the frame to realize that now, the scaffolding matters more than the surface. The premium is no longer in the doing, but in the _design of the doing_. It's one of those things I simply couldn't have learned any other way, and now that I know it, I can't *not* get it out. I have no idea if my practice is a viable business, but I do know that the perspective is sound, and I can build in confidence around that until the market is ready. That's the real power of a sabbatical.