On Getting Yourself Unstuck

So it appears I’ve kind of boxed myself into a rather unproductive corner with the writing of this book. You see, productivity has always been this complicated dance I’ve had with myself for years now. I’m better at it now than I used to be, but it’s still a constant effort to keep myself consistently moving forward and ticking off items on my never-ending checklist of life. 

This book, The Free Agent Manifesto, is one of those items, and an important one at that. It is a much needed outlet to verbalize the values that drive my work, but also my life; a way to answer countless questions — both spoken and unspoken — that have been aimed my way for years. I’ve been unconsciously wanting to write some version of this book for more than a decade, and consciously wanting to write this version of it for the better part of a year.

Now, I know myself very well. I know just how many projects fill my brain at any given moment, and I know just how easy it is for them to get shelved if I don’t act on them quickly enough. I also know what it’s like for a project that isn’t financially generative (yet!) to drag on for eternity, waiting in the wings while I scrape together five minutes here and ten minutes there to work on it. I know that projects like that need new and innovative forms of incentivization.

With this book, I knew I could buckle down and finish it all in a few months if I wanted to. The chapters were short, the ideas were all fresh and top of mind. And after all, I wrote my very lengthy, academically-dense, 250-page thesis in just under 4 months, didn’t I? This was going to be a relative walk in the park. So I came up with a format that would force me to stay disciplined and on track. (Or so I thought.) Around mid-August of this year, I offered it as a “live edition” book on my website that people could subscribe to with a one-time fee. I released the Cold Open and the first chapter for free. And the remaining seven chapters would drop every two weeks starting September 15th. Plus, all the subscribers would have lifelong access to bonus essays and quarterly Q&A calls since this is going to be a neverending project. People paying for it would mean that I would feel obligated to deliver the goods on time. Plus, this whole “live edition” format was a direct demonstration of my free agent philosophy: I had no real patience for the slow wheels of traditional publishing and I didn’t like binding myself to pre-existing systems; this format let me sidestep all of that and retain most of my profits for myself. It was an active case study of what it meant to live as a free agent. So convinced was I in the ingenuity of this format that I even put a countdown timer on the upcoming chapter on my website so that me and my subscribers (thankfully only a small handful since I hadn’t advertised the book widely) could see exactly when it would drop.

It is now September 23rd. And I am only halfway through Chapter 2. 

You see, discipline wasn’t the problem this time. The whole “live edition” experiment was doing its job very well and keeping me on track. I was writing everyday, I was extremely consistent in my commitment to the book. But here’s where I miscalculated. I strapped myself to a very unforgiving format at a very busy time in my life. Within just the last four weeks, I had two travels lined up, a conference to attend, a publication design project for a client on a tight deadline, another publication design project that’s just ramping up, and two guest lectures at the end of this week that I’m currently preparing for. So yes, there was time to write everyday, but simply not enough time to buckle down and finish the chapter by September 15th like I’d wanted to. The subscription model, the countdown timers, all of it served to apply a consistent amount of pressure, which would work just fine if it was modulated and calibrated more carefully to match my current tolerance level at the moment. But it wasn’t, because there were too many other things applying their own forms of non-negotiable pressure. There’s a line between keeping yourself disciplined and straight up choking yourself. 

September 15th came and I realized I wasn’t going to finish the chapter. So I moved the countdown timer to 11:59pm on September 17th. That was the day I was travelling to San Francisco and spending half my day in transit. I had this deluded idea that I could use my six hours on the flight to finish writing the chapter. I didn’t. That outcome was pretty obvious in hindsight. So I moved the timer again to September 23rd, 11:59pm. I was back in town on the morning of the 21st, so I’d have that whole day plus all of 22nd and 23rd to finish it. Except that still didn’t account for the fact that my first week back was chock full of meetings (scheduled by yours truly), and two guest lectures at the end of the week that I had to prepare for.

So this morning — the morning of the 23rd — I finally let myself acknowledge there was no way this was going to happen on time. This is the moment I’ve always been irrationally terrified of all my professional life: admitting to myself that something I want to do is not going to turn out the way I’d originally planned. And yet, every time I’ve actually mustered up the courage to admit that to myself, it has always proven to be a profoundly transformative moment. Because the minute I admit it to myself, my brain immediately starts plotting new creative solutions designed to fit within this new set of circumstances — solutions I’d never have had the mental space to cook up before. 

The minute I realized that this countdown was proving to be the exact opposite of productive, I started coming to terms with new non-negotiables: 1) I had to get rid of that goddamn countdown timer; I needed to just take each chapter as it came and give it the time it needed. 2) If I couldn’t deliver the chapters by their originally promised dates, if I had to make the releases more flexible, that meant I had to refund the small handful of subscribers that I had so far. (And thankfully there were only a few, so I could actually afford to do that!) It was a matter of principle after all; they had paid a fee in anticipation of specific things, and if those terms were going to change, they deserved their money back. I’m still letting them retain their subscription for free, which is both an apology, but also a token of appreciation for supporting the book in its early and evolving state. I wasn’t particularly worried about telling them either, because I knew that would simply take one earnest, well-written email. (Someday I shall tell you all about my theory of how any problem in the world can be solved with a well-written email… but I digress.) When I decided on this path, my mind suddenly and wonderfully freed up. Gone was the self-imposed pressure of the countdowns and the timers and the subscriptions. Now I had a clean slate where I could retain the parts of the process that worked and say goodbye to the ones that weighed me down. I was now free to pursue this book in the way it deserved, liberated from the many shackles I had overenthusiastically clamped around it in my effort to be “disciplined.”

And that’s when I realized, this entire episode was a moment of learning that fit right into the book. This slight change of course produced so much relief and liberation that it reminded me of a crucial aspect of being a free agent: the ability to creatively adapt to any situation. Free agency is not really about making a ton of money or always having fun or never having to do boring things like filing taxes. Being a free agent is about knowing how to navigate the moments in which you feel stuck. It’s about knowing how to get yourself unstuck from any situation, including (and especially) the ones you get yourself into. It’s about building the stamina to do that, to be unfazed by the feeling of being locked in, and knowing there’s always a creative way out of it. 

I remember a similar scenario two years ago when I was writing that aforementioned 250-page thesis. I was doing my masters’ at RISD and it was a week before my department held its annual symposium — our final official presentation of our thesis research to our academic community. I was writing a rather lengthy thesis on internet memes. I’d already finished writing it; I was done with the basic requirement of my degree and all I had to do now was make a 20-minute presentation. But I was also producing my thesis as an interactive, multimedia artist book, which was most certainly not a requirement and something I was doing simply to further my own creative book-making practice. I had gotten this fantasy lodged in my brain that I would debut this artist book at the symposium along with my presentation. What that meant, practically, was preparing not only my 20-minute presentation but also producing this very elaborate artist book from scratch in a mere two weeks (something that would truthfully require at least two months). It was an utterly deluded plan, in hindsight. But I was hung up on the intoxicating fantasy of debuting this book at this event, of having people gathered around me, ooh-ing and ahh-ing as I demo’ed the book. For about a week, I really tried to make it come true. I lost several nights of sleep, I constructed an outer box for the book (which turned out really shoddy and was way too big to be structurally feasible), I printed out the various pages and ephemera in a haphazard manner. And it just wasn’t coming together. Yet I couldn’t give up on the dream of it. (I still hadn’t worked on my actual presentation, by the way.) And I remember so clearly, four days before the symposium, I sat myself down and forced myself to face the truth: there was no earthly way this artist book was going to be ready in time for the symposium. I cried like a baby that night. This was the first time I had ever let myself properly mourn the loss of a deluded, work-related dream. I’ve spent almost three decades side-stepping my own time-related delusions, ignoring my own planning fallacies [1], and never letting myself fully absorb the disappointment of a fantasy not quite playing out the way I wanted. This time was different; this time I allowed myself — forced myself — to feel the pain of that fantasy shattering. Acknowledging that it was already dead, that it could never have lived, and letting myself really mourn its loss. And you know what happened? Within about half an hour of crying my eyes out about it, I came out on the other side with new realizations and new opportunities that didn’t exist before. I suddenly gained a perspective I didn’t have before when I had my fantasy-driven blinders on — I realized I was way too attached to the romance of this lone symposium. In fact, it wasn’t even that big of an event. It was just for the liberal arts faculty and a handful of students at RISD, all of whom would be perfectly satisfied and impressed by my 20-minute presentation alone. I realized that it was rather limited to think of this event as the ultimate stage for debuting this book — why was I thinking so small? When the book was ready, I could probably whip up some kind of exhibition around it, do talks with it, and so much more. I was so fixated on that one symposium that I hadn’t considered there may be far more interesting spaces to show off this book to a much wider audience. (And I did, at multiple events over the coming year.)

[1]  Coined in 1979 by Daniel Kahneman and Amos Tversky that describes the phenomenon of severely underestimating how long a task will take to accomplish.

Changing course can be one of the most liberating and empowering things you can do, but you have to learn to give yourself the permission to do it and discover what new and unexpected things emerge on the other side of it. While acknowledging a limitation (or even an impossibility) can seem insurmountably daunting, it’s actually incredibly freeing. Remaining in stubborn denial of a limitation makes you keep trying to blindly step around it, and that prevents you from creatively problem-solving for it. But the minute you acknowledge it, your brain automatically starts devising interesting and creative solutions to negotiate with it. It took me a very very long time to learn that — 31 years to be precise — and I’m still relearning it every single time a project doesn’t go my way. And each and every time, I’m awestruck by how profoundly it transforms the structure of my thoughts, feelings, anxieties and assumptions, creating a new order in which different ideas and possibilities can emerge. This bonus essay was birthed in exactly that kind of crucible. The minute I realized I had to rethink some aspects of this “live edition” rollout, I realized this was yet another manifestation of free agency, and it became yet another angle I could write about. I didn’t think I’d be writing any bonus essays until after I was done with all eight official chapters, and yet here we are. I felt a burst of inexplicable inspiration to write about it now, without waiting, without making it too long like the other chapters — here was a moment of raw inspiration to lean into. This shift in course opened up an unexpected opportunity to add a new piece of content, a new facet to the book that hadn’t occurred to me so far. It didn’t ruin the integrity of the book; in fact it enhanced it.

Change and instability and unpredictability are constants. It’s almost a guarantee that things rarely ever go the way we plan. Building the stamina to weather those unpredictabilities is the only way to be free of them, to be untethered to their consequences. And when we can’t change course on the fly and find new creative ways to get where we want to go, that’s when we feel stripped of our agency. We feel forced to do things in ways that feel wrong or unintuitive, or we’re forced onto completely different paths that we never intended to take. Getting where you want to go despite things not going your way is a subtle but crucial skill to master. And it’s one that requires constant reminders, relearning and practice. To this day, I forget that I can still get where I want to go even if things don’t go my way. I can still get there via different and perhaps even better means. It just takes some unfettered creativity and ingenuity to unshackle yourself from whatever assumptions, rules and systems are keeping you stuck — quite often they’re ones of your own making, and those are the hardest to let go of. In a way, it’s easy to rebel against someone else’s rules. It’s much harder to do it with your own. But that’s usually where the most transformative shifts lie.

I’m sharing this little episode as a bonus essay, because it exactly embodies the essence of The Free Agent Manifesto project. It’s a book that’s in a constant state of evolution, discovering new facets and dimensions of what it means to be a free agent. It doesn’t end with financial freedom or entrepreneurship or freelancing or whatever else you might associate with it. It’s a way of being that seeps into everything, concerned only with the central question of what it means to live and work with a high degree of agency. To know how to get yourself unstuck.