It’s been two months since I left RotoWire and struck out on my own. At first, I was just writing about whatever was on my mind, and it felt normal and natural, like someone had given me the exact tools I needed to do the work for which I was meant. But the lack of structure, the lack of a viable plan to turn it into a livelihood, the ease of blowing it off, going out for food and drinks, or spending too much time on Twitter began to weigh on me. What was I really doing? How long would I want to keep it up? How was I going to earn a living? Selling RotoWire was good, but not set-for-life good.
I’ve set up both my sites (chrisliss.com and realmanwould.com) with contribution buttons, but I didn’t offer automatically renewing payment options (the best way to generate reliable income) because if I’m dinging your credit card every month, then I owe you work. And I didn’t just retire from arguably the best job in the history of humanity (not just that it was fantasy sports, but that 90 percent of my job in fantasy sports was to play in leagues and be myself) to get on another treadmill with a new set of obligations. A more reasonable person would tell himself being one’s own boss, working on the material one chooses was enough, and owing people work was just part of making a living. But I am not a reasonable person. I want to work on what I choose, when I choose it, not owe anyone anything and still earn enough money to live more than comfortably. (Once we normalize streaming sats for work on a per-article basis and get rid of the cumbersome credit card interface, via a payment processor, it will get easier, but we’re not there yet.)
As it turns out, I am generating enough content presently that I would feel okay about auto-renewals, but that’s not the point. The point is that I could take six months off, walk the earth, so to speak, and I would not feel like I let anyone down or stiffed anyone out of anything. Those are the conditions under which I want to work. If the work is owed, it’s done under coercion. If the work is done of my own volition, it’s pure. Well, nothing is perfectly pure, but it’s as good as I can hope.
So I’ve erected an obstacle to getting paid (no renewals, something on which I might reverse course), but that’s not the only one. If you want to get paid for content, you typically need to provide people with the kind of actionable advice they most urgently want: how to make money, how to lose weight, how to get laid. But I won’t market myself as that because: (1) If I knew how to make money, I wouldn’t be writing about figuring out how to make money on my terms; (2) I know how to lose weight and I will share it with you now for free: time-restrict your eating (fast), eat fewer carbs and exercise; and (3) I am more or less married (not legally, but it’s been 11 years, we have a house, a daughter and a dog.) Do you think I’d be stupid enough to get married if I knew how to get laid?
Seriously, though, while I can’t offer you what you want, I have to come up with some kind of value proposition. I try to think of it as the Steve Jobs’ (and I’m paraphrasing): don’t give people what they want, but what they don’t yet know they want. What might that be?
It’s not simply entertainment — there’s lots of that for free everywhere. Writing and podcasting must be entertaining, but it’s a high bar to get paid for entertainment alone. It’s not information, either — I have no special inside access to non-public information, and there is virtually no subject on which there are not many more learned and expert sources than me. Moreover, I am not RotoWire with a real-time feed of curated, actionable news or a Bloomberg terminal for financial information.
I’ve thought about this for the last few weeks, and it dawned on me what I have to offer is the application of critical thought to things of importance.
The reason I left RotoWire — aside from it being sold, getting paid, no longer owning the entity for which I worked, having bosses and prospectively getting paid less than when I part-owned it and took a share of the profits — was I no longer felt fantasy sports was important enough to devote myself to full time. Given the seismic changes happening in the world, it felt like a distraction. I still have my NFBC teams and enjoy rooting for them, but it’s not where most of my focus is anymore, as you can tell from my writing, podcasts and Twitter account. I no longer had it in me to talk for eight hours per week about fantasy sports on the radio. A 15-minute weekly guest spot on my old show is enough.
One’s work isn’t only about money, it’s the purpose too. I want to do something that matters, to apply whatever skills I have in service of something important. There are two pieces to this, one, what is important to the individual — managing money, managing health and managing relationships (we’re back to making money, losing weight and getting laid!), but it’s more an attempt to understand what’s going on in the financial system, how to take care of one’s health in an environment encouraging poor consumption habits and profiting off the inevitable illness therefrom. (I talk about being a parent and dealing with people too, but the only possible value-add there is to serve as a warning of what not to do.) Overall, the focus isn’t on actionable advice, though, it’s critically assessing what’s going on and cultivating awareness. Awareness doesn’t guarantee anything, but it’s a necessary condition for a proper response.
The second piece is what’s important to society. What’s the best way to think about it, influence it socially, economically, politically, ethically? You can be in great health, have socked away dozens of bitcoins and have a beautiful family, but if the compliance police kick in your door, you are still fucked. You can be a great surfer, but it won’t help you if there’s a tsunami. Given the unprecedented shift in western society over the last few years — yes, we really had lockdowns, and they really are creating a “disinformation” governance board to police your speech — it’s important to raise awareness and draw firm lines before it’s too late. It’s important to convey the urgency of this to as many as possible, including those who only vaguely understand something’s off and quite understandably do not want to contemplate what’s possible if we tread deeper down this path.
I am compelled to talk and write about what’s important, to be ruthlessly loyal to what I take to be true, even if it angers or upsets people who were colleagues, peers and friends. The stakes are too high to go along to get along, and my aim is to persuade everyone who is persuadable to draw an uncrossable line too. Freedom of expression, (freedom to be wrong even), freedom to decide what medicines to take or not to take, freedom to leave your home without government permission — these are foundational to any kind of world in which I want to live and raise my daughter.
I cannot promise I’ll be successful in persuading anyone going forward — though I have had people DM and email me to attest the podcasts and writing have influenced them — or at least helped them feel less alone when thinking along these same lines. But as long as these foundational principles are under attack, I will try. The best case scenario is we are successful, those who would seek to control our speech, thoughts and movement are beaten back, and we never find out whether our standing up made any difference whatsoever. Best case, people who free-rode think, “How paranoid you were for no reason!” when part of the reason it turned out that way is so many people drew the line. I don’t have to tell you what the worst case is.
The only paid content to which I subscribe right now is to Glenn Greenwald’s Substack. I get access to all his articles and podcasts in my email box, and honestly, I almost never read them. (Ironically, after drafting this, I did read his take on the Roe v Wade discourse, and it was excellent.) But I subscribe because I am glad he exists, that he is doing real journalism while the so-called journalists are running public relations for powerful people who ever-more-desperately need it.
It’s a version of Immanuel Kant’s Categorical Imperative: “Act only on that maxim you would will to be a universal law.” Do I want people selling “How to increase your engagement on Twitter,” “How to make a six-figure income drop-shipping" (is that still at thing?) to thrive, or do I want more Glenn Greenwald, calling out the hypocrisy and craven opportunism of the world’s most powerful factions? Do I want a world where everyone supports real journalists or life-hack specialists? For me, it’s an easy call, and I suspect most of the generous people who have contributed to my work have likely done so for a similar reason.