At its core, accounting is a system of accountability. But what is “accountability,” really? I thought it would be interesting to explore the idea in detail. Accountability has multiple dimensions. There is accounting for the finances in a business, which is the most obvious application. There is accounting for the physical inventory of a store that sells goods. We account for our time, what we do with our money, and how closely we follow our plans. There is the kind of accountability that can be measured on a scoreboard. This is the logical and relatively non-emotional side of accountability. We write down what we did, what we have, what we are going to do, and what we hope to accomplish.
But humans aren’t logical—we’re emotional, and that brings baggage to accountability. In any group, someone’s bound to use the scoreboard to prove they’re better than someone else. If we get to design the scoreboard, we might rig the metrics to make ourselves look good. Or we’ll try to game the system—focusing on the numbers instead of the reason behind them. And when that doesn’t work, some people will flat-out lie. The more baked-in accountability becomes, the more people tie their identity to the numbers. That’s not always a bad thing if the right things are being measured. No matter what, though, every system can be gamed.
The Freelance Life: More Bosses, Less Structure
The past few years I’ve been reflecting on how to incorporate accountability as a strategy for individual motivation. As a self-employed freelancer, my accountability structure is a bit different. Contrary to popular belief, self-employment does not mean being your own boss unless you are financially independent (which I’m not). In my experience, being self-employed means having a lot more bosses. Running a business comes with built-in accountability to a degree. Clients are naturally incentivized to hold me accountable for the things they are paying me to do. Nobody has a natural incentive to hold me accountable for the important-but-not-urgent initiatives in my business. I think there are a lot of well-meaning but misguided ways that people commonly try to solve this problem. One such way is by arbitrarily externalizing commitments. People fail to acknowledge that if you want someone to hold you accountable, you have to give them a reason to. People are self-interested creatures. Someone might be willing to do you a solid here and there by sending you reminders to do your workout or ask you if you’ve worked on your screenplay this week. But if you want somebody to truly hold you accountable, you either have to pay them or find a way to devise a structure of mutual benefit.
The Problem With “Accountability Buddies”
One common structure of mutual benefit is the classic “gym buddy” arrangement. Two people both benefit from a mutual structure when they both have a desire to change the same habit. But there are some inherent limits to this type of agreement. First off, you have to find somebody who has a sufficiently compatible goal to yours. If the desired habit is constrained to a certain time of day, then you also have to find someone whose schedule works with yours. All of this is possible and there’s plenty of evidence it can be done. But here’s the difficult part. You have to find somebody who is sufficiently self-aware to recognize what they actually want. It’s easy to fall into the trap of thinking someone else can keep you on track when you’re not fully sold on the goal yourself—but that rarely works out well. You have to learn to practice discernment in the choice of accountability buddies. You have to find someone sufficiently self-aware when it comes to what they say they want; otherwise they’ll flake and then resent you for making their flaws more apparent. They might even blame you for their own decision to quit.
I often remember the old Zig Ziglar quote: “If you go out looking for friends, you’re going to find they’re very scarce. If you go out to be a friend, you’ll find them everywhere.” I believe the same is true for accountability buddies. We have to learn how to be accountable on our own. And here is one of the biggest missing pieces. Ultimately, I am accountable to myself when it comes to my own business. Nobody in the world will ever care about my business more than I do. Nobody will care about my personal goals or ambitions more than I do. No one will ever care about my personal life mission more than I do. So it’s a fallacy to think that somebody else can hold me accountable to these things if I won’t hold myself accountable. The internal work that each of us must do alone is the deep digging to decide what we are truly committed to. We’re not looking to fake commitment; we’re trying to uncover what’s already there. We’re not looking to conjure up a commitment out of thin air; we are looking to find the commitments we were born with.
Commitment Mining
Discovering one’s true commitments is a lifelong process that never ends. Our commitments don’t change over time any more than our DNA does. But our self-awareness grows over time. In my early twenties, I thought I was committed to a career of being a computer programmer. In my early 30s, I thought I was committed to a career of being a writer. Now, as I rapidly approach 50, I’ve come to realize that my commitments are not defined by job titles, but by my mission to build thriving communities. I’m not here to do something; I’m here to build something. Just as my thought process about my commitments has changed over the last 30 years, I expect I will continue to discover more over the next 30. Just like anyone else, I’m learning what I was made to do. I am revealing the proverbial statue inside the block of stone as life takes the unwanted pieces away year by year.
One practice that I have adopted is question journaling. Sometimes, if I am mulling over a complicated problem, I will write out my question as clearly as I can articulate it in a short and direct manner. I now always do this before bringing a question to anyone else. I ask myself what question I think I need the answer to and then I make my best attempt to write down what I already know about how to answer the question. The more regularly I practice this habit, the less I need it. I find myself naturally reframing questions more often when I use the tool of writing in journaling. When I bring a truly complex problem to the table, the next thing I will often find myself doing is slicing the problem into different aspects. For example, if I’m trying to think about how to get new clients, as I often do, this is really a cluster of problems that needs to be broken down. First of all, the question then becomes, who are the clients I’m trying to land? What problems do they have that I can solve? Where should I fish for clients? Does my messaging need to change at all? Etc.
When I’m journaling about a complex problem, I’m not fixated on trying to find the answer, because the nature of complex problems is such that there is no simple one-stroke answer. Every time I crack one little piece, the whole mess starts to feel a bit less tangled. Sometimes, there is a tipping point when it comes to solving complex problems. We are always potentially one simple problem away from unraveling the whole mess. I think about it like solving a jigsaw puzzle. Sometimes all it takes is placing one more piece, and then everything else starts to fall into place. We have to be patient and accept that it may take a while to get to that point.
Quantity Over Quality… to Get to Quality?
Externalizing accountability is not a good way to solve complex problems. But it is a fantastic way, when we identify a habit that will consistently solve a small part of the problem, to make sure we keep the necessary habit in place and prevent backsliding.
Here’s where it all comes together. This blog post that you’re reading right now is the result of a recent experiment I’ve tried with accountability. A writer friend and I have started texting each other each morning to talk about what we are writing. We decided to do this for 30 days. So now I’m curious about how sustainable the strategy will be. The experiment got me to write this blog post. Will it continue to get me writing more things? I like to think maybe I’ve cracked something open, but I have to factor in the recency effect and the novelty of a new idea. The real test will come over time. I get the sense that I have found a simple tactic that will at least lower my writing resistance by a smidgen. I am hopeful that there is at least some degree of sustainability, as a similar tactic has worked with my Substack. There was one pivotal cup of coffee I had with someone who suggested that I write on my Substack on the 10th and the 25th of every month. He said he was going to get on my case if he did not see me keeping up with this schedule. I have no idea if he’s actually reading the Substack or not, but in any case, I have been keeping up with the publication schedule on my Substack for the last few months.
Experiments, Not Eternal Contracts
This experiment got me thinking about a story I’ve seen floating around online. Supposedly there was a college professor somewhere who divided a class into two groups of people and tasked their students with making clay pots. Half of the students were instructed to turn in one clay pot and advised they would be graded on the quality of the pot. The other half were told to turn in as many pots as they could produce and advised that they would be graded on the number of pots they turned in regardless of quality. According to popular internet lore, the students who were graded on quantity produced better quality. Who knows if this ever happened, but the idea is useful in any case as a thought experiment. What I needed was a way to accept the inherent imperfection in my writing and send each finished piece out the door anyway. Externalizing accountability seems to fit the bill because I have a natural desire to write. That’s the key piece I didn’t realize years ago.

(Side note: I really wasn’t trying to make myself look like Geppetto with a Pinocchio version of myself. I still have a ways to go with training ChatGPT to make images in my likeness…)
When I look back over my life at the various levels of success that have either motivated me or failed to motivate me during earlier years, I can see one of two patterns always occurring. On the one hand, there were the unsuccessful times where I was trying to conjure up motivation out of thin air by using external accountability to force my behavior to change. In the more successful cases, I was using external accountability as a diagnostic tool to uncover my true inner motivation. There were times when I stumbled onto the key to success when I didn’t even know what I was looking for. The most obvious example comes to mind during the phase between 2010 and 2012 when I was forcing myself to write in an unnatural way. The exercise did not successfully produce the output I initially envisioned, but I did become more aware of what I was actually trying to accomplish.
Using accountability as an experiment is the main takeaway of this article. We all have to go through a learning curve when it comes to understanding what really drives our behavior. I think the practice is especially valuable for people like me who have a lot of creative ideas. There’s a lot to be said for trying a short-term experiment and seeing what happens. For instance, you can try forcing yourself to do something for an hour or 15 minutes and then see if your thought processes have changed by the end. You’ll know you’ve identified a true commitment when you find something that you still can’t stop doing even when you don’t feel like it. I don’t know how to describe the phenomenon any more clearly. You’ll know what I mean when you experience it for yourself. Meanwhile, the best thing I can suggest is to make only finite-term commitments and keep experimenting to see what lights your fire.
There’s no substitute for having your fire lit.