Iteration is Everything
Photo by Markus Winkler on Unsplash
I was recently reading a wonderful piece by Dan Luu titled What to Learn, in which he talks about what’s worked for him in terms of guiding his one personal development. In it, he talks a bit about taking generalized advice on what to learn, which he doesn’t think works:
I took generic internet advice early in my career, including language advice (this was when much of this kind of advice was relatively young and it was not yet possible to easily observe that, despite many people taking advice like this, people who took this kind of advice were not particularly effective and people who are particularly effective were not likely to have taken this kind of advice)...
In retrospect, when people said things like "Forth is very productive", what I suspect they really meant was "Forth makes me very productive and I have not considered how well this generalizes to people with different aptitudes or who are operating in different contexts".
This is a good point, something like “specifics matter; what works for a particular person or a particular situation might not work for other people or situations”. He then segues into what he’s found does work for him, which is leaning into revealed strengths he possesses, especially where they cover weaknesses or gaps others might leave vulnerable.
One thing that's worth noting is that skills don't have to be things people would consider fields of study or discrete techniques. For the past three years, the main skill I've been applying and improving is something you might call "looking at data"; the term is in quotes because I don't know of a good term for it. I don't think it's what most people would think of as "statistics", in that I don't often need to do anything as sophisticated as logistic regression, let alone actually sophisticated...
Another way to find these is to look for things you can't help but do that most other people don't seem to do, which is true for me of both "looking at data" and "having an adversarial mindset"... Poking at the limits of a system to see where it falls apart doesn't feel like work to me; it's something that I'd have to stop myself from doing if I wanted to not do it, which made spending a decade getting better at testing and verification techniques felt like something hard not to do and not work. Looking deeply into data is one I've spent more than a decade on at this point and it's another one that, to me, emotionally feels almost wrong to not improve at.
What strikes me about this argument is that he’s talking about places to improve that he wouldn’t have broadly known at the beginning of his career, and focus on skills he had to have experience to know were valuable. It doesn’t necessarily stand out in the article, but that means he had to revisit where he was at in his personal learning and adjust; if he hadn’t, he would still be primarily learning programming languages that people recommended without much thought as to whether they made sense for his needs and the needs his current situation demanded. Instead, he’s developed a skill-set he doesn’t even have a name for, but is highly customized for his needs; this seems to have been an absolute win, but it demanded a certain kind of thinking and openness to do.
I work at Clipboard Health where this kind of thinking is often referred to as “constant reiteration”. The idea is that situations are never what you initially expected them to be and change constantly. To keep up, that means you need to change constantly as well, adjusting plans and yourself to fit the needs of the day. I came to Clipboard from a series of jobs where the expected performance standards were more about constant, consistent repetition than frequent pivots, so I’ve learned a lot since arriving about how staying aware of the benefits of change can help with personal growth and task-effectiveness.
Reiteration is a Mental State
Until I entered an environment where reiteration was the norm, I didn’t realize how easy the trap of “making every day the same” was to fall into. There’s a certain allure to being able to consign a large part of your workday to mental autopilot. Making every day the same essentially lets you sleep through a lot of your work, but in a way where nothing ever improves. You can call it falling into a rut or routine, but the effects are very literally the same; if improvement requires change, then this mindset by definition doesn’t allow for improvement.
A mindset of reiteration is the opposite; rather than being easy and mindless, it’s difficult and active. If making-every-day-the-same mindsets allow you to disengage, reiteration mindsets contrast by active engagement in everything you do. To constantly reiterate, you have to constantly be awake, looking at every aspect of a task or project to see where you can improve. It means looking at every incoming piece of data with an attentive eye, figuring out where it fits into the ever-evolving picture of what you are trying to get done and how it sheds light on new opportunities or risks. But that difficulty allows for change, which allows for improvement.
Not every task is the same in terms of how many improvements it demands, by the way. In some jobs the landscape changes every year while in others it changes every minute; a day-trader is going to have to think on their feet and pivot a lot more than a bricklayer, for instance. A person in a job in a more static field would be ill-served by trying to change more often than the situation demanded, and actual constant changes have the potential to act a lot like planning paralysis.
When we say “Constant Reiteration” we are aware of the fact that constant reiteration doesn’t actually mean constant change; it means constant awareness looking for needed changes. It means engagement with the job on a level that goes beyond getting through the day and week. It’s about constantly updating your priors of what your task is and what your goals are, so you can be optimized to handle the changes reality forces on you as quickly as possible.
This doesn’t just apply to tasks; it’s also something you want to encourage in yourself. Dan Luu talks about various ways he’s pivoted his learning as he progresses through his career, and you can tell it’s natural for him to do that. He’s a constant improver; he’s always looking for the next way he can learn and improve and become more than what he’s been. But this isn’t the default for everyone; a lot of people eventually fall into a pit where they know enough to get by and don’t spend the extra energy they need to get ahead.
Personal reiteration follows the same principles as reiterating your plans for a particular task. It means looking at who you are every day with a focus on improvement. It means watching your work and the world around you to know what improvements to work on. Your time is limited; blindly learning new skills just isn’t time-efficient enough compared to the kind of optimized direction you can give yourself by being awake in your day-to-day life, noticing the demands of your world and improving yourself in specific ways to meet those demands head-on.
Reiteration is Environment-Dependant
Returning to the task reiteration/personal reiteration relationship, I think both rely heavily on maneuvering yourself into an environment where those things are not only accepted but rewarded, especially if you aren’t a Dan Luu type of person who treats that kind of improvement as naturally as breathing, something you’d do regardless of the difficulty and rewards.
In some business settings, frequent changes to plans are seen as a sign of poor planning rather than a sign of flexibility. I’ve been in those environments, and it’s tough to improve a process when changes are thought of primarily as something you do to repair rather than something you do to reach greater heights. I was really pleased when I got to Clipboard Health and found that a lack of changes was usually viewed as a sign of a lack of engagement rather than something people should be comfortable with; it was clear that whatever else my new job might be, it wasn’t one where saying “I think we should reassess and do this instead” was considered a bad sign.
On a personal level, I think I’ll never again in my career go into an interview without asking some piercing questions to my interviewers. I’ll be asking questions like “Do you have an example of someone on your team who picked up a new skill, and how that helped the team?” and “How do you deal with stagnation in your people and projects?” to try to make sure I find that, just as at Clipboard, the management is looking for and expecting the kind of self-improvements I have to make to eventually become the kind of person I want to be. I think for people like me where self-improvement tends to be a bit harder, finding that kind of environment is vital; having a workplace that encourages and rewards reiteration at a company values level is a gigantic help for that kind of motivation.
Reiterate your Reiterations
Like any other thing you want to improve, reiteration itself benefits from an awake-and-aware mindset. For instance, I’ve recently spent a lot of time thinking about how sometimes reiteration doesn’t mean changing what you are doing or altering your overall direction; it means leaning into the same thing more. It’s easy for me to think of reiteration as all big, bold changes, but sometimes it also means looking at something that’s working and saying “OK, how can we do more of this or do this harder to squeeze even more benefit out?”.
I know that’s likely pretty obvious to most, but it’s not a mindset that came easily to me. That meant to pivot to something better meant that I had to get better at pivoting in general, that I needed to change into being better at changes themselves. I mentioned earlier that some companies view frequent changes as a sign of trouble; fostering an understanding that this isn’t always so and learning the nuanced differences between “always having to change” and “always fine-tuning for best results” is another example of the kind of changes to how you change that improve your methods of improvement themselves.
When I write for the company blog on an average day, I usually use the corporate “we”, speaking in a company third person with the aim of explaining who Clipboard Health is. Today I didn’t do that, because I wanted to make it clear that this is a concept that I think starts from an individual level; fostering a culture of change necessarily demands that somebody takes those first steps and makes it clear that active reiteration is both acceptable and beneficial. I was lucky enough to come to a company that already had that kind of culture, but for many people reading this, a move towards constant reiteration as a value might have to start with a single absolutely significant change; you yourself changing how you work and approach improvement and blazing the way. That sounds hard, but it’s also what you deserve: growing means changing, and if being “awake” is necessary for that, someone has to be the first to wake up. It won’t be easy, but it will be worth it.
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