
There are very easy ways to stay out of the doghouse in the two major careers I’ve had: being a teacher and being a lawyer. This would be some way of checking the boxes that would not necessarily be the heart of the substance of being a good teacher or lawyer. However, they were very important for compliance and when the bosses would need to answer to their bosses or clients.
In teaching, I can’t tell you how many teachers I’ve known who had excellent relationships with students and put a lot of effort and thought into their lessons.
But they could get into a lot of trouble for not having a lesson plan. I knew teachers who were put on performance improvement plans because they really struggled to have lesson plans. My teaching program taught me how to have a good lesson plan, but when I had to teach three classes and different grade levels a day, not every lesson plan could be the best.
Sometimes, my lesson plan would be a continuation of the previous lesson when my class did not finish the lesson. My lesson plan would not always anticipate every student action, but I got the sense these lesson plans were what my bosses were looking for when they came by.
Having a lesson plan every day did not make me the best teacher in the world, nor do I think it made me a very good teacher who could anticipate the ins and outs of every lesson. But usually, the lesson plan could help me anticipate certain challenges or more individualized student needs.
Another way I often saw teachers get in the figurative doghouse was grading. Other teachers and I often had to put in two grades a week to keep student grades updated. The worst thing that could happen was big surprises near the end of the quarter for students, so I understood the importance of this. I taught what is known as self-contained special education, which means I had smaller classrooms with students with moderate to severe disabilities.
This meant I had fewer students than your average general education teacher, so this was a very easy requirement for me to keep up with. I could put in my 2–3 grades a week, and if it were a week I was having trouble keeping up, there were various classwork and participation grades I could put in.
But teachers who had the usual 30 or more students with four classes a day would, for very obvious reasons, struggle more with this. Especially with grading deadlines at the end of the quarter, early in my career, I once saw a missing grades report that I was on. I endeavored to never end up on that report again because it seemed like low hanging fruit to dodge getting in trouble, but I knew other teachers who did struggle with this and could get reprimanded, particularly when they were particularly high-stakes grades (like grades for graduating seniors).
Again, grading and lesson planning were not indicators of relationships with students or how engaging someone could make a lesson. But these simple, contractually obligated tasks as a teacher often have a lot of implications, like when someone more high up than the principal comes to audit the school. I also saw it from the student and parent perspective of being surprised at the end of the quarter if there was a drastic change in the grade.
It was not just grading and lesson planning. There were also obligations like submitting progress reports for students with individualized educational plans (IEPs) as a special education teacher. I saw how teachers could be very overwhelmed and not have enough planning time to keep up with all these tasks, but before I became a teacher, proficiency in these tasks was something I wish I drilled down sooner.
. . .
As a lawyer in private practice, there is a similar task that even some of the best lawyers in the world struggle at: time entry. This is the act of billing your time to the client. Early on in many lawyers’ careers in private practice, they are told the importance of putting in the time they are billing to clients daily and consistently.
I have been to several trainings about this, and every lawyer gives a similar takeaway: you can be the best lawyer in the world, but if you’re consistently bad or late on your time entry for billing, you will get yourself in unnecessary amounts of trouble for being days or weeks behind.
I don’t see it from the client’s perspective, but it is better to have consistent bills than to be surprised. I’m still somewhat new to this and endeavor to put in my time every single day and then monitor whether I made any mistakes in my narratives in the morning.
It’s not the substance of what makes me a good lawyer, but I’ve been to three or four trainings on how incredibly important this is, so I tend to be a bit proactive about this. I make sure to make the narratives pretty detailed and specific (probably too specific), like “analyze case law and statute in order to determine issue X in response to Y claim from opposing counsel,” and I’ve heard stories about lawyers who have been weeks behind.
Anyway, I’m not as much of an expert on this, given I have only been an attorney for four months, but the importance of billing reminded me starkly of the bare minimum checking the boxes activities as teaching, and fortunately, people have been happy with me for my billing entires.
. . .
Are these checking the boxes activities sexy? Are they glamorous or what people dream of doing when they become a lawyer or teacher? No, they are not. I suspect there is a version of this in every profession — doctors and social workers have to keep detailed records, and the military prioritizes punctuality, men being clean-shaven, etc.
And I never went into work every day as a teacher dreaming about how to write a great lesson plan or grade assignments. I spend about 15 minutes a day putting in my billing entries as a lawyer and making sure my narrative adequately captures what exactly I did. This can be somewhat inconvenient with my work style of spending 20 minutes doing one task and then switching to another 20 minutes later (especially for long term, time-intensive projects), but I usually have one timer going that I can stop and then shift to another one.
Regardless, I have learned how important the bare minimum of checking the boxes is, and how easy it is to nail down the basics as a prerequisite to doing the tasks that really matter. My motivation is mostly not wanting to get in trouble, and checking the boxes has largely helped me avoid that and allowed me to focus more on the substantive parts of my work — legal research, writing, etc. Not needing to worry about being in the doghouse about putting in grades, submitting progress reports, communicating with parents regularly, or writing lesson plans allowed me to focus more on my actual student interactions and what I was actually teaching.
Again, I think someone in every career and profession might be able to relate, and these tasks can become routine, annoying, mindless, or all of the above. I eventually came to see that’s how the world worked. And I came to see it as a reason our bosses don’t get in trouble with their bosses for reasons we don’t always see.
I wish I could tell a younger version of myself to appreciate the importance of the mundane — the part of the job that includes administrative checkboxes and compliance-related tasks. There was a lot more of the boring and administrative than I expected, and it isn’t ever going to go away.
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This post was previously published on Ryan Fan’s blog.
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Escape the Act Like a Man Box



