Structuring my workday for personal productivity and incentives

Without trying to sound too much like a #girlboss-in-recovery, I’ve been trying out a new way to structure my workday.

Here’s the goals tl:dr;

Here’s the structure tl:dr;


This part got kind of long and personal, feel free to skip to High Level Goals if you just want to hear about what I’ve been trying out

For some context, I’ve worked in a lot of different settings and work situations, starting with the week I turned 15 up until now (at age 35) – omg, 20 years of labor exchange! But most importantly to this topic, I’ve worked a lot as a consultant (billable hours, which takes different forms based on set lump rate, FTE contracting, or standard by-the-hour freelancer) and I’ve also had several standard salary-jobs at both biggish (not actually that big) companies and small ones.

Also the work that I’ve done has been software engineering, something-similar-to-that-e.g.-systems-designing-structuring-ops-whatever-etc’ing, and something I categorize as “explaining technical concepts to clients.” This latter part has been a big part of my job up until recently, working in Support-supporting technical roles in my last two jobs (4 years).

This full-time “solutions/integrations” kind of work doesn’t easily fall into the way I’ve grown accustomed to thinking about work, which is through “billable hours.” It’s also the kind of work that is inclined to burn people out, and I was feeling a lot of that early last year. I ended up switching jobs and am actively trying to manage the burnout feelings. I still deeply enjoy the part of the job that involves helping people with what they want to achieve, and I don’t get worked up over the occasional rude dude. That’s the easy stuff. I think what causes the rapid path to burnout is lack of control over the workday.

(And, of course, organizational disfunction, but that’s just.. a whole other topic entirely. I just want to note that burnout is largely a structural problem and not someone’s personal failure to keep up in systems that are out of wack with living a healthy life!)

For whatever reason, I felt that I was able to thrive in that kind of chaotic environment. At some point, though, I started to realize that it wasn’t so much that I was “thriving” but rather that I am fueled by fear and anxiety and other very-millennial graduated-into-a-recession feelings. It served me well for a very long time, but overall I started to understand that the constant stress of random pings throughout the day, always “being on” and responding to the most important fire of the moment, and the constant context-switching was causing my brain to be on high-alert all day every day.

(And I don’t have to add this caveat but I want to: I’ve been lucky to work for places that are extremely thoughtful and kind in terms of work-life balance and understanding this kind of stuff, so the pressure is all coming from myself, internally – not external pressure)

All of this is to say that I switched back into a traditional engineering role a few months ago, so my day is now very unstructured. I have very few meetings, and what I do is largely up to me to determine.

So now that I’m working my way back into this mindset of “having focused time on one thing” again, the performance anxiety I was having around “Quick! Panic! What’s the most important thing to do right now to help A, B, C, … all the way to Z?” morphed into “Ohmygod am I doing enough? What am I doing? Do I even know how to write code? What did I even do all day if I didn’t end up with a perfect PR at the end of it?” kind of anxiety. Again, this is all coming from just me, not from outside forces. I started going to therapy to help me deal with this exact thing. She calls it the harsh superego but I’m not gonna get into all of that, but yes, I was disappointed that my brain comes up with something to get stressed about, no matter what the job is.

High level goals

First, what am I trying to achieve?

I want to:

As a smaller goal, I was previously working with this mindset of “jumping between tasks” as a way to motivate myself. I’ve always worked that way – I work on something because I currently don’t want to do the other thing. It’s like cross-procrastination-productivity or something. That’s how I’ve been balancing my work for the past two months, but that means I am inclined towards small-easy work when the big-interesting-challenging work gets put off.

Finding some structure

If you’re not familiar with the pomodoro technique, it’s basically setting a timer for whatever interval works best for you (the de-facto is 25 minutes) and working until that timer buzzes, and then setting another, shorter timer to take a short break (usually 5 minutes). I won’t go all into the theory behind this, but I’m not the only one who has used it in the past as a way to trick myself into getting started with whatever the necessary task is instead of procrastinating or fumbling around with a few different things. In theory, it helps me from straying off to do whatever else might pop into my head while working. It reminds me of this scene from Peep Show where Mark teaches Jez how to read.

Like probably almost every software engineer, I’ve tried this on and off with not much success. But I’m trying it again this time in a way that fits my overall needs by adding some day-level structure.

Merging consulting mindset with salary-job mindset

A large part of this goal is making sure I feel productive during my day. When you work remotely, with a focus on async and flexible work hours, it can be hard to know when the workday is “done.” I enjoy working a mostly normal schedule (Dolly Parton’s 9-to-5) but occassionally there’s life reasons that can cause a timeshift or I just mentally or physically feel that forcing myself to work through specific times don’t work for me (and doesn’t benefit my employer, either), so taking a break and coming back to something after a walk or a snack or a meditation can help with that. I’m very grateful to be able to have this kind of work structure. But it still puts me in the position of feeling like “When am I done? What is enough?”

When I was doing consulting work, I just billed hours so it was easy. I could do that when I wanted and work towards the specific goal, broken into smaller goals-tasks. With a salaried position, there’s a history of the “hours you are at the office are hours working”, but we’ve seen a shift in that, especially in the tech sector, and this shift precedes the pandemic.

There’s a lot of discussion on what constitutes a full workday. I spent a lot of time thinking about this when I was doing consulting full-time, by binging podcasts like The Freelancer’s Show. The general consensus is that as a freelancer, you are only billing for that “I’m really working right now” working hours, and the expectation you should set for yourself is that you aim to spend around half of your “full time” doing “billable hours” work and the other half towards sustaining and growing your business, and attempting to do more than 20-ish hours a week of billable time is going to lead to being burnt out. I’ve definitely pushed it past that for reasons of necessity, and even going up to 30 is probably okay depending on the type of work, but that’s the general idea. (And also why freelancers need to charge double whatever an hourly rate equivalent would be, but again, that’s another digression).

Okay, so my work experience means I have experience with that specific consulting mindset (I charge you for hours working towards your goal, but not the time I spend billing you & other admin work) and also the “you are in the office from at least 10am to 6pm and that’s work, no matter the ratio of time spent chatting at the water color or writing code or doing standups”. How can I merge the two to make myself feel happy in a “remote, async, many different time zones” work culture (the environment where I’ve spent the last 4+ years, and many have spent the last two years)?

Mapping out my day

It’s not clear how much time people spend working when working in the latter, salary-type configuration. There’s been a lot of writing on this, and I feel like the conclusion is that people probably actually get 4 hours of “"”real””” (triple scare quotes) work done per day. Joel Spolsky, in 2002, says he felt like it’d be around 3 hours of productive, “real” work where you are in this kind of “flow state”.

With that in mind, I started structuring my day like this:

(Aside question: When does Afternoon become Evening?)

Documenting my day

pomodoro outline

For each time block, I start the timer and write my goal and the time, and then I note what I am doing as I go along.

I use my remarkable2 for this because I love my remarkable. I use a template that is a 4-up storyboard layout where I can state my time-restricted goal, when I start the pomodoro, and then lines where I can write what I actually did during that time. I set this up for Morning, 10 Poms, and Evening, which makes 3 pages. This can detail the things I tried or steps I took to think about something, what I learned about or wrote about while working on something, or if something came up and it took me off-course (like if my previous block was doing communication work, and then one of those pings come back and turn into a 30min meeting instead of The Thing I Intended To Do).

This forced reflection helps me think about how I’m spending my time, which I think is one of the foundational pomodoro goals.

10 Pomodoros

Okay, now into these 10 pomodoros for a minute. I’m approaching the pomodoros as a guideline rather than strict rules. I think that’s probably was messed me up about trying out the technique in the past – You MUST work 25 minutes and MUST break at 5 minutes and you MUST repeat 3x, etc etc. Again, that’s my harsh self speaking to me. I decided to follow those rules, but not feel like they’re so rigid.

By not so rigid, I mean that if the buzzer hits 25 and I’m really achieving something or wrapping up something, I’ll keep going until I get to the natural stopping point. If I feel like I’m fumbling a bit, I stop at 25 because the break will help me. Similarly, if my 5-minute timer runs out but I’m in the middle of a conversation with a colleague and that has to go on for a bit longer, I’m not going to be like “Listen dude, my pomodoro says this conversation is over.”

Also, yes, I’m counting meetings as 1 or 2 pomodoros, depending on length, and tend to round up that time due to the context switching or prep involved with those meetings.

Doing 10 pomodoros is five hours of work if you count the 5-minute breaks, and a little over four hours if you don’t. I do count the 5-minute breaks because when I’m not tending to basic biological needs, I’m checking in on Slack or other things that are essential to my basic job functions. To me, this has been working out to be around a full day’s worth of effort along with the morning and evening prep/tidy-up work. And because I’m flexible about all of these boundaries, it ends up taking me through a basic 9-6 (which could end up being a 9-8 if I need a long break or breaks in the day, or 10-7 when I get a late start, or 9-4 if I’m really up on it, whatever).

Brief thoughts on “banking time”

Due to my consulting/billing-hours mindset, this kind of structure puts me in a position where I mentally “bank hours” – if I’m really on fire, I can keep going and get a lot done, and then feel like I can “use those banked hours” on days or weeks when I don’t get so much done. Again, this is just like how my brain has ended up thinking and overthinking about this, so I’m not saying it’s a healthy way to think about things, but it helps me out. At my previous job, I had to track all of my hours and just hit X hours a week (35), and I’d find myself working a 10-hour Monday and end up with a half-day Friday due to how I was working at the time, and I still sort of work that way. Also due to hormonal fluctuations and the attitude of my uterus, I do have weeks where I’m really highly focused and high-energy (week before I’m ovulating) and weeks where I’m really dragging and feeling low-n-slow (the week before I’m menstruating). You’ll have your own times and reasons for moving faster or slower (childcare, sensitivity to the news cycle, the world is ending soon and nothing matters actually, friends in town, Your Sport’s Team’s Problems, etc).

Some other reflections


At the end of each day, I feel like I have something I can look back on and say “Hey, I did all of this today!” and feel good about that, rather than thinking “Did I even work today? It feels like I just wasted my whole day.” In my previous pattern of “latest-fire-driven-development”, I didn’t worry too much about whether I was getting things done because the accomplishments were so quick – I was always helping someone and moving on. But with software engineering where so much of the time can be spent working towards something through means of trying-failing-retrying with different approaches, or thinking about a strategy before writing it, or knowledge-building while puzzle-solving, … it can feel like you’ve “done nothing” until you arrive at the right answer. This has helped me a lot with realizing that the entire work-work part of writing code is the investigation rather than just the outcome.

I’m still testing this out, so I don’t know if it’ll work for me long-term. It could also get me in the right mindset so that I don’t need these kinds of guardrails in place to make me feel like I’m accomplishing my goals.

What do you think? Do you do something similar to structure your day? What have you found works and doesn’t work for you? Am I a total monster for thinking this much about how I work?? Too much or not enough? Sound off in “the comments” (yes, this blog does not have comments, but you are probably reading this on a platform that does have them).