A Beginner's Life


10 min read
cambridge summer

I took a trip recently to see my friend Bill Bounds in Atlanta. In the course of catching up, he asked what seemed like a fairly inoccuous question: “what are you working on, and for whom?”

I then stammered through 15 minutes of the different projects I was working on. Customer Happiness team building (a hiring activity, which as a people and schedule-intensive thing is really tough for me), a fairly major project (organizing and contributing to a product update, which I’d never done before), and covering a full part of our support process (the technical lead role, which is one that takes a lot of time and focus). Along with those things, I was trying to keep up with my consistent leadership and marketing rituals, which I believed crucial to building a successful company.

Bill patiently listened to my entire response, taking occasional sips from a cup of coffee. When my stuttering, stop-and-start explanation finally ground to a halt, he said simply, “sounds like you’ve got a lot going on.” He was right.

My inbox was growing weeds, my Trello board was full of “immediate” projects that required my attention, and I permanently had the feeling I was missing or forgetting something. I was preoccupied in meetings, unable to focus on the conversations and people I was working with, and my work relationships were suffering. Since I wasn’t able to say “no", sometimes opportunities just got silently pocket veto’d – lost in my inbox somewhere.

It’s easy in retrospect to diagnose my condition: I wasn’t in control of my schedule, had stretched myself too thin with big projects, and on top of that, my down time was completely swallowed up in a cycle of working on nonessential things that seemed really important (the endless “fires” that crop up in our daily work).

One of my interview questions revolves around the idea of prioritization – given too much to do and not enough time, would an applicant be able to prioritize, or would they simply expand their bandwidth to accommodate? But I wasn’t following my own advice – I needed to get clear on what I could meaningfully contribute to, and what was best undone, or given left to others who would be even better or more energized by the opportunity.

I could write several blog posts on all the re-organizing and re-prioritizing work that went into getting me back on track, but today I just want to talk about the concept of zero. I’ve been inspired by several zero-based practices, and I want to share them with you in the hopes they improve your time management, your focus level, and your relationships.

To-do list zero

The first two areas I tackled were my email inbox and my Trello board. I was using Trello for my work list – blog post ideas, futuristic product concepts, bugs, “this week” to-do items, immediate items. Every time someone would look over my shoulder at the board, they would shudder and fall back aghast. It was bad.

I started by re-organizing my Trello board, and moving my lists from being time-based (this all needs to be done now!) to project-based. Each list was related to the different “hats” I wear at work. This activity had the immediate impact of clearing out almost half of my Trello cards, because I got to ask myself “is this really important?” each time I moved something. I dropped entire lists that weren’t related to my core contribution to the company and my own personal growth.

Still, multiple lists left me somewhat un-organized and un-prioritized. Which were most important? It was weird, but I felt like I needed another layer of organization.

Inspired by a post from Asana CEO Dustin Moskovitz called Mindfulasana, I re-opened a dormant Asana account. To be honest, the initial impetus was to see what a product created by such mindful-focused folks looked like.

Because it was an experiment, I only added a single days worth of items from my Trello board to my Asana list – and kept it conservative. If the items stayed on the list for multiple days, I could safely remove them – they were backed up in Trello cards. But removing them meant they stopped cluttering up my to-do list view, which allowed me to focus on what was clearly more important.

At the end of each week, I empty the Asana list, and start again from scratch. To-do list zero lives.

The second practice of to-do list zero: new “urgent” actions still get examined and properly prioritized.

Urgent issues come up almost every day, especially when working on a growing web product. But I was in constant context-switching mode, always jumping into the latest fire and leaving the last one unsolved. I knew this was ultimately unproductive and chock-full of mental clutter, so I needed a new approach.

To-do list zero means no issues go straight to the Asana board – first, they must be added to the Trello list. This forces me to pause and reflect – which list do they go on, and where on the list? Sometimes, this pause is enough to make me realize I shouldn’t work on them at all, or that, when examined critically, the urgent issue isn’t big enough to deter me from my big goals.

When when someone comes to me with an urgent issue, I don’t start from a place of “I can solve this!” (which is hard, because I get pretty happy pleasing people), and instead I start with “no”. I might add a Trello card, or ask the issue-bringer to open a GitHub issue, but I don’t add it to my Asana list until I’ve carefully considered whether it needs to be done today. Remember, urgent issues masquerade themselves as important issues all the time. In my experience, most things that seemed critical to fix in the first moment, look unimportant even five minutes later. Don’t forget to breathe before diving in.

Lesson Learned: The to-do list and inbox creates a constant mental load to carry. Find ways to comfortably eliminate the trivial and keep even the vital that you aren’t currently working on out of view.

Bonus: Oh, I also adopted Mailbox, and have found their “later” and “lists” functionality incredibly liberating.

Zero-based scheduling

My fiancé Marisa, a physical therapist, checks in with me between patients. When she’d ask “how’s your day so far?” and I’d answer “ugh, nothing has gotten done yet” she would push further, and helped me identify my scheduling nightmare. I had said “yes” to so many recurring meetings, I was losing two full days of my week just meeting with my co-workers! This also meant time I should have spent making progress against project action items was spent updating folks that “no progress had been made."

In reading the book Essentialism I learned the concept of zero-based budgeting. Instead of using the previous budget as a baseline, accountants start at zero, and force every item on the expense report to justify itself before getting added to the budget.

And so zero-based scheduling was born. Instead of supporting the status quo of recurring meetings, I re-examined each for it’s value to my work, and my interest in preparing adequately for it. There were standing meetings where we decided on a weekly schedule, because that’s what Google Calendars provides, when biweekly (once every other week) would do just fine. 1:1 meetings have been a great example of that.

This critical examination practice has also made me better at declining meetings I won’t be able to add to, or worse, I’ll be distracted during and therefore won’t take anything away.

Try this exercise: draw five empty boxes for the days of the week, and add in the meetings you know are on your schedule. Any that you forget? Cut instantly. Any that you find yourself sighing while adding? Re-examine critically. Any that are at the wrong time of day? Re-schedule. We get caught up in the flow of our weeks and forget we can take control of our time.

Zero-based scheduling has been a godsend for me, and (secretly) those I work with. Instead of forced conversations when I’m really thinking about something else, the removal of recurring meetings means I’m choosing to engage in conversations (albeit less frequently), and being deliberate about that being a learning and curiosity time for me. It’s led to deeper, more meaningful conversations, which keeps me excited for my next one. The perfect type of cycle.

Lesson Learned: If not controlled, our schedule will fill up with unnecessary meetings. Move all conversations possible to asynchronous medium (like email, GitHub comments, etc.), and examine critically before adding any new “standing” meetings.

Backlog zero

I’ve been spending a lot of my time between the support and product realms, learning what our customers want from our product and setting a vision for bringing that to life. Part of that process was consolidating a long list of known issues, and creating a uniform process for bridging the gap between our customers experience and engineering to-do lists.

Emboldened by my personal to-do list clean out, I went hog wild, removing issues that seemed extraneous, or that should be resolved through careful product thinking (and not just jumping in). But even after whittling down the list, I was left with the question of which comes first: major projects or maintenance issues?

Our CEO Chris sent me a link to a talk on product and team management by Peter van Hardenberg of Heroku. While the talk in it’s entirety is excellent and totally worth watching, Peter covers my exact conundrum in the Q&A segment (~31 minutes in). He describes the concept of “backlog zero”, which you’re probably aware of but never gave vocabulary to. If a bug or issue has been open for six months, and it never rose to the level of importance where it needed doing, you should safely close it.

I attacked our Trello board of maintenance tasks with new rigor, and started pruning our lengthy GitHub issues list as well. Sometimes, things that seemed like major customer issues at the time turn out to never come up again, and we can safely close the issue until it becomes important enough to tackle.

While there is consistent progress being made towards our big goals, a shorter issues list makes it scarier to review, and we’re able to slot those smaller projects in as we go. This cadence creates increased the feeling of movement and product velocity, which has definitely had an impact on my personal and team morale.

So those are some of my recent zero-based practices. It can be so easy to create a never-ending to-do list, fill an overbooked schedule, and spread yourself thin on multiple “priorities”. These approaches have made it easier for me to clear to neutral and be deliberate about what I want to work on, and when. As a result, I feel more in control of my time and my growth.

I’ve found myself, for the first time in a long time, thinking about big vision items. I’m excited about the future.

P.S. Every week, I send out a short newsletter with links to my favorite articles. When I write a new essay, that will be included as well. Sign up to get your copy.