How I manage a packed calendar while keeping my sanity

A few lessons learned from being a product design lead and manager at a late stage startup.

My calendar each week is packed.

I’m in meetings more than I’m not. I don’t have much downtime at work.

Dialpad, my company, has a meeting heavy culture. And we’re well aware. We even tried making Thursdays “no meeting Thursdays,” but our culture is still the same. We don’t have less meetings, we just cram five days of meetings into four days.

We’ve even started bending the rules. “No meeting Thursdays” isn’t free of meetings, it’s just free of recurring meetings like 1:1 and stand-ups.

I couldn’t find a time that worked for everyone on the other days, so can we meet on Thursday this one time?

- My team, every week

On top of this, Dialpad is distributed across many time zones. Since I’m in EST, which sits between GMT and PST, I rarely have much “quiet time” when others are off hours but I’m working.

That might sound dire, but my situation is not unique. Over the years I’ve picked up a few ways to reclaim some time and attention.

A realistic representation of my work calendar each week

Here are a few ways I use my calendar to ensure I’m not constantly in meetings:

  1. Exercise: I exercise 30-45min every morning. I usually start my workday around 7:30am and work for a couple hours. Sometime between 9am and 11am, I block out time to exercise. While I could exercise before work, I like how a mid-morning workout breaks up my day. I create a block on my calendar to ensure it happens.

  2. Lunch: Similar to exercise, eating lunch is something I do every day (duh!). Since our team is distributed across time zones and cultures, it’s never lunch time for everyone. I create a block on my calendar for lunch. Sometimes I move it around to accommodate my team, but if push comes to shove I’ll decline a lunch meeting. “I’m here in this meeting but camera-off because I’m eating” is not a healthy way to have lunch.

  3. Tasks as blocks: If I have an important task I know I need to do on a given day, I’ll create a calendar block for it. Sometimes I create a 30min block titled simply “catch up on notifications” I’m I’m getting behind. I use Amie to drag items from my to-do list onto my calendar.

  4. “Ask first”: If I see small opening between a wall of meetings, sometimes I’ll fill it with one of these. The message: Meetings are not off limits, but ask before booking cause I might need a break.

  5. 🔬 Focusing: A good ol’ fashioned “Deep work, don’t book this.” I try to do this at least once or twice a week.

  6. “Don’t book if you need my full attention”: I have this block on my calendar at 4:30pm every Friday. The message: Meetings are not off limits, but you’re not going to get 100% of my brain or energy.

To prevent unnecessary meetings from landing on my calendar, I’ll sometimes respond to invites with one of the following:

  • “Do we need to meet or can we discuss this over chat?”

  • “Do I need to be there? Can you just tell me the result of the meeting afterwards?”

  • “Can you send the agenda / design file ahead time to review so our meeting doesn’t go over time?”

It’s not perfect, but it helps

So that’s what I do to keep my calendar from spiraling out of control.

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After finishing The Manager’s Handbook, the chapter on hiring made me realize this is a weakness of mine, especially recruiting. It’s so easy to procrastinate this and gravitate to other parts of the job (like designing).

Linear’s Conversations on Quality interviews product designers and leaders about what “Quality” mean to them. Interesting hearing how different folks approach this from different angles.

Datawrapper visualized every recorded death on Mount Everest, citing the cause and altitude of each. Morbid but surprisingly interesting.

I love this piece by Mandy Brown where she wrestles with the idea if we need to be on social media in order to reach people.

Farnam Street’s Shane Parrish wrote a series of books about understanding big ideas. This series looks a little dense for me, but I really enjoyed Shane’s last book.

The US’ most important climate elections this fall are local since state lawmakers influence how states set clean energy targets and whether they seek to access federal funding for climate initiatives.

Google and Amazon are investing in small nuclear reactors (low carbon) power for their data centers. Last month Microsoft announced Three Mile Island will reopen to power its data centers. Tech giants, who have made strong commitments to using clean energy, and are willing to pay through the nose for it.

🏛️ From the Archives
A favorite article I periodically re-read

It’s election seasons in America again, and as always there are a ton of issues up for vote. One of them is guns (I fucking hate guns), which prompted me to re-read Why I’m Afraid of Americans.

Thanks for reading ✌️
- Ted (@tedgoas)