Episode 52: How to better manage your time

I have 5 calendars I actively manage on a daily basis. There are consulting projects, side hustles, advisory roles, volunteer work, career, travel and relationship related work streams.

I live by my calendar for each one and have experimented with different evolutions of how to effectively manage all the things I need to do. In the past I have experimented with project management tools like Trello as well as a simple running to do list in a new note each day.

Over time I have settled into simple, repeatable systems that help me track all the things across all the projects. Here’s the breakdown and how it’s evolved:

Browser

My entire system is built around the browser. I was an OG Opera user for mobile and web browsing. I then moved to Safari for the integration of icloud keychain, but missed the chrome extensions. I was a tab hoarder but found solutions like OneTab really helped keep the clutter to a minimum.

I used to separate chrome browser per project/workstream, but found permissions to be very challenging. I would constantly accidentally open a work doc from my personal email and vice versa. (Chrome eventually released profiles that solved for some of this but I had already moved away at that point).

Enter Arc. Arc allows you to setup different profiles and then multiple spaces per profile. My current system is Profiles: Personal, Consulting, Side Hustle, Work. Each one has different spaces (think completely separate browser tied to different emails). A quick swipe lets you access the next space. Each one has custom folders, pinned apps, and look/feel making it perfect for switching across projects throughout the day.

Note: advice I was given from a TechStars alum was always avoid working on anything side hustle/consulting related on main hustle device. Try to keep things 100% separate. If you don’t your main hustle can claim IP rights to whatever you’re working on.

Tasks

v1: I used to use a Trello board that had all my incoming tasks prioritized automatically by due date. I loved the automations in Trello - few examples:

• move a card to the appropriate column based on due date - e.g. when it’s two weeks out, this week, and today

• move a card to due in a week after it’s been blocked for 3 days; keep a label called “blocked” to remind me that I need to treat it differently

• progress status of “big rocks” - i.e. all the tiny tasks rolled up to a single project/goal so I always knew how many more tasks I had

Cons:

• I started to run into limits with automation without paying. After paying, I had multiple boards per project/workstream but then felt I had to bounce around too much to get a clear view of what I needed to do.

v2: iOS reminders app. The iOS 16 massively upgraded the reminders app. Now they had smart filters and a dedicated ‘grocery’ section that categorized the items in the list based on the name - e.g. pantry items, meat, etc for easy organization.

Workflows:

• reminders based on location: e.g. when I sit in the car (focus mode: driving) and my location is set to home, remind me to grab the amazon returns.

• reminders based on messages: e.g. when I message my wife remind me to ask about dinner reservations for next week

Cons:

• the filters didn’t always work properly - I tried to replicate the filters based on timing (to only see what was short-term important) but then things just wouldn’t show up (probably conflicting logic I created) and then I abandoned it

v3: I have switched to google tasks. For each calendar I create a set of lists and since calendar is always open, I have this task list easily accessible. Bonus is when using the ‘tasks’ format in google docs (and assign to yourself) tasks show in the task view on your calendar.

I find it helpful to create 15-min events at the end of my day for all the to-do’s and then transfer them over to google tasks for further organization and tracking.

This has been the least friction to setup and it’s helpful to decrease the amount of apps I bounce around between.

Time tracking

When I got in the zone, I used to go hours without moving. I felt like I was making good progress but had constant pain in my back, tight hips, and dry eyes. I also found it harder to get into flow state mode. Enter the pomodoro technique and a pomodoro timer.

There are many free digital versions (and even physical versions if that’s your thing) but the basic idea is after a long stretch of flow state (e.g. 60 minutes) you should take a break for ~5-10 minutes and then come back. This technique helps you continue your flow state longer. After 4 repetitions you take a longer break. For deep work I like 50 minutes of deep work and 5 minute break. I can usually get through two rounds before meetings.

Calendar

I use Google Calendar for everything. I make sure I share each calendar to my personal, so I have a single view of all events on a daily basis. I always have a calendar, drive and mail pinned for each email across my different Arc spaces.

I also add all calendar accounts to my mobile google calendar app, so I can create/edit invites from any account on the fly. I share my wife’s work/personal calendar to my personal as well as TripIt where I keep a record of all travel plans. I use iCloud concerts/events/apps that don’t have a calendar integration which syncs with my personal GCal account.

I use reclaim.ai to automatically block time on my work calendar when I have a personal commitment to ensure I don’t get double booked and cal.com (OSS alternative to calend.ly) to show latest availability across the various accounts.

There are a lot of productivity gurus out there telling you one tool or system will change your life. The key is knowing what comes easily to you and where you struggle first and then designing the system to maximize your strengths / cover your weaknesses second. That’s the key to making the system have a big impact even if the system is very simple.

As always, feedback is a gift and I welcome any/all feedback on this episode. See ya next week!

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✨ Special thank you to Gigi Marquez who suggested I start this newsletter 🙏