The Calendar Habits that are Currently Changing My Life

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A Simpler Time. Simplifying. Simplicity.

Themes of conversations I’ve been having a lot of with clients and friends over the past couple weeks. As we are building successful businesses and making more money and having more impact and growing in our careers, how can we stop and remember…

What’s it all about?

What really matters?

How can we go through our days and our weeks and our lives feeling free?

How can we simplify?

While I’m all for some life-changing magic of tidying up, I find that my own feelings of simplicity and freedom have more to do with my calendar and how I’m spending my time than how I’m folding my sweaters. For me, when my calendar feels out of control, my life feels out of control. And when my calendar feels aligned, my life feels more aligned.

As a result, my relationship with my calendar has been a constant work in progress. Since starting my business, I find myself unintentionally repeating some of the habits I learned in the corporate world - back to back meetings, double and triple booking myself, and packing my day with commitments from 7 am until 6 pm. Changing these habits is still a work in progress for me, even after running my business for over five years.

In recent months, I’ve been looking more closely than ever at the calendar habits that create more simplicity in my life...at the practices that make me feel more free...and that ultimately allow me to have more positive impact by focusing on the things that matter most. Here they are.


Do a 2-Week Look Ahead, Each Week.

This has been the most transformative process I’ve implemented recently (credit for this practice goes to Jake). Each Sunday or Monday, Jake and I sit down with our calendars, and look out at the next two weeks. What do we have going on? What shared commitments do we have? What logistical considerations do we need to think about for the weeks ahead? And what shared time do we want to block off to hang out, have dinner with friends, or take the pup to the dog park?

While I’ve been in a solid rhythm of doing my own weekly review for the past several months (which I also love), the process of the shared look-ahead has not only made my life feel simpler, but it’s helped to create shared accountability for non-work-related things that we want to prioritize. I can’t recommend this process enough.

Create White Space.

Schedule at least 30 minutes of white space (ideally more, when possible) each day to “zoom up” from the whirlwind and think critically about the things that matter most. To increase your odds of maximizing this time, make a note about what you want to focus on. For example - do you want to use this time to identify key priorities for the week ahead? Do you want to use it to connect with a client who you haven’t talked to in awhile? Or do you want to use it for quiet thinking and reflection? Schedule the block on your calendar, along with a note about its purpose.

Schedule Meeting-Free Time.

Reserve a half-day free of meetings once per week, to focus on strategic work and big picture projects. If you are part of a team, I recommend implementing this practice as a team. Collectively identify a block each week that could be free of internal meetings, and create an agreement to preserve that block.

Several of my clients have done this by creating a block of time each week that is free from internal meetings, and it has increased both the happiness and the overall impact of the team, by giving each team member a sacred block of time for heads down work each week.

Be Specific.

Be as specific as possible about what is happening within each calendar block, to increase the likelihood of it happening. For example, instead of relying on a recurring calendar hold that says “focus time,” add specific details about how you want to use your focus time during your 2-week look ahead. Otherwise, it’s very easy to allow this time to be overtaken by meetings or lower impact work.

Look Critically at Meetings.

Think critically about which meetings you need to be a part of. Ask, “what specific impact can I have in this meeting?” If you’re not sure, have a conversation about whether it really makes sense to attend. If you lead or manage others, have this conversation with your team members. How does the team feel about the effectiveness and relevance of weekly and monthly meetings? Are the meetings serving the overall purpose of the team, and the organization? Are there any changes that need to be made? The 2015 State of Enterprise Work Survey found that “wasteful meetings” were employees’ top obstacle to getting work done. Improve your approach to meetings as a way to improve your overall outcomes.

Be Realistic.

Schedule buffer time after meetings that often run long. If there are certain client conversations that always take longer than the scheduled hour-long block, add a 30-minute block to your calendar after each of these meetings so you can plan for the overage. Plan ahead so that you can feel prepared, rather than feeling as though you’re constantly running behind.

Add commute time and meeting transition time to your calendar - and base this on the “worst possible scenario” (lots of traffic, lots of red lights, seeing several colleagues in the hallway) versus “best possible scenario” (no traffic, all green lights, and seeing no other humans on the way).

Schedule Personal Commitments.

Add personal items - even small ones, like going to the grocery store - to your calendar so that you can plan for them as part of your day, rather than trying to “squeeze them in” to an already-packed calendar. As part of your 2-week look ahead, think about all of the priorities in your life - especially the priorities that span beyond work and client commitments - and the ways that you want to honor these priorities over the course of the upcoming two weeks.

Peter Drucker once said, “what gets measured gets managed.” For many of us, our calendar is a measure of how we spend our time. Being intentional about our calendar allows us to be intentional about our days, our weeks, and our lives.

“How we spend our days is how we spend our lives.” - Annie Dillard