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2 / Does your calendar reflect your priorities?

August 7, 2022

Welcome to Issue #2

This week I caught up with Paul Millerd, author of The Pathless Path and Boundless.

Paul and I talked about “infovores,” people who love to read and learn as much as vegans love cauliflower appetizers.

I’m absolutely one of these people. It’s not uncommon for me to pull a book down from a shelf in the middle of a call. It’s a regular ritual for me to clear the piles of books off my desk at the end of the week to quite literally start the next week with a clean slate.

A friend of Paul’s asked him, “But… like… what do you do for fun?” Paul’s answer? Reading.

If you’re sitting there saying, “Damn, I’m not an information vacuum cleaner, Andy,” then that’s fine—few people are.

How is this relevant to newsletter for founders trying to build businesses and work on themselves? Founders have to cover so much ground once they get the rumblings of product-market-fit that they couldn’t read all the helpful stuff even if they dedicated their calendar to a hot-dog-eating contest of information consumption. So how do you learn? How do you level-up?

One way is to hire a coach. For example, one of the CEOs I work with told me this week that when other CEOs as what its like to work with me, she says that I’ve read just about every book and blog post and I can “prescribe” the right idea or half page of a book at the perfect moment.

Other ways include finding newsletters like this one, pruning your twitter feed to be filled with people learning about things you’re interested in, and finding a group of CEOs to meet with on a regular basis (I’m starting one of these soon in San Francisco).

The takeaway? Even if you’re an infovore building a company, “hire” others to do the work for you and benefit from what they learn and synthesize.

Big Idea #2: Does Your Calendar Reflect Your Priorities?

A conversation I had with Keith in 2014 or 2015.

Last week I introduced the “big idea” section, and after some feedback, I decided to break this section up into “theory” and “practice.” I’ll use “theory” to teach the concept, and I’ll use the “practice” section to showcase an application.


Years ago, I sat at dinner with Keith Rabois and he told me one thing that’s stuck with me: “Your calendar should reflect your priorities.”

Every founder I work with will, at some point, express frustration that something isn’t right. Hiring isn’t happening fast enough. People building stuff that isn’t aligned with the vision the CEO has. You name it. And almost every time the issue lies with time management.

When this happens, I’ll ask my client what the top three priorities for the business are over the next 3-6 months. If they can’t answer that, then answering that question becomes priority number one. Once we have a list of three, I’ll ask them to pull up their calendar.

Their calendars usually look like a graphic designer took six games of Tetris and then layered them all on top of each other in the most panic-inducing pattern possible. Hiring is usually a top priority, but I always chuckle when I see two thirty-minute interviews for a whole five-day week on the founder’s calendar. And they wonder why hiring is progressing at a glacial pace.


Keith’s time management principle of having your calendar reflect your priorities takes discipline but is pretty straightforward to apply. Whatever your top priority is, you can’t spend 2-3 hours on it in a week and expect to make progress. Top priorities require a minimum of 15-30% of your attention in a given week.

First, you need to be clear about what your top three-ish priorities are for a given period. When you set your priorities, set a rough goal for each one for how much of your time you’d like to allocate to those priorities. For example, you may say hiring is the top priority, so you set a goal of spending 30% of your week on hiring related tasks.

Second, once you’re clear on your priorities, you need to make sure you’ve blocked meaningful chunks of time (phenomenal read on time blocking here) on your calendar for each of those priorities.

And third, you need to defend your calendar throughout the week. As a founder, there are endless shiny objects that come wrapped in calendar invites or emails from investors and reporters. But if they’re not a top priority, then you need to jettison them from your calendar.

Fourth, I recommend auditing your calendar regularly. If you said you wanted to spend 30% of your week on hiring, how did you do? If your calendar reflects reality, you can look at all the events at the end of the day on Friday. You can also keep a private slack channel, message that channel every time you switch tasks, and have your EA classify your time in a report at the end of the week.

If your calendar regularly reflects your priorities (and the right priorities), I promise you’ll be happy with the results.

Reads & Resources


I always think of this article’s title as “Why Standups Suck.” The author, Andy Johns, led growth for Facebook, Twitter, Quora, and Wealthfront—an impressive resumé. He lays out a terrific alternative to standups that focuses teams on action items and decisions instead of individual updates. If you’re running standups and you haven’t read this piece, it’s like saying you love romance movies and refusing to watch The Titanic.

From Twitter

“People think progress is a line that goes straight up and to the right. But the truth is that it’s a zig zag.” A wonderful coach I learned from describes resentment as “refusing to accept what you cannot change.” Progress will be non-linear. There will be ups and downs, and you cannot change that. When you accept progress’s zig-zag up-and-to-the-right-eventually wave, you can learn to ride it instead of fight it.


If business had a Jedi council, I’m confident Seth would not only be on it but he’d be the Grandmaster. He simplifies what other people endlessly complicate. In this episode, he talks with Tim Ferriss about his book This is Marketing. My favorite takeaway is on the importance of finding “your smallest viable audience” when choosing a market to start a business in.


Published by The School of Life (an institution devoted to providing the emotional intelligence education we never got as kids), I think On Being Nice is an essential read for founders who struggle with how to balance being kind and candid or direct or frank. My favorite line to keep in mind: “A fundamental path to remaining calm and kind around people, even in very challenging situations, is being able to distinguish between what someone does and what they meant to do.” (p. 28)

Dice Roll

Ethan Mollick is a Professor at Wharton studying innovation and entrepreneurship, and he regularly tweets research on such. I’ve never been at a company that didn’t have an issue with people showing up on time at least some of the time. This research shows that asking people to show up on time isn’t just about being a stickler, though. Late starting meetings are less effective, creative, and productive.

That’s all for this week. I’m looking forward to what’s next!