I’m a CEO who felt overwhelmed by life and work. I thought an executive assistant would fix things but I was wrong — here’s what worked instead.

This as-told-to essay is based on a conversation with Noah Greenberg, a 35-year-old co-founder and CEO of Stacker based in New York, about productivity hacks and how to build your perfect week. It’s been edited for length and clarity.

I started my company, Stacker, with three other co-founders in 2017, and it’s been almost eight years. In a nutshell, we’re a platform for helping distribute brand content as earned media.

At the end of 2020, I was feeling out of sync, overwhelmed by my calendar, and overwhelmed by life and work generally. People put meetings on your calendar, life happens, and it’s really easy to feel like it has to be that way, even if you’re frustrated. But over the past few years, I’ve really benefited from thinking about what could be better.

I’ve had to ask myself, “What does an ideal workday look like, and how do I realistically put the pieces in place to make that happen?”

I realized that my calendar was just a bunch of stuff thrown on in no particular order, with no real intention. Once I started calendar mapping, I started living with intention and feeling more productive.

My schedule and calendar had several issues

As CEO, I do a lot of external meetings scheduled in advance. I realized my calendar was getting filled two weeks in advance, and when my team really needed to talk about something, they’d look at my calendar and they wouldn’t feel comfortable asking if I could move things around.

Also, things got scheduled that didn’t need to be a priority. I’d end up with a zebra calendar, which is half-hour meetings, half-hour breaks, and repeat. I learned that if I could stack those meetings back-to-back, then all of a sudden, I would have a full hour and a half free to actually get things done.

I got an executive assistant who didn’t work out, but introduced me to calendar mapping

I only had an executive assistant for a few months because, in the end, I felt like I didn’t need one. I thought it would be helpful, but I felt very uncomfortable not sending my own emails, even as simple as scheduling a calendar invite.

The biggest impact of hiring an executive assistant was that they taught me about calendar maps, which is having a separate calendar with set blocks of the day planned out. I schedule blocks for things like internal work, internal meetings, external work, and deep focus time. I also try to have a weekly in-person breakfast blocked off. When I’m scheduling things now, I try to put them in the blocks I saved for them.

I even use it in my personal life. On my calendar map, I have “cook for friends” once a month on Thursdays. It may not actually happen on that date, but it reminds me to schedule something.

The more people I’ve talked to, the more they say an executive assistant will sometimes do this for you.

A yearly three-day silent retreat also helps my productivity

I also did my own three-day silent retreat at the end of 2020, booking an Airbnb, driving to upstate New York, bringing a journal, shutting off my phone, and leaving my computer at home.

I decided to spend the time completely offline from work, assessing what was working and what was causing me anxiety about work. I do this every year now. It was so transformational for me.

Being away from your phone and computer for three days can really help open your mind to what could be different.

There have been podcasts and books I’ve read. But even with all of those inputs, the best source for finding what works for me is self-reflection. It’s looking at my calendar and being really honest with what makes me happy and what makes me unhappy about how I spend my time.

I print out my calendar retroactively to see how well I actually use my time

I read something a few years ago that Jeff Bezos prints his calendar out and looks at everything that he did that month. He will cross out the things where he said that, if he could go back in time, he wouldn’t have attended.

I do this a few times a year now. I think it’s pretty intuitive. Reviewing, circling things that work, and crossing out things that don’t, it takes five minutes. The real meat of the work is taking action on that.

At the end of last year, there was a meeting that was my least favorite of the week. It was a topic that I was really excited about, but I dreaded it every week. So, I sat down with that team, and we completely changed the makeup of that meeting.

I now calendar map my personal and professional life once or twice a year

I’d say overall, people have been very receptive to me taking control of my calendar, and essentially my life, this way. I think what helps is having conversations to help people understand why you’re making the changes or blocking out the time.

Every year, if not every six months, I calendar map my work and personal lives together. My goal is to look back at the week on a Friday afternoon and say, “That’s the life I want to live; that was a great week.”

If you have a productivity hack that you would like to share, please email the reporter, Agnes Applegate, at [email protected].

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