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I'm Brent Chudoba, Calendly Head of Biz Ops, and This Is How I Work

Illustration for article titled Im Brent Chudoba, Calendly Head of Biz Ops, and This Is How I Work

Location: Atlanta, GA and Charleston, SC.

Current gig: Head of Business Operations, Calendly.

Current mobile device: Pixel 3 XL.

Current computer: 12” MacBooks for work and home. And an iMac used only for WFH video conferencing.


One word that best describes how you work: Juggler.

What apps/software/tools can’t you live without? Looking at my menu bar and dock, I can spot the critical ones quickly: Chrome, Slack, Todoist, Evernote, Trello, Password manager (not saying which one), Spotify, Pocket, WhatsApp, Dropbox, Monosnap, G-Suite Apps.


What’s your workspace like? I try to stay fairly minimalist, and have nearly identical setups at work and home. A 27” monitor, laptop stand, Magic Trackpad, Magic Keyboard. Other items include an Anker power-usb hub with 1 foot cables for USB-C, Micro-USB, and Lightning to charge anything I need. And then a Leuchtturm1917 notebook with a couple Muji 0.5mm pens.

What’s your best time-saving trick? I manage several different people and several different functions at our company. What I’ve learned is that anytime I have an idea or topic for someone, it’s best to add it to a list to cover with them in our next scheduled meeting. Most things aren’t urgent and some things that could distract you right now, may not even be worth spending time on by the time your next meeting rolls around. Shared lists or tools for managing 1x1s or group meetings are critical for this. Another bonus, but related time hack, is that I have my own short URL. So I don’t have to use bookmarks or navigate to things that I visit a lot. I just create a short links that get me to the most common web URLs that I need to visit and type them in. Can’t remember your Linkedin profile to share? I can always remember mine:


What’s your favorite to-do list manager? Todoist. It is fantastic. The recurring reminders and quick adds are what made it a huge win for me. Until recently I was on Wunderlist for years but sadly after they were acquired by Microsoft they went into what seems a state of product purgatory.

Besides your phone and computer, what gadget can’t you live without? Toss up between AirPods and Garmin 645 Watch.


What everyday thing are you better at than anyone else? My fingers don’t dance on the keyboard the way they used to when I was an investment banker, but I’m still damn good at building quick models in Excel or Google Sheets and my formatting is on point.

What are you currently reading? That Will Never Work by Marc Randolph. Marc was the original founder of Netflix. I’m about halfway through and enjoying it on audiobook while I start to ramp up training for a marathon.


What do you listen to while you work? Mostly country. Mostly Midland. Thankfully they released a second album because the last couple years was just the same album over and over again.

Are you more of an introvert or an extrovert? Introvert.

What’s your sleep routine like? I’m a very firm believer in the science behind sleep, especially after spending over a year working directly for the queen of sleep herself, Arianna Huffington, as COO & CFO of Thrive Global. I try to get at least 7 hours a night. I travel weekly for work and have two kids under the age of four. So while the start and stop part of my “routine” can be a moving target, my best practices like limiting phone use, lots of water, cool temperature, are consistent.


Fill in the blank: I’d love to see Rich Roll answer these same questions.

What’s the best advice you’ve ever received? Two always come to mind:

  • First, given to me directly from my former boss Dave Goldberg who was at the time CEO @SurveyMonkey. We were talking and I was frustrated about a complicated issue. He said to me, “I can’t say yes to problems, but I can say yes to solutions.” That was a quick way to get me to focus on presenting something that we could actually take action on.
  • Second, something I heard on Tim Ferris’s podcast from Ray Dalio. He said, “There are only two things you need to do to have a great life. 1) Figure out the best decisions to make 2) Have the courage to make them. I think this is very true since whenever we look back at mistakes, the culprit is either not seeking enough info to find the best decision, or being too scared or lazy to make it.

And that is how I work.

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