🟢 How to Intentionally Underperform, New DoorDash Podcast, and Greenlights

PROGRESSION: February 2023

Okay, we’ve got a jam packed email this month so let’s jump right in. I keep kicking around the idea of sending a shorter email twice a month but for now we’ll roll with the status quo. 🤷 Open to your feedback!

Books, Articles, etc.

Greenlights by Matthew McConaughey (Book)

Excellent biography about a fascinating human. McConaughey tells countless interesting life stories and his Texas accent makes the audio version a lot of fun. Here’s one that resonated. 

In 2010, McConaughey was coming off a decade-long run of successful romantic comedies but he wanted something different. He felt pigeon-holed. He wanted roles that would stretch him. So he told his agent that he was done making rom-coms. No more. He knew the rebrand would take time. Romantic comedy offers kept coming in, but no offers for the roles he was looking for. Months went by. No offers. A full year went by. No offers. He told himself to be patient but it was eating at him.  

One day he got a multimillion dollar offer for a romantic comedy. He said no. The studio kept coming back with a higher price. He said no. Ultimately they offered him $14.5 million. “I declined the offer,” McConaughey writes. “If I couldn’t do what I wanted, I wasn’t going to do what I didn’t, no matter the price.” He had enough money to wait things out. But his passion was acting and it pained him to sit on the sidelines. 

Matthew McConaughey went two whole years without an acting job. But his patience eventually paid off. A role that interested him came through. Then another. And another. He went on to have one of the hottest movie streaks playing starring roles in Interstellar, Mud, Dallas Buyers Club, and many others.

McConaughey’s story is a good reminder of how hard change can be. People want us to look or act a certain way. They’ve gotten used to who we’ve been in the past. It’s easier if we don’t change. Becoming the person you want to be requires patience. But if you bet on yourself, and hold true to what you believe in, even when it’s hard, it will be worth it to you in the end. 

Leading with Empathy | Keith Yandell Interview by Lenny Rachitsky (Podcast)

Keith Yandell is DoorDash’s Chief Business Officer. He was my first boss at DoorDash and the man who persuaded me to join the ~250 person startup back in 2016. 

In this interview, Keith shares how to lead with empathy, the importance of openness in the workplace, tips for hiring, and how to make big decisions when teams are competing for resources. Keith is a great leader and I highly recommend giving this a listen.

Apple Podcasts | Spotify | YouTube

The Creative Act: A Way of Being by Rick Rubin (Book)

Rick Rubin is one of the most successful music producers of the last several decades, producing albums for a wide variety of artists including the Beastie Boys, Aerosmith, Metallica, LL Cool J, Weezer, and Johnny Cash. 

I knew little of Rubin before this book and I still know little about him after reading it. That’s because it’s not biographical. It’s a book on the creative process. The chapters are short, each having a nugget of wisdom Rubin’s he’s learned through years of creating. Here’s one that resonated.  

Part of the process of letting go is releasing any thoughts of how you or your piece will be received. When making art, the audience comes last. Let's not consider how a piece will be received or a release strategy until the work is finished and we love it.

Observations

Question of the Week: What Will You Intentionally Underperform at? 

This question came from a startup CEO who was struggling to manage all the tasks in front of her. You’ll inevitably underachieve at something. When you decide in advance what you’ll fail at, you take control and eliminate any shame. Click here for the video. 

Don’t Focus on the Gap. Focus on the Gain Instead.

Top performers are keen at identifying the gap from where they are today and where they want to be. Herculean effort gets poured into closing that gap. But often that gap can feel so distant it becomes paralyzing. We lose the motivation to move forward.

When I see clients beat themselves up like this, I challenge them to do the opposite: focus on the gain. A simple question gets them there: “Go back to the person you were 12 months ago. What would that person think of the person you are today? What progress have you’ve made?” They’re always surprised by how far they’ve come. We then spend time celebrating those wins and highlighting personal growth.

To read the full article, click here.

Podcast Interview: Navigating Career Changes (with Al Dea)

I recently had the opportunity to sit down with Al Dea to be interviewed for his MBA Insider podcast. In our conversation I share my thought process behind big career transitions and how I navigated those successfully. I also opened up about the challenge of moving from LinkedIn to leading HR at DoorDash.

Finally, we dive into the launch of my executive coaching business and how I’m helping leaders thrive. Here are links to the full interview: Apple Podcasts | Spotify

Gratitudes

I’ve found power in regularly expressing gratitude so I’ll continue the habit. I’m grateful for the early DoorDash team. Last week I caught up with someone I hired shortly after I joined the company. She’s become a good friend and it was fun reflecting on the hard, crazy experiences we went through together. As I thought about it, those relationships weren’t formed in spite of the challenges we faced, they were formed because of the challenges. Often it’s the hard experiences endured together that build lasting relationships. 

If you've read anything worth sharing I'd love to hear about it. And do let me know if there's anything I can do to help you.  

Nathan

Learn about coaching | Read my blog

If this was forwarded to you and you'd like to sign up, click here