4 Lessons From 4 Years at DoorDash

Four years ago I left a comfortable job at an excellent company to join DoorDash, a Series C startup that had ~250 people. At the time, DoorDash was far from a sure thing. Several competitors had gone under and many were prophecying we were next. It’s been an incredible ride so far and while we’re just getting started, I want to reflect on lessons learned during this period. Here are four that stand out. 

1) Optimize for learning and impact 

Hours after coming to DoorDash’s San Francisco headquarters to interview, I got a call from the recruiter. Tony, the CEO, was about to leave town and wanted me to come in early next morning for a final interview. I had enjoyed meeting the team but this was a quick turnaround for a meeting of this magnitude. I had to work late that night and would have little time to prepare. 

The first part of the interview seemed to go well as I answered questions about my experiences in both HR and finance. But things went south when he asked me to share two new things I had learned over the past month. My mind went blank. I totally froze. 

After several seconds of silence, I answered his question but the examples I gave weren’t concrete. Trying to save the interview, I told him I knew my answer wasn’t impressive but that the primary reason I wanted to work at DoorDash was so I could accelerate my learning. And it was true! In my prior role, I was feeling comfortable but somewhat stagnant. I wanted a job where I could constantly learn. I wanted to have real impact. 

When the job offer came I was ecstatic. While the compensation package was less than what I was making, I knew I had to accept. I told myself that even if DoorDash wasn’t successful I’d still learn a ton. I’m grateful I accepted and my hypothesis held true. I’ve learned more over the last four years than I could have imagined. I’ve found that when we optimize for learning and impact, especially as we grow our career, the rest will take care of itself. 

2) Your limits are far beyond what you think they are

My first few weeks at DoorDash were a rude awakening. I had gone from an individual contributor on a highly structured HR team with well-built processes to leading a small, understaffed HR team. I was both player and coach, responsible for making key decisions and successfully executing them. While this was the key reason I decided to join DoorDash, it was very much a “be careful what you wish for” moment. 

Each morning I’d wake up filled with anxiety, my stomach in knots. I did my best to show up at work confidently, but I felt like a total phony. I’d experienced imposter syndrome before, but this was so much more. The sheer volume of work was challenging, but it was also the pressure of executing. I felt a tremendous weight on my shoulders. I had been hired to do an important job and I continually questioned whether I was up for it. 

A few weeks after starting, I had a conversation with my dad. Overwhelmed with work, I told him I thought I made a bad decision by joining DoorDash. This startup life just wasn’t for me. I didn’t think I could be successful. He listened for several minutes as I shared the challenges in front of me. He finally jumped in and asked if going back to my old company was an option. I quickly replied that it wasn’t. He then said, “Well, it sounds like the only path is to move forward. Just get up and do your best every single day. I’m sure things will work out all right.”

I sought to follow his advice. The boats had been burned at my last company. There was no turning back. I knew I needed to keep going. The knots in my stomach continued each morning but would subside after I got to the office. I sought to focus on the work and nothing else. I found that I needed to reframe can I do this? to I can do this

I learned that my limits are far beyond what I thought they were. I’m confident this applies to all of us. We can’t truly know our limits until we’ve tested them. 

3) Set boundaries

You don’t join a company like DoorDash if you’re looking for a slow and steady pace. While I had done 100-hour weeks as an investment banker early in career, my life had changed. I had a family with three young kids. I wanted to prove that I could handle the startup life but I didn’t want to abandon the things that were most important to me. 

On my first day in the office, I tried to feel things out. Most employees were younger than me and didn’t have kids. Was there room for someone like me? How could I fit in? Many at DoorDash stayed late and ate dinner together so I decided to join them. After the meal, my manager pulled me aside and asked what I was doing. I explained my desire to build goodwill with the team. He pushed back, saying that he needed me for the long haul and that if I don’t find a way to manage work and family I wouldn’t last long. He knew my priorities and was there to support me. 

This conversation empowered me to set boundaries. I had a long commute so I committed to leaving the office at 5 pm every day so I could be home with my family for dinner. On the flip side, I would wake up early and get to work before everyone else. This schedule wasn’t easy but my wife and I partnered to make it work. We welcomed our fourth child while at DoorDash and I made time to serve in my church and in the community.  

Had I not made the commitment to leave by 5 pm I don’t think I would have lasted more than a year. Setting boundaries was essential. 

4) Pause before placing judgment 

Kevin Delaney tells the story of a farmer who lived in a village on the outskirts of a town. One morning the farmer went out to plow his fields and found that the gate of his stables was open and his only horse missing. The neighbor noticed the empty stable and commented, “What terrible luck that your horse has run away. How will you farm your fields?” The farmer replied, “It could be good, could be bad, who knows. But I’m sure it will all work out.” 

Later that afternoon the farmer was mending his fence, and he noticed a thundering rumble growing louder and louder. He looked up to see his horse charging towards the open pen, followed by a team of wild horses. In a matter of minutes, there were a dozen horses secured inside the yard. The neighbor couldn’t believe his eyes and exclaimed, “How lucky you are! Yesterday you had only one horse and now you have a dozen.” The farmer looked at the horses and replied, “It could be good, could be bad, who knows. But I’m sure it will all work out.”

The story continues with several events that initially appear bad immediately followed by one that appears good. The farmer refuses to pass judgment at the moment they occur. He knows that there’s no value in wasting precious energy in constant judgment. 

I’ve learned the same goes for our careers. During my time at DoorDash, countless things have happened (getting layered, new manager, team reorg, etc.) that on the surface seemed to negatively impact me. In the moment I’d get frustrated and start spiraling. On one occasion, I considered leaving the company. Most of these situations, though difficult in the moment, turned out to be just what I needed. 

Endlessly debating whether things are good or bad is a waste of time and energy. I’ve now sought to live by the motto: Come what may and love it. We can’t always control what happens to us, but we can control our mindset. 

The last four years at DoorDash have been an absolute roller coaster. We’ve come a long way, but we’re just getting started (yes, we’re still hiring!). I’m fortunate I’ve been able to be a part of the journey and grateful for the amazing people I work with. There’s nothing better than doing meaningful work with people you care about. 

Onward and upward.

This article was originally posted on Linkedin.

The Most Important Story You Will Ever Tell (Episode 14)

Click here to listen to the podcast version

The most important story you will ever tell is the story you tell yourself.

I’ll say that again, the most important story you will ever tell is the story you tell yourself. 

One of my professors, Curtis Lebaron, shared this with our class many years ago. I didn’t fully know what he meant at the time, and I’d like to explore it further today. 

The stories we tell ourselves start at a young age. We love labels. Our society loves labels. In high school we label people as jocks, or we label people as nerds. When I was in high school there was a group that dressed in all black. We called them goths. Not sure if that’s still a thing. 

Why do we label? Labels make it very easy to categorize things. Labels make a complex world appear simple. Labels allow us to tell easy stories. But labels can be very dangerous. We know the danger of applying inappropriate labels to groups of individuals–we call these stereotypes–but have you stopped to think about the danger of the labels you apply to yourself? Have you thought about the story you tell yourself about who you are? 

I’ll share a personal example. Throughout most of my life, I have told myself the story that I am not creative. I was never fond of drawing or painting. Art class never was fun. Part of the reason is that I’m color blind. In 2nd grade I had a very traumatic experience where I was made fun of by my teacher and classmates for being color blind. In front of my class I shared a picture of my “green frog” but I had colored it brown. Everyone laughed at me.

I told myself: I am color blind. I don’t like art or drawing . Therefore, I am not creative. That story, which was repeated regularly, turned into a fixed mindset towards all things creative. Whenever an assignment in school came up that required creativity, I shied away from it. I told myself, I’m just not a creative person. That’s not me. 

This story stayed with me until I joined LinkedIn on the compensation team. I had a few projects I was leading and my manager pushed me hard to be creative. I still remember when he used that word. It was like fingernails running down a chalkboard. I didn’t tell him, but in that moment I thought, oh no, that’s not me. 

My manager and I had several conversations on the topic of creativity. I decided to give it a try, so I read a lot of articles and a couple books on the topic. My favorite book was Steal Like an Artist from Austin Kleon. I highly recommend this book and it helped shift my perspective on what creativity is and super practical ways we can be more creative. 

As time went on, I changed that story. By trying to act in a way that was creative, and by telling myself that I can be creative, a virtuous cycle was forming. I was becoming more creative. The change didn’t happen overnight but I made consistent progress. 

Over the next year, I wrote a book–something I had never done before– learned to edit video, learned how to market a book, and developed several other skills. 

Back to LinkedIn–I later left the compensation team to join another group that was highly analytical. We were working on a large data integrity initiative and my team was tasked with coming up with a creative way of making it stick. One person in the group said–I’m not creative. You’re the creative one. What should we do? I was tempted to say that I’m not that creative either but I owned it. I had been labeled as someone who was creative, which was in line with the person I was trying to become, and I wasn’t about to ruin that.

The lesson for me was that if you don’t like the story you’re telling yourself, you can change it. As I wrap up that example, I’m tempted to add that I still don’t feel like I’m very creative but I’m not going to say that. I can be creative and the more I work at it, the more creative I will be.  

This example focuses solely on creativity, but the stories we tell ourselves can cover anything. You might be upset with your spouse because he was rude to you or didn’t clean up his messes for the last few days. Another person might have the same experience but tell themselves a story about how her spouse has been working hard at his job, has gone out of his way to cook a nice meal for you, and is tired and needs some comforting.

Here’s the challenge for this episode — start to notice the story you’re telling yourself about everything. Your boss was late again to your 1:1. Does that really mean she doesn’t care about you? Your colleague has been dragging their feet on a project. Does that really mean they are incompetent 

When you catch yourself in this way of thinking, pause —- then say, the story I’m telling myself is ______. What’s a different story I could tell? 

Stories are incredibly powerful. They shape how we view the world and how we view ourselves. Always remember that we have the power to rewrite our stories. We have the power to change.

Don’t Follow Your Passion! Do This Instead. (Episode 7)

The most popular career advice out there is that you should follow your passion.

“Do what you’re most passionate about!”

“Find a job you love and you’ll never work a day in your life!

You hear it all the time. While well-intended, I’ve found this to be the worst career advice that’s out there. In this week’s episode, I’ll explore why you shouldn’t obsess over finding your passion, and discuss three practical things to do instead.

As a reminder, the Not Your Parents’ Workplace Show is now available as a podcast:
– Apple: https://apple.co/2T8URbu
– Spotify: https://spoti.fi/3dPs2so
– Google: https://bit.ly/3bECFwu

5 Ways to Unlock the Power of Mentorship in Your Career (Episode 6)

Mentorship is critical to career growth and the benefits of mentorship include faster promotions, salary growth, and increased job satisfaction.

But finding the right mentor can be challenging and it’s not always clear how to build an effective mentoring relationship.

In Episode 6 of The Not Your Parents’ Workplace Show, I cover why mentorship matters, four ways to attract a mentor, and creative ways to find mentorship.

5 years ago I published Not Your Parents’ Workplace. In the book, I wrote about the challenges I faced in 2008 when I had a front-row seat to the largest bankruptcy in US history. Given today’s economic environment and career challenges, I’m kicking off a YouTube series where I’ll share lessons I wrote about in the book as well as lessons I’ve learned since.

3 Daily Practices to Thrive During COVID-19 (Episode 5)

I don’t know about you, but for much of this COVID period, I’ve been in survival mode, learning on the fly how to cope with this new reality. But recently, I was challenged to look at things from a different perspective.

Rather than merely survive during this period, what if it were possible to truly thrive? What if it were possible in one year to look back and say that we experienced more personal growth and were more productive during this time than any other?

Over the past few weeks, I’ve come to believe that, while difficult, holding a new perspective is possible. In this video, I share 3 daily practices for thriving during COVID-19 and any other challenging period.

For more videos, click here.

How to Develop a Career Competitive Advantage (Episode 4)

In 2012 I read a book that had a profound impact on me and shifted how I think about my career.

That book is The Start-Up of You by Reid Hoffman and Ben Casnocha.  The authors argue that we can develop a competitive advantage by answering questions regarding our assets, our aspirations, and the market realities.

1) Assets: What are you inherently good at? What do you have going for you? These can include soft assets (knowledge, skills, connections) and hard assets (cash, investments).

2) Aspirations: Where do you want to go in the future? What do you want to do? Who do you want to become?

3) Market Realities: What will people actually pay you for? Where is there a market demand?

In my latest video, I dive into these three critical questions, sharing how these questions inspired me to make a career pivot and how they can help you build a career competitive advantage.

Fortune Favors the Bold (Episode 3)

Being bold is important in all aspects of our lives, but it’s especially critical in our careers. I learned this lesson firsthand when my friend Ned’s boldness and creativity helped him find his dream job.

In Episode #3 of the Not Your Parents’ Workplace Show, I walk through why fortune favors the bold, share the story of how Ned landed the job, and provide two tips on how YOU can be bolder than ever.