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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.