At 9:30 every Monday morning this summer, I have a Zoom call with an entrepreneur. She’s one of my Duke students who decided to skip the typical path of taking a summer internship in order to pursue her startup, and we’ve agreed to do a weekly call in order to provide some consistent advice and accountability.
But 9:30 on a Monday morning is early for a meeting. At least, it is for a 20-year-old. Personally, I have two young children, which means I’m lucky to still be sleeping at 6:30 most mornings. But that’s not the case for this entrepreneur. Every time we talk, she’s clearly exhausted. Finally, I asked if she wanted to push back our meeting time.
“No, no, no,” she insisted through a yawn. “It’s my fault. For some reason, I’ve got myself into a terrible work cycle where I don’t get started until 1:00 in the afternoon and then work until 4:00 in the morning. I’ve got to stop doing that.”
“Do you feel like you’re getting your work accomplished?” I asked her.
“Yes,” she said.
“Do you feel like you’re making good progress?”
“Yes,” she agreed again.
“Is there anything you’re not able to do during the hours you’re working that you need to be doing?”
She shrugged. “Not really… no.”
“Then why do you want to change your schedule?” I asked her
“I guess because it seems like I’m supposed to,” she shrugged.
“That’s not a good reason,” I told her. “One of the worst ways entrepreneurs sabotage their productivity is by trying to conform to what they think is a ‘normal’ work process. And, believe it or not, it can destroy your company. Trust me… I know from experience.”
My first co-founder was (and still is, I suppose) one of the most talented people I know. I worked with him for well-over a decade, and we built multiple companies together. Officially, he was always the person in charge of our product, but, really, his mind worked in a way that made him brilliant at just about anything the company needed, and I often relied on him to be the “brain” of our business while I did more of the work executing it.
However, for as brilliant as he was, he had unbelievably strange working hours. He would work late into the night and into the morning, then he’d sleep the entire day. In fact, we would occasionally have morning meetings where he was still working from the previous night and I was already starting on my next day.
As his co-founder, keeping synced with his crazy work schedule was frustrating. And it wasn’t just frustrating because he was rarely around to collaborate with during the day. It was also frustrating because it meant he constantly wanted to be talking with me late in the evenings after I thought I’d finished my workday. I’d be sitting on the couch with my wife in the evenings to unwind while watching some TV only to get a call from my co-founder that would inevitably have me on the phone until 1:00 in the morning.
At some point during our startup journey together, I decided the company couldn’t have a co-founder who wasn’t able to work within the concept of “business hours,” so I confronted him. “We need to get you working like a normal person,” I insisted during one particularly frustrating late-night conversation. “You’re never in the office when everyone else is,” I scolded. “Our staff almost never sees you,” I added. “And, quite frankly, I’m tired of having to be on the phone with you until all hours of the night. We need to get you on a normal schedule.”
“I know, I know,” he said in a conciliatory way that surprised me. “I don’t know why I work when I do. But you’re right that I need to fix my schedule.”
Excited about his willingness to adapt, I helped him devise a plan to shift his schedule. We created a calendar, scheduled daily meetings he needed to be at in the middle of the day, and even scheduled personal training sessions in the mornings that would force him to go to sleep early so he could wake up and get to the gym. Within a couple weeks, he was working “normal business hours,” and I felt like I finally had the co-founder of my dreams.
Except there was a problem. For the next month, the entire company became much less productive.
What I didn’t realize when I tried to “fix” my co-founder and his operating schedule was that his schedule wasn’t some strange quirk. It was fundamental to our company’s processes and operational efficiencies. In other words, it was a huge part of how we got so much work done.
Functionally, my co-founder was operating a second shift that kept our company productive 24 hours a day. Even those late night and early morning meetings that felt so frustrating were actually adding dozens of hours every month to our operational productivity simply by getting me working more hours.
To be clear, I’m not necessarily arguing any of this was good or healthy from an emotional or lifestyle standpoint, but, in terms of producing output for our business, the strange schedule was a way of increasing our output. When we took that away, the company struggled. We either had to hire more people to overcome our newfound inefficiency, or we had to go back to our old way of operating.
“What did you do?” the founder I was mentoring asked when I finished sharing the above story with her in the same way I’ve shared it with all of you.
“We slowly drifted back to our old habits,” I said with a shrug. “I’m not sure it was the right choice, but it’s what happened.”
“So does that mean I shouldn’t change my schedule?” she asked.
“My days of trying to change people’s natural operational schedules are long over,” I laughed. “What you need to understand is that there’s a reason you’re operating on the schedule you’re currently on, and, judging by the results so far, it seems to be working well for you. Do you really want to risk sabotaging that?”
“But isn’t it weird that I work through the night?” she wondered.
“Weird by what standards?” I asked. “Big, established companies have standard business hours because they have employees and customers who need to operate within a routine. Ultimately, if your company grows, I suspect it’ll probably need to follow more normal business hours, too. But, right now, you’re building a startup. Startups aren’t nine-to-five jobs. Startups are a way of life. It doesn’t matter when you wake up or when you go to sleep, you’re going to be working on it. Worry less about when you’re working and more about what you’re working on. That’s much more important. If you’ve got a good workflow and you’re making solid progress, don’t risk sabotaging your productivity by changing something that doesn’t actually matter. That’s what I did, and it almost killed my company.”