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On Monday, January 12th, 2015, I was starting my second week as the VP of Sales at PatientPop, a seven-person startup in Los Angeles. Except I wasn't in Los Angeles. Jennifer and I lived all the way across the country in Brooklyn, where I'd started building a small sales team out of a WeWork in lower Manhattan.
That three-hour time difference was a lot tougher than I expected.
I'd get up at 5:00 or 5:30 a.m. and work on sales strategy before anyone else at the company HQ was even awake, then meet my team around 8:30 a.m. and spend the day with them before heading home around six. Back in LA, the executive team was still working hard in the middle of their afternoon. Meetings and messages kept flowing in until 9:00 p.m. New York time, and pretty soon I found myself working fifteen-hour days, five days a week.
At first, I thought this was a pretty smart move. Most of the other executives had been software leaders for a decade or more, and I was this new 33-year-old kid (in their eyes) trying to prove I belonged. Working extra hard and being available whenever someone needed me felt like two easy ways to separate myself from the pack.
And I was right. Everyone praised my work ethic, how reachable I was, and how quickly I got things done. It felt awesome to be recognized by people I respected, especially when I was still trying to establish myself in this brand new, important role.
My wife, Jennifer, wasn't nearly as impressed.
She warned me early on that if I kept making myself available at all hours, everyone would start expecting it. And once they got used to me being available whenever they needed something, changing that expectation was going to be incredibly difficult.
I definitely heard her, but I also didn't do anything about it. After all, my strategy was working just the way I'd hoped. The company was growing quickly, the board was thrilled, and I was building a reputation as the guy who would do whatever it took to win.
As that first year rolled on, the 8:00 and 8:30 p.m. meetings became my new normal. Nobody ever stopped to ask whether I was free, and I never spoke up if I wasn't. How could I? In these fast-moving startups, everyone's working hard, and I figured I needed to do the same, and then some.
But after a while, it started taking a massive toll on my social life, my marriage, and my mental health. I found myself exhausted all the time, and I certainly didn't enjoy spending almost every waking hour working. But I had a hard time imagining myself telling the whole executive team that I couldn't keep doing it.
Their praise had become part of the problem.
I'd spent the better part of my first year building a reputation as the guy who was always available, and people admired that about me. Imagine getting complimented for your hustle and availability, and then turning around and asking if you could have fewer late-night meetings. That felt so nerve-racking. I thought it would make me seem less committed, less hardworking, or less deserving of this role I'd worked so hard to get. I still needed to prove myself!
The part I hadn't really considered was that I already had.
We'd absolutely smashed all four quarterly goals, the board was exceptionally pleased, and the CEOs were calling PatientPop a "sales and marketing" organization. How validating. Here I was, with plenty of evidence that I could do the job, yet I was still behaving like the new guy who needed to impress everyone.
As the year came to a close, I finally decided to speak up and say something.
I flew out to LA for a week at the home office, and during an executive meeting, we went around the room talking about what was going well and what wasn't. I ran through my whole spiel about how sales and marketing were performing, shared some of the things I was working on fixing, and then took a deep breath and told everyone that the hours were starting to take their toll on me.
I remember feeling so intimidated saying that out loud in a room full of people whom I admired so much. I'd spent the whole year showing them how hard I was willing to work, and now here I was face-to-face, telling them I wanted to work a little less.
Their response completely floored me.
Everyone listened, took my concerns seriously, and vowed to put together a concrete plan to solve the problem. Nobody rolled their eyes, questioned my commitment, or suggested I wasn't working hard enough. That said a lot about the leadership team and made me feel even better about my decision to join the team at PatientPop.
From that point forward, I continued delivering quarter after quarter of strong growth, without wrecking myself the way I had during that first year. I ended up only missing one quarter out of seventeen in my career at PatientPop.
When I look back at the job, I don't think working those long hours was a mistake at the beginning. I was young, ambitious, had tons of energy, and was trying to establish myself in a very important role. Working extra hard helped me earn the trust and respect of my colleagues, and I loved being part of a company that was growing so fast.
But I kept working that way long after I'd earned that trust. I was so deeply concerned about maintaining the reputation I'd built that I never stopped to ask myself if my behavior still made sense.
And it turns out, the people I was so worried about disappointing were happy to help me make a change. I didn't see that coming.
Sometimes the hardest part of proving yourself is realizing you don't have to anymore.
I think a lot of people get stuck for far too long doing things that made sense earlier in their careers. Maybe you spent years saying yes to everything someone asked of you because you wanted them to notice your commitment. Or worked every single weekend because you were so desperate to get ahead. Hell, maybe those decisions worked! You worked to earn that big promotion, or built your first successful business, or finally got the respect you so desperately craved.
I've learned that getting what you want doesn't mean you'll automatically change how you behave, though. There’s a huge risk that you’ll continue making all of the same sacrifices because you're worried that stopping will somehow unwind everything you've accomplished.
I know I felt that way. I'd spent almost a year worrying about what my colleagues would think if I worked fewer than 15 hours per day, without even giving them a chance to tell me how they felt. Turns out, when I finally asked, they were perfectly happy to help.
I don't think I could've earned the same respect working fewer hours from the very beginning. To this day, I feel confident that was the right move. But as I entered my second year at the company, I felt like I'd earned the right to find out whether 15-hour days were still necessary.
At some point, it makes sense to stop asking, “Can I keep this up?” and start asking yourself, “Do I still need to?”
