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One of the hardest days of my life was the day I decided to hire my own boss. I cofounded Looksharp six years ago and had been through the trenches. From cutting founder salaries and narrowly raising a seed round in 2010 to losing key employees at key moments, we had dodged more bullets than James Bond. Yet, through the challenges, we built a successful company with millions of users, a phenomenal team, and backing from some of the best investors in the world.
When my cofounder brought up an interest in hiring someone more experienced than me in the marketing role, it caught me off guard, but it shouldn’t have. Our team was expanding, our marketing budget was ballooning, and we needed to develop new channels that I had never built before. Surely someone who’d been there before could execute faster?
Sound logic aside, when you fire yourself from the company you built (because that’s what you’re doing), none of this matters — you are going to feel awful. You’ll have to defuse yourself from your identity as a founder and come face to face with the fact that you might not always work at the startup you spent years building.
Here are some of the lessons I learned going through this process that I hope will help other founders, early employees, or anyone else who has to hire above them. It happens a lot and, while it’s never easy, I ended up learning more in the last year than just about any other time in our startup’s life.
Lesson 1: Accept the Change
As the hiring conversation evolved, I had trouble sleeping. My mind was racing, and I was full of personal disappointment. In the midst of the talks, I decided to take a trip to Vancouver to help clear my mind.
On my first night there I was staying at a hostel, and at 3 in the morning I was still awake. Suddenly, my 6’5’’ hostel roommate came back from the bars. He spent 15 minutes trying to climb into his bunk before giving up, turning around, and throwing up all over his suitcase. The scene was absurd, funny, and for whatever reason pulled me out of my negative headspace. Sure, I was torn up about my job, but at least I had a clean set of clothes to wear the next day.
In that moment I decided life is too short to be angry; I was going to stop resisting change and accept it. This decision made all the difference. I started sleeping better and became happier overall. When I got back to San Francisco, I had to go to work every day and face the reality of finding my replacement, but by accepting the change I was no longer pulled in different directions.
Lesson 2: Learn to Meditate
In one of Ben Hororwitz’s best blog posts, he says, “By far the most difficult skill for me to learn as CEO was the ability to manage my own psychology. Organizational design, process design, metrics, hiring, and firing were all relatively straightforward skills to master compared to keeping my mind in check.”
It’s a fantastic quote because it shows that even the best leaders deal with immense psychological pressure when running a company.
The most effective tool I found to help me through the stress of this change was meditation. There are a million articles out there about meditation, but for me, the key was to practice for 10 minutes every morning. My goal wasn’t to find calm; it was to spend time reflecting on my upcoming day, prioritizing what needed to get done, both of which made it easier to focus on the task at hand rather than the thoughts in my head.
Lesson 3: You Will Grow as a Person
As an entrepreneur, when you hear Elon Musk say that “Starting a company is like staring death in the face,” you get a sense of pride, because you can relate to the statement in a way that 99.9% of the world cannot.
The hardest part of this change was to let go of the immense pride I had in my identity as an entrepreneur. In the end, this was one of the best parts of the process — it forced me to reflect on everything that led me into entrepreneurship and I knew would drive my success on future companies and endeavors. I realized that Looksharp was one of many companies I hope to build, and learning to handle hard decisions creates a personal resolve that can only benefit you in the long run.
Finally, it helps to have the genuine support of your team. I’m thankful to my coworkers, mentors, and the fantastic investors at Subtraction Capital, all of who were thoughtful and supportive throughout this process.
If you are ever in the doldrums of a big change at your company, feel free to reach out (firstname.lastname@example.org). Otherwise, onwards to building something awesome.
Note: There are a few other articles on this topic that I highly recommend including Fishkin’s blog on swapping drivers and Jonathan Strauss’ post on Replacing Oneself. In both cases, it is worth noting there is a big difference between replacing a CEO (“The vision person”) and a founder in marketing or engineering.
Nathan Parcells is cofounder and VP of Marketing at Looksharp, a series-A backed tech company that helps students launch their career. Outside of data-driven marketing Nathan enjoys rock climbing, writing and coffee.
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