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Why applying to 100+ jobs doesn’t work
When I was entering the job market in early 2023, I caught up with my friend Fadeke. She had just started a really good job at DigitalOcean. She shared her process with me, and let me know that she did fewer than 20 job applications. This quantity was a really helpful anchor for when I…
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Creative energy: Generative mode vs. explosive mode
When I told a good friend of mine I wrote a blog every day while I worked a full-time job, they responded, “I don’t know how you find the energy.” I actually generate energy from writing the blog every day, I tried to explain. If I didn’t write the blog every day, I would have…
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Opportunistic vs. strategic
If you’re doing things right, people will knock on your door with business opportunities. Every so often, one of these opportunities will catch your attention. While you already have a strategy—a path you’d outlined to get where you wanted to go, and a list of things you decided not to do—you’re figuring out how to…
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Reconsider your definitions
One of my clients was a co-founder of a company that had raised $60 million in funding before they signed on my editorial studio to work with them. We met to discuss the project, and it went well—they liked the strategy and were ready to kick off. Towards the end of the meeting, he wanted…
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To minimize overthinking, set and adhere to a time constraint
Doechii made her mixtape, Alligator Bites Never Heal, in a month. She says, “If I sit with art for too long, I start to overthink. Then you start over editing. Suddenly you can find yourself with a completely different picture. That’s why I set a hard time limit. I told myself: ‘Whatever I get done…
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Leaders trust people, not AI, to be accountable
You trust a person to deliver on a promise because they’re incentivized to. If somebody doesn’t do their job, they risk losing their income. If they lose their income, they will feel pain. The incentive creates accountability. AI doesn’t feel this pain (yet?). While they’re capable of doing many things, one of its few shortcomings…
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Free lunches
Early in my life, I learned the motto, “There’s no such thing as a free lunch.” The implied lesson is to be careful around somebody offering you something for free—because there’s usually a hidden cost. They must have something to gain from it, and that’s why they’re giving it to you for free. While that…
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If you’re embarrassed by your early work, that means you did it right
Anybody who does anything worth doing knows how difficult it is to get through the early work. While you have great taste, your skills aren’t at the level you need to match it yet—so you make work that falls short of your vision. It feels mildly embarrassing at the time, but as the years go…
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You won’t think your way out of overthinking
Overthinking—making and updating plans, gathering information, talking to people—is only useful for protecting you from the pain of reality and the hard work it takes to learn. It is not useful if you actually want to achieve your goal. What is useful is doing. Because you’ve already thought so much about it, you probably aren’t…
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Who you are vs. how you appear
I recently came across The Luddite Club co-founder Logan Lane’s speech at MoMA R&D Salon 48 entitled, “No More Likes” (via Alex Vadukul). Her closing message really resonated with me: There’s a certain vulnerability unique to younger generations, having grown up digital natives. For the youth of today, the developmental experience has been polluted. It’s…