May 20, 2025, 9 a.m.

Notes on delegation

Draft's Letters

Thanks for your patience while we were out in sunny, profoundly warm Mexico. I watched a thunderstorm roll in while drinking coffee on my balcony, overlooking the Caribbean, and I felt really grateful to be alive, doing what I do for all of you.

A few small announcements:

  1. I’ll be doing teardowns at MicroConf Remote tomorrow, May 21, in the morning. MicroConf is one of those extended-family things that I’ve been honored to attend over the past few years, and I’m really grateful to be on some form of stage for them. Please come through & heckle!
  2. I was quoted on the App Collective’s latest episode on the topic of how we vet trusted partners. Don’t call us, we’ll call you.
  3. Not a Draft-y thing, but we enjoyed this A/B test. Not a very high sample size, but you’re dividing by zero, so.

Okay, actual letter time.


One of the fun things about going to a new-to-me community’s conference is when you get to zoom out & determine all of the things that they value. MicroConf, for example, loves emphasizing the necessity of charging more for software, for moving upmarket, for reducing the cost of marketing. I was once part of a community that loved the whole creative-person success story, and they emphasized vulnerability, tradeoffs, making sure their audiences were consulted.

This conference was all about how to make your life as easy as possible as a manager of humans: when to hire & fire, how to delegate, etc. The theory, I suppose, is that you are freeing up psychic space & discretionary time to think about the long term, to think in general as opposed to execute.

This works well for businesses that are larger than us. Draft has been 2 people since nearly its inception. Once we got into a place where our hair was sufficiently on fire, we hired an assistant, and as mentioned, we did a bad job training her until, one day, we didn’t, and then our hair became less on fire.

But I like executional work. I like both talking about the quality of the offering and actually providing the offering. And I want to keep doing things I like, because truly why else do I have this job.

And so perhaps the challenge now becomes a question of how to delegate well, and be more discerning in what I can do v. must do. It might be an unknown-unknown sort of thing, or a do-it-now thing, or the sort of thing where I work unthinkingly and don’t realize I’m spending time on activities that I don’t strictly “need” to be.

If this resonates with you and you’ve come up with your own solutions, I’d love to hear them.

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