Tools for MGMT: Episode 112

Monthly planning, $100k for icons, benefits for the self-employed, read receipts

Good afternoon from my girlfriend’s parents’ back porch in the Carolinas. It’s been a lovely time down south. Back to New York tomorrow.

My name is Ethan. I manage a screenwriter and a comedian. I started this newsletter to regularly send out a few links that I think other managers will find interesting. Thanks for reading this 12th edition!

Monthly Planning
In many ways, it feels like all bets are off after November 3rd. With that said, we’ve still got a month left in 2020. Yesterday I completed my planning for October – following a process that I started at the beginning of the pandemic in March and have iterated on since. I’ve talked to a few of you in the last week about your goals for the month ahead, and wanted to share my planning system:

  1. First, I block out 2-3 hours for this planning (sometimes I do it over 2 days).

  2. Then, I make a copy of this Monthly Planning template from the good people at Ultraworking, and fill it out entirely. It’s not the most intuitive document tbh, so you might find this guide helpful.

  3. Next, I take a blank sheet of paper and fold it into 6 parts (ugly digital template here) and write out the following by hand with a blue pen:

    • Things I can’t control: an ever-growing list…

    • Things I can control: basic stuff (ex: publish this newsletter every Fri.)

    • Monthly Habit: one habit I am focusing on for the month. October’s habit is to review my todo list each night and reschedule or delete anything that didn’t get done. September’s was to complete this mobility sequence every night (made it 26/30 nights).

    • Top 3 Priorities: capped at three priorities that are attainable, controllable, and that I’d be proud of myself for accomplishing 😀

    • Secondary Priorities: a longer list (10-15 bullets) of which I can reasonable expect to get halfway through during the month, but often have less control over…

    • Tertiary Priorities: a shorter list of items that would be nice to get done, but rarely do. I try to avoid carrying over any tertiary priorities from month-to-month and either delete or upgrade them.

      For the Top 3 Priorities, I try and avoid including anything that I don’t have (almost) full control over. For example “Close X deal for [Client]” would not be a top priority for me because I am so often relying on others…

  4. Finally, I spend 5 minutes reading over that piece of paper each morning – and try to schedule time for the highest priorities while making peace with the inevitable distractions and new things that pop up.

Six Figures in 6 days
A designer I’ve followed for a few years wrote an inspiring post on his blog about his iOS 14 icon set, which has generated $100k+ in sales since he tweeted his homescreen setup on 9/20. A bit that stood out to me about the benefit of having some slack in your schedule for when inspiration strikes:

Freedom of a clear schedule allowed me to take action as soon as the inspiration hit, which was incredibly important to maximize exposure. Inspiration is a productivity-multiplier, but it's perishable—so act quickly.

I’m thinking about all of this in the context of there being a growing appetite, appreciation, and willingness to pay for digital art… combined with a slate of free or low-cost tools for distribution (like Gumroad, Shopify, Stripe).

And indeed, my favorite visual artist has been drawing a ton lately. If you’ve come across any artists monetizing their art in interesting ways, please send along…

September 24, 2020

Portable Benefits
Many of you are self-employed, or have 1099 income that supplements your W2 income. I recently came across a company called Catch, which automatically sets aside certain percentages of your (self-employment) income for taxes, retirement, savings, vacation, and health insurance starting at $1/mo. In addition to automating, Catch can make quarterly tax payments to the IRS directly, and help you compare health insurance plans and obtain coverage from the app.

While all of this can of course be done manually, I’ve personally experienced friction with recurring todos like “set aside X% for savings” or “compare health insurance plans” that I know I should be doing. YMMV, but I do see a significant psychological benefit in having as much automated as possible.

Another company that keeps popping onto my radar is Collective (recently rebranded from Hyke… good choice) – which I’ll discuss more in a future dispatch.

Read Receipts + Email Tracking
Finally, I’m curious for your thoughts on read receipts. Some of the most communicative and responsible people that I work with have read receipts turned on in Signal (by default) or iMessage. But even so, I’m glad there’s a way to preview messages without having to “open” them.

Email tracking is a different, more insidious matter. I hate the idea of anyone knowing when (and how often) I’ve opened their email. To combat this, I use the PixelBlock extension in Chrome and have “ask before displaying remote images” toggled off in Gmail on iOS… both of which are not airtight solutions. Unfortunately, I’m a huge hypocrite in that I’ve used Superhuman off an on over the last year (which has “read statuses” turned on by default) and can think of numerous scenarios where it is beneficial to know if someone has opened your message… I just cringe when that “someone” is me.

This was inspired by an interesting debate about email tracking on HN from earlier this week. I’d love to hear your thoughts, also. Lmk?

Ok, I’m off – but here are a few more reads for your weekend ahead: