✔️ To Do: One Small Business Owner’s Checklist

“Alice in Responsibilityland” by Liana Finck for The New Yorker

Dec. 2, 2023: To Do¹

1. Renew health insurance

   1. Run Gusto payroll report to reveal meager take-home pay this year

      1. Determine if this will yield higher or lower government subsidy, reducing the otherwise $1,800 per month sticker price for a family of two—more than double the cost of your first car.

         1. Muse over whether it’s time to move abroad, given how much you hate the health care system in the U.S.

   2. Seethe in rage upon receiving two bills from your annual doctor’s visit for routine lab work totaling $922.07 and $318.51, instead of $25 each.

      1. Wait on hold for thirty minutes with insurance company agent, seething further at bureaucratic ineptitude stealing your precious time.

   3. Figure out asthma situation ever since contracting COVID for the first time the day after Christmas last year.

      1. Wonder if this is officially “long COVID.”

         1. Wean off medication working wonders but hobbling vocal cords.

2. Cancel a slew of subscriptions to simplify expenses and reduce overhead.

   1. Determine how to gracefully apologize to anyone who might be offended.

3. Continue daily yoga streak.

   1. Remind self that 2023 word of the year was thrive. Only one month left to turn things around.

      1. Continue half-hearted attempt at losing pandemic and marriage 20 30 so that at least some of your clothes fit again.

         1. Kick sugar habit.

            1. Finally try those mberries your friend raved about.

      2. Buy and assemble standing desk. Marvel at the new view for Zoom calls.

         1. Still, swear off Zooms and video calls in the new year.

      3. Determine source of gremlin sitting in lefthand side of lower back.

         1. Is this 40?

      4. Start pondering word/theme for 2024.

         1. Miracles ended up apropos for 2020 😂

            1. Perhaps faith this time. Your usual logic has run its course.

4. Figure out how to clear calendar in the new year by pausing most business activities, after last month’s lightning bolt “download” telling you to do this.

   1. Determine WTF meant to do with life. And work.

      1. Keep following creative spark.

         1. Attempt to listen quietly as new direction reveals itself.

   2. Browse summer internships at venerated media institutions in New York City.

      1. Close browser tabs upon realizing they pay minimum wage for full-time work-weeks, and you have already committed to #3.

5. Announce the upcoming pause to your private membership community.

   1. Record a bonus episode for them, speaking from the heart instead of a script.

      1. Finish recording after thirty minutes, blinking in disbelief that after you hit “stop,” none of it saved. Everything you said is gone.

         1. Whine to your spouse like a baby. He says maybe there was something in there that wasn’t meant to be shared.

            1. Re-record a shorter, crisper version.

            2. Rejoice now that the earlier one got erased, despite annoyance at tackling this twice.

   2. Spend two weeks drafting and refining the community announcement email.

      1. Schedule it to go live.

      2. Due to a quirk of Substack settings, realize in horror—again—that the email went to 3,000 people instead of the intended 65, but only after your attorney replies with, “What’s going on? Everything OK?”

         1. Respond to say that, “Yes! Everything is fine!” 😂😅🫠

         2. File ticket with Substack support ending in, “Please explain . . . I’m mortified.”

            1. Support responds. 🤦🏻‍♀️ It was your own fault after all.

               1. Scold self for forgetting the highly nuanced tripwire that by inserting a paywall break in a Founding Member message, you nullify the narrowed recipient list. Free preview goes out to all.

6. Plan solo episodes to air in February announcing that both podcasts will be paused indefinitely.

   1. Figure out how to make friends again, now that you won’t be conducting eight to ten guest interviews every month.

   2. Question whether you are shooting yourself in the foot—and perhaps sabotaging your own success—by pausing your shows after achieving the current levels of chart and production momentum.

   3. Question when and whether to update website bios to reflect that you may no longer be an “author and podcaster.”

   4. Ponder whether you should re-release best-of episodes during the time off.

      1. Decide against this; too much work.

7. Turn attention instead to Substack growth and improving the quality of various offerings across your three newsletters.

   1. Cast skepticism at #7. Would it be like staring at the sun for too long again?

      1. Try to earn back your bestseller badge, after it disappeared as quickly as it came two weeks ago.

         1. Shoot! See 7a: now you are staring at the sun again. Stop that.

8. Sweat while checking credit card balances.

   1. Start preparing bookkeeping now for tax time in the new year—the sooner the refund, the better.

      1. Update emoji balance sheet. If only accountants would accept this.²

         1. Berate self for not doing a better job adding to retirement savings over the last thirteen years. Your 27-year-old self thought you’d be a multi-millionaire by now 😭

   2. Consider how many IOUs you owe yourself across various accounts you’ve robbed in the last three years. Or is it four years now? It’s all a blur.

      1. Pray you’ll be able to take your hands out of these cookie jars soon.

      2. Contemplate whether it’s time to sell remaining stocks to re-fund those accounts.

      3. Ponder what new business activities would generate enough revenue at one time to: pay yourself and your taxes and your business operations and then still have enough left over to cover not only the current month’s household expenses but the previous ones you’ve racked up.

9. Plan a virtual or in-person event to celebrate the second bookiversary of Free Time.

   1. Figure out how to sell the next 3,000 copies in a far-fetched attempt to hit the magic number of 10,000 before March 22, 2024, hoping to spark a new wave of momentum.

      1. Barring that, ponder how to give away the next thousand copies so that at least the work continues making its way into the world.

   2. FIGURE OUT WHY AMAZON STOLE HALF OF YOUR REVIEWS AND NOW YOU ARE AT 92 INSTEAD OF THE HARD-EARNED 144.

      1. Seethe in rage at faceless monopolistic bureaucracies. Again.

10. Write a reminder note to future self about how much time, work, energy, and money goes into book publishing, and how little comes back out.

    1. DO NOT FORGET THIS when the urge to create the fourth book hits.

    2. Stubbornly dream anyway, because books have always been your balm and best friends, and for the analog fun of creating an artifact in the world.

       1. Research print on demand.

       2. Perhaps you’ll make a tiny zine.

          1. Make a note to self (and an Artist’s Date) to browse bookstores in the Lower East Side where these are in vogue.

          2. Wonder if you need to be a 20-something MFA to participate in the ‘zine scene.

11. Find a hip-hop class in the city to rekindle a lifelong love of dancing.

    1. Make sure it’s one where a 40-year-old can futz around in the back behind all the lithe, perfectly flexible, stellar-at-choreography-memorization, actual Broadway dancers.

       1. On a recurring basis, carve out the three hours it takes to leave the house, wait for the subway, people-watch and/or meditate during the thirty-minute train ride, sign in, situate yourself in the room, take the class, thank the instructor afterward, then hop on the next subway home.

          1. Ensure it’s not dark out when attempting this three-hour block.

             1. Grow discouraged upon seeing the various schedules; the classes you’ve found are all at night.

12. Catch up on the alarmingly tall pile of newspapers and New Yorkers stacking up in your home ever since you started on Substack, lest you reveal yourself to potential guests as the reading material hoarder you are.

    1. Remind self the house is too full of piles to have guests anyway.

       1. See 6a: now you really won’t have any friends.

    2. Vow to clear clutter and give away books in the new year.

       1. Consider putting craft books down to catch up on these publications, plus the hundreds of unread digital articles waiting in your Substack inbox.

          1. Craft still has a delicious hold on your attention, so ignore #12 for now.

13. Start contemplating what the next ‘Doh post will be about.

    1. Worry that you are all out of ideas and stories.

    2. Worry that your stories are too Debbie Downer.

    3. Worry that your readers are starting to worry about you.

       1. The next deadline is approaching, so you must cast a) through c) aside! Don’t break the twice-weekly streak now, you’re five months in.

       2. Remember that some of your favorite posts came at the last minute, and that you are glad to have stuck to your arbitrary commitment so far.

          1. Contemplate what will happen if you hit a pocket of success and no longer have ‘doh to write about.

          2. 😭 who are we kidding. Upcoming election year will make 2023 shenanigans look mild in comparison. Survive ‘til 25.

          3. Remind self that “success” would be a good problem to have, and that

          4. More ‘doh will inevitably follow. Such is the nature of life.

14. Spot another cockroach on the kitchen counter as you make your morning coffee.

    1. Recoil in horror.

       1. Spray it vigorously with your pet-safe essential oils spray can in self-defense. Leave the belly-up carcass on the counter for spouse to discard. Hey, progress, at least you didn’t rouse the house by screaming.

    2. Figure out how to get rid of these disgusting vermin for good. Again. 😩

       1. Listen in full-blown paranoia to the creaks and pops in the kitchen while everyone else sleeps. Is it a family of cockroaches making their nocturnal rounds? What are they trying to tell you?!

15. Make a dent in email today, never-ending email. 😭

    1. That dent wasn’t good enough. You’re back where you started.

       1. Make another dent on another day.

          1. That dent wasn’t good enough either. Now you have more than the previous two combined.

             1. Make another dent on another day.

                1. Declare defeat, putting up your holiday autoresponder until January, buying yourself time.

16. Consider reducing the prices on your website for programs that are not selling.

    1. Or maybe remove them from the top navigation altogether.

       1. But your book mentions them, so if you do hide those pages, you’ll need to set up a redirect for those URLs.

          1. Do nothing instead.

    2. Contemplate adding new services in the new year.

       1. Search inside yourself and come up empty on the energy required.

          1. Do nothing. For now. See: pause.

17. Contemplate, again, whether it’s time to leave New York City.

    1. Is the jig up?

    2. Scan for any inkling of intuition that it is, in fact, time to move.

       1. Crickets.

          1. Reaffirm that, in your heart of hearts, you still want to do whatever you can to stay.

             1. ❤️

1. This format was inspired by NaNoWriMo cofounder

Grant Faulkner

’s The Art of Brevity; with special thanks to Chapter 6 for pointing to Jennifer Egan’s “To Do.”

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