258: To Do—A Small Business Owner’s Checklist (Rolling in D🤦🏻♀️h Crossover)
8 Dec 2025 · 17 min
Jenny Blake reads a Rolling In Dough essay that's a numbered to-do list for solo business owners: health insurance, subscriptions, bookkeeping, content pauses, community emails, sales, mental health, home life. It's the small victories and anxieties that actually make up running a business.
Chapters
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This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.
Welcome back Free Timers.
Today I'm bringing you another Rolling In Dough essay. This one was a runaway hit. I had no idea, as usual when I wrote it, that it would be. But I remember my friend Adam texting saying, your post today was so great and the comments are on fire. I was out. I had family visiting. This was in the first week of December. I just had no idea that it was resonating so deeply and for that I am truly grateful. This one now takes the cake as the most popular, the most commented on, the most viewed post in six months of Rolling in do so. I thought it'd be fun to share it here with you before reading you the post. I want to give credit to NaNoWriMo.
Co founder Grant Faulkner.
I participated in NaNoWriMo, which is national Novel Writing Month in November, and it was the first time in almost a.
Decade of attempts that I actually completed 50,000 words. I didn't write a novel, I just promised myself that I would write every day and that I would hit that word count toward Rolling in dough. Types of ideas while doing NaNoWriMo, I read Grant Faulkner's book the Art of Brevity and in chapter six of that book he points to Jennifer Egan's To Do. It was a To Do List style post that she wrote for the Guardian.
And so one morning when I was trying to hit my word count goal, I thought what would my to do list look and sound like? If you want to read the full post, I'll put the link in the show notes and I highly encourage you to subscribe to Rolling In Dough if you're not already. You can do that@itsfreetime.com secret that's itsfreetime.com.
Secret or rolling in doh.substack.com without further ado, I bring you to do one small business owner's checklist.
December 2, 2023 to do number one renew health insurance a Run gusto payroll report to reveal meager take home pay this year. Determine if this will yield higher 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. Muse over whether it's time to move abroad given how much you hate the health care system in the US 1B 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. Wait on hold for 30 minutes with insurance company agent seething further a bureaucratic ineptitude stealing your precious time. 1C figure out asthma situation ever since contracting Covid for the first time the day after Christmas last year. Wonder if this is officially long Covid wean off medication working wonders but hobbling vocal cords. 2. Cancel a slew of subscriptions to simplify expenses and reduce overhead. 2a. Determine how to gracefully apologize to anyone.
Who might be offended.
3. Continue daily yoga streak. 3a. Remind self that 2023 word of the year was thrive. Only one month left to turn things around. 3 aye continue half hearted attempt at losing pandemic and marriage. Strike out 2030 so that at least some of your clothes fit again. Kick sugar habit maybe finally try those emberries your friend raved about. Buy an assemble standing desk. Marvel at the new view for zoom calls. Still swear off zooms and video calls in the new year. Determine source of gremlin sitting in left hand side of lower back is this. 40. Start pondering word or theme for 2024. Miracles ended up apropos for 2020. 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. 4a. Determine WTF meant to do with life and work. Keep following creative spark. Attempt to listen quietly as new direction reveals itself. 4b. Browse summer internships at venerative media institutions in New York City. Close browser tabs upon realizing they pay minimum wage for full time work weeks and you have already committed to number three daily yoga. 5. Announce the upcoming pause to your private membership community. Record a bonus episode for them Speaking from the heart instead of a script. Finish recording after 30 minutes, blinking in disbelief that after you hit stop, none of it saved. Everything you said is gone. Whine to your spouse like a baby, he says. Maybe there was something in there that wasn't meant to be shared. Rerecord a shorter, crisper version. Rejoice now that the earlier one got erased, despite annoyance at tackling this twice. 5B spend two weeks drafting and refining the community announcement email. Schedule it to go live 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 okay? Respond to say that yes, everything is fine.
Laugh, cry emoji Sweat emoji melting emoji.
File ticket with subsack support ending in Please explain I'm mortified.
Support it was your own fault, after all. Scold self for forgetting the highly nuanced.
Tripwire that by inserting a paywall break in a founding member message, you nullified the narrowed recipient list. Free preview goes to all six. Plan solo episodes to air in February, announcing that both podcasts will be paused indefinitely. 6a. Figure out how to make friends again now that you won't be conducting 8 to 10 guest interviews every month. 6B question whether you're 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. 6c question when and whether to update website bios to reflect that you may no longer be an author and podcaster. 6 d Ponder whether you should re release Best of episodes during the time off. Decide against this. Too much work.
We'll be right back just after this.
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This message may be shocking to many millennials. If you are one, you might want to sit down right now. Loads of people are searching the following on depop Low rise jeans, halter top, velour tracksuit, puka shell necklace, disc belt. You likely placed these in the dark of your closet in 2004, never to be seen again. But if you can find it in yourself to dust them off, there are a lot of people who will give you money for them. Sell on Depop, where taste recognizes taste.
7. Turn attention instead to substack growth and improving the quality of various offerings across your three newsletters. 7a. Cast skepticism at number seven. Would it be like staring at the.
Sun for too long again?
7B. Try to earn back your best seller badge after it disappeared as quickly as it came two weeks ago. 7C shoot C. 7A. Now you are staring at the sun again. Stop that. 8. Sweat while checking credit card balances. 8a. Start preparing bookkeeping now for tax time in the new year.
The sooner the refund the better.
8B. Update emoji balance sheet.
If only accountants would accept this.
Berate Self for not doing a better job adding to retirement savings over the last 13 years. Your 27 year old self thought you'd.
Be a multimillionaire by now crying emoji.
8C. 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. Pray you'll be able to take your hands out of these cookie jars soon. Contemplate whether it's time to sell remaining stocks to refund those accounts. Ponder what new business activities would generate enough revenue at one time. 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. 9a. 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. Barring that, ponder how to give away the next thousand copies so that at.
Least the work continues making its way into the world.
9B. Figure out why Amazon stole half of your reviews and now you're at $92 instead of your hard earned 144. Seethe and 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. 10a. Do not forget this when the urge to create the fourth book hits. 10b.
Stubbornly dream anyway because books have always.
Been your bomb and best friends.
And for the analog fun of creating.
An artifact in the world, research print on demand. Perhaps you'll make a tiny zine. Make a Note to Self and an artist's date to browse bookstores in the Lower east side where these are in vogue. 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. 11aMake sure it's one where a 40 year old can futz around in the back behind all the live perfectly flexible stellar or choreography memorization actual Broadway dancers. 11b. 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 30 minute train ride. Sign in, situate yourself in the room, take the class, thank the instructor afterward, then hop on the next subway home. Ensure it's not dark out when attempting this three hour block. 11C grow discouraged upon seeing the various schedules.
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 that you are.
12A.
Remind yourself the house is too full of piles to have guests anyway. Now you really won't have any friends. 12b. Vow to clear clutter and give away books in the new year? Consider putting Kraftbooks down to catch up.
On these publications plus the hundreds, if not thousands of unread digital articles waiting in your substack inbox.
Crafts doll is a delicious hold on.
Your attention though, so ignore this for now.
13. Start contemplating what the next dough post will be about. 13a. Worry that you're all out of ideas and stories. 13b. Worry that your stories are too Debbie Downer. 13c. Worry that your readers are starting to worry about you. 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. Remember that some of your favorite posts came at the last minute and that you're glad to have stuck to your arbitrary commitment so far. 13d. Contemplate what will happen if you hit a pocket of success and no longer have dough to write about.
Crying emoji. Who are we kidding? Upcoming election year will make 2023 shenanigans look mild in comparison. Survive till 25. Remind self that success would be a.
Good problem to have and that more dough will inevitably follow. Such is the nature of life. 14. Spot another cockroach on the kitchen counter as you make your morning coffee. 14 a recoil in horror. Spray it vigorously with your Petsafe essential oil 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.
14B figure out how to get rid of these disgusting vermin for good again. 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. 15A that dent wasn't good enough. You're back where you started. 15B make another dent on another day. 15C that dent wasn't good enough either. Now you have more than the previous two combined. 15d make another dent on another day. 15e declare defeat putting up your holiday autoresponder until January, buying yourself time.
16. Consider reducing the prices on your website for various programs that aren't selling. 16a or maybe remove them from the top nav altogether. 16b but your book mentions them, so if you do hide those pages, you'll need to set up a redirect for those URLs.
Do nothing instead.
16C Contemplate adding new services in the new year. 16d Search inside yourself and come up empty on the energy required. 16e. Do nothing for now. See also pause.
17. Contemplate again whether it's time to leave New York City. 17a. Is the jig up? 17b. Scan for any inkling of intuition that it is in fact time to move crickets. 17c. Reaffirm that in your heart of hearts.
You still want to do whatever you can to stay.
That's a wrap on the To Do List post, and I have to give a big thanks to Ben who wrote in the comments.
18.
Give self a break.
If you want to read the full post, I'll put the link in the show notes and I highly encourage you to subscribe to Rolling in Dough if you're not already. You can do that@itsfreetime.com secret. That's itsfreetime.com secret or rollingindo-o h.substack.com have a beautiful rest of your day. Thank you so much for listening.
If you've listened this far, you get a gold star.
Thank you.
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