If you are cracking open a brand-new calendar to bring fresh organization to 2020, you may have Anna Bond to thank. And speaking of thanking people, you may have her to thank for that too.

Ms. Bond, 35, is the chief creative officer of Rifle Paper Co., which has sold nearly 750,000 planners since 2015 and more than 500,000 thank-you cards last year alone.

She and her husband, Nathan Bond, the company’s C.E.O., started Rifle out of his parents’ garage apartment ten years ago (choosing the name simply because she liked it, not for any connotation of shuffling through papers). “We had absolutely no clue what we were doing,” she said.

But their company has been operating at a profit almost from its beginning, Ms. Bond said. “We have never taken on any investment or taken on any debt at all,” she said. “It was a common-sense approach.”

Rifle employs more than 150 people between its headquarters in Winter Park, Fla., its nearby warehouse where orders are fulfilled and its office in New York. Its offerings have expanded to include wrapping paper, gift bags, phone cases, book covers, sneakers, rugs, wallpaper, water bottles, mugs and pillows. All bear Ms. Bond’s signature floral designs that she, a former art student, creates with brush in hand, using gouache paint.

She got started designing posters that advertised Mr. Bond’s band performances, back when they were dating. Friends started asking her to do their wedding invitations. After she did invitations for her own wedding, orders started pouring in.

This was 2009, still early days for social media. People were making more connections with friends old and new by computer and phone. One might think this would spell doom for the old-fashioned letter writing industry, but some saw an opportunity to market its specialness. Small-batch stationery companies sprouted all over the Etsyverse. Rifle has been one of the few to have broken through to a larger market that includes legacy brands like Crane & Co.

The Bonds also have three young sons — Ford, 4; Ronan, 20 months; and Louis, 8 months — and so when we spoke with Ms. Bond in mid-December, her own planner was stuffed: both with last-minute details for her family’s 2019 celebration and ideas for how her business will approach the December 2020 holiday season.

11:30 a.m. I arrived to our New York office in SoHo after a photo shoot. I flew in from Florida on Sunday night. I come once a month to meet with the designers here. Most of the day I was with Trish Whalen, our president, and Debs Camplin, the new creative director. They worked together at Kate Spade.

12:30 p.m. Over lunch, we continued to talk about holiday 2020 ideas, because a few key accounts would like to see previews. We reviewed cards that need to get to the printer. We ordered take out from Sweetgreen and ate at the conference table in the office. In Florida, nobody eats at their desks. I didn’t think that was weird until we hired New Yorkers and they would say, “Where is everyone?” And I would say, “They’re out taking their lunch break.”

2 p.m. Trish brought up some big collaborations she wants me to consider. I passed on most of them. We have a capsule collection at Anthropologie of mugs and travel accessories, categories we have not yet fully developed. Anthropologie wants to keep some of that going and I did say yes to that.

7 p.m. I went back to Greenwich Hotel and ordered room service (spaghetti). I was in bed by 9:30. One of my goals when I come to New York is to sleep. Child-free sleep is a deep, magical sleep.

7:45 a.m. I had breakfast with a friend in the pretty parlor room at the hotel. He works at the Art Academy and we’ve been talking about our doing a workshop with the students, where we would end up with a limited-edition print.

9:30 a.m. I did a few emails. We use Slack at Rifle, so I checked in on some Slacks from the Florida team. I personally like Slack for group-chat back-and-forth conversation, whereas email is good for discussions you need to keep organized.

1 p.m. We had an epic two-hour meeting discussing our spring marketing initiatives, so that I can go to the creative team in Florida to talk about how we can support it all. We had lunch during the meeting. I ordered from a random Japanese place I found on Uber Eats.

3:30 p.m. We reviewed some 2021 planners and a few tech samples. Like an AirPod Pro case we are making with Case-Mate.

4 p.m. I met with one of our designers. We were talking about holiday concepts for 2020. We made advent calendars this year for the first time and they’ve been very popular. So she showed me a few concepts for next year.

4:30 p.m. I met with a designer about what we are doing for our Keds collaboration for 2021.

5:30-6:30 p.m. I reviewed and approved some social posts. I try to delegate some of that work but any direct communication with the customer is so important. It’s never a waste of time.

6:30 p.m. I left for La Guardia Airport and got home around 1 a.m.

6 a.m. Ford, my oldest, got up and requested some bread and butter. I pleaded with him to wait until breakfast time. I gave in.

7:50 a.m. I took Ford to school. Ronan, my middle son, came for the ride. Nathan stayed home with the baby. I stopped for coffee on the way back, cappuccino at the good old suburban Starbucks. I have learned the importance of drive-throughs since I’ve had children.

8:15 a.m. I hung out at home with Ronan and Louis, the baby. When the nanny arrived at 9:15, I showered and went to work.

10 a.m. Nathan and I share an assistant. When I get in, she and I do a quick touch-base. She’s helping with our Rifle holiday party, so we talked about that too. We’re doing it at a venue in downtown Orlando. It will be employees and their significant others. We also invited local vendors. We’re expecting about 250 people.

11 a.m. This is when I did my most urgent task of the day, which was actually due on Friday, half a week before. I was reviewing 17 new cards, the final files that would be sent to the printer. They are all cards that I painted and that the creative team cleaned up and prepped for print. They will be available at the end of January or early February. All of our cards are printed locally in Florida, so the turnaround time is quick.

2 p.m. One of my designers popped in and we wrapped up discussions about our 2021 planners. We are making changes to the packaging.

2:30 p.m. I had my standing meeting with the V.P. of marketing and our project manager. We talked about the sales and announcements that will happen on the website for Christmas so I can brief the designers on anything we might need from them. I met with the senior marketing designer and she showed me social posts that are going up during the weekend.

5 p.m. I had the final meeting about the planners. I had asked for little revisions, we are trying to make our packaging more consistent. There are some updates to the fonts.

5:30 p.m. I saw the time and it just hit me that we had a guest coming to stay for a few nights. I raced home. The guest room doubles as a nursery and the sheets were clean, but the kids play on the bed while I put the baby to sleep. So I changed the sheets and freshened the room. I moved the baby’s stuff into our room.

6 p.m. We had the normal evening routine of feeding the kids and putting them to bed. I had intended, again, to make dinner but we decided to order in. Nathan and I caught up with our friend and hung out.

10:30 a.m. I arrived to the office. We have a small retail store in front of our offices and we do a Christmas sidewalk and I checked out how it was going. We sell any of our products that are slightly flawed at a discount, and it’s quite popular locally.

11 a.m. I did a few emails and hand-lettered a quote that will post on social media sometime next week. Normally I paint everything in gouache but I have these Japanese paint pens that feel like paintbrushes but are more like markers. I have been using them for lettering.

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