Book#150: Annie Knows Everything by Rachel Wood

  

Annie Knows Everything

Rachel Wood

 Released: April 7th, 2026

My 16th book for 2026 was Rachel Wood’s “Annie Knows Everything”.

This was my April book from Book of the Month club.  The last one I read from them was the classic All Quiet On The Western Front.  I ducked out for a few months as I relocated, but my first book for ordering was this one.

I've grown a greater appreciation for Rom-Coms.  Stories like Beach Read, Pumpkin Spice & Everything Nice were feel good reads that you could sit down with a latte and enjoy in a coffee shop somewhere.  Plus, you open yourself up to a world of other readers who enjoy the genre more.

Annie Winstead finds herself on the chopping block of layoffs for her company.  Thanks to her best friend Carrie in HR, she is transferred to a new department that she does not have the slightest idea about.  By building up trust with her team, and growing a deeper personal relationship with her boss, she establishes herself.  When a planned IPO is mentioned, she works to save the jobs of coworkers who are next for layoffs.  Due to this breach, she is fired, and has to resolve things with her family, and hopefully win the heart of her new beloved.

Along the way, her sister is getting married to someone she dislikes due to an infidelity during the engagement.  She navigates her new relationship while attempting to sabotage her sister's.  

A lot of the book revolves around office relationships, startups, technology companies, layoffs, and themes of love.  Annie has to come to terms with various changes in her life, and adapt with them.  It's a feel good story.

Here is what I learned:

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• Annie Winstead works for a productivity software company.

• Dedicated to my parents, who met at work.

• “Statistically, the most common days of the week to be fired are Monday or Friday.”

• Suzy is the copywriter.

• She was behind the slogan, “Tick your to-do list off one Taskio at a time.”

• Annie’s best friend Carrie works in the HR Department.

• Annie and Carrie started at Jotter, a start-up that was then bought out by Taskio.

• Tech guys are either enormously socially awkward computer geeks or cocaine-snorting sales leads that speak in gibberish.

• Annie’s sister Shannon is renegades to a man named Dan that is not highly regarded.

• Taskio is doing structural changes due to difficult market conditions.

• Naomi Evans is the head of Data Strategy.

• Annie’s job is saved when Carrie deletes the opening and “accidentally” puts her in role, citing technological challenges.

• Taskio is spread across 5 floors in one of the World Trade buildings with views of Manhattan’s Financial District and the Hudson River.

• Taskio is a digital version of a cork board with notes and notices.

• Naomi gives off girlboss vibes when speaking at town halls.

• Annie wears a getup called “Hot Steve Jobs”.

• Naomi is out on maternity leave.

• Annie introduces herself as the new data strategist.

• The Scratch Kitchen, also known as the “canteen” is a restaurant on the 25th Floor used as a meeting space and watering hole.

• The company pantry is like an enormous general store.

• Connor Reid is the interim department head.

• SQL means Structured Query Language.

• Annie is not skilled in Excel.

• Murphy’s Tavern is the de facto meeting place of the Product Team.

• Annie once had a crush on Andy.

• He once got to second base when he grabbed her nipple at the office Christmas party.

• Lee is going to try for a job at TrustPilot.

• Annie is from Canada.

• Carrie once saw a man from Merrill Lynch.

• Annie and Leon do research.  They call current customers and ask for feedback.

• Alex is a UX Designer.

• Alex has diplomacy skills of a hostage negotiator.

• Brad Pincer is VP of Corporate Development.

• Connor is his personal assistant.

• Martha is moving back to Philly. 

• Martha is a designer.

• Martha enjoys Vodka Sodas.

• The company also employs a Connor Jones.

• Connor Reid loves hot dogs.

• Andy struggles to quit smoking cigarettes, especially with the firing.

• A dinosaur named Brian with a butterfly net, guides you through the quiz.

• Connor is has been with the company 9 years, is 32, single, and his mother is his emergency contact.

• Annie lives in a 4th-floor walk up in Greenwich Village with her roommate Sam who owns the place.

• Sam’s sister moved to DC for a job.

• Sam works part-time at an experimental art gallery that doubles as a nightclub once a month.

• Annie is from small-town Ontario.

• In Sam’s universe, relationships are strictly casual.

• Sam is famously mean.

• LaGuardia is the cursed pit of nothingness.

• “The blessing and curse of this place has always been the same: time passes, but nothing changes.

• Dan is a walking Gap ad.

• Uncle Bill is the resident party guy of the family.

• Rib fest will the last weekend in July.

• Shannon dropped out of college to be closer to Dan.

• Dan works in local government.

• They live with her parents to save for a home.

• Dan ran for public office.  He campaigned against a fictitious golden eagle that he only beat by 57 votes.

• Shoeless is the neighborhood bar.

• The Millers are thinking about downsizing.

• Shannon is coming to New York for a Realtor’s Conference.

• The big dress shop from Dream Dress is in New York.

• Annie is short for Annabelle.

• Connor has never been trick or treating.

• Annie once bought a purse from a thrift shop and found $40 in it.

• Connor once won a chess tournament at Disney World.

• Connor: I won, obviously.  But I’ll never truly be sure I beat him fair and square.

• Connor never misses a beat when it comes to sarcasm and humor.

• Annie once won a competition where you invent your own ice cream flavor.

• Shannon and Annie shared a car all through high school.

• Annie has forgotten stuff before causing Shannon to turn the car around.

• They inherited Grandma’s Old Honda.

• The local golf course, King’s Glen, was Shannon’s preferred venue of choice for the wedding.

• Shannon has been replaced at the conference by the top salesperson from the previous year.

• Annie’s ice cream flavor was “Coco-nutty”. It had a coconut mascot with a barbell saying “I’m here to get shredded.”

• Annie’s keycard is deactivated again.

• Annie’s coworkers are Ben, John, and Martin.

• Ben is a tall wiry redhead in a striped long-sleeved rugby shirt.

• John is shorter, curly hair, and Harry Potter-style glasses.

• Martin is the shortest, impeccably dressed, and sporting jet black hair.

• Martin is the team’s court jester.

• Martin moved to Pennsylvania in the 4th grade.  He puked on himself the first day, walked home to change and was sent back to school.

• Martin is a legend on the Hinge dating app.

• Annie writes a passive aggressive corporate response.

• Annie did not take a date to the prom.  She went with Thomas as friends.

• Connor reports to Brad.

• Annie made out with Thomas on the dance floor.

• Annie is tasked by Connor to find out why nobody is using the dashboard.

• Jim is Connor’s barber.

• Annie wants Ben to date Carrie.

• “Workplace relationships are forbidden? If that were true, this place would have no need for annual layoffs; we'd lose ten percent of the workforce after every Christmas party.”

• Annie has feelings for Connor.

• Subu is catering the Lunch & Learn.

• Subu is an extremely New York-famous food truck.

• 2 packs of Oreos can do a lot to restore your inner calm.

• There is a rumor that Brad does not have a computer.

• Sam’s gallery “Le Nal” is an anagram of its address on Allen Street.

• Traffic is the backing track to everything you do in NYC.

• Annie uses her training on DinoCode to fix an index coding issue.

• Ben likes pistachio cookies.

• Martin likes white chocolate cookies.

• Krumes, the bakehouse, has the best cookies in the city.

• Krumes is about the size of a basement cupboard.

• Krumes has only one rule: Only one box per customer.

• Almost half a pound of dough goes into each cookie.

• Ben and Connor were college roommates that have always worked together.

• Connor was the 5th employee hired at Taskio.

• Taskio was a lot better in the early days.

• The Grand Bazaar is the oldest flea market in the city.

• Mr. Shaw was one of Connie’s favorite teachers.

• Mr. Shaw teaches science.

• Annie kisses Connor.

• Carrie and Sam smoke weed.

• There is a weekly team meeting every Monday at 10:00am.

• Jotter tracked user engagement a lot differently than Taskio does with the dashboard.

• Connor and Annie plan a date.

• Annie’s sister’s visit is known as “Operation Liberate Shannon”.

• Shannon wears expensive things.

• Daniel accompanied Shannon to NYC.

• They are staying in Dumbo.

• Connor gives Dan and Shannon a tour of the facility as punishment.

• Shannon considers herself the “hot one” and Annie the “cute one”.

• “It just goes to show the old saying is true: you can’t polish a turd.”

• Everyone drinks Margaritas, except for Dan, who has a Paloma.

• “The streets reek of garbage.”

• Shannon insults Annie, claiming her surprises ruin her life.

• Annie gifts tickets to a standard up to Shannon and Dan.

• Connor invented DinoCode.

• Shannon’s Bridal Shop of choice is in SoHo.

• The bridal shop offers glasses of champagne.

• “I slept with Connor and my sister told me she hated me.”

• Taskio is planning to go public.

• Annie plans with the Integrated team to build a product that will save their jobs.

• “The product department's all-hands meeting is a quarterly get-together where the entire department (plus a few interlopers) meet to brainstorm and share updates about what they're working on. In theory, this leads to innovation. In reality, this leads to mudslinging.”

• Brad is a panic attack on legs.

• Annie is fired for a breach of confidential information.

• “How could I forget?  Annie knows everything.”

• “My words land between us with a dull thud. There's a difference in the way we've been arguing. Everything he said was true. Everything I said was mean. The hurt and disappointment is etched all over his face.”

• “Samantha is not a comforting person by nature. Need a hug? Don't go to Sam. Need someone to give you an honest opinion about your bad haircut when it feels like everyone else is lying? Sam is your girl.”

• “When I tell her my life is ruined, she scrapes her butter knife across a piece of toast and tells me you must not have had a very good life then.”

• Annie visits Shannon’s house for the first time.

• Annie and Shannon duel with inflatable tubes.

• “Don’t underestimate the value of a good blowjob.”

• “I don't even bother with outrage, just go with it. Now that it's decided I'm leaving, I want to get going as soon as possible.

• I feel an almost desperate urgency to get back and make things right.”

• Sam and Carrie hook up.

• Connor and Ben quit Taskio.

• Shannon’s wedding sucked.

• Sam plans to move Carrie in and move Annie out with Connor.

• Connor, Ben, and Annie start their own company.  It’s a Coding Academy.

• Annie was the first graduate.

• Rachel Wood owns a bookstore in Edinburgh, Scotland called “Rare Birds”.

• Falling in love is as act of optimism.

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Overall, pretty decent rom-com.  Shows a bit about city vs. suburb mentality.  The story is genuine and heartfelt.  I liked it.

Recommended.

On to Book #151: “Hey…Wait A Minute.  I Wrote A Book!” by John Madden.

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Need to catch up?  See previous blog post: Jason 3D: A Comprehensive Exposé on Friday the 13th Part 3.