A Day in the Life of a Double: Meet Caitlyn
At Double, no two days look exactly alike, but they all have one thing in common: making busy peoples’ lives easier. Doubles are expert multitaskers who create structure out of chaos and calm out of noise.
Take Caitlyn, for example. Based in Chicago, she supports a real estate developer and a nonprofit director, balancing investor decks in the morning and grant spreadsheets in the afternoon. Most Doubles, like Caitlyn, support more than one executive. The secret to doing it well is focus. Whether she’s preparing for a board meeting or wrangling travel plans, Caitlyn’s attention is fully on the task (and the executive) in front of her.
Morning: Setting the Stage
Caitlyn’s day usually starts early with a check of her executives’ calendars and inboxes. Doubles are trained to spot the small problems before they become big ones, and Caitlyn’s no exception. This morning, she quickly rearranges a double-booked meeting and rescues an exec from an accidental 6:00 AM call request. Crisis averted before coffee number two.
Inbox triage is an art. While her executives sleep, Caitlyn filters, flags, and files, clearing the decks for the day ahead. "Circling back" emails are sorted. Calendar invites with no agenda are declined. She knows her executives' priorities better than their to-do lists do.
Midday: Deep Work, Strategic Support
By late morning, Caitlyn shifts to deeper work. This is exactly the kind of proactive support that sets Doubles apart. For her real estate client, that means reviewing leases, coordinating with architects who all have different visions for the same lobby (don’t ask), and prepping materials for an investor meeting. Presentation design is one of Caitlyn’s strengths. When she sends over the board deck, it’s polished enough to win awards or at least prevent awkward questions about mismatched fonts.
Meanwhile, her nonprofit client needs updates on grant applications and budget reporting. Most Doubles manage multiple systems and tools. Caitlyn flips between Notion, Airtable, and QuickBooks like it's second nature. Budget anomalies don’t stand a chance.
While working across clients, Doubles stay synced using the Double app. Task lists are updated and transparent so nothing slips through the cracks, even when the day gets busy (because it always does).
Afternoon: Flexible, but Focused
A Double’s day is all about flexibility. Caitlyn might be finalizing travel plans for an executive headed to a last-minute conference or coordinating with vendors for a board dinner where everyone’s dietary preferences read like a logic puzzle. (Gluten-free, vegan, dairy-sensitive, all at the same table.)
Double’s assistants aren’t just task-takers. They anticipate. Caitlyn preps weekly reports without being asked, schedules prep calls ahead of deadlines, and nudges stakeholders early enough to keep projects moving without stepping on toes.
Inboxes get another sweep. Calendar holds get another check. Travel itineraries get a final polish to avoid late-night “where’s my hotel confirmation?” emergencies.
End of Day: Setting Up Success
Before signing off, Caitlyn updates her project boards and leaves clear notes for each exec, summarizing what’s done and what’s on deck. Transparency is a big part of how Doubles work. It’s not just about getting things done but making sure the client sees the road ahead. And yes, one final look at Slack. There’s always that one person who thinks 7:00 AM meetings are a good idea. Caitlyn rescues the morning once again.
Why It Works
Caitlyn’s day shows what makes a Double a real asset. They aren’t just assistants. They’re operational partners who create space for their clients to focus on the big stuff. Doubles bring proactive support, attention to detail, and calm professionalism to every interaction. Whether it’s inbox zero or board deck heroics, they keep the wheels turning and the stress low.
3 Things Caitlyn’s Execs Say About Her
- "She just gets how to make everything easier. Calm under pressure and lovely to work with."
- "Caitlyn is the rare kind of assistant who can handle both the numbers and the nuance."
- "She brings order, clarity, and a level of polish that instantly builds trust."
3 Tips Caitlyn Has for Execs
- "Start the week with clear priorities. It saves a lot of back-and-forth later."
- "Give your Double real ownership. Trusting us with bigger pieces makes everything more efficient."
- "Simple, quick updates work just fine. A quick Slack or bullet-point email is usually all we need to stay in sync.”
Want a Caitlyn on your team? Schedule a call with our team to learn more about working with Double.