Last updated: 2026-09-17
A task shows up. You know how to do it, so you do it. No pause. No question. You just start.
That’s the default, and it’s expensive. Not because any one item is huge. Because you never evaluate whether it should have been yours in the first place.
Does this sound familiar to you?
The real difficulty is remembering to outsource at all. So I recommend a repeating task in your project management tool, every 2-3 days, with one line: “What can I delegate?”
When it fires, look at your plate. If something appeared since the last check, decide on the spot. Offload it, or keep it on purpose. The prompt keeps delegation top-of-mind so you stop defaulting to doing the work yourself.
Create that recurring task today, in whatever tool you already open. The question has to show up on a schedule or you’ll forget to ask it.
The tiny work that drains you
Manually paying bills. Searching for a buried email attachment. Tracking team schedules in a spreadsheet. Each one looks too small to fix.
Together they drain hours, energy, and attention.
Run a Time Squander Audit. Identify the small, recurring tasks that shouldn’t still be manual, then automate them. Auto-pay for the bills. Keyboard shortcuts for the stuff you repeat all day. A team management app like TeamSnap instead of that spreadsheet.
You’re after mental energy and attention here. Time comes back as a side effect.
Write down your top 3 time squanders. Pick one automation that would remove the worst of them, and set it up this week.
Brooks’s three levels
Brooks breaks delegation into three levels. This is usually where people get honest with themselves.
Easy. Tasks you hate or you’re bad at. Dog poop pickup. Plumbing. Handing this off feels obvious, so most people can get here.
Medium. Tasks you can do but don’t enjoy. IKEA assembly. Grocery shopping. You’d survive Saturday spent on it. You’d rather not.
Hard. Tasks you’re good at, even tasks you enjoy, that still consume disproportionate mental bandwidth. Trip planning. Bookkeeping. This is the uncomfortable one.
Most people stop at Level 1. True leverage comes from Level 3.
Are you still holding a Level 3 task because you’re good at it? That’s the trap. Skill is not a reason to keep the work. Name one Level 3 item you’re doing right now. That’s the one to outsource.
The $200 rule
If you struggle to calculate ROI on personal tasks, skip the spreadsheet. Set a fixed monthly budget instead. $200, specifically for buying back time.
Grocery delivery. Cleaning. A task-based freelancer for the annoying errands. The constraint makes the decision small enough to actually try. You’re running an experiment, not rebuilding your whole life.
This is the entry point if you’ve been treating outsourcing like something only CEOs get to do. Set that budget for next month and spend it on purpose.
Taste the benefit, then graduate
Task-based services like Fancy Hands are built for one-off, specific work. They handle the hiring friction. You send the annoyance, it gets done.
A dedicated executive assistant is a different bet. Over time you get compounding benefits. They learn your preferences. They start anticipating what you need. They make decisions on your behalf.
Start with a service so you can taste the value. Then graduate to a dedicated EA when you want long-term leverage.
This week, take one specific annoyance and run it through a task service. One thing that’s been sitting on your list.
When you’re ready for an EA, I recommend starting at 5-8 hours a week. Part-time. Not a full salary on day one. Most people overestimate the cost and underestimate the value of even a few hours of delegated admin. You feel the mental bandwidth first. Then you scale the hours.
Keep the first week simple. Inbox triage, so you’re not hunting through mail. Calendar blocking, so the hours you need for real work actually stay blocked. That’s enough to start.
Watch your energy
The true value of outsourcing is the mental space and energy you recover.
Outsource cooking and grocery shopping and you might save 5 hours. You also remove meal planning, shopping, and cleanup from your head. That recovered attention is what makes room for higher-quality creative work, or for actually being present with family.
Clock time is the easy number. Energy tells you if it worked. Track how you feel before and after you hand off a recurring task.
Pro tip: the walk-in hack
When a restaurant looks fully booked online, have your EA call. Or call yourself. Use client language: “My client is interested in your signature dish…” Ask for a seat, politely.
Restaurants often have hidden capacity for walk-ins, or they can accommodate a request if a person actually asks. Digital interfaces hide that. Persistence and social skill get it back.
If you keep losing the reservation game, pick up the phone. This is the human piece apps still miss.
Open your tool of choice and create the repeating task: “What can I delegate?” Every 2-3 days. When it shows up, answer it.
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