The biggest outsourcing decision of my life went the wrong way, if you only read the spreadsheet.
When our second child was born, I ran the numbers on going back to work. Childcare for two kids in California was going to run roughly $50,000 a year after tax, which meant I would have to earn well over that just to break even on someone else spending the best hours of the day with my children.
The spreadsheet could make a case for going back.
Salaries compound. Careers stall when you step out. Retirement contributions matter. Every responsible voice had a point.
But the spreadsheet was not the whole calculation.
The human answer was different: I would be trading my time for salary so I could pay someone else to spend that same time with my kids.
That trade did not belong to the life I was trying to build.
I am telling you this up front because this piece is going to argue that you should pay other people to do more things for you. I do not hold that position cheaply.
The point is not “outsource everything.”
The point is to actually run the math, because most people never do in either direction.
Buying back time only works when the hour you reclaim goes somewhere worth living.
The question I stole from real estate
I spent years in private-equity multifamily real estate. Before any acquisition, you ask one question about the property: what is its highest and best use?
Not what is it currently doing.
What could it produce, and what is standing in the way?
Nobody asks this about their own hours.
That gets especially strange as income rises. When your employer promotes you or raises your pay, they are publicly declaring that your time became more valuable. Then most people go home and keep spending that newly expensive time exactly the way they did when it was cheap: cleaning, errands, returns, admin, yard work, the same Saturday routine they have run for a decade.
It feels responsible.
Frugal.
Grounded.
But the question changed.
The old question was: can I save money by doing this myself?
The better question is: what is this hour worth now, and what could it become if I bought it back?
Run your real number
Start with your real hourly rate.
Not your salary divided by 2,080. That number flatters you. If you want the math without building a spreadsheet first, start with the Value of Your Time calculator.
Take what actually lands in your account each month and divide it by the hours the job really takes: commute, Sunday-night email, recovery time, the dead hour after a draining meeting where you are technically home but not really available to anyone.
That is closer to your real number.
For most people, it is lower than they guess.
And it still makes half the to-do list indefensible.
If your hour is worth $40 and a cleaner charges $25, you are not saving $25 by doing it yourself. You are buying the right to spend a $40 hour on a $25 task.
Sometimes that is fine. Maybe you like cleaning. Maybe it resets your brain. Maybe money is tight and the math still says keep it.
But at least tell the truth about the trade.
Grocery delivery might cost $5 to $15. The round trip to the store might cost an hour, decision fatigue, and six things you did not mean to buy. That does not automatically make delivery right. It does make “I am saving money” less obvious than it sounds.
I know this math cold, and I still skip delivery some weeks because pushing the cart myself feels like virtue.
That is the part nobody tells you: the flip is not a switch you throw once. It is an argument you keep having with an earlier version of yourself, and that earlier version is a stubborn negotiator.
Where the math becomes obvious
The first thing we handed off after moving abroad was cleaning.
In Portugal, our cleaner cost about $8 an hour.
Eight.
The math was not close. It was not even really math. It was a confession that the only thing stopping me had been the identity of being someone who cleaned his own house.
Those hours went to the kids, writing, investing work, and occasionally doing nothing useful at all, which is underrated if you have spent years treating every free hour like a slot to be filled.
I have never once stood in a clean kitchen wishing I had done it myself.
But there is one condition, and it is the whole game.
The trade only pays if the reclaimed hour goes somewhere.
Time with your kids. Deep work. Exercise. Learning. Real rest. A walk with your spouse. The work that might become the next chapter.
Fine.
Reclaiming an hour from the supermarket to spend it scrolling is just paying for a different waste.
Print it, stick it on the fridge, argue with it.
The things you should never outsource
Now the part the optimization crowd gets wrong.
Not every task is a task.
I drive my kids to school. There are services for that. The math could make an argument for delegating it.
But those twenty minutes — the half-finished thoughts, the strange questions, the last check-in before they walk into their day — are not an errand. Hiring that out would not free my time. It would cut out something I actually want.
Gardening fails almost every hourly-rate test ever devised. Home-grown tomatoes are the most expensive tomatoes you will ever eat.
Grow them anyway, if growing them puts you back together.
Time spent on what genuinely sustains you is not spent. It is invested.
The highest-and-best-use question applies to almost everything except the things that are yours because they are yours.
The skill is telling the two apart honestly.
“I fold the laundry because it is meditative” is sometimes true.
Sometimes it is a story frugality tells to keep its job.
This week: the audit
Do not think about this in the abstract. You will nod along and change nothing.
Do this instead. It takes half an hour.
- List every recurring task you did last week that someone else could do: cleaning, errands, returns, admin, yard work, repairs, bookkeeping, scheduling, inbox triage.
- Next to each one, write what it would cost to hand off and the hours it took you.
- Sort the list into three piles:
- Hand off now: costs less than your hour is worth, and you do not value doing it yourself.
- Keep — it is mine: school runs, gardens, workouts, rituals, anything that genuinely belongs in your life.
- The squirm pile: things you are keeping but cannot clearly defend.
The third pile is the interesting one.
Full disclosure: I redo this audit every few months, and my squirm pile has never once been empty. It just rotates membership.
The usual suspects are small admin tasks that look harmless in isolation and somehow eat the edge off an entire afternoon.
The flip: nobody announces it. You have to notice it yourself.
Where you are on the curve matters.
If you are early, time-rich and cash-poor, aggressive DIY may still be right. Keep it.
But if the base is built, the income is higher, the calendar is crowded, and you are still living like it is year one, nobody is going to tap you on the shoulder and tell you the math flipped.
Consider this the tap.
The real question is not what the task costs. It is what the hour could become.
Friday goes after the squirm pile: what happens when frugality stops being a tool and becomes who you are.
Reply and tell me: what ended up in your squirm pile — the task you are keeping but cannot defend?
— Ashleigh