What Do You Happily Pay Someone Else to Do?
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Here's a hopefully fun question for today — what do you happily pay someone else to do? Have you rotated through a few different “someones” enough to offer advice on what you like or don't like? Have you ever made the opposite decision and STOPPED paying someone else to do something?
We've talked a lot about this in the context of things like upgrading personal services, using a personal assistant, hiring a cleaning service — as well as discussions over on CorporetteMoms about leveling up your childcare and even hiring a housemanager.
What I Outsource
The big ones for me are home cleaning, grocery shopping, and tax preparation, but I've considered meal prep services. I haven't had good experiences with travel planners thus far, but it's the kind of thing I'd consider if a friend had a great recommendation.
Home cleaning – I have gone through a few “someones” here; we've worked with maybe six different services over the years… and there's absolutely an element of fit there. There was the woman who unloaded the dishwasher without knowing where anything went, and then made weird choices like putting knives, pointy-side-up, with the spatulas. There was a service that weirded me out by walking around taking pictures… after their first clean. I could see it making sense to do with the homeowner, like “I like it when this pillow goes here…” but otherwise it creeped me out. (Maybe she had taken “before” pictures also, and that was her goal? I don't think it was that bad, but what do I know…) There were amazing ones also, including a one-woman show where we trusted her so much we would have let her organize our closets.
Grocery shopping – I've used this off and on over the years, but I've been steadily using it for about five years now. I like being able to build my grocery list casually in the app, and then have someone else who actually knows where things are run around to find things… we also tend to make good use of prepared food from the grocery store like pre-portioned, sliced apples, mirepoix, and (sometimes) pulled rotisserie chicken.
Tax prep – Hey, I went to law school, I know that the Tax Code is extensive (and mysterious and important!)… and ever since then I've decided to let someone else know all that stuff! I've only had two accountants. The first one was a lovely old man a friend had recommended, but when he nearly missed a huge thing (a first time home buyer's tax credit that I don't think is available any longer), that was our last visit to him. We've been with our second guy for 15+ years now and I really like and trust him.
Readers, what's on your list — what do you happily pay someone else for? Have you rotated through a few different “someones” enough to offer advice on what you like or don't like? Have you ever made the opposite decision and STOPPED paying someone else to do something?

Cleaning, for sure. I also send more dry cleaning/laundry out than a lot of people do. Taxes, for real for real. As for groceries, we get Blue Apron weekly and have for years (although I am starting to lose my patience with their recent fulfillment issues), and I also order from the supermarket online and then do curbside pickup (although there’s no charge with a minimum order). Weekly lawn service and more significant yard work seasonally.
Also I pay a fee to a travel agent to get discounted airfares.
Change my oil. Wash my dog. Mow my lawn. Weed my beds/garden.
These are things I used to do myself in my younger days when I was broke and had the time.
Along those lines, waxing the car.
And I have my lawn guys come in the fall and do two leaf clean ups. Raking leaves just left me a sneezy, runny mess and I am happy to pay to have that done.
Snowplowing is a must for me. I thought I could handle it myself for a few seasons and I was miserable.
For housecleaners and yard stuff, I’ve landed on having them come a few times a year. Housecleaners come for a deep clean before Thanksgiving and in the spring. I had biweekly cleaners for years, but the prices kept going up and the level of service kept going down. It was super useful during a particularly busy season of life and there are some weeks where I miss it, but having the deep clean every six months or so really helps.
Lawn guys come for spring and fall cleanups, mulching, fertilizing, and any bigger projects that would take my whole weekend. I handle weekly mowing myself because I discovered that I actually like having 90 mins to walk around my yard and listen to an audiobook.
Mowing the lawn and laundry.
Dry cleaning, or just pressing, a LOT of stuff., and other than during the pandemic, I have not cleaned my own house in two decades.
Picking up dog poop! I already have a house cleaner, a pool guy, gardener, and a food delivery service, so dog-poop-picker-upper was the fun new find this year!
Paying my accountant to do the taxes is the best money that I spend each year. Having a house cleaner about 6x per year always feels great and worth the money, but I don’t enjoy having someone weekly or biweekly. I currently do my own yard because it’s so small that I cannot justify paying someone else to do it. I would pay someone to cook for me 4x per week because neither DH nor I enjoy cooking and I insist on a very healthful diet for myself and I have significant food limitations.
Weekly housecleaning and half day daily house manager who helps with the joys of multi school drop off. Then she comes back and does laundry, resets kitchen, preps food for dinner, and does random amazon returns, fills cars with gas etc. This has been gamechanging.
House cleaning, lawn mowing, all car maintenance/service/cleaning even if it’s having the folks at Autozone install my windshield wipers (okay the service is free but it’s because you paid for the product), taking care of my horses, I have paid someone to thrift treasures for me, tailoring (I sewed as a kid but nah for now), bike maintenance and service, personal training/designing workouts, home maintenance/service (I have no desire to learn to do anything more than change an air filter), as much as I can really. Although, I enjoy grocery shopping, so I do that myself!
Wax my underarms. I’ve been going to the same aesthetician for 20+ years. We know each other so well, and have helped with parental problems. We’ve been through a divorce and a spouse’s suicide together. She’s wonderful.
I’m very low maintenance, but underarm waxing is one of my very few indulgences. Razors and I do NOT get along in that area of the body!
I outsource lawn mowing, an annual gutter cleaning, and about half my tailoring. And about every other grocery shop I order “click and collect” to pick up my groceries bagged from the store. I too prefer to choose groceries in person, but when I’m busy, it’s a life saver.
When I was a contractor, I had an accountant, but this involved so much work from me, and only just paid for itself. If I need such a service again I will use a local finance/tax app instead.
I yearn for a twice yearly deep clean done by somebody else, and I hope to add this to my budget next year.