I always feel like there's a whole rule-book of "how to Do Life" that I didn't get, for this easing-into-the-upper-middle-class and/or doing-serious-business-stuff shit, that other people just know, because of who their families are and who they grew up hanging out with.

I gather the version of that I did get was the middle-class version—which some others didn't get and have a similar "wait, that's just normal?" reaction as I do to the upper-middle stuff. Like 90% of that's basically credit-related—how credit cards work and how to use them, how to build credit, how to buy a house (generally with a mortgage, so, still basically a credit-related thing), that kind of stuff.

I've noticed similar things when it comes to paying others to do stuff for me. Having a house cleaner come in for the first time was fucking weird. Still is, really. I can't relax, feel like I ought to be helping. Or paying someone to do work on my house that I could do—tiling, drywalling, some light electrical, plumbing, most general home-improvement stuff. It feels gross—I don't think it does for those who grew up with that stuff being normal. I suspect it's a barrier to advancing in business, because those attitudes carry over. Delegation is weird to me. Being someone's boss is horribly uncomfortable. The notion of starting a business and hiring employees to take over stuff I've been doing feels icky and wrong, and no amount of one part of my brain telling another part to knock it off makes that go away.

Yep I'm with you, I am absolutely loathe to hire anyone to do something I could do myself. I've done major home repairs, painting, flooring, kitchen and bath remodels, I do almost all my own auto repairs and maintenance, I do my own laundry, I clean my own house, I cut my own grass. I have neighbors who just pay for someone to do all that without a second thought.

There are certain tasks that you would never do yourself, such as surgery. And there are certain tasks like changing your oil where anyone with patience and diligence can do it themselves. It's just a question of whether you want to spend the time to learn it and do it.

Responding to a C&D letter from a Fortune 50 company, I would posit, is more like performing surgery than changing your oil. The cost of being wrong is rather high.

Right, that's the "I could do myself" part.

Though I've generally been disappointed with the legal services I've hired. Law and medicine seems like most professions, there are some really good practitioners and a lot who are mediocre but have passed the minimum required qualifications, and it's hard for an outsider to immediately spot the difference.

Speaking of surgery, here's an analogy that might be helpful.

Five years ago I had a catastrophic ankle injury I suffered while running in Moab. Two broken bones, lots of torn ligaments, and otherwise irreparable damage without serious surgery.

I interviewed a whole bunch of surgeons before I decided where to go under the knife. And I don't remember where I got the advice, but someone told me the most important question to ask is: "How many times have you performed this specific surgery (a Maisonneuve fracture repair)?"

I eventually found the Steadman clinic and a doctor who had already performed the exact surgery I needed nearly 100 times. Everyone else's answer was less than 5. Some even answered 0. The surgical clinic I used had signed pictures of professional athletes all over the wall. I found the true specialist, and I'm very thankful that I did.

Even bad lawyers and surgeons are expensive. When you have a bet-the-business legal issue, do plenty of advanced interviewing to make sure that the one you hire has plenty of experience with the exact issue you need help with. If it's not obvious that you've found the right person, keep looking.

> Law and medicine seems like most professions, there are some really good practitioners and a lot who are mediocre

This is accurate, in my experience. It's what makes initially finding a lawyer (or doctor, or therapist, or auto mechanic, or etc.) a painful experience. You have to expect to go through a few before you find one that works for you.

Then, when you find one, treasure them for the pearls that they are.

The weird bit is when doing it yourself turns out to be more of a hassle and more expensive than paying someone else to do it. Around 15 years ago I decided to learn how to change my own oil. Even after excluding the fixed costs (I bought little ramp things to drive the front of the car up on while I worked underneath, and a container to drain the old oil into), I was surprised at the per-change costs: the cost of the oil itself (and the new filter), as well as the cost to properly dispose of the old oil. Ended up being more expensive than just taking the car to Jiffy Lube and leaving it with them for an hour or so.

That was the first and last time I ever changed my own oil.

Feel ya. Disposal is a pain, and if you mess up, it's a trip to home Depot to get some chemicals to clean your asphalt. That was fun when my apartment had me parking in a shared garage...

Oil is simple and easy enough that I just get it changed with my inspections. There are things that, even if you're competent enough to monitor and do yourself, is still better getting a second pair of eyes on. That said I wouldn't do jiffy lube or other stop and go oil shops... Too many noobs there where the chance of them effing it up is higher than myself. I once had a tire buldge when I was younger and broke AF, they replaced the wrong tire and I had to drive back to convince them they changed the wrong one (big old bubble in the sidewall), took a bit to convince them they changed the wrong one since they refused to admit fault. Thank God I took a picture before that was clear enough to place the bulb right on the text in the exact same spot.

I'm having similar concerns around my diy for some electrical and gas work. Yeah technically I can do it myself to code, but I'd rather inspect someone else's work and not deal with the liability of fucking it up myself. Just because I can do it doesn't mean I can do it to the level of a quality professional, and I'm now wealthy enough to actually get the pros and not just the journeymen. There's something about paying for quality work that just feels good. So long as you can respect the labor, it feels great and not so weird to hire others.

That said, I've had a few coding projects I've subcontracted in my home due to lack of time to those on roughly equal grounds as myself. It feels a bit weird, especially for tasks with unknown bounds but worth it for the time and schedule savings. I'd rather not wait another 6 months and spend my personal time when I have a laid off friend who just wants some bar cash.

As long as Jiffy Lube doesn’t put the new oil in the radiator.

Sometimes you do things yourself because that’s the only person you trust.

But oil changes are one of those “do it yourself once so you understand it and then let Walmart do it” kind of things.

I've had shops do all of the following (not at the same time but each has happened before I stopped letting them change my oil):

  - fill with the wrong weight oil
  - not change the filter
  - not tighten the new filter adequately, resulting in leaks
  - install a very low quality "no-name" filter
  - overfill the oil
  - overtighten/strip threads on the drain plug.
  - leave tools under the hood.

And that's just oil changes, one of the simplest things a shop can do. Maybe it's because they put their least skilled people on it, but it doesn't incline me to trust them for anything else.

> Having a house cleaner come in for the first time was fucking weird. Still is, really. I can't relax, feel like I ought to be helping.

A long time ago, I had a house cleaner come in once per week to do deep cleaning stuff. It was quite a luxury! However, I always spent a couple of hours cleaning the house in preparation for their arrival.

What I've noticed is a shift with age and wealth. When I was young and poor, I had time and energy in abundance and never hired people to do anything for me (excepting for specialized things like medical care). Now that I'm old and more comfortable, I don't have any issue hiring people to do things I can technically do myself.

I look at it this way: whether you hire someone or DIY it, you're paying something to get it done. If not money, then time and effort. I just pay in the manner that, big picture, costs me the least. When young and poor, my time and effort was worth less than actual money. Now, money is often worth less than my time and effort.

Is it worth paying $50 to have the neighborhood kid mow my lawn for me? Younger me would say absolutely not. Current me says absolutely.

I would guess later in life when your insurance agent or tax prep person find out you didn't fill out a will yet and introduces you or encourages you to have an attorney write one with you. Now your family has an attorney! That or going through a family estate.

A coworker's wife's friend is an attorney. So he's "his family's attorney" now, because of course he is. My landlord is a dentist, so he's my dentist now, because of course he is... That's how it mostly works... I guess :P

The only time I've ever needed a lawyer was for a small side business I had at the time. One of our customers had an unpaid invoice that was past 90 days, and they were not responding to phone calls. Happily, my business partner's brother was a lawyer and she asked him to send out a dunning letter. We had the money within days :-)

Yea, they're a useful bunch, especially if you know one. Back when I worked for an e-commerce site, we were deciding if we're gonna implement package splitting CoD (cash on delivery) for multi-package orders, or if we're gonna just slap the entire sum on the first package (this seems like an easy enough job, but when you have many shipping service APIs you have to work with and you have automated CoD back-reporting that goes into your invoicing, it becomes annoying). We did the easier thing and just sent a pre-drafted dunning letter to people who took the CoD-less packages for free and did not pay for the first one with CoD. Worked like a charm.

> she asked him to send out a dunning letter

Honestly, I think that about 1/3 of the value I get from my lawyer is the power of his letterhead.

The rest is explaining contracts to me, explaining risks and exposures of things I'm planning to do or that have been done to me, educating me about aspects of law I need to know on a daily basis, and such.

A tiny percentage is helping with large things like selling my business, negotiating major contracts, defending me against legal attacks, and that sort of thing.