How to find discounts that shouldn't exist (without feeling like a shameless mooch) Part 1: WHOMST to ask

Ask (artfully!) and ye shall receive

Welcome to Imperfect Working Order—where we survive capitalism while sick and do it as fancily as possible, running microbusinesses, smooching hotties (well, one hottie, currently), and rolling with MEeps and regular peeps alike.

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Let’s not poop ourselves: one of THE biggest influences on our health is MONEY. (Thanks to Jodi Ettenberg for raising this thought in Curious About Everything #47.) That’s one major reason I started Imperfect Working Order—to help you make, find, and keep more moolah.

When it comes to discounts, I’m not talking about using discount codes or hitting sales. Credit card breaks, Capital One Shopping codes, and affiliate links are brill, but you can save even more with this one weird trick (heh).

Here’s what everyone misses: the best discounts are asked for.

And if “asking for a discount” just sparked a little cringe? Stop that right now. There’s a WAY to ask that won’t make you feel like a tap dancing orphan or a grabby grifter. Instead, you walk (well, click) away feeling quite classy, stroking your (vegan) fur collar with a (vegan) leather gloved finger while smugly congratulating your smart self for knowing the method.

You cannot get these discounts any other way, so gird up ye loins, quit leaving money on the table, and LFG.

Get in, sickie. We’re going discounting. Artful discounting.

The first rule of artful discounting is asking the right people.

Knowing you’re approaching someone ready to give, who won’t be remotely put out by your ask, will grease your gumption.

So, who are we asking?

1. Ask: Big Corporations

Big corporations budget for a certain number of discounts—and they often STILL make a tidy profit off you at a reduced rate.

They also benefit from unprecedented tax breaks. Your measly little discount request simply doesn’t register on their bigass bottom line.

Consider negotiating: internet providers, car insurance, online megastores, ALL of your monthly subscriptions, even utility companies. Scripts coming in Part 2!

I’ve negotiated a $4/mo New York Times subscription, scored Adobe Creative Suite for half-price for years, and even been comped entire Amazon orders—all through extremely polite, friction-free conversations and text-chats.

2. Ask: Hospitals + Labs

Most hospitals are non-profits and/or funded through the government, which means they are REQUIRED to have assistance programs.

These assistance programs are usually funded from multiple sources: federal, state, and local dollars. You have paid your fair share into these coffers, bebe.

What’s more, hospital billing is set up for INSURANCE to pay, not you. Often just asking for an itemized bill is enough to jog them to bill you less. They’ll knock off the $42 bandaid that insurance doesn’t blink paying, dropping your bill or even obliterating it completely. This works even if you’re using insurance.

In 2020, half of all hospitals spent less than 1.4% of their operating expenses on assistance. They will not go out of business because of you. Promise.

Healthcare isn’t affordable for most, so it’s a huge PITA for hospitals to get paid at all. They know this.

Hospitals do not want to spend the money to hound you on their bill. They want it PAID, even if they pay it themselves. So they’re often very generous with no-interest payment plans on top of forgiveness and discounts.

On the flip side, they don’t really care if you somehow scrimp together the funds and pay—that’s ALSO easy-peasy for them. No one at the financial aid office will argue with you when you try to pay them in full, even if you took out a second mortgage or sold your cat to do so.

In my town, you can make six figures and still qualify for some forgiveness with enough (non-medical) bills. There are other discounts if you’re not up for forgiveness, too. My hospital has a 5% “early pay” break…but you have to call and request it.

After years of forking over 15% of my income to my local hospital, I finally found out I qualified for TOTAL, everything-is-free-assistance for a year *going forward*, on a moderate salary. In fact, I had qualified all along. I just never asked before.

I can’t go back and get back what I spent—enough for a paid year off, a down payment on a home, or a big retirement boost—but I can save my limited resources going forward.

Another reason to take forgiveness if it’s offered? Other medical providers sometimes have a forgiveness system that makes having local hospital forgiveness an automatic forgiveness in kind on their end. When I mailed my hospital forgiveness award letter along with an application to outside labs like TrioSmart, my bills were forgiven in full.

3. Ask: local health providers

You’re probably a “frequent flyer” at your dentist, acupuncturist, chiropractor, counselor, or PT by now. (Yay.)

Consider this: they could have spent ad money and overhead to attract and intake 10 new patients, or they could just keep you as their loyal repeat customer for free.

Even if you’re not a frequent flyer, you know who gets hit up for healthcare provider recommendations all the time? Sickies. Your providers know you’re basically Yelp, but better.

Finally? If their business does well, it’s going to get bought out, at which point it usually becomes either a corporation or a hospital. Either way, the owner gets a tidy sum. If it’s just taking off, then new providers often just want to get people on the books and word of mouth rolling. You can help with on both counts.

Most indy providers have a place where BOTH of you can save—for instance, my dentist gives me the cost of a credit card transaction fee as a break if I write a check. Another dentist knocked $200 off just because I asked (and maybe because I had to have at least four serious procedures with him over a number of years). My PT office just took a copy of my hospital forgiveness form as reason enough to write off a year’s worth of appointments—in advance.

A gifted bike bell is just ONE part of what made this trike possible…someday I’ll do a whole post.

4. Ponder before you ask: local small businesses

Small businesses make the local world go ‘round, and many relish giving back where and when they can.

Often, they’ll extend the senior discount if you’re disabled, or just give you a “what the hell” 10% off if you ask. Ones that have been in the community for a long time are usually safe bets with established discount policies.

That said, local businesses also don’t get the benefits big corporations do, and often run on tight margins—check the vibe before you ask. Unsure? You can always ask if they have any sales or specials on the horizon.

Shoutout to my local secondhand outdoor store, where the owner grabbed an extra bike bell out of his garage to gift me for my trike.

5. Don’t ask: your friend’s business

Never ASK for a “close friends and family” discount…but graciously accept if it’s OFFERED.

Here’s why: I’m a small business owner myself. If a client asks for a discount, cool. I can look at my financial picture and know if that makes good business sense. If it doesn’t, they shot their shot and can decide if they want to still be my client or not. No harm, no foul.

If a good friend asks for discounted work or product…the stakes become the friendship itself, not the business particulars. I refuse to make that calculus. I’m not entirely opposed to mixing friends and money, but I do approach it with caution. I keep business and deep friendship separate as much as possible.

When I want to buy something from an entrepreneurial friend, I offer to pay full price. It’s partly selfish: I want to establish myself as a full client in their business, with a working relationships separate from our friendship. That means I’m not getting the “friend rate”, but I’m also not getting the “friend treatment”…where it’s okay to be late or offer up the dented goods because they really couldn’t afford to take me on for less than their advertised price in the first place.

This doesn’t mean you can never get the friends and fam discount. I’ll offer if I can do something for a friend or family for free or cheaper. And I often do! Many of my friends have spruced-up resumes, proofed websites, or industry intel I’ve dished out for free. I’m glad they took me up on it…and I’m glad they didn’t ask me to. (Sidenote: be generous wherever you can. This is how we build communities and microbusinesses. Look, I’m doing it right now: free discount advice!)

I have been the grateful recipient of faaaaar too many sweet gifts of talents and time from fellow solopreneurs: a perfect fall day photoshoot, gorgeous handcrafted jewelry, creative consultations, smart business advice, brilliant life advice, these beautiful cards made by an ME/CFS patient, top shelf coffee, and so many more.

Okay. That’s the who. Next week? We’ll hit the how. STAY TUNED.

In the comments:

What was your finest asking-for-a-discount moment?

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Speaking of asking…

It’s my birthday this week! My wish: for you to share this post with at least one sickie, sickie supporter, or literally any human who could benefit. (I mean…who couldn’t?)

And speaking of other discounts…

• Get $100 when you open a new Ally high yield savings account using this link. (Gives me $50, too.) Minimum deposit is $1k. I’m so mad no one told me about high yield savings until I was nearly 40.

• Get a $200 bonus (and then up to 3% cash back forever) on a no-fee card with American Express with this link. (I get $75.) Hot tip: go through their “special offers” to really load up on cash backs. I use Amex for both business and personal.

• Take $60 off a Liberty Trike like mine with this link (I think it gives me $60, too?) For the cheapest deal, get the “Classic” (aka, old, aka, mine) model or a refurb.

• If you feel a stirring to support this work, you can Venmo my “parent company” @flyingbicycle or fulfill my wildest replacement toothbrush head dreams on MyRegistry (my b-day is Wednesday!). Thanks in advance!