Chapter XXXVI: Creating or Dealing with Elaborate Door Security While Doing DoorDash or Uber Eats

Perusing information on X lately is a bit of a gamble what with all the quackery and other questionable content seen there in the Elon Musk era. You still see videos pertaining to DoorDash and Uber Eats, though, and it’s usually controversial content—like deliverers rebelling against no tips as just one example. Recently, I saw a related video that stood out from the others. It was about a woman who sets up elaborate safety procedures at her door when having food delivered from Ubers and Dashers.

Now, I can’t say for sure if any of that was really true. Evidence is there it might have been done as a set-up to gain clicks. But it seemed overly elaborate to be a fake. 

With increasing mentally ill people out there today, it’s more than possible many people create their own security procedures at their front doors when having food or drink delivered. I mean, we’ve already seen evidence people with short fuses are out there delivering—probably because they have no other means of income.

This doesn’t demean being a Dasher. All of the ones I encountered when delivering were friendly and intelligent individuals. The ones who might pose a threat are perhaps more likely to avoid conversations with their fellow deliverers anyway. And I wouldn’t blame anyone for setting up basic or complex security at their door when having something delivered.

What’s really going on out there, and would you put up with someone’s detailed security measures to deliver food to their door? Also, let’s expand with whether you’d do the same with an Uber or Dasher delivering to your own abode.

How Far is the Security Going?

Based on the above video seen on X, it’s mostly women taking these measures out of precaution. You can’t blame them in the age we live where you’re never really sure who’s lurking around your house. No doubt men are doing the same security here and there.

For the record: I never encountered a customer who directed me to a security process in delivering their items. Then again, the “Leave the order at my door” note on the app was always a signal they didn’t want to answer in person. It’s the simplest method to bringing a safe delivery method. Some people don’t even trust that, though, considering people have their food stolen off their doorsteps far too often.

I always worried that someone was going to steal a food bag near a customer’s door, particularly when having it exposed to anyone walking or driving by. I’d frequently see strangers walk past while seeing me drop the bag at someone’s doorstep. In many cases, however, the customer opened the door to retrieve their food mere seconds later, often murmuring “Thank you”, or just waiting until I was out of view. 

Once in a while, I was given specific directions to deliver the item to the customer’s back door, a shed, or some other nearby, isolated area. This was usually because they’d have food bags stolen before at their front door, or because the front area wasn’t completely accessible.

While I never encountered someone giving me security directions in-person, it appears it’s becoming an increasing trend. What happens if you encounter someone like this, including a multi-step process to make it safe for the person?

This could delay you since time is always of the essence when it comes to prompt deliveries. Regardless, the customer is always right, and you should (arguably) go along with it.

Should You Talk to Uber and DoorDash About What the Customer Did?

If you happen to encounter an overly elaborate door security procedure that wastes too much time, you should definitely call Uber or DoorDash agents to tell them what happened. The customer may get a talking to on taking too much of your time in delivering safely. That person may have to come up with a simpler solution for you to deliver without it feeling like a prolonged, multi-step authentication process.

In the X video I referenced above, it showed the woman in question implementing several extended security procedures to ensure her own safety. One of those was spreading salt on her walkway to capture the delivery person’s footprints. She also forces the delivery person to put on a handcuff outside her door before handing off the food to ensure the deliverer doesn’t invade her home.

It didn’t stop there. She also has the delivery man show his I.D. card, including providing his fingerprints for a complete background check. Then she sends out a remote-controlled drone to capture the guy’s car license plate. This ensures it’s a real delivery person and not an illegal immigrant or other fake. The drone also follows the car to make sure it moves out of the area and doesn’t linger (see my blog piece about “lingering”).

Unfortunately, the one who posted the video called the woman a “liberal”, giving an unexpected political bias to who might do this. The woman in the video made a good point, nevertheless, about how she can’t trust anyone anymore. 

If this is true, would you feel comfortable setting up a similar security protocol at your home?

Getting Your Food Faster

Some people just want their food handed to them due to being in a hurry. You may be one of those people, hence having to deal with an Uber or Dasher handing the food off to you. Would you trust a deliverer handing food to you at your door—including if you were home by yourself?

Well, I’ll tell you this: I’d trust myself since I was always a reliable and conscientious deliverer for Uber and DoorDash. But, I’m consciously aware that others aren’t like me and are basically forced into delivering food to survive. 

There’s been concern about illegal U.S. citizens delivering for a while, despite Uber and DoorDash now providing better methods to make sure real residents with licenses work for them. Traffic offenses are also scoped out through a background check done once per year. Not that this would completely eliminate any potentially psychotic people out there.

From your perspective, imagine a deliverer delivering your food, yet you fear the delivery person looking a bit creepy when spotted on your Ring camera. You need your food fast and don’t want it dropped off at the door. What are you going to do since you’re the only one home?

Outside of building a security moat loaded with piranhas, your best bet is to speak through your Ring camera when the person rings the doorbell. You can just tell them to place it at the door since you’re likely feet away inside anyway.

This makes for a good compromise without forcing the deliverer to go through ridiculously long security measures. Oh, and it helps to have dogs who bark at your door as proof you’re completely secure. Dogs intimidated me more than once at many front doors.

Trusting Your Deliverer

One of the most satisfying things about doing DoorDash and Uber is that you’re going to have a lot of repeat customers after a time. If you stick with it for at least a year, you’ll start delivering to a group of regulars you’ll get to know. When I had to deliver to these people, we’d chat in text like longtime friends. 

It’s here where you’ll know right where to go and what to expect every time. Best of all, the customer has complete trust in you based on your past track record. That means either a routine tip amount or more during each visit.

Those of you who live in slightly smaller towns or cities will probably have repeat deliverers. Get to know them by chatting in the provided text boxes (without flirting). You’ll be able to have worry-free deliveries this way based on a long-standing track record. Just don’t set up quicksand in your yard for the still mysterious guys delivering from Amazon.

In Chapter XXXVII, I’ll look at the issue of high commission fees from DoorDash and Uber. If you wonder why these delivery services aren’t being used in your favorite local restaurants or fast food places, it’s usually due to thin margins. This could affect you and DoorDash in some restaurants starting their own delivery services.

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Chapter XXXIII: Past and Future Issues with Self-Employment Taxes When Doing Uber Eats & DoorDash

Maybe it’s still inevitable that death and taxes are still inevitable, even if the latter is now potentially on the chopping block. And perhaps death can be overcome someday under certain circumstances. While the chances are possibly lesser than 50/50 President Trump will eventually eliminate American income taxes, let’s assume taxes (including self-employment taxes) are still going to be around for a while. DoorDash and Uber Eats will most definitely still warn you about that.

One thing I learned as a freelance writer before the Uber/DoorDash days was, self-employment taxes are a massive head scalp. If you make up to $30,000 or $40,000 per year with your own business, you can expect to pay about $3,000 annually in non-withheld tax. While I paid a little less with DoorDash and Uber, it was still expensive. The IRS continues to think you can pay all that in quarterlies, due four times per year. But, when other expenses get in the way, it’s often challenging to pay even those amounts.

It’s one thing to think about, seriously, if you start working for DoorDash. Some people with no experience paying SE tax still don’t realize you’re an independent contractor when delivering food & drink. And this often gets people into tax debt, something I admit happened to me. 

Don’t sit around assuming the IRS and/or income taxes are going to become extinct before the end of 2025. If you’re adamant on doing Uber Eats or DoorDash to make extra money, it’s time to plan a self-employment tax strategy until further notice from the President of the United Taxable States.

Let’s dive into what you might have to pay, how to lessen that amount, and what taxes may look like in a future DoorDash world.

Will You Have to Pay $3000 in Self-Employment Taxes?

Yes, it’s very possible you’ll have to pay in the neighborhood of $3,000 if you do Uber or DoorDash a lot. I met a few people during my Dashing times who told me they did DoorDash as their main job. You really shouldn’t, despite the extreme temptation thanks to the freedom of working your own hours and driving open roads. 

I learned the hard way that making money while working from home or via car has a steep tax price. You’re basically chained to the U.S. economic system of having to work for a company (mostly on-site in their workplaces) if you want your taxes withheld.

This was one reason I had to start working for Amazon after working as a freelance writer for 15 years. Anyone who’s gone through self-employment tax hell probably made the same moves due to the 15% SE tax bracket.

Again, just don’t do DoorDash as your only job since you’ll likely end up making far too much money that’ll be taxed. Your best bet is to just make it a side gig with another job. The ideal sweet spot is to simply do DoorDash once per week on a day off. This can fill in well to help you make extra income without getting a steep tax bill by the following April.

There’s still many who do Uber and DoorDash more than three days, though. If you insist on this, be sure to set aside money to pay your quarterlies. This can be a major challenge if you have other expenses you have to pay each month. Unless you have some money set aside for emergencies (and many don’t nowadays), I recommend not doing DoorDash beyond one or two days.

Just keep in mind Uber and DoorDash will ultimately try to push you to deliver as often as possible. Much of that is corporate hype, though it’s entirely up to you based on what you need to do. In the chance you have no choice but to use DoorDash as a means of making money, the best scenario is to work out a payment plan with the IRS after you get the tax bill. This is something I had to do. Fortunately, the IRS became more like a kind uncle in recent years in helping you set up long-form, time payment systems. 

With major IRS cuts recently, however, perhaps the existing agents aren’t as kind as they were over the phone.

What About Adding Tips to Your Taxable Income?

The recent “No Tax On Tips Act” in Congress leaves it open now to many employees being able to write off tips as an exemption rather than part of income. While President Trump will supposedly sign this if it passes in both houses of Congress, it’s only designed for restaurant and hospitality workers. Because Uber and DoorDash deliverers are independent contractors, no taxes on tips there won’t yet apply.

Yeah, you probably just scoffed at that piece of info. It also broaches another discussion on whether you should report any tips you get from DoorDash when filing your taxes. If you’ve already done Uber or DoorDash, then you know most customers tip through the app. With this, any tips you get are already on record and added as income.

Once in a while, though, you’ll get tips in cash from your customers. During a delivery run to an outside town here in the valley of Oregon, I received a $100 cash tip from two women who realized I had to drive a bit of a distance to get there. “That was a long fucking drive, right?” One of the women said. “Yeah”, I uttered while my eyes bulged out at the sight of a hundred dollar bill in the other woman’s hand.

It’s cash tips like this that bring a lot of ethical debate when filing your taxes. Considering it’s cash, some might say it’s all under the table and doesn’t apply. Tax professionals will say you absolutely need to report cash tips in the chance the IRS audits you. Others may even say the chances of you being audited are slim, unless you’re making $100,000 per year as a Dasher.

In this case, I say it’s up to you whether to report cash tips. Most of the cash tips I made while delivering were generally from a few bucks to $10. Only occasionally did I receive bigger cash amounts from wealthy families living in the hills of my city.

One thing for sure is that any tips added through the apps will pump up the income you make. Just going by the base pay would otherwise lessen your earnings by far.

What is the Future of Self-Employment Taxes While Doing Uber and DoorDash?

I’d lobby tirelessly (if having the time) to abolish self-employment taxes in general. But I don’t think they’ll ever go away, unless income tax is abolished while Trump is in office. Those of you who do Uber or DoorDash over the coming year or beyond will likely still have to pay SE tax on every penny you make.

By chance income tax goes away, it might attract more people to sign up to deliver for Uber Eats and DoorDash. The only reason many people still want to do food deliveries is no doubt because they don’t initially realize how deep of a head slice self-employment taxes will give them. 

You might want to know that DoorDash has been lobbying in Congress to get tax exemptions for those earning tips while delivering. The company wants gig workers who work through apps to enjoy the same tax savings as W-2 employees. Their goal is to add this to the “No Tax On Tips Act”, which still isn’t law at time of this writing.

Reportedly, Uber is advocating the same thing for their drivers and deliverers. Just when you thought corporations like this are greedier than ever, they’re morally standing up for the deliverers to at least save on their taxes.

You can probably say that the IRS scares DoorDash and Uber anyway. The more taxes people have to pay on delivery earnings, the least likely anyone else will want to do the same. 

Once the reality of self-employment taxes gets out there, the stats may already show the majority of Uber deliverers and Dashers are those just stuck in it due to inability to have any other job.

It’s best to say use DoorDash and Uber in moderation—something you’d say to all your food and drink recipients. 

In Part XXXIV, I’ll cover detours in making deliveries, something you’ll need to think about if roads are blocked—or blocked by trains—while in a rush to deliver.

Part XXXI: Delivering From or To Adult Stores When Doing Uber Eats/DoorDash

Just about every town or city has an adult store, and that’s usually plural. They’ve been around, legally, for decades throughout America, with many questions and rumors still permeating about what really goes on in those shops. While always talked about by many, let’s not forget they’re run by human beings who also need food & drink delivered to them after, uh, working long hours. And you might even find some rare times when you have to deliver an item from one of them.

For the record: I’ve never picked up a sex toy to be delivered to someone—or at least that I was aware. I’ve seen sex toys and dolls in sealed boxes while working at Amazon, btw. Regardless, I’ve heard stories about people picking up sex toys to be delivered to someone as another category to miscellaneous deliveries.

What I have experienced, officially, is delivering to several adult stores. The big question is: Would you want to pick up from or deliver to one of these stores? Not everyone is going to be ok with such a thing. 

My first time delivering to one allowed me to see the inside inventory in all its glory. Let me tell you what you might experience and how to go about it in the right way without embarrassment if you suddenly find yourself there.

Would You Pick Up a Sex Toy Order for Delivery?

According to my research, there haven’t been a lot of deliveries like this. But it’s not that it hasn’t happened once in a while. Some people buy naughty items through sources like Walgreens (a place I picked up from quite often), plus pharmacies. In many of those pick-up scenarios, I never saw what was in the boxes. Walgreens was especially secretive on what I was picking up for a customer.

Apparently some adult stores have worked with DoorDash to get things delivered to people fast. Rather than wait several days for a mail delivery (or going in person), some people want their vibrators—now. 

I still remind you that I delivered a lot of miscellaneous items when doing Uber and DoorDash. If I ever delivered an adult toy, it must have been with the “unknown” packages. My guess is Walgreens is where it must have happened if it ever did—namely because they have a pharmacy there. They likely offer various things not openly showcased directly in the store.

While the evidence is there such deliveries have happened for some people, finding out that’s what you’re delivering brings a lot of questions. Would I have delivered a sex toy or related item had I known this is what I was picking up?

I probably would have since nothing was off-limits for me, as long as it paid decently. You have to imagine if someone wants any of those products immediately, they’re willing to pay extra or a large tip to get it to them. 

Yeah, when it comes to human satiation, food and sex are likely #1 and #2 for a lot of individuals. When someone’s in the mood, they’re in the mood, regardless if it’s also Popeye’s chicken.

The bigger question is whether someone like you would deliver a sex toy with the knowledge you were delivering that very thing. I know a lot of people, and I’d say it’d be half against and another half who wouldn’t have any problem. 

Always live up to your own ethics when it comes to what you deliver with Uber Eats and DoorDash. If you’re under 18 or delivering with your kids, it’s probably a good idea to stick with the food without having to answer a lot of questions. If you’re a couple working together—well, it may be one of the best scenarios. The customer seeing a couple delivering their sex toy may go over better than a single guy or woman.

Would You Deliver Food to an Adult Shop?

You might face the same dilemmas delivering to an adult shop, even if it’s more inevitable if you decide to deliver food & drink. During my two years doing Uber Eats and DoorDash, they’d occasionally have me deliver to other businesses that might be deemed controversial by some.

For the most part, it was delivering to cannabis shops, something that seemed apropos considering even the owners and clerks get the munchies. Delivering to those places never bothered me in the least, though there was always the scent of weed in the air when going in to deliver.

But then, one day, I got a delivery order to Eva’s Boutique, a popular lingerie and sex toy store franchise here in the Oregon valley. This was a standard McDonald’s order, though had never delivered food to an adult store at any time prior. The initial thought was, it’d be no big deal since I’d certainly been around these products before—if not in a retail environment.

You always think you won’t be embarrassed going to an adult store—until people start seeing you park by the door. Being a straight guy, people in the periphery seeing me park at Eva’s offered up a few curious stares. And, naturally, it had to be right next to a busy street here in Salem, Oregon where anyone I might know could easily see me go in.

As with most businesses, I thought it’d be an easy delivery, as in leaving it at the front counter. Yet, once inside, it appeared there wasn’t anyone around. The woman clerk was busy helping a couple interested in the lingerie inventory in the back of the store. This required me to walk through all the aisles to hand the McDonald’s bag to the recipient.

Winding through the aisles enabled me to see nearly every item in the store, including a little detour through the vibrator section. Yes, that also brought on a few interesting side eyes from other customers inside, mostly women.

I finally found the clerk inside. She let out a slight giggle as she saw me standing there, next to an aisle of lubricants while offering her the McDonald’s bag. It was the ultimate clash of Americana in one little store. Instead of handing the bag to her, though, she told me to set it over on a nearby counter. 

And out I went, adding another line to my DoorDash delivery experiences. This happened a few other times afterward, albeit being much quicker by dropping off right by the door. Since then, I’ve always wondered how many other DoorDash customers have had similar experiences and how they reacted.

Here’s my advice: Always stay professional and don’t act flustered or embarrassed. You’re going to encounter a lot of interesting places and situations when you do Uber Eats and DoorDash, so always act like you’ve already seen it all. Perhaps you already have if you’re grown up enough.

On the other hand, you might have to explain away delivering to other places, as I had to. After delivering food once to a fertility clinic to help women get pregnant, I had to tell a co-worker why I was going in there after being seen. 

If you have to explain to a family member, friend, or co-worker why you were seen by them going into an adult store, it’s best to have some ID on you proving you deliver for DoorDash. In that regard, I almost wish DoorDash would send business cards to prove you work for something nearly resembling the CIA.

In Part XXXII, I’ll be looking at the problem of paying self-employment taxes when working for Uber Eats & DoorDash. If income taxes are abolished (under President Trump), would it increase those who want to deliver food to the public? 

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