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How to Live Your Life Entirely On-Demand in Chicago

One writer shows how to get things done without ever leaving the house.

Illustration: Marc Rosenthal

I’m a homebody. I work from an office that doubles as my guest room, and my perfect Friday night involves my couch, some wine, and Shark Tank. Lucky for me, practically every week brings a new on-demand service or app that makes leaving the house unnecessary. With this collective help, I wondered, could I take staying in to an extreme-sport level? Become a shut-in for five whole days while still keeping up with workouts, shopping, grooming, and so on? And how much would all this cost? I was about to find out.


9 a.m. Renee from Prestige Personal Fitness, which offers in-home training in Chicago and the western suburbs, shows up for my yoga session. We set up our mats in my kitchen (suddenly I wish I had done a better job sweeping), and after an hour of downward-dogging, I feel centered. The class is more casual and less rigorous than those at CorePower or Yogaview, my usual studios, but you can’t beat all the personal attention. Since Prestige offers a free introductory session, my Zen comes at no cost!

4 p.m. For the week’s dinners, I signed up with Evanston-based Meez Meals, an online home-cooking delivery service. You select meals from five offerings, and the ingredients—measured and prepped—get delivered with recipes. I ordered three dinners for $55.

A messenger arrives with a cooler. He lingers a little long at my front door, and it’s not until later that I wonder if I should’ve tipped.


8:30 a.m. Fabian (yes, his real name), another Prestige personal trainer, shows up. He brings a kettlebell, a 15-pound weight, resistance bands, and a Bose mini-speaker. We do an hour’s worth of 30-second exercises in my daughter’s playroom, and I’m hurting when it’s over. My waistband will surely thank me. My wallet? Not so much. My session costs $72.

6:15 p.m. A superfriendly 2­0-something guy from Dryv, a local laundry and dry-cleaning service, arrives to pick up my clothes. He tells me to expect a text in the next day or so to schedule the return. There’s a $20 minimum on all orders, but Dryv’s prices ($4 for a blouse, $5 for pants) are on par with my regular cleaner’s.

7:45 p.m. For dinner, I make roasted Brussels sprout tacos with Sriracha aïoli from Meez. Since I don’t even have to chop the ingredients, it seems more like assembling than cooking. The dish is a little bland—the recipe calls for exactly zero spices—but it sure beats my usual Trader Joe’s frozen enchiladas.


8:35 a.m. I’m nearly out of milk and Swiffer refills. Normally, I’d walk to my neighborhood CVS. Today, I try Postmates. The online service, which expanded to Chicago in March, is like Uber for deliveries. You request whatever you need through the app, and a prescreened courier picks it up within an hour. I log in my order. Seconds later, I receive a notification that Postmate Dwayne has accepted my request.

9:09 a.m. Dwayne texts me: “There’s a sale on Swiffer pads, buy one get the second half off. Do you want to take advantage?”

“Are they the dry Swiffer pads? Not the wet ones?” I respond.

Dwayne sends me a photo of the pads in question, and in less than 20 minutes, he’s at my door, goods in hand. He even used his CVS card to get me the sale price. I want a Dwayne always.

Dwayne tells me he receives 80 percent of the delivery charge, which varies by distance, but in my case is $5, plus a tip. Postmates adds a 9 percent service fee. All in all, my $13 order comes to $23. Ouch.

2:30 p.m. For the past few days, Taylor from Chicago’s Girl on the Go, a personal assistant service, and I have been e-mailing. “I don’t do serious cleaning, though I’m happy to tidy up—and no heavy lifting,” she said, explaining that she weighs only 115 pounds and was once asked to carry a bookshelf down three flights of stairs. “Everything else is fair game.”

Services start at $50 an hour, with a two-hour minimum, so Taylor and I agreed to a two-hour errand list: get gifts for my nephews, pick up my overdue license plate and city parking stickers, buy light bulbs, take bags of clothes to the Salvation Army, and—just to test her mettle—call Comcast to get me a better deal on my cable TV.

I had to give her my driver’s license, my vehicle identification number and registration, my Comcast account information, and the last four digits of my Social Security number. (Yes, I am practically begging to have my identity stolen.) Now she’s at my door, bearing the gifts and my stickers, and she takes the old clothes off my hands. She promises she’ll call Comcast later. (Dwayne who?)

7:48 p.m. Taylor e-mails: “It turns out I only have 15 minutes left for you. If you want [to buy] more time, I will gladly call Comcast.”

Knowing how long Comcast loves to keep people on hold, I ask Taylor what she could do in our last 15 minutes. She says she can’t think of any 15-minute tasks. I consider asking her to read to me—I’m behind on book club—but it seems too cruel.


7:58 a.m. My dry cleaning returns, two minutes before my 8 to 9 a.m. delivery window. It’s delivered in a reusable garment bag—not the usual cheap plastic. I already paid through the app. Again, am I supposed to tip? Awkward!

8:55 a.m. My self-imposed house arrest ends soon, but I don’t want to look like I’ve been a recluse. So I book a blowout through the cleverly named TheStylisted, an in-home hair and makeup service that uses a network of local stylists. On the app, I look through photos of their work and choose Athina, mostly because of her $40 price point. (Blowouts range from $40 to $100.)

When she arrives, I tell her that I’m usually too lazy to blow-dry my naturally curly hair. The last time I had it professionally done, I explain, I hated it. I even show her a photo of the botched job. But Athina reassures me she can straighten out my kinks. She’s right: My hair ends up looking great. The best part: I’d turned on the Today show, so no forced salon small talk.

7:30 p.m. Dinner—my final and favorite Meez meal—is crispy won ton cups. The company warns that you’ll likely have leftover peanut sauce. I drink it for dessert.


10 a.m. The last time my friend Callie visited from Brooklyn, she left a dress behind. That was three years ago. A better person would have returned it by now, but that would require getting myself to the post office. (Yeah, right.)

Until today. ShipBob, a local startup, provides on-demand shipping. You upload a picture of whatever you want to send, and a “ship captain,” in a white captain’s hat (I’m not making this up), will pick it up within 30 minutes. ShipBob uses the cheapest option—in this case, $2.90 for FedEx Ground, plus a $5 pickup fee.

Three years and $7.90 later, Callie is getting her dress back.

8 p.m. I end the week like anyone would: with a drink. Through DrinkFly, a Chicago-based mobile delivery app, I order two bottles of wine from Galleria Liqueurs in Old Town. Using the app doesn’t seem any different from ordering directly from the store. No matter. Thirty minutes later, I’ve got a glass of red wine in hand.

The week over, I ask myself whether I would use these services again. Dryv, ShipBob, TheStylisted, sure. The others, not so much. And when the next blizzard hits, Taylor should expect to hear from me. I haven’t forgotten those unused 15 minutes.


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