Confessions: My Two Months Driving Lyft in Chicago

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Mr. Sierra, taking notes. Click photo to view COA Instagram.

Last year, the ride-share company Lyft offered explosive financial incentives in order to generate a gold rush of business into the Chicago market.  The bonuses being low-hanging fruit, I signed up as a driver last fall and banged out my 100 rides.  But I walked away with more than just cash.  Unlike my usual flâneurie, which is immersed in urban anonymity, Lyft driving opened access-ways into human experience unlike any I’ve known.  First a question—a curiosity blooming into a discussion—then suddenly an entire human life opens before you.

Friday, October 16, 2015

By Cloud Gate in the Loop, I pick up a family—a mother, father, and two middle-school girls.  They’d treated themselves to dinner on the town and were headed back now to the suburbs—about a 40 minute trip. Hearing the parents’ accent, I begin speaking to them in Spanish, usually a welcome gesture of intimacy among fellow Latin-Americans. But it seems the father, having by his admission “come 20 years ago to work hard in this country,” wants his family to speak only in English. So my questions in Spanish remain unanswered, or answered strictly in English.

I tell them I’m an English professor, and the father’s face illuminates.  He turns and prompts his 12-year old daughter to tell me about her biome project in school.  Her English is without the spot or blemish of an accent.

At the end of the trip, he gives me a knowing look and thanks me for being “respectable and hard working,” and wishes me well “in this country.”

Minutes after I drive away, the Lyft app informs me he has given me a $50 tip.

Saturday, Oct 31

Halloween. The entire north side is an all-immersive outdoor masquerade.  I have my “Weekend Party” Spotify playlist going. By Wrigley Field, five women pack into my car, each dressed as the devil.

“Hey I’m sorry, guys, but the maximum amount of passengers is four.”

“Just drive!”  The eyes of one of them flash.

Against my better judgment, I do.  The ride isn’t long, anyway; just to Wicker Park.

The devil sitting upfront whips her head over: “Looky…who…we have…here.  So who are you?”  I notice with my peripheral vision how thick and dark the eyeliner is around her eyes.

In response, I begin telling, at first haltingly but then with increasing acceleration, of my beautiful wife and our child on the way; my life here with my wife; I’m doing Lyft because we’d like to travel this summer with our beautiful child…our life preparing for child, travel, my home and fatherhood, and oh the joys of wife and child…  

As I drop them off, I see that my flood of words has swept their party into silence.  

As her friends walk away, the woman upfront turns back through the open window: “You should know that tonight you came this close to the devil herself.”

Friday, November 13

I pick up a roughly 33 year old man at an Irish pub in Old Town; his destination address pops up on the Lyft app in Englewood, in South Side Chicago.  As he enters the car, I click on my “Jeremih Radio” Pandora station.

“Whaddup player?  What you up to this night?” I ask.

He’s just getting off from work at the small gastropub where he works as chef.  After a few minutes of small talk about his work there, he admits that, while it’s decent, he feels they’ve been undervaluing him of late.  So he’s been trying to move on.  Just the day before, in fact, he got a job offer at a competitor restaurant.  I’m surprised at how conflicted he seems by this, feeling like he’s betraying his current workplace, “Like I was cheating on my girl.”  For reasons I can’t quite understand, he seems to want to convince me he was justified in taking the new offer, as if my opinion of him really, deeply, mattered.  This new job was offering better salary and greater hope of advance—and who could blame for that?  I told him I certainly didn’t: “You gotta do you!”

Halfway through the trip we pick up his girlfriend, and he continues to recount his experiences in the food industry.  His stories go chronologically backward, so that as we’re crossing over into Englewood he’s now telling of his first chef job seven years ago.  His girlfriend sighs, “Ah I remember that busted job you got, just after jail.”

Before they leave, I ask for the address of the new restaurant, so that I can find out if everything “you been claiming about ‘dem cooking skills is true!”  I step out of the car and give him a gangsta hug. I eek out words, feeble in their sounding, with which I hope to encourage him:  “I got my money on you!  You best show them how we do. You never look back, you hear?”

“Never, ever look back,” he repeats solemnly, looking down.  What I suspect is true.  My belief in him matters.

Saturday, December 5

I pick up a roughly 30-year old couple on Randolph Street, out for a night of, as they put it, “getting smashed,” and I take them about 20 minutes away.  A few minutes into small talk, the woman suspects something: “Are you…from Chicago?”

“No, I moved here five years ago from New York City.  And wow I love it here!”

The mood in the car changes.  “And you hated it back in New York, right?”

“I’m sorry?”

“The piles of trash. The insane people.  My brother moved there and he pays three times the rent for a tiny shoebox apartment.  I went to visit and couldn’t wait to get out of that hole.  Didn’t you just absolutely hate it there! —”

Her boyfriend’s eyes fleetingly connect with mine in the rear-view mirror: “But…NYC…isn’t so bad, Ashley—”

“Yeah, if you can keep it like 800 miles away!”

After minutes of this, Ashley’s tone transforms. “But Chicago is the best place in the world, the best city ever—like ever, on the entire planet!  You can walk to the beach and it’s clean and people are so friendly all the time.…”

As I drop them off, I’m not sure if they can see me holding back tears (I feel I have to live up to NYC’s soulless reputation); the boyfriend hands me a five-dollar tip.

Ashley pauses before closing the back door: “But do you miss it?”

“I’m sorry?”

“Like do you want to go back there, or do you love it here?”  The boyfriend, already at their front door, turns around in wait.

As I figure what I’m going to say, Ashley closes the door and staggers away.

Friday, December 18

When a roughly 22-year old woman enters the car at 2am, and I ask my customary “Having a good evening?”

“Just ok.”  Her voice suggest she’s been crying.

As I’m still trying to figure out whether she wants to be left alone or engaged, she asks, “So you like driving Lyft?”

“Yeah!”  Ok she wants to talk.  “I’m an English professor, and I’m trying to earn a little extra cash for when my wife, child, and I go overseas for my sabbatical in two years.  I’ve always dreamed of writing my first book by the sea in Puerto Rico, and Lyft helps me save up for that time away.”

“So you’re a professor?  Where?”

“Trinity Christian College.”

“That’s a—Christian college.  So are you—Christian?”

Given the tone of her inquiry, along with her young age, it’s clear that for this ride I’ll be wearing my professor hat.  “Why, yes, I am!” I respond.

“I recently dedicated my life to following Christ,” she continues.  “Just a few months ago.  The only problem is —” and here she pauses, apparently deciding whether to back off or proceed — “the only problem is…my boyfriend is an atheist, and he feels I’ve betrayed him. Tonight we broke up.”

“I’m so very sorry to hear that.”

I continue driving for about four blocks.

“Well I once had a relationship, when I was your age, that suffered great stress when I too made the same decision for my life.  My partner saw me as having abandoned her on the path we were on together, even though this is the last thing I intended.   We too broke up.”

“Was that the right decision, sir?  I really need for someone to tell me: Do you think…I’ve made the right decision?”

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Erick Sierra

Erick Sierra

Erick Sierra lives in Pilsen, Chicago. Visit his website at