The misplaced energy of professional ambition

When the going gets tough, the bets get safer, we guess. 

Chicago’s aging startup dads are still trading the same few hundred million back and forth across their “innovations.” Mediaocean, an ad tech company founded by Groupon’s Brad Keywell, is acquiring 4C Insights, a “data science” company founded by Northwestern professor Alok Choudhary, for $200 million. 4C Insights ostensibly helps advertisers coordinate their spending across social media and television, technology Mediaocean can integrate into its own platform as it advises big companies on where to buy ads. 

Psst, y’all, over here: What’s a “television ad”?

Electric vehicle startup Rivian raised another $2.5 billion. Which, we get it, self-driving Amazon delivery trucks is a real post-capitalist dream/nightmare. But how many billions does it take to get an idea into production and start turning a profit? It’s potentially good news for the 350 employees in the downstate Normal factory, but it would be even better news if Rivian was making cars people couldn’t stop buying. 

Speaking of Amazon, it continues to gobble apace, with plans for a huge distribution center staffed by hundreds of people near Midway airport. 

Then there’s all the action around healthcare. We don’t know if you’ve heard, but there’s a pandemic, and a bunch of people seem to think the answer is in, you know, more profit from healthcare instead of more access to it. Oak Street Health, a primary care provider that focuses on older folks and Medicare patients, is planning to go public and get huge, estimating that its market size could be as large as $325 billion. 

Also capitalizing: GoHealth, which made a $914 million IPO last week. The online insurance broker immediately saw its shares drop in value, and Crain’s had a completely on-brand response ruing the real problem here: Dual-class stocks that allow GoHealth management to retain control instead of ceding it to investors. A health insurance middleman hitting the market at near a billion dollars in the middle of a medical catastrophe and the concern is shareholders may not make enough money and get enough say in how the company prioritizes profits? Yeah, that’s not the problem we were worried about. 

Meanwhile Livongo, which tracks personal data and “nudges” people with chronic conditions to avoid risky behavior, is getting a lot of attention and money because the market has decided it’s “a tech company in healthcare clothing.” Hmm, yeah yeah yeah, where have we heard that before

If you ever find yourself thinking, “Wow, ghouls will really profit off of anything,” we regret that we must make you aware of a new and damning fact: Highland Park-based Grassroots just made the world’s largest cannabis company with an $830 million acquisition by Massachusetts-based Curaleaf. Ah, yes, Highland Park, Illinois, and Wakefield, Massachusetts, two municipalities that should most definitely be cashing in on the legality of marijuana. Surely those profits will go directly into decriminalization and social justice reforms. 

We do have a couple of pieces of truly delightful news. One, eco-friendly cleaning maker Method is expanding in Pullman, with plans to add 200 jobs. We love to see a job today that doesn’t actively harm the future. 

Speaking of harming the future, the New York Times finally did a good and published a little piece on which corporations go against all their lovely statements by donating to anti-immigrant, anti-women, anti-LGBTQ, anti-black candidates and organizations. Oh yes that’s right money! We can see where yours goes!

Jobs, Glorious Jobs
Marketing and Administrative Assistant at ACM Strategies
The homepage tagline says “We turn workers into activists,” which, are we secretly working for this company? The woman-owned firm needs a junior person to help support unions and progressive candidates, a decent way to make a living in our opinion. 

Policy Fellow at Chicago Community Bond Fund 
Put those record donations to work and end cash bond! Yes the max listed salary is $50,000, but someone great should take this job (especially if you don’t have to support yourself and can do it for the pay offered).

Marketing Director and Content and Communications Manager at Levenfeld Pearlstein
LP tries real hard to tell you it’s a different kind of law firm — one that favors collaboration, transparency and community. Worth checking into because surely these are relatively stable jobs with decent pay.

Senior Specialist, Digital Properties at Exelon
Maintain the energy company’s website and intranet. Post content, prepare reports. About as electrifying as you’d imagine, but bet they’ll pay for continuing ed so you can stay ahead. 

Inspiration of the week

“In the present moment, in a time when the pandemic has caused so much uncertainty about the future of so many industries, professional ambition begins to feel like misplaced energy, as helpful to achieving success as chronic anxiety.”

—Maris Kreizman on the joys of working in publishing, and the reality of working under capitalism

Ambition is a tricky thing. Get swept up in it, and you forget to question whether the levels you’re moving through have any value at all. As Maris writes, “What if the things for which you’ve been striving no longer feel important because they’re the spoils of a rotten system that needs a complete overhaul?”

We have said it before and will continue to: Succeeding at capitalism isn’t an accomplishment. Professional movement can’t be subbed in for personal success. Trust us we have tried. If your ambitions are dependent on the respect of others, well, you can spend a lifetime striving and still get nowhere. 

Instead, consider what you really want to accomplish: equality, independence, agency? Identify the systems and people standing in the way, and put your ambition not toward changing them, but upending them. 

Forward this email to anyone who has ambition to spare. They can sign up here, and we will give them some ideas on where to put it.

Got a tip on an excellent job? Reply to this email, send us a new one at, or reach out on Twitter.

Good jobs

And all the things we mean when we say that.

So, OK, we’re still in a pandemic and a recession right? Because you know how sometimes you’ll look at your bank account and be like, “You know what, I don’t have any money anyway, why not buy these shoes?!” Well it seems like every business is doing exactly that. 

Uber is trying to buy Postmates for $2.65 billion in spare change, creating a fearsome competitor for Grubhub, which is set to be acquired for $7.3 billion in stock by Just Eat

Allstate is also doing some emotional shopping, buying insurer National General for $4 billion. And while Walgreens isn’t outright acquiring VillageMD, it is investing $1 billion in the healthcare startup in the hopes of opening up to 700 clinics in its drugstores in the next five years.

Yeah, those stimulus checks really were like winning a plush banana stuffed with newsprint after playing $50 in carnival games. 

Aon, meanwhile, must’ve had good luck in the couch cushions, because it’s reversing its 20% pay cut, paying back the money it withheld and adding 5% on top of it.

Is there, like a secret vaccine we don’t know about? Or were all the gifts to businesses just that good? (Kidding, we know it’s the more depressing one.)

At least our not-at-all-benevolent overlords are throwing some crumbs our way. Facebook is planning a DeKalb data center that should be good for “hundreds” of construction jobs and a steady 100 operations jobs once it’s done. Why? Lol new tax incentives that make the project a dream deal for Facebook, a company that brought in $70.7 billion in revenue last year. 

We can’t honestly believe this is where we’re at, but United is now the only company behaving logically, announcing plans to potentially lay off 36,000 workers, most of them unionized. We hate it, but we at least kind of understand it? Although laying off up to 45% of actual workers and only 30% of management seems like not the perfect ratio, all things considered. 

Despite, well, everything, there are some real signs that workers might come out of this with a few more rights. Chicago enacted a fair workweek law Wednesday that forces employers to provide work schedules in advance, and pay a premium for any last-minute changes. That, plus a bump in the minimum wage to $10 an hour statewide and $14 an hour in Chicago puts us closer to something like livable conditions for the most vulnerable workers. AND, new sexual harassment and discrimination protections give service workers in the hotel and casino industries more avenues to report incidents, while all employers will be required to report harassment and discrimination complaints to the Illinois Department of Human Rights. 

That’s especially good, because getting this shit out in the air finally seems to be working. Case in point: Cards Against Humanity is looking to unionize — and management is promising to honor it — after it got caught out being a creepy, garbage place to work.

Jobs, Glorious Jobs
Associate Manager, Social Strategy at Beam Suntory
This is a brand social role, which means you’ll be hands-on with strategy and execution for a portfolio that includes Jim Beam, Maker’s Mark and several sought-after Japanese whiskies. Downside is that you'll also be handling community management and consumer inquiries.  

PR Manager at Goose Island/Virtue Cider, Social Media Coordinator at Virtue Cider
Meant to note in the last job that alcohol sales are not in a great place right now, so we’ll leave that here for your consideration/interview question.

Press, Public Affairs & Projects Officer for the British Consulate-General
Lead communications and public diplomacy in Chicago and the Midwest. We definitely don’t have public diplomacy among our LinkedIn Skills, but if you do this is a rare find.

Writer (Personal Finance), Writer/Expert (Travel Rewards), Assistant Assigning Editor at NerdWallet
Journalist friends, these 100% remote opportunities are for you.

Tool of the Week
The Aspen Institute Digital Anti-Racism Pledge Tracker. Step one: Make sure a company has said something meaningful. Step two: Hold them to it. Because you know there are a lot of companies out there hoping maybe we’ll all just forget. h/t to Hustler Kate for sending this in.

Inspiration of the week

We tend to romanticize this economic history, saying that good factory jobs have been replaced by bad service jobs. But in truth, there is nothing better about banging hubcaps onto cars on a moving assembly line than about serving hamburgers in a fast food restaurant or changing bed linens in a hotel. The difference between these types of jobs is mainly that industrial jobs were frequently unionized and service jobs are not.

—Richard Rothstein in The Color of Law, a book that just takes your high school history lesson on de facto segregation and lights it on fire. There’s an eight-minute video of the basics making the internet rounds, but we highly recommend reading the whole book. Our dude is a Grade-A no-nonsense grump, and the book flatly and mercilessly lays out all the lies we like to tell ourselves about how the American economy works. This particular nugget isn’t even germane to its focus on legal segregation — it’s tossed off in a footnote. A footnote!  

We’re not going to try and tell you an inarguable case for reparations is a “fun read,” but we did bark-laugh several times while reading The Color of Law, and got caught shouting out advice to historical actors like we were watching a slasher film. So let’s say it’s an interactive book. 

Forward this email to anyone who knows all jobs should be good jobs. We can’t unionize everyone, but if people sign up here, we will constantly remind them that unions are one way to take the power back.

Got a tip on an excellent job? Reply to this email, send us a new one at, or reach out on Twitter.

The Grateful Generation says sorry

Here we are again. A bunch of brands Columbusing into Juneteenth and making it a holiday did not solve racism. We are more tired than we’ve ever been, and the inspiration of the week might finally explain why. But we are still taking stock and taking action every damn day, even if it means tapping into our very strongest Regina George energy just to mean girl people into better behavior.

The tactics don’t have to be noble when the battle isn’t. 

The Illinois unemployment rate is down, but the job cuts aren’t over yet. Northwestern University is looking to knock off another 150 to 200 people via buyouts, and WBEZ cut 12 jobs in the face of a deficit four times as big as the one caused by the 2008 financial crisis. Cool. Who needs information?

Also learnding: Cards Against Humanity, which has been outed as another racist, sexist trash heap of a company. Are you telling us that a bunch of suburban white kids who made a fortune turning Apples to Apples into something more offensive didn’t know how to build a supportive workplace? 

That honestly might be what passes for good news this week, given that the major hiring announcement comes from Amazon, which is looking to hire another 2,000 people for south suburban warehouses. 

OK, OK there’s some more good news, in that the Rockefeller Foundation is planning to invest $10 million across 10 cities, including Chicago, to help minority-owned small businesses get credit and keep their communities from getting gentrified by big box retailers. Worthy goals! But if you are literally a Rockefeller, don’t you think you could afford to flex more than $1 million a city? Because that’s not going to do much to fill a gap this size

Jobs, Glorious Jobs
Digital Manager at Revolution Beauty
The U.K.-based cosmetics company formerly known as Makeup Revolution is looking to drive online growth in the U.S. It’s tough times for makeup, sure, but that $7 Shape Tape dupe is about as pandemic-proof as it comes.

Director of Content at UPshow
The company turns TV screens at venues — restaurants, gyms, stores — into marketing displays. So many questions, right?

Staff Writer, Brand Studio at Built In
Write branded content and social media copy for the tech jobs hub.

Director of Marketing & Communications at National Runaway Safeline
Act as marcom director, creative director, senior writer, graphic designer and head of social for the 45-year-old organization keeping runaway, homeless and at-risk young people safe. It's a big but important job, and rare in its mention of a TikTok strategy.  

Inspiration of the week

The 9-5 and Working Girl of our era was The Devil Wears Prada, which taught us that the best way to deal with a bad boss and a toxic workplace is to quit. But, if quitting wasn't an option — either because we cared too much about our careers or lacked the funds to just stop working — we were supposed to find ways to exist within the broken system, by heeding the unspoken rules, watching our own backs, and privately fixing things when they went wrong. Along the way, many of us did more than just survive a bad situation. We learned how to thrive within these environments, becoming devils ourselves. We, the Grateful Generation, owe you younger people in the room an apology.

—Journalist Connie Wang, writing on how older millennials actively propped up the systems holding us down by combining “the worst parts of modern careerism with recession-bred shell shock.” 

Ooo, ahh, too sharp, it burns! God, how much time and effort did we spend scrambling to make the rules work for us, instead of looking to rewrite them? We joke about our feminist socialist business newsletter, but you don’t have to go too far back in the archives to find the same kind of bullshit bootstrap rhetoric. It’s so, much, nicer to believe that underneath it all there’s some fucked up kind of meritocracy, if you just learn the tricks. It’s why we started this letter. We thought that by telling more people what doors might be opening and closing, we could help them get to the front of the line. We didn’t really think about who those people would be, or who they’d be putting behind them. 

It is true, you can beat the system. But you can’t ever believe for a second that it’s on merit. Succeeding under capitalism isn’t a skill, it’s a birthright. 

In my last job, I made less than the men I nominally managed and needed an intermediary to present my ideas to the CEO, lest we risk me being alone in a room with him. It didn’t occur to me to quit. When a mentor asked me to join the union, I said no, that I wanted to keep my managing editor title. I was 24, and I was grateful. 

I can’t go back. I can’t go back to Tuesday, when I listened to a man talk down the value of my company to a client. I will spend the rest of my life trying to remember to ask who, exactly, is on the team before I agree to be a team player. 

I just hope that’s not true for you. I hope this recession doesn’t make you grateful. I hope the fact that Breonna Taylor’s killers still walk free doesn’t make you give up. Because until the team includes everyone, it’s not worth playing for.

Forward this email to anyone who’s grateful. We can’t help them forget, but if they sign up here, we’ll remind them every day they don’t have to be.

Got a tip on an excellent job? Reply to this email, send us a new one at, or reach out on Twitter.

“I can’t believe I’m gonna say this … ”

… but we’ve had enough words. 

We write a letter every two weeks fueled almost entirely by a sense of righteousness, and we do it for fun. So we know how good it feels to write yourself above The Problem. It can make you feel like you’ve done the work, like all that waits now is gratitude.

But if you are not Black and you’re spending energy on something that makes you feel comforted right now, it’s worth asking why that is. Just about every organization we’ve ever come in contact with — including plenty of racist ones — have issued a carefully worded statement in the past two weeks, as if every “BIPOC” and “accountable” is some sort of defensive brick in an unimpeachable wall of allyship.

We’re glad to see everyone talking and reading. We just want to make sure we don’t see anyone soothed. We’re all big, we know where to donate and how to show up. Create the systems you need to keep going, but point them toward doing the work. Because if we focus on getting the performance just right, we’re never getting out the door.  

It’s also go time for layoffs. And no, we didn’t spend a lot of time massaging that transition so it landed softer.  

Other businesses are just fully giving up the ghost, including Medicaid managed care plan NextLevel Health. Bad news not just for its employees, but its 56,000 patients, all of who will have to transfer to a new plan. One key reason for the closing: the lack of capital available to minority-owned businesses. NextLevel saw an acquisition fall through a couple of months ago, and couldn’t find the funding needed to continue. 

Not a problem for GrubHub! Despite increasing regulation and uncertainty about the future of its business, Amsterdam-based Just Eat is acquiring GrubHub for $7.3 billion in stock. That’s nice for them. 

The new company will be the largest food delivery provider outside of China, and will keep its North American headquarters in Chicago. This is theoretically good news — if the rumored Uber acquisition of GrubHub went through, there would pretty much not be a GrubHub anymore. Still, hard to be excited about something that avoids any antitrust regulations by virtue of being globally huge. 

Despite all the grim news, there are some positive signs. Unemployment is theoretically falling, stocks seem on the verge of rebounding and some companies are making plans for growth. Ford, for one, is expanding its Southeast Side factory despite constantly starting and stopping production due to COVID-19. 

It’s almost like businesses are using the pandemic as an excuse to cut costs and collect bailouts under the guise of a tanking economy, just so they can plump up future shareholder profits. Couldn’t be, could it?

Jobs, Glorious Jobs
Director, National Initiatives and Content Strategy at Feeding America
Content pros, step up: Not only is this a director-level position, but it’s also at a nonprofit whose work has never been more important as food insecurity rises because of COVID-19. Plus we’ve heard they pay pretty competitively.

Digital Product Manager and Influencer Marketing Coordinator at Equilibria
Jumping into the highly regulated CBD industry via a women-led company that makes bath bombs sounds super dope. And Equilibria fancies itself a “high-growth, omni-channel premium CBD platform for women,” so get that money.  

Manager of Communications & External Relations at ConAgra
The packaged food giant recently recalled Healthy Choice Power Bowls that may contain small rocks, but pfft, that’s nothing that a seasoned journalist can’t handle.

Job, Inglorious Job
Recruitment Marketing Manager at Uline
Convince people to work at Uline, a box manufacturer in suburban Wisconsin run by a couple of Trump nuts who regularly push politics on their employees. Oh yeah no, good luck with that. We’re sure you’ll get all the top talent lining up. With pitchforks. 

Inspiration of the week

“I can’t believe I’m gonna say this, but I see hope. I see progress right now, at this moment.

I don’t want to overstate this, but there are significant swaths of people and communities that are not black, that to some extent have some perception of what that pain and that suffering is. I think that’s different.”

Ta-Nehisi Coates expressing a new sense of cautious optimism. Let’s all do the work this weekend to make sure he doesn’t have to take it back.

S/O to hustler Scott Smith for this inspiration, which came from his very excellent “Notes From Your Dad” letter.

Forward this email to anyone who’s perceptive. They can sign up here for bi-weekly reminders to turn those feelings into actions.

Got a tip on an excellent job? Reply to this email, send us a new one at, or reach out on Twitter.

Panic. Just not about jobs.

Well, things went back to normal for a day at the Ford plant. Then two people were diagnosed with COVID-19, things had to shut down, and it’s pretty much been off and on since then. That’s about as good a representation of the past two weeks as we’re likely to get: No one knows anything and all we can do is try, fail, hope and try again.

So anyway, happy Illinois reopening day!

Aon is celebrating in what might be the most horrifying way possible: nominating a panel of peers to judge colleagues’ requests for more money. Oh no thank you we’d rather die. So Aon decides to cut everyone’s salary by 20%, then asks people to come back and beg their anonymous peers for the money they were promised? Get the actual fuck out of here. Can you imagine? 

Also — yeah, we’re not done with this — can you imagine what this will do to the no doubt already existing salary gap? You’re going to tell me 20 random people won’t view men’s salaries as more necessary? Or that people from minority groups will be as willing to put themselves in front of an anonymous panel to demand more money? 

Boeing kept up that morale-building theme — telling 6,700 employees earlier in the week that their jobs would be eliminated today. Love to keep ’em guessing! Lenovo’s also got the Motorola people on their toes, saying it’s considering vague cost-cutting plans. Yeah, unless a recession makes people real nostalgic for Razr phones, we imagine there will be another round of job cuts at Motorola. 

Others are planning to double down. Real estate firm @properties is picking up stakes in other brokers and looking to franchise its brand starting with an expansion into the Southeast. It’s also planning a partnership with Guaranteed Rate to offer mortgage lending, so, potentially good news for both Chicago companies. 

University of Chicago is also getting the good news, with a $10 million gift to study cancer-fighting cellular therapy. That should keep a couple of scientists happily employed. 

Which is good, because the merger of four South Side hospitals has been called off after the state refused to give them hundreds of millions of dollars without a public plan in place.  

Jobs, Glorious Jobs
Here are some newly posted opportunities for you or smart people you know:

Digital Marketing Specialist, SEM at Reverb
Not sure what the musical instrument market is like right now, but there’s a good chance people are selling. You could be set up to make significant strides in customer acquisition when buying picks up.

Executive Director at Recovery on Water
Lead operations and fundraising at this important nonprofit that provides fitness and social support for breast cancer patients and survivors. ROW’s longtime, much-loved ED is taking off for a similar role at another rowing organization, so bring your best.

Director of Marketing at TimeDoc Health
The chronic care management platform just secured a $5.7 million Series A round of financing, so get in there and grow that business. And the job post insists “WE ARE FUN!” so that’s worth looking into.

News Writer at the University of Chicago
Like many colleges and universities, UChicago recently announced it was freezing salaries and slowing hiring. So this job must be pretty necessary and relatively stable, not to mention the university coming off a record $8.5-billion endowment last year and whatnot.

Digital Marketing Manager at Xtreme Xperience
The exotic car experience company says it’s on a mission to make Ferraris, Lambos and McLarens accessible to everyone who has ever dreamed of driving one. Not the worst purpose, tbh.

Social Media Coordinator (Part Time) at Ride Chicago
Content creation, community management, and email and paid marketing at the motorcycle school.  

Head of Content (Part Time) at Leafwell
Would imagine this part-time role at a medical marijuana card company — now with telehealth — could grow into something more. 

Tool of the week
Your body. We are particularly talking here to fellow white people who are feeling frustrated, angry, embarrassed, but not afraid. Because people of color have to carry that fear every day. 

There are plenty of things white people need to do. But while you’re watching and reading and learning, take a beat to think about what you can do directly to lift just a little bit of that fear. 

Yes, that means not using 911 as a weapon. It also means knowing your skin is a weapon. 

You know which way the sympathy goes. It’s on us to do the work of actively rejecting it — and to do that work without a hint of self congratulations. Guaranteed that for every time you catch your privilege and interrupt it, there are 100 times you’ve benefited and claimed not to notice.

For white women especially, our bodies are used to create, perpetuate and condone racism and violence. You didn’t ask for it, but you’re a part of it. And until you use your body against it, you’re a participant.

Your money is good too: Support Reclaim the Block

Inspiration of the week

I am sick of everyone in this community who tells me to stop creating a panic. How many of us have to die before you get scared off your ass and into action?

—Activist Larry Kramer, back when there were 418 people dead from AIDS. Now that number is somewhere around 32 million. Larry Kramer was a difficult person, and there are no doubt people who feel more comfortable now that he’s dead. That rage made him a singularly effective face in the battle for gay rights and gay lives.

Creating change depends on being unlikable. So in honor of Larry Kramer and in solidarity with protestors putting their bodies on the line to force recognition of black lives, think about what you can do this week to make someone uncomfortable for being wrong.  

Forward this email to anyone who’s ready to make others uncomfortable. They can sign up here for bi-weekly inspiration.

Got a tip on an excellent job? Reply to this email, send us a new one at, or reach out on Twitter.

Loading more posts…