Zahara Bassett Credit: Courtesy of Life Is Work

Zahara Bassett fell on the floor of her best friend’s house exhausted from a long day of making $9 an hour and barely getting by. She was working as a housing monitor for TransLife Care at Chicago House, a transitional housing program for transgender people who have nowhere to stay or are reentering society. All the while, her friend’s crib was her temporary housing while she worked the job, and the two were joking amidst their stress. “I was like, ‘Girl, life is work. Ugh, I can’t catch a break.’” As she told the story to the Reader, Bassett recalled, “I was just tired.” 

Bassett, a Black trans woman, grew up on the west side of Chicago, struggling with housing and job security. She came out as trans at 13, and was kicked out of her home by 16 for having the audacity to do so. 

Unbeknownst to Bassett, that night at her friend’s house she had coined the moniker for her future nonprofit where, 16 years later, she’d celebrate three years as its executive director. Life Is Work is a Black and trans-led nonprofit  headquartered on the west side that has so far this year already supported over 600 Chicagoans with access to free housing, clothing, job interviews with multiple employers, and STD testing services. And that’s just the tip of the iceberg.

Being a high schooler at Crane Tech Prep was no reprieve from being expelled from Bassett’s home. The school attempted to make special accommodations for her to abate the likelihood of harassment and make her feel included, to no avail. She could use the faculty bathroom, for instance, but that meant she had to take two flights of stairs down to get to that restroom even if her classes were on the third floor. She also had to get dressed for gym 15 minutes before the rest of the students. Nonetheless, she was chased home and assaulted by male classmates who lived in nearby housing projects. “[The school] did try to work around me,” Bassett said. “But it was so uncomfortable and I felt so ostracized, it made me drop out at the time.” 

Left without housing or school support as a young teenager in the 90s, Bassett hustled to find a job. She was hired for a gig at McDonald’s, but was dismissed the first day she walked in. “Right on Randolph and Dearborn, I’ll never forget that,” Bassett said. “That woman said, ‘We don’t hire people like you.’” The same thing happened a month into her next job at H&R Block. Her peers told her job the tea, as they would call it. Someone let Bassett’s employer know she was a trans person, and Bassett was fired on the spot. 

Feeling broken and unsure of what to do, she went up north one night to hang out with her friends on Belmont. “This guy pulled up and offered me $200 and I jumped in [his car]. And the rest was history. I’ll be honest with you,” she said. The 39-year-old remembers this entry into sex work and escorting like it was yesterday. “I was like, ‘OK, this is my new job.’ And I made it my job for ten years.” 

Life Is Work
5463 W. Chicago, 312-796-6020,

Food pantry and Solidarity Closet open daily for those in need. Call to inquire about other services. Life Is Work maintains an Amazon Wishlist for those who wish to donate goods to the food pantry. Additionally, the organization recently launched their sixth annual Meals for Christmas campaign.

Bassett found chosen family amongst a group of other transfeminine teens in sex work, who jokingly called their cohort “the Mattels,” after the American toy company that manufactures Barbie dolls. 

Bassett received her GED from Malcolm X College’s West Side Learning Center in 2003. By 2007, she left sex work and landed her first full-time, on-the-books job at Chicago House, where she stayed until 2013. 

One of her main takeaways from working for Chicago House was realizing that more community services were needed, and those resources didn’t always need to be placed on the north side, where Chicago House was situated. For example, when Bassett began medically transitioning as a teenager, she often would have to take two-hour rides on public transit to the north side to access hormone therapy.

“If you notice, many leading organizations [that serve trans people] in Chicago are on the north side or are in neighborhoods that are considered ‘safe.’ None of them are in the hood,” Bassett said. “So we want people to come from out of their lived areas, where they need services, somewhere else to get services? That sounds so redundant and ridiculous to me.” 

Life Is Work headquarters Credit: Courtesy of Life Is Work

From 2013 to 2015, she was working as a receptionist at Broadway Youth Center (BYC) when she noticed the community’s need for education about pre-exposure prophylaxis (PrEP), a medicine that reduces the chance of getting HIV from sex or injection drug use. PrEP was new at the time. The numbers of newly-diagnosed, HIV-positive youth was starting to rise at BYC, and the idea of an antiretroviral medication taken as a preventative measure intrigued her to educate herself. 

“Oh, my God, I love Broadway Youth Center. That was one of my favorite jobs. We started in a basement. It was real grassroots work,” Bassett said.

That experience pushed her into a role at Howard Brown Health recruiting patients for a research study, which monitored people taking PrEP and kept track of whether they continued to take their medication as prescribed. 

All the while, Bassett worked behind the scenes to raise money from friends and on Facebook each holiday season to cook and distribute meals for unhoused people on Christmas Day. She’d usually raise between $1,000 and $2,000 each year to “make it happen.”

“People used to think I raised all this money. I didn’t really raise a lot. I used to stretch it, because I knew how to stretch money. I come from a Black grandmother [who is] from Mississippi; we can make anything out of anything,” Bassett said.

Bassett was so ruthlessly fundraising for Christmas meals on Facebook that Brave Space Alliance hired her in 2019, initially on contract, to spearhead fundraising and external relations. She eventually became director of development for the then-young nonprofit. When COVID-19 hit, Bassett and her team opened up a food pantry overnight and were able to persuade Barack Obama to endorse it. Bassett’s team ultimately fundraised $1.2 million for the food pantry in its first year.

Life Is Work was formally born in 2020, when Bassett had trouble withdrawing funds raised from a Christmas GoFundMe fundraiser. The website compelled her to incorporate as a nonprofit to get the money. Bassett and her team originally planned to keep the nonprofit focused on Christmas meals, but her friend had vacant apartment units to fill. Since Bassett has always been passionate about helping people acquire housing, she took that opportunity to launch the housing-focused leg of Life Is Work, getting seven people into living quarters during the organization’s first year. 

Life Is Work staff members and community partners Credit: Courtesy of Life Is Work

Bassett wasn’t new to launching ambitious endeavors, and she knew she wouldn’t escalate her vision without funding. Using her preexisting strong ties with Howard Brown Health, Bassett submitted a proposal for her vision and Life Is Work was awarded its first grant, worth $15,000, for supportive housing. The Chicago Foundation for Women also supplied a rapid response grant for $7,900, and Bassett secured other seed money from private funders. 

The new organization then needed an office from which to run services. Bassett was driving down Chicago Avenue to visit her grandmother when she saw the future home of the enterprise.

“I saw a space for rent, but I was honestly going in just to see if I could get one storefront. By the time I walked out, I was at two for the price of one.” Amazon donated furnishings for both offices and the food pantry, including a refrigerator, cabinets, and flooring. 

The nonprofit looked different in 2020 than it does now in 2023, but during that time period, Life Is Work offered an impressive amount of community resources. The organization ran a workforce development program called Visions that trained people looking to work while giving them jobs at Life Is Work’s resale shop. Today, Life Is Work partners with Amazon and Target warehouses to get people on-site interviews. This program helps many former sex workers looking to transition into long-term nonsex work jobs. Life Is Work also partnered with Purpose Workforce Solutions, a downtown workforce development program that offers weekly paying positions for 18 to 29-year-olds. 

Bassett’s organization will soon introduce a new job readiness program that helps interested people train to be community health workers. The Life Is Work resale shop transitioned into Solidarity Closet, a free clothing resource for Life Is Work clients. Life Is Work’s two storefronts now host a food pantry, a space where clients can discreetly be tested for STIs, and administrative offices. Life Is Work programs continue to be run primarily by Black and trans staff and volunteers. 

Life Is Work’s housing program connects with government-funded partner agencies that have apartment buildings all over the city. Life Is Work also participates in the federal Housing Opportunities for Persons With AIDS (HOPWA) program through their partnership with Chicago AIDS Foundation, which finds housing for people who are either HIV positive or at high risk of contracting HIV.

Life Is Work headquarters Credit: Courtesy of Life Is Work

Chicagoans on the U.S. Department of Housing and Urban Development’s (HUD) waiting list to receive public housing may qualify for Life Is Work’s programs and automatically become part of the nonprofit’s caseload. These clients have expedited housing possibilities through Life Is Work’s partnership with HUD.

E.H. (who requested to go by his initials), 33, received services from Life Is Work earlier this year while going through a breakup from a long-term relationship. The breakup took a hard hit on him, including making his housing situation precarious. 

“I started off staying with my niece and then I went to my brother’s. After that I went from motel to motel,” E.H. says. “Then, I was wearing out my welcome at my mom’s [place] and my aunt’s, and then I just got too overwhelmed.”

E.H. learned about Life Is Work from the housing advisor at his doctor’s office. Within a few weeks of submitting his application, he was taken on a tour of an apartment and waited just under two months for the process to conclude. 

In comparison, some people have been on HUD’s public housing waiting list for over a decade. Through Life Is Work, though, his experience is expedited. Now the born-and-raised Chicagoan is excited to say he moves into his new one-bedroom unit this month, and he has it all to himself. 

“So, when I came across Life Is Work, they really picked me up off the ground; they really helped me out,” E.H. says. “It was a long wait, but it was worth the wait.”

Bassett recounts the evolution of Life Is Work with pride, but she seems most proud to run this nonprofit powerhouse specifically on the west side, where she knows there is a tremendous need for organizations like hers. She spent her career privileged to walk into rooms with her white counterparts, she tells the Reader, and never retreated from her insistence that big-name nonprofits need to focus their resources on places other than the over-resourced north side. 

“I sat in rooms with leaders throughout my work always saying well, ‘Why aren’t we doing anything on Chicago’s west side?’” Basset said. “You would think I was a Girl Scout or something, because I used to run up to the executive directors like, ‘We should do some services on Chicago’s west side!’ But nothing ever happened.” Bassett said that cis- and white-led organizations claim they exist to support transgender Chicagoans but often don’t prioritize representation in their staff, which she finds confusing.

Life Is Work headquarters Credit: Courtesy of Life Is Work

Bassett said she opened Life Is Work to prioritize Black trans women. “[Although] I opened it for the prioritization for trans people,” Bassett said, “we’re not turning away anyone that needs help. But we needed space that was affirming for trans and trans-identified people when they walked in, where they felt safe enough to get the services that they need.”

Life Is Work hosted a Trans Day of Remembrance event called “New Era Together 2.0” in November at Venue West Chicago. The organization partnered with Brave Space Alliance, Chicago Therapy Collective, Center on Halsted, and Lace to Liberation, a group that provides gently worn shoes to LGBTQ+ folks experiencing life challenges.  

Life Is Work also hosts a Trans Visibility Pageant that’ll be going into its third year in 2024. The organization is planning an even larger event next year as they will partner with the Chicago Department of Public Health for a trans health and wellness summit during Trans Week of Visibility. The organization will bring resources, ideas, and workshops from fellow groups in and around Chicago to share and exchange knowledge in an open summit.

Looking back on her life Bassett gives a humorless laugh at all the hard circumstances that precipitated her ability to support west siders in the way she’s always envisioned doing. “It just gives me pause to laugh and know that something is more powerful than the universe that I’m in; that it still protected me and afforded me the life that I’m able to live now.”

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Volume 53, number 3