We’re in Chicago: LaShawn Holloway
What is your current role? How would you describe the work that you do?
I am the Inaugural Director of Chicago Partnerships at Braven and responsible for fundraising efforts in Chicago. It is a national non-profit. I work with local partners, philanthropic organizations, and our Chicago Board. The work comes down to relationships and managing them internally, working with the Chicago program team and learning about what they need, staying informed on what’s happening on the ground with our Chicagoland area fellows, and being able to connect externally with all the different groups I share. If fellows want more access to healthcare, how do we bring in our healthcare partners for exposure? It’s all about internal and external relationships and being able to share, like sharing fellows’ stories out to partners to see the impact their dollars make. I enjoy the core of the role, relationships and connecting people and resources.
What was your Chicago Scholars experience like?
I was a part of Chicago Scholars 1.0, when the organization was a scholarship organization. Then 2.0 has been described as the high growth area, where it went from serving scholarships, to becoming the best college access and success organization in the country. There was the birth of the Lift team. Then version 3.0 arrived. It was the birth of career and leadership development. My experience as an Alum came in around the 1.5 area. I entered the organization with a scholarship and they were moving away from that.
It was a unique experience, and I valued having a college counselor in CS —my counselor literally told me about the school I ended up attending. I didn’t know schools beyond the Ivy Leagues. The counselor was instrumental in sharing all the schools they were familiar with, and Simmons was a perfect fit. That’s attributed to CS. The scholarship and the rigorous college counseling was vital. I was the type of kid to apply to 23 schools. But I could only do that because CS paid for the application fees. It was helpful for a first-generation college student, and that’s a lot to pay. Once I started college, it felt transactional with CS. I didn’t have a Lift team. Then in junior year, I got CS emails again, “If you’re back in town, we’d love to invite you to a bowling social.” I went to that and went to another event that was hosted by a CS career partner.
That was my start to re-engaging. I appreciated being invited back into the fold because I had all those touchpoints junior and senior year, but there was a pause after college. After that point, when I was figuring out the next steps, CS was a network to tap. I reached out, but didn’t have any staff’s email address. So I just emailed DJT (former Chicago Scholars CEO). Didn’t think she’d respond, but she did and we had lunch, which led to connecting with Sasha Pena, who was ad hoc in supporting Alums looking for jobs. That was my first time in the current office. As a Scholar, there was a dingy office that was unwelcoming. This was the first time seeing the new office. I met with Sasha and learned that there was a temporary full-time position as an executive assistant to DJT. This led to me being the first person to lead alumni engagement work. CS was pivotal in these key transition moments and helped to refine and identify my skill sets.
The throughline of the most engaged alums, is that there were moments or experiences that cemented the connection to CS. Some of the Alums, if we invited them to a board meeting or retreat, would join board members for lunch. Ask the Alums to be speakers. Those are the moments that you will never forget CS.
How did Chicago Scholars support you to be the person you are today?
The first thing early on was the network piece. The socials and leadership development sessions. Because I went away to Boston for college, a lot of my network in Chicagoand high school ties had severed in most cases. My network was in Boston. When I was coming back to Chicago, it was those sessions and engagement points before graduation that reminded me I had the CS network and that was a helpful starting place. Rebuilding my network here as a young adult was a center point. Having that lunch with the CEO was a game changer. I was in my first job out of college and I learned a lot. The last 6 months of my time there were challenging times. I was able to unpack that with the CS CEO at the time. I was struggling to see the lessons to take away and she helped me see everything critically. Really instrumental in being prepared to start another role and take those lessons and apply them forward. CS was my second job out of college, early 20s. It helped me to learn basic skills, like appropriate ways to send an email internally and externally, interpersonal relationships, work politics. I wrote something when left the org, that I think would be helpful here. I reflected on my almost 5 years there. In essence: I really appreciated working in a space that allowed me to play and explore and really say and try different things. I worked out my skillsets, became a masterful event planner and built up my superpowers. That role allowed me to figure out what the next steps could be, which led to master’s program.
What advice would you have given yourself just after being accepted into the program?
Trust—it’s okay to trust the people who are experts in the college counseling space and the staff, who care deeply about your wellbeing and success and growth. You don’t have to do this alone. You have a community, resources you can access, so just ask for it. Don’t feel embarrassed, ashamed, or like you should know. Humble thyself, you don’t know what you don’t know. Ask all the questions. And boldly ask all the questions. Don’t feel like you can’t do that, because it’ll only help.
What advice do you have for current Scholars?
I’ve told younger scholars all the time, you are so blessed. There are so many more resources, the curriculum is so good, and I didn’t have access to 75% of the things you have now. Truly go to the workshops. Don’t miss a workshop. Try to attend all of them, take notes, ask questions. While all content might not be applicable, take note. Lean on mentors and staff. Show up to the extra things that aren’t required, that’s the sweet spot. Those are the moments you’ll remember the most. The session you go to, the industry roundtables where you met someone who works a job you’ve never heard about. It helps to open the mind to all of the possibilities that may unlock a passion you didn’t know existed. Good to have a goal. And try to be as open as possible and attend these events that are designed for you.
What does being from Chicago mean to you now?
When you’re from Chicago, and that was all I knew, I almost was immune to the complexities and beauty of the city. It wasn’t till I went away, lived in Boston, and had to describe to people in Boston about Chicago. I remembered feeling like I had to defend my city. Then I realized that I thought I was naïve and immune to the fuller picture of who Chicago is in the melting pot of culture, food, and architecture. I was proud to say I was from Chicago in Boston. Some would be impressed, and others would ask if it was dangerous.
To my core, I’m still proud, born and raised here. I’ve been able to have an impact here, specifically in education and career spaces. I think that there’s a lot of opportunities that the city can really hone in on, like the business community. And I think economic wise, there are still opportunities for people to just partner. Find those bright spots and areas where we can double down. The next generation of leaders are being set up for success and won’t have to take on the deficits of decisions policymakers have made. One word: hope. I still feel hopeful in all that can be in this city. I don’t want people to lose hope in Chicago. It hurts to see people leave because of the cost of living or rising violence. I don’t want to give up on my city.
What do you wish people knew about Chicago Scholars, as well as the city of Chicago?
That’s the beautiful part. You can’t talk about the city without talking about this organization. And you can’t talk about the organization without talking about the city. I think it’s still beautiful that to this day, CS is the largest college access and success org. The seven year model is beautiful. So much influence of younger people that are 17/18, in a prime time to really mold, support, and launch them much faster before they even reach college, and the supports in college. And support after. Those pivotal points are huge. CS isn’t just about the ”have the young people gone to college?” That’s all good and dandy, but it’s the transitions from when they’re in school, figuring out the college transition. The fact that CS can be there as a constant, a family. Especially considering the makeup or our Scholars. CS helps when Scholars feel like they are at a loss. As they transition after graduation, it’s a big unknown. And having that constant unit, family, is instrumental in helping them and us as professionals. More than just getting them into college with scholarships, but there is also that constant unit.
Chicago: Almost parallel. Oftentimes I say around Chicago being a big city, but it’s small. Once you are plugged in, you’re plugged into everything. In the CS network, you’re in the Chicago network and vice versa. You’re in a deep network. Who doesn’t want consistency in their life? That’s what I wish people knew. There are pockets of units and a network that is supportive and illuminating in the seasons of self, in discovery.