Janet Nester Olszewski

I met Janet what feels like a (good and meaningful) lifetime ago - we were both Fellows for Education Pioneers in 2015. Since then, I’ve had the privilege of following her professional and personal journey. 

Her path to her current role as Director of Grants Strategy and Development, at Oakton College, is a living testament that a career doesn't have to be linear to be deeply impactful. Originally from Ohio, Janet’s college path began in the world of journalism. She was drawn to the field wanting to both learn new things daily, where no two days were the same, and to educate people about the world. This early passion for storytelling and information-sharing eventually led her to an internship with the Associated Press in Athens, Greece.

However, a fork in the road appeared with an option of a different kind of service: education. She was able to make both opportunities work, by deferring and subsequently joining Teach For America (TFA). She spent a three-year stint in Phoenix teaching third grade, and while in Chicago in the next phase of her career, maintained her roots in journalism by working part-time as a reporter. This period was a unique moment of realization; she found she was able to do both, though the news industry,  as we knew it before, was on its way to collapse.

When she started her work at Start Early (formerly Ounce of Prevention Fund), it was in direct services for families and children, and she remembers not just the intensity of the work, but also the lack of language about the personal well-being of those taking care of others. She subsequently took on roles of increasing responsibility in managing programs. At her last job, she received leadership coaching, and is candid about how vulnerable she had to be to look at the feedback and what she was learning about herself. 

Being laid off and having eight subsequent months with this knowledge was also life-changing; there were moments of feeling like an imposter. But the knowledge she received informed the roles she applied for and the professional choices she made. While she has always been detail-oriented, what that looks like for her has shifted: with a large portfolio, she makes strategic decisions about where to dive deep and where to hand off. 

Janet with her husband Rob, and daughters Dayla and Helena

We reflect on conflict avoidance so often a reflection of our familial and cultural upbringing – the behaviors we are taught at home. She continues to work on this skillset but acknowledges that it can be a source of discomfort. She is a Midwesterner (and points out that Cincinnati and Chicago are VERY different), and for her the strong experiences of her childhood included being a girl in a family of 3 siblings. She reflects fondly on not just her grandparents, but neighbors - Norma and Otis, who came from a rural background, who took on that role and became family.  It was unusual to not stay where she grew up but doing so helped her meet people from different backgrounds and perspectives.

When I ask her about what keeps her going, she reflects that her whole career has been ensuring equitable access to education and she has held a variety of roles in service of that. One of the formative childhood experiences that led to this was being separated in academic groups when in school – which essentially were groups for kids considered smart versus not. It wasn’t that she wasn’t in what was considered the “best” group but both that she was surprised about being there but also the likely counterintuitive outcome of that approach. The way she sees it with kids is that everyone is in a bag of popcorn; we just pop at different times.

Janet with Dayla and Helena at the 2026 Oakton College Commencement

She sees firsthand at the community college, how students come in with disadvantages, and she constantly asks herself, what I can do in my Grants role to support them. She has also started a consulting practice, and at the time of this interview, was leaving soon for Michigan to audit teacher training. 

Personally, she looks at the period where she wasn’t working full-time for the first time since High School, and this was a unique moment of pause for her to assess what is important outside of work. She is focusing more on things for her physical well-being, from yoga to triathlon training (WOW). She is volunteering more, and regrets not having started earlier, finding it incredibly fulfilling. It helps that she now has a 7 minute commute and more manageable scope, ensuring a better balance between work and family.

Looking ahead, she sees herself continuing to build structured policies and systems that support students and administrators alike. Her upbringing, where gendered expectations were prevalent, drives her to create environments where everyone has a seat at the table.