Cara joined Teach For America after college and spent her first two years at Perspectives Charter Schools in Chicago, followed by a third year at Catalyst Charter Schools. It was her first real job - she was 21 and focused on surviving the classroom. Like every Chicago public school teacher, including those at charter schools, 9% of each paycheck went to the Chicago Teachers' Pension Fund. But at the time, she wasn't looking closely at her pay stubs, and her school wasn't exactly spelling it out.
When she left teaching, Cara knew she had money sitting with the city. She just didn't know how much, and she had no idea how to get it back.
The maze nobody wants to enter
For 13 years, reclaiming her pension contributions stayed on Cara's to-do list - and stayed at the bottom. It wasn't that she forgot about it. It was that every time she thought about tackling it, the process felt impenetrable: unfamiliar forms, a pension system she'd never interacted with, and no clear starting point. Each year that passed made it harder to begin.
"The worse you think it is, the less you want to look at it."
Cara also carried a misconception that many charter school teachers share: she didn't think she was part of the Chicago Teachers' Pension Fund at all. She believed charter school teachers were separate from the district pension system. In reality, all Chicago charter school networks - Perspectives, Catalyst, Noble, Acero, KIPP, and others - contribute to CTPF. Nobody had told her otherwise.
On top of the pension, Cara had old 401(k)s scattered across former employers and no IRA to consolidate them into. The pension was just one piece of a larger financial tangle she'd been avoiding - and the avoidance was fueled by something deeper than procrastination.
"There's a lot of shame connected to lack of financial literacy, especially in your 30s. I worried there would be judgment about me looking into my pension fund almost 15 years later."
The push she needed
In early 2026, a friend and fellow TFA alum who had just gone through the process himself texted Cara asking if she'd ever looked into her CTPF money. Consolidating her retirement accounts was already on her mind - but she hadn't been able to start. He recommended Recess, and Cara reached out.
What got her past the shame was her first conversation with Recess.
"'This is really common' echoed in my head after we hung up from our first call. What a relief to hear I wasn't a lazy idiot for leaving money on the table for this long!"
A packet in the mail and a trip to the bank
Recess prepared all of Cara's CTPF paperwork and mailed her a complete packet with step-by-step instructions - each form had highlighted sections showing exactly where to sign. Because Cara's name had changed since her teaching days, a marriage certificate copy was flagged upfront and built into the instructions so nothing would get rejected.
"What I received in the mail was a beautifully curated packet with instructions and highlighted sections on each form where I needed to sign or fill out information. Recess provided a pre-stamped envelope, so all I had to do was drop everything in the mail and wait."
Cara took her forms to Charles Schwab, where Recess had helped her open her first-ever IRA. They notarized and signed everything in one visit. She dropped the pre-stamped envelope in the mail - and within weeks, CTPF confirmed that $13,135 in pension contributions had been deposited into her IRA.
What changed
Getting her pension back wasn't just about $13,135. Having someone demystify the process - and make it safe to ask questions - changed how Cara thinks about the rest of her financial life.
"Because I had a support person to de-mystify the process and create psychological safety to ask 'dumb' questions, I feel totally empowered to move my other accounts into my new IRA."
The scattered 401(k)s from years of moving between jobs? She's consolidating those now. The IRA that didn't exist before Recess? It's the foundation for everything going forward.
Sound familiar?
Cara is one of thousands of former Chicago teachers - including many charter school teachers who don't even realize they were part of the pension system - with contributions sitting unclaimed in the Chicago Teachers' Pension Fund. If you taught in Chicago and left before hitting 10 years of service, there's a good chance you have money waiting too.
Find out what's yours - free.
Recess handles the forms, the notary, and the follow-up. You just sign.
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