Erin Frey: Assistant Professor, Yale School of Management

We were delighted to welcome Dr. Erin Frey, an assistant professor at the Yale School of Management who studies how people rebuild their careers after a serious mistake, as our March 2025 White Collar Support Group Tuesday Night Speaker Series presenter. She came to tell us what the academic research actually says about second chances, and where that research stops cold. You can watch the full recording above.

If you are bracing for how people will treat you once they know, give this hour to Erin. Her first study followed military trainees who were made to wear a pin on the uniform announcing to everyone who saw it that they had violated a core value. They called it the scarlet letter. What that pin did to the people wearing it is not what any of them expected, and our members recognized the shape of it within minutes.

Why second chances come with a punishment attached

The trainees kept their careers, and they paid for it. Demoted, stripped of rank, pulled off their normal jobs, and marked. So they did what most of us would do. They hid the pin and they changed the subject.

You cannot hide a pin. Supervising officers and peers walked up and asked the blunt question, what did you do, and the trainees had to answer. Erin’s finding is that the answering is the whole mechanism. Three things came out of being forced to talk, and not one of the three was what the trainees had braced for. The strangest of them has to do with who goes on to offend again, and why telling the story over and over made that less likely.

Which leads to the uncomfortable half of her conclusion. Organizations almost always bolt a punishment onto a second chance, and Erin thinks that reflects something durable, and not very flattering, about human psychology. But without that pin, none of those trainees would have said a word to anybody, and none of the growth would have followed. Sit with that for a minute.

Our search results are the scarlet letter we cannot remove

Something happened in the chat while Erin was talking. Members started messaging me and each other, all landing on the same thought at the same moment. The pin is a search result.

We wear ours in the search engines, permanently, legible to every employer and every new acquaintance before we open our mouths. Our group works the policy side of that through our right to banking initiative and our pardon and expungement work with people like Professor Mark Osler, and cultural change of that kind can take twenty years to arrive. Page one of a search today is a different problem, and it is the one Drew Chapin walked us through in his own session.

So I put the question to Erin on the recording. If the shaming thing is what forces the conversation that lets a person move forward, is the pin we cannot remove doing work we have never given it credit for? Her answer is worth the trip to the end of the hour.

What the research says about jobs and relationships after prison

The existing research on employment after incarceration is thinner than you would guess. The piece of it that surprises almost every room is company size. The employers most willing to hire someone with a record are either very small, under twenty people, or very large, and there is close to nothing in the middle. Most of us walk in assuming the big names are the closed door. Ron Bauer has told us about the other route, building the thing yourself, which runs all through this research too.

The rest of it is better news than our members expect. White collar cases have measurably better odds of landing stable work than other categories of offense, and most of us land back in middle-class careers eventually, even when the first job out looks nothing like one. Her most robust finding is not about employers at all, though. People forgive far more readily than any of us anticipates, families included, and what she says can happen to a marriage after prison is the part of this hour most worth passing to your spouse.

Then came the caveat that reframes everything before it.

it really is not specific to, um, the experiences of people trying to rebuild their lives after, um, white collar, uh, crime.

All of it describes formerly incarcerated people in general. Narrow to white collar cases and the shelf is bare.

So, this is actually become the focus of my work, because there’s so little that we know about it.

She is fixing that with confidential one-on-one interviews, reviewed by the Yale Ethics Board, with people who have been incarcerated for a white collar offense and people who are about to be. I sat for mine and found it cathartic. Details are on the Professional and Personal Restoration Study page, and anyone who has heard Tom Hardin or Brian Cuban tell their story here knows why the telling matters.

About Dr. Erin Frey

Dr. Erin Frey is an assistant professor at the Yale School of Management, where she studies how workers recover after major mistakes and how and when organizations and society give them second chances. She has asked that question inside the U.S. military, entrepreneurial training organizations and the entertainment industry, and her current work is on people rebuilding after incarceration for white collar crime. She received her BA from Harvard College and her PhD from Harvard Business School, and previously held faculty positions at the University of Virginia and the University of Southern California. When we first discussed the study, she warned us to be careful what we wished for, because she publishes what she finds.