20 Years Of The Harvard Portrait Project: Q&A With Creator Tony Deifell

Tony Deifell returned to HBS to recreate portraits of subjects 15 years later. He also asked them to reflect on their original essays.

You also asked some of the subjects to reflect on their original essays 15 years later.

Yes, an instructor wanted to ask some students that were in the early years of The Portrait Project to reflect on their essays, so I ended up coming back to campus. We focused on the Boston area students because of logistics, and I took them back to the same place on campus where I took the original and I would try to recreate it as aesthetically as possible.

How did their reflections differ from their original posts? Was there a theme in the new answers?

Well, they partially write to the original prompt, but in reflection on their first essay. I also do alumni gatherings and we would gather in small groups and talk about what we wrote. It was great because it self selects for a very reflective, cool group of people, and it prompts a very meaningful conversation.

So I’ve heard a lot of responses on how people were reflecting on their original essays, and I got a sense of the overall trend. The same thing came out when we did the class project. Initially, alumni feel a little cautious about reflecting on the material because they’re not doing exactly what they wrote. It’s almost like they should feel some shame about the fact that they didn’t follow through on exactly what they wrote. But when they hear that that’s the case for every other student, the shame turns into this recognition that, “Wow, life has a lot of twists and turns, and things we don’t expect that we have to incorporate into our lives. Our values can evolve, our opinions can change. It’s the exact kind of reflective quality that the project is about, but when you have the benefit of a 10-year gap between things you wrote, it really helps precipitate reflection.

Has the theme or subject matter of these MBAs’ essays changed in the 20 years of the project so far? I know, just through our reporting at Poets&Quants, there is a bigger emphasis on DEI, climate change, and other social issues in business students now than there was probably two decades ago.

Yes, and I want to map it out at some point. In terms of being more socially conscious, subjects like activism come up more frequently; people wanting to stand up for a certain right, or an issue, or to be a voice for a group of people who are not often heard in the media.

Speaking out about identity issues became stronger. I think people going into nonprofits and entrepreneurial realms just became more prevalent. You used to say that people go into nonprofits to do good and go into for-profits to make money. That’s not necessarily the case now.

For example, a guy named Jeff Barkas from this year’s batch, wrote about his grandparents who were very active and could do everything–until they couldn’t. He wrote how his family, all of a sudden, had to get all their paperwork and finances in order and many of his grandparents’ last good days were signing legal and financial paperwork. At a time when you should be spending time on relationships, you’re spending time on paperwork. So, he is starting a for-profit company that serves families like his, to help families prepare for aging so you can focus more on meaningful things. To me, who cares if it’s a for-profit or nonprofit, it’s something that does good in the world.

The other trends that I’ve seen is around gay, lesbian, bisexual, and transgender identity. In my year there were students I knew that they were gay–and I don’t think I knew any transgender students–but they wouldn’t put it in their essay. It was several years before anybody acknowledged that they were gay in the project. Then, that started happening more. Then, more students wanted to sort of wave a flag about it because it wasn’t talked about enough, and their work was about changing these stereotypes and more actively talking about it. More recently, it’s evolved to where it’s just actually woven into the essay. It’s who they are, but it’s not the purpose of the essay. I think that is very reflective of the societal shifts we’ve had.

I would say also that mental health has, in the last few years, gone through a similar pattern as with LGBT+ students. People have begun to acknowledge that as a part of their identity, which is nice, because I think that’s one of the last vanguards of things that people are shedding shame around and are willing to talk about publicly.

What’s next for the project?

One thing I want to do eventually is put together a book, not just repeating the stories and the pictures, but having connective tissue and follow up interviews with the students as well. I have this idea where I’ll just sit down and read all 712 essays, or however many there are at the time, and interview students and write about the lessons the project can offer.

What are you doing now?

I live in San Francisco, and I have a 10-year-old son. I’m running a company called Awesome Box, which is a web service for people to collect photos and stories by inviting other people to participate. Then, it rolls all them up into printed products. So, it’s not like just making an online photo album, but they are collected into a nicely designed box with cards that has a picture on one side and a story or a memory on the other. It’s 100% customized for the customer.

It’s in the realm of things I’ve cared about, which is rallying a community of people to tell stories and to create a meaningful object that will last.

In your original 2002 essay, you wrote about a blind student whose photography helped you see the cracks in the sidewalk you normally just walked over. She mentioned how her cane gets stuck in those cracks and made it difficult for her to navigate in the world. Looking back 20 years later, how would you reflect on what you wrote in 2002?

I love metaphors and how powerful they can be. I encourage students to search for them in their essays, too.

I focused on that metaphor because I knew that it could capture a lot more than even I knew at the time. Me not seeing those cracks in the sidewalk was because of the privilege that I have, and it was me trying to remove the blinders from my eyes and see the world more realistically and authentically.

Looking back, The Portrait Project has actually been one of the manifestations of what I wrote about in my essay. I wrote about cracks in the world that needed repair—especially ones that often go unnoticed. Personal storytelling is a powerful way for people to become aware of cracks, which often comes from privileges we have due to race, class, gender, education and more.

Over 20 years, students in the Portrait Project have told stories with candor and vulnerability that have changed how I, and hopefully many others, see.

See the entire Harvard Portrait Project collection here. 

DON’T MISS: A selection of some of Tony Deifell’s favorite essays and portraits from the Class of 2022.  

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