Senior lawyer, filmmaker explores questions about retirement in latest documentary

Stephen Herman fell in love with photography as a teenager growing up in British Columbia, Canada, and extended his passion to filmmaking shortly after he turned 50 in 2010.
The longtime civil litigator filmed, edited and produced several videos with his wife Evelyn Neaman, who worked in program management at the Justice Education Society, before deciding to focus his lens on retirement. Retirement on Trial, a documentary Herman and Neaman released in 2023, explores the challenges lawyers face when preparing (or not) for life beyond practicing full time.
Herman, who describes himself as a “retiring lawyer” with Watson Goepel in Vancouver, talked with the ABA Journal about what he learned and hopes to share with other lawyers about the psychological and emotional aspects of retirement. The interview below has been edited for clarity and length.
Starting from the beginning, one thing you mentioned in the film was becoming obsessed with retirement. Can you tell me more about that?
I’m going to say two things, and I talk about them in the film. Number one, there was a seed planted because of my mom’s disastrous retirement. I don’t specifically mention it, but she spent 20 years with depression and anxiety. This was a woman who was really quite joyful, maybe a tad anxious, but absolutely in the depths of depression and anxiety. And I didn’t have any doubt it was because she retired to a purposeless life.
The second one was I think I had a lifelong fear of death. I can even remember as a teenager when my grandmother died, thinking, “I’m afraid of dying.” And I didn’t do any therapy with that; I just kind of lived with it and shoved it under the ground. But it did come bubbling back up when I hit 50 and really had a recognition that there was more to life than the practice of law, and I needed to explore that.
I joked the other day when we screened the film, after talking about myself, I said, “Well, the film’s not really all about me.” And then I said, “Well, you know what, the film is really all about me.” I mean, that is quite true. It’s the story of how I found something outside of law in pretending I was a documentary filmmaker … And then I thought, I need to get my colleagues to talk about how we’re going to prepare for retirement, right? And not when we’re 65, but when we’re 50, and there’s some road ahead.

What are some of the reasons it’s so hard for lawyers to begin planning for retirement?
At the first screening in Vancouver, where I live and practiced my whole career, I found this hat [that says “director”], and I thought, Oh, this would be so funny, because all my colleagues will see me standing up there. I’m Steve Herman, a lawyer. I’m not a famous lawyer, but a lawyer, and I’m going to put on the hat and pretend I’m a director.
What started as a joke became profound insight, because what I kind of realized is that we go through our career as lawyers wearing a hat that says “lawyer.” And the truth is, when we showed the film to some judges on Friday last week, I said, “I think one of the challenges of leaving your role as the judge is you’re wearing a hat that says ‘judge,’ and it is uncomfortable to say, all of a sudden, I’m going to take that hat off.” I think that’s a huge part of why it’s hard for lawyers to leave.
A lot of lawyers and judges you spoke to for the film addressed that and also talked about how they overcame some other challenges. Which lessons stand out to you?
I was sure that my gift to the legal profession was that I was going to say, “Here is the formula for successfully preparing for retirement. At 50 years of age, you need to start mapping out the things you’re going to do. You have to plan.” And then I went and interviewed our former provincial premier Ujjal Dosanjh. It’s not in the film, but I said to him at one point, “Well, Ujjal, tell me what your plan was if you didn’t win the federal election, and, you know, become the right-hand man to the prime minister?” And he said, “Oh, I didn’t have a plan. If that happened, I would take some time at that point to figure it out.”
That’s been very, very insightful, and helped me with accepting that if I thought there was one path to retirement, there is absolutely not. I think for many people and certainly anxious lawyers like myself, it is comforting and important to do some preparation, but I think some lawyers will be just fine saying, “I’m going to work until this point, and then I will stop. I will live with that discomfort for a while, and that discomfort will generate some options.”
In the film, you share what lawyers are doing after they retired. I can imagine it might give other lawyers who see this some ideas on what life could look like after practice.
One of the comments we’ve had is that we interview people, all of whom have moved into something new in their second phase of life. I don’t think that’s quite true. Jan Lindsay, for instance, the former president of the Law Society [of British Columbia], had cancer. She’s a grandmother, and she bakes. [Former prosecutor] Anita Ghatak did some post-legal career education but is traveling and not working.
One of the things I say in the film, and it’s sincere, is that I regret the fact that our profession has this ethic of “you are all in, or you are all out.” I, for instance, consider myself relatively unique. I’m associated with a firm, but I will wander in at my usual time at 10:30 or something, and I’m going to leave the office before the traffic gets bad at 4. I do think for many lawyers, that would be an absolute sweet spot. But the challenge is it’s hard to slide that model into the compensation-focused model of virtually every major law firm.
We recently interviewed my cardiologist who said, “Oh, I’m never going to retire,” and also, candidly, “Half of my colleagues have struggled after retirement, and I think it would be better if they didn’t have to retire and drop off a cliff, but could just start to work more infrequently.”
Are you planning a second film or conducting interviews for something else?
We are planning on a second film. What’s really lovely is the first film has still got lots of legs. I mean, this film’s been around for coming up to three years and now we’re talking to [the ABA Journal]. That’s pretty good for a film. But when we screen the film, invariably, if lawyers bring their friends or spouses who are nonlawyers, but are teachers or professors or doctors or therapists, they’re walking away saying, “Oh, it’s the same for us.” And so, we came up with the idea of making a film that is somewhat more universal.
Since making the first film and working on the second, have your personal thoughts on retirement changed?
The answer is yes. I could never have contemplated that anybody at the American Bar Association would want to talk to me about anything. I think I was a capable lawyer in British Columbia, but not with anything really important to say. And so, that’s been the really dramatic change. I get not only to talk about the value and benefit of finding something outside of your legal career, but I can say, “Look at me. Maybe don’t be a filmmaker, but I made this up as I went along, and it is very fulfilling.” I’m ticking off a lot of boxes. I’m helping people. I think it’s purposeful. It is intellectually stimulating.
The last thing I do want to comment on, because you talked about resistance to retirement—when we were at the ABA Commission on Lawyer Assistance Programs conference in Colorado, a psychiatrist spoke about the distinctions between capacity and competency. I want to address that more in the next film. The reason I do is, I think, for a lawyer to say after 30 or 40 years, “I’m no longer competent,” or to have a colleague come and say, “You know what, I think you’re no longer competent,” is overwhelmingly difficult. However, I’m hopeful more and more lawyers will be comfortable saying, “I’m still competent, but I’m now in my 60s, and I don’t have the capacity to run 250 personal injury files as I did when I was 50. I don’t have to be so embarrassed about that.” That’s a message I would really love to get out.
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