Episode 65: Jim Henderson (Attorney/Singer)

Meet Jim Henderson! He's an attorney and singer here in Watertown. In this wide-ranging conversation we talk about his early years in law (including winning a state supreme court case as a junior associate), the importance of different parts of his life beyond his law work such as his musical practice, how he homeschooled his kids and why the arts played a big part in that, and running for Massachusetts Secretary for State as an independent (and getting almost 3% of the vote). 

We do a dive into a part of his current work of getting questions on the state ballot, how he got into that field, the behind-the-scenes process of drafting the language, the political strategies involved, the questions he's worked on in the past and the four that he's currently working on this cycle. Then we end with his musical project Crooked Mowth and the story of reconnecting with his birth father in his 40s. 

Released October 17th, 2025

(Click here to listen on streaming apps) (Full transcript below)

Learn more about Jim, the lawyer at law.jdhenderson.com

Learn more about Jim, the singer at crookedmowth.com

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Transcript

Matt: 0:07

Hi there. Welcome to the Little Local Conversations Podcast. I'm your host, Matt Hanna. Every episode I sit down for a conversation with someone in Watertown to discover the people, places, stories, and ideas of Watertown. This time I sat down with Jim Henderson, who is an attorney and singer here in the city. We dive into lots of different topics. Just a quick note before we jump into the conversation. Wanted to let you know about the little local holiday giveaway I'm doing for the podcast. Anyone who signs up as a Little Local Friend, monthly supporter of the podcast, will have a chance to win one of the over $1,000 worth of prizes that I'm giving away from local businesses and organizations that have been on the podcast. Head on over to Little Local Conversations.com slash friend for more information. Alright, now we'll get into the conversation with Jim.

Jim: 0:52

I'm Jim Henderson. My day job is that I am an attorney. I have a solo practice in the basement of my house in East Watertown. I primarily work on business matters for small and medium-sized businesses, a lot of transactional work. I also do estate planning for individuals and families. And as hopefully we talk about later on, I also do work on ballot questions. So that's what I do professionally. Beyond my professional work, I am also a singer. I have performed in the midwinter nee Christmas Revels in Cambridge seven times. And I am currently a member of a four-voice a cappella group called Crooked Mowth. And have been living here in Watertown for three years now, and am very happy to be here. It was the proverbial downsize of our lives for my wife and me, and moving into a place that has a more vibrant community was something we were looking for and I think we have found here in Watertown.

Matt: 1:54

Great. All right. Well, we'll dig into all those different parts of your story. Let's start. I always like to go back in time first, kind of like, you know, where did you grow up? How did you get interested into those various interests you just mentioned? You know, what's your origin story?

Jim: 2:10

Sure. I will get to the fun tangent aspect of this story in a little bit. But I was born in Boston, grew up in Wayland, so Bostonian, born and raised. My father was a law professor at Boston University when I was a young kid. So grew up in a household where law was sometimes a topic of the dinner table. Because of the nature of my dad's work, there were a couple of years in which he served as a visiting professor. So there were a couple of years where I didn't live in Wayland. Lived a year in Boulder, Colorado when I was in fourth grade. And then three years later, in my seventh grade year, we lived in Charlottesville, Virginia. So again, very much of a Bostonian, but had a couple of these opportunities, at least as a kid, to see other parts of the country. So graduated from Wayland High in 1983, got my undergraduate degree at Princeton University, went straight to law school at the University of Michigan Ann Arbor, did that for three years, came back to New England, joined a law firm right out of law school in Stamford, Connecticut, lived there for four years. During that time, I met my wife Morgan, got married down in Connecticut, and then we moved back to Boston, now 31 years ago, and actually lived in Wellesley, so didn't live in Boston proper. Had two kids who are adults and married and doing great things in their lives. So we lived in Wellesley for 15 years, lived out in apple country in Stowe for 13 years, and came to Watertown three years ago. That's the chronology.

Matt: 3:45

Yeah. So then I know you said your father was into the law field, but how did you get interested in? Was it just that, or was there some moment where you're like, actually, law is interesting to me too?

Jim: 3:57

It's a good question. So part of this will be a little bit of an indictment of my youthful self. So at Princeton, I got my undergraduate degree in economics. And I started off thinking I'd be either a math or a physics major and came to a pretty quick conclusion of two things. One, even though how well I'd done in high school in math and physics, damn, there were some really smart people at Princeton doing that work. But also I found that the theoretical side of that stuff, while on one level still fascinating to me, was not enough to sort of feed my interest. So I channeled my undergraduate work into economics so I felt it could be more practical. How does this stuff really work in the real world? And so to swing back to how I went to law school, again, having a father who was a law professor certainly had an influence on my sort of on what I would do. I mean, my dad joked when he was an undergraduate, he thought he might go to medical school, and then he decided he couldn't stand the sight of blood, so he had to go out to law school. My situation wasn't quite as stark as that.

Matt: 4:58

There was nothing gruesome about economics.

Jim: 5:00

Nothing quite so gruesome about economics. But, all right, I want to do something that's sort of practical out of college, but I didn't have any other really good ideas at the age of 21. And so the law was certainly familiar, and the idea of going to law school seemed like a perfectly fine thing to do in the era of LA law back in the late 80s. So I went off to law school. But the work I did there and sort of where I focused my interests in law school were not the areas of interest that my dad was where his expertise was. So I did carve out my own little path there. The one thing I would say, this is where the indictment is on myself, is that if someone came to me today and said, I want to go to law school, I would ask them why. Not so much they you shouldn't do that, but in the sense of you should have a reason. And I don't think I had a good reason to go to law school, other than it was the next thing to do. I mean, I could have pictured myself going down lots of different paths in my life. I mean, go back and say, I mean, had I said, all right, if I'm interested in practical stuff, let's do engineering rather than economics, that could have taken me down a whole different path. But with that said, it's not that I dislike going to law school. I enjoyed my time there. I think I've done well professionally. I have a group of friends, so I mean, outside of having practiced law for 35 years, so the best thing that came out of law school is the group of friends with whom I still participate in a fantasy baseball league for 35 years.

Matt: 6:28

It's not as niche anymore.

Jim: 6:30

It's not as niche. Yeah, truly at that time is quite the niche thing. And we've always had it as a purely pride league. So there's no real money at stake. It's just sort of the bragging rights amongst this group of lawyers.

Matt: 6:41

Yeah, yeah, yeah. But so what type of law, you said you carved out your own area, so what were your interests? What did you get into in your field?

Jim: 6:49

So my interest in law school was focusing on business-related work. Again, thinking economics. I turned 60 yesterday. And so I look back and say, all right, I was, I mean, again, a naive to the ways of the world, 21-year-old turning 22 when I started law school. And so if I'm an economics major, I'll do business stuff. And so that's what I focus on. I mean, one can take different courses in law school, and one can either choose, all right, I want to be a litigator. So you take your civil procedure and your criminal law or what have you. And or you can take, I mean, how do you do contracts and how do you deal with the sort of business aspects of law? So I did that in law school and came out of law school, sort of thinking, all right, great, I'm gonna work for a law firm and do corporate work. And one of the interesting turning points in my early law career, which I think really did have an impact on sort of my approach to my practice, not necessarily the area of my practice but my approach, the law firm I was with in Connecticut lent to me for six months on a full-time basis to Connecticut Legal Services. 

Jim: 7:50

So rather than working with corporate clients as a young associate in the law firm, I was doing day-to-day work with people who had unemployment claims or other small, I mean, small but very personal topics on a daily basis. And I would go in, I'd go into their offices rather than the corporate law firm offices and found an enjoyment in working with, I mean, people who really could use my help as opposed to the corporations for whom I was just a grunt associate. I had one particular client had a need for state support, state welfare, for lack of a better term. And she had applied to the state of Connecticut and was denied. And the reason why she was denied is because the state had said, we actually notice that you are a, you’re a legal resident, but an immigrant to this country and not a citizen. And the state was requiring her to provide information from her sponsor, from her immigration sponsor. But her immigration sponsor turned out to be her ex-husband's sister, who, by the nature of the ex-part, was not particularly forthcoming and being supportive. And so my client from Legal Services could not provide the state. And so the state said, no, you can't have welfare from the state, which is an important distinction. 

Jim: 9:07

And so I actually argued to the courts in Connecticut that they were not permitted to make that distinction. That if we were talking about federal welfare, federal welfare, you could say, are you citizens? Are you not citizens? That's sort of 14th Amendment stuff. But the state doesn't have that right to make that distinction between somebody who is a citizen and a non-citizen. State can say, oh, if you live in New York, we're not going to give you welfare. But if you live in Connecticut. So I made that argument, essentially on 14th Amendment grounds. And again, as this junior corporate associate, I actually ended up taking this case to the Connecticut Supreme Court and won. I mean, I actually found out I'd won while we were on our honeymoon. But it was particularly satisfying to help this one person who really had a need for somebody who could advocate for their interests. Now, I didn't go into legal services. I continued being a business lawyer, but I think to this day, I mean, my interests have always been sort of helping somebody, maybe again, a business person, someone who but it's the individual, it's not the big corporations. I'd much rather find clients who are individuals who are buying a business or selling a business or who are trying to do something on their own. Again that sort of entrepreneurial spirit. And so that relates to the type of work I do today. So it's still business stuff. I still like the entrepreneurial aspect of the business work. Say, all right, but what about the estate planning side of things? That's really personal stuff. That's not business stuff, but that's really helping somebody or somebodys address a very personal concern. So again, that's a personal aspect. I really enjoy that. So. 

Matt: 10:42

Yeah, you like talking to a face rather than looking at a page in numbers.

Jim: 10:44

Completely. Completely, completely. And I think my clients over the years have appreciated that aspect of me. So that's the feedback I tend to get. Very satisfying.

Matt: 10:54

Sure. Yeah. So where did you go from after that? Because you know, it's a pretty big early case for you to do to come down from your high a little bit before you moved on to something else.

Jim: 11:03

Well, again, my wife and I, as I said, found out I'd won that case on our honeymoon. So we just gotten married, and I can't remember where we were in the process there, but I had pretty much decided around that time that I wanted to not continue at that law firm and wanted to come back to Boston. Now, Morgan, my wife, had also applied for and had been accepted into a master's program at Simmons College up here in Boston. And so coming back to Boston for me, coming to Boston for her. And I mean, I joined a smaller law firm than the law firm I was with in Connecticut, and was with them for 11 years and learned a lot. I mean, part of what I gained out of my time there was the connection between business work, corporate work, business work, and estate planning. And the law firm actually encouraged me to get a master's degree in tax law, which was very helpful. But I mean, I was there for 11 years, and a couple of things happened in the course of those 11 years. One, importantly, we had kids. And so that sort of had an impact.

Matt: 12:01

On everything.

Jim: 12:03

On everything. And I also rediscovered my opportunities to go back and sing. So I had sung all through elementary school, high school, college, not so much law school, even while I was practicing in Connecticut, had found opportunities to sing, stopped when we had kids, and stopped while I was sort of pursuing this master's degree, but rediscovered the importance of that part of my life. So went back into singing early in the 2000s. And because of sort of the confluence of working for this law firm I was with in Boston, had become less than completely satisfying. And we had made the decision to homeschool our kids, wanting to have a more hand in that. And also wanting to think about having a more flexibility in my life to be able to go and do a little bit of performing. So in 2006, I left that law firm and started my own practice, working out of my house at that time in Wellesley. And the motivations for that were very much a wanting to do all of these things and have a hand. So a wanting to have a direct hand in the homeschooling process with our kids and giving myself the challenge to be a solo attorney and see if I could actually generate some work and actually keep food on the table. And on top of that, find opportunities to perform in ways that would have been hard if I were still working for a downtown Boston law firm. That was one of the biggest shift in my life and certainly a relatively considerable leap of faith. And thankfully, when I left the law firm in Boston to go on my own, I did have clients who came with me. Again, I couldn't guarantee that. There's at least one of these clients that remains with me to this day, which is very satisfying and hopefully a testament to actually at least being a decent lawyer. But that was a big change to go out on my own.

Matt: 13:47

Yeah. Yeah. And during that time then, were there any other milestones or big cases or stories that were particularly noteworthy?

Jim: 13:56

Well, again, I think the the noteworthiness things were not in the law, in the sense that, I mean, it was certainly a challenge to go out and all right, now I gotta fend for myself and hope that people will like me enough to hire me and maybe a little bit of word of mouth. I had at that stage had not yet embraced the concept of good professional networking, which I did discover at some later point, which has been a much better thing. But I think the real turning points and the real changes was being able to be involved in my kids' lives. I mean, when we decided to homeschool, we were living in Wellesley. Wellesley, for better or for worse, has a pretty good school system. And so to make that decision, say we're opting out of that and to do something else is, I mean, I don't know if risk is quite the right word, but at least it's it's a leap of faith that you're gonna give your kids, you're not gonna handicap them or you're not gonna disadvantage them in any particular way. Spoiler alert, we didn't. But being able to match time that I had spent working on client work with time where I could be hands-on with the kids. At that time, we were part of a homeschooling cooperative that was at that time based in Acton. And so we are before we moved to Stowe, we were traveling between Wellesley and Stowe. But it was very much of a, we are helping to raise our kids in a way that hopefully that will do well by them, but it's also we're making it a real personal commitment to them. And I think we both felt that as a really important part of our parenting decisions. 

Jim: 15:22

It was also putting your money where your mouth is. If you're gonna do this, you gotta be in on it. One of the reasons, I'll just harking back to the decision to homeschool, one of the reasons we opted to homeschool our kids was we felt at that time, at the time that kids were approaching school age, that because of the emphasis on the MCAS, schools were going to be de-emphasizing the importance of the arts. And I've already talked about my interest in music. Morgan, she had a background in theater, and I had done theater work as well. And so the idea of putting our kids in school and have them not have that exposure was just an anathema. So sort of, you can't do that. And so going back to where I was about sort of leaving the law firm into the homeschooling was making sure that our kids had their own exposure to the arts in some form. And so I’ll offer a couple of quick stories of that. So perhaps the funniest, mostly true, I think, stories on it. So with our son, he had done a bunch of little kid things. I mean, he did a little kids' course, he did a like semester of Suzuki violin. And so when he was nine, he said, Mom and dad, can I take a year off of doing music? And he said, Fine, that's okay. But in a year, you gotta pick something. We don't care what you pick, but you're gonna have to come back and do something, but your choice. So a year later, as we were planning for a big family trip to Scotland, our son went to Morgan and said, All right, I know what do I want to do. You can probably see where this is going. 

Matt: 16:48

Yes. 

Jim: 16:49

He wanted to play the bagpipes. Now, I think I mean the apocryphal part of this story is that we think that he probably thought, all right, and mom can't find me a bagpipe teacher. Little did he know at the age of 10 that his mother was quite industrious and quite capable of finding him a bagpipe teacher, which she did. And our son, to his credit, he followed through and became a fairly accomplished bagpiper. And he still plays a form of the bagpipes to this day, so I'm told. So we also had found interesting dance opportunities. So our son actually had done a little bit of ballet as a little kid, but we had also been connected in with sort of the folk dance community in the Boston area. And I had performed in 2006 in the Christmas Revels, and so I had been sort of come to learn of the Morris dancing community. Since I don't Morris dance, I won't go into that in a big way. But we found a person who in Sudbury who taught kids Morris dancing. I thought it was like a really nice activity to do. So we got them into it, and both kids ended up doing that. But with that little background, such one of my more proud moments was in 2009 when again I was in the Christmas Revels, but my both my kids performed in the Christmas Revels that year. And it's not a unique thing to have that parent-child thing in the Revels, but I got to experience it. And it was really cool. And I mean, there was like an opening night. There's one point where in one of the pieces in the show, so I said to myself, damn, I'm doing this. And my kids are on stage with me for this show. It's not just me. And so the Morris dancing, while our daughter doesn't do it anymore, my son today still does that. 

Jim: 18:21

Again, there's this tangential story I'll fill you in later on that ties into this, but he still does that today and as actually in this somewhat niche world, really, really good at it. Very proud of that. So anyway, I look back at certainly in that period of being noteworthy, were not so much about the law work, but again, looking at my kids. Now, I'll throw one more interesting sort of thing here. There are a lot of things I'd done that had been politically active over the years. So I'd worked on various campaigns over the years. I did a little bit of work on a congressional campaign while I was in Connecticut. I was a delegate to 2002 for Robert Reich when he ran for governor here in Massachusetts. Actually, in 2004, I actually was a delegate to the Green Party National Convention and had sort of always toyed with the idea of, I mean, should I run for office at some point? And whether I'm a glutton for punishment or just daring or stupid or what have you, but in 2010, I actually ran for Secretary of State here in Massachusetts as a progressive independent candidate. And my thinking at that time was that I'd seen good candidates go up against Bill Galvin at the time in Democratic primaries and get smoked because Democratic primaries are, I mean, or party primaries are sort of very insular things, and they're also happen at a difficult time of year to get people to focus. And so that it's really an insider's game. I said, all right, I'm not gonna play the insiders game. I'm gonna run as an independent, so if I can get on the ballot, at least I'll get on the November ballot. Now, spoiler alert, I didn't win. But I mean, the fact that I did get on the ballot and got just under 3% of the vote statewide. And that was a campaign with no money. So it was, again, it was foolish in some ways to do it, but an experience that I don't look back and regret in any way. It was an experience that sort of helped me out in some things I've done subsequently. But it is an interesting challenge to go into that. And if I knew then what I knew now, I might still run but there's things I would have done differently.

Matt: 20:21

Sure, you can't know everything your first time. What was your slogan? What was your.

Jim: 20:27

I have no recollection. It's been 15 years to this point since then. But it was an interesting process. And again, a miracle I got on the ballot at all. But there's a reason at least for trying.

Matt: 20:38

No, I mean that takes a lot of effort and gumption and all that stuff to get that far. So and three percent is not, you know, that probably beat Mickey Mouse. 

Jim: 20:47

Yes. Had I gotten three percent, I could have created my own party in the state. But that's. 

Matt: 20:51

That's a whole other level. 

Jim: 20:53

That's a whole separate issue that I hadn't sort of counted on, or certainly not a motivation at that time to do that.

Matt: 20:58

Yeah. So that could kind of lead us into do you want to talk about some of the work that you're doing now?

Jim: 21:04

Sure. So I began doing ballot question work leading up to the 2020 election period. So I had starting back in the early 2000s, I had been an advocate for ranked choice voting and had spoken on the topic. I actually had an op-ed in the Boston Globe in the mid-aughts on the topic. And then after Maine adopted ranked choice voting in their elections in 2016, I was part of the group that came together right after here in Massachusetts to begin work to try to get ranked choice voting on the ballot here. And so I had background with the folks who were the leaders, I mean the other leaders of that group, and had sort of became part of the executive team there. And because I was, in fact, the lawyer in the group was primarily responsible for any legal issues that came up in that process. But I was also an advocate. I mean, I would go out and spoke around the state on that topic, doing podcasts and cable TV and radio things on that topic. And we had thought about maybe trying to get it on the ballot for 2018, but felt we didn't have enough time nor we had enough money. And so we deferred our goals to do the ballot work until 2020. Well, when that became more a reality, I had reason to get more familiar with the actual law behind doing ballot question work as counsel to this effort. At a volunteer meeting, it was in Framingham. I actually met a fellow by the name of Tom Bean, who I came to learn after the fact was essentially one of the primary ballot question attorneys in the state. But he was not there because he was trying to get the work. He actually liked the idea, wanted to be supportive. But having learned that, I said, all right, Tom, teach me more. 

Jim: 22:40

So he and I worked together when dealing with the ballot question process with the attorney general and all that. And so I learned under his wing as to how you actually really truly get a question on the ballot. So the 2020 election comes and when everything shut down for COVID, we actually had to deal with some interesting issues at that time because part of the ballot question process. I mean, people listening to this in the fall of 2025 may have been accosted by somebody in a grocery store having to sign petition papers. But there are two periods during which one has to collect petitions. One, it's the fall of the odd-numbered year. So again, now 2025, but fall of 2019, you would have collected signatures. But if you get past that initial hurdle, there's actually a second period in which you have to collect signatures, which is usually the spring of the even numbered year. So next spring you might hear it, but in that case, it would have been May and June of 2020. And as we were approaching that time period, it was clear that the standard processes for collecting signatures were not going to be available because people were just not going out. This typical, hey, I'm going to stand in front of a grocery store and collect signatures. It wasn't going to happen. So we actually petitioned the SJC, the Supreme Judicial Court, for a special ruling that would apply only to that election that would allow the electronic collection of signatures. It's an idea I would still like to see implemented. But we actually, I mean, not only were we able to convince the court, but the other thing about me is I'm also a geek.

Matt: 24:10

I mean, the fantasy baseball.

Jim: 24:12

Fantasy baseball, but I mean I did a podcast 20 years ago, and I do video editing when I can. But as a geek, as a computer geek, I actually was able to describe to the court how it could be done. And so not only was we were asking for a ruling for the court to allow it, we actually needed to provide some guidelines because we couldn't rely upon SJC to necessarily know the technical aspect. So it was an interesting mix of, all right, we're still doing ballot question law here in a very special set of circumstances, but it was very satisfying to be able to present something to the court and have them say, all right, great, that seems useful. We're gonna support what you've proposed. And we were able, I mean, we and others were able to go out and get electronic signatures to get the question on the ballot. So that was an interesting there. Anyway, so sadly, in my perspective, the ranked choice voting effort did not succeed. I will blame the pandemic for that. But having had that experience, and again, I'm a solo attorney, I thought, all right, well, let me see if I can go out and do more of this work. And so I was actually referred to a fellow in early 2021 through my networking group who wanted to present a question on the ballot. And I said, all right, here's a chance for me to actually do this for somebody else. 

Jim: 25:25

And as it turned out, this particular fellow had never done anything like this, was prepared to self-fund this effort. So he needed some help on the legal side, but also needed a little bit of help understanding the call it the politics of it. He hired me and I actually helped him write his question and go through the attorney general process. And we had vociferous and well-funded opponents who tried to get the ballot question sort of knocked off at the initial stage. We got past that. And so some of you may recall. So in 2022, the one ballot question that passed that year was on dental insurance of all things, which was the one I worked on in 2022. And so, again, very satisfying to work with this fellow and actually help him get a ballot question and have it succeed at the ballot box. So that was great fun. All right. Now I've gone through two election cycles. 

Jim: 26:13

So I'm going to the third election cycle. And so for the 2023-2024, I was actually approached by a couple of different groups and ended up working with only one of them at the end of the day. So the group that was pursuing the full minimum wage for tipped workers question. Again, that was a place where I was brought in to help write the question and then deal with the issues at the Attorney General's office in getting the question certified and to begin the process there. Now a few more people knew that I did this work. Sadly, that question did not succeed a year ago, not for the want of the legal work. And so, again, in the odd number of years, sort of, hey, I'm out there prepared to do that. And actually got hired by three different groups this year, who at the end of the day sort of pursuing four different ballot questions right now, that all of which got certified by the attorney general in September. And it's now a little, I mean it's a little bit of expanding practice. The next time I'll have this opportunity will be, again, spring of 2027. So it's very cyclical in nature and very concentrated in time. But the the opportunity to do work on the questions which I have a hand in are ones that all have sort of real political impact, could have real political impact in the state. Political impact that I support. As a solo attorney, I can choose what I take and what I don't take. So I've not been approached to do anything that I didn't agree with. I've been able to agree with things I have taken on. 

Jim: 27:35

So the questions which I mean, again, all these are being collect signatures are being collected now for these questions, but I worked on the question that would actually address the state primary process. So I again I talked about earlier about the challenges of the party primary process when I ran for Secretary of State. Well, so this initial question, which is petition A, would change our primary process to get rid of party primaries altogether and create what's referred to as a top two primary, where all candidates regardless of party, so far as they qualify, would appear on one primary ballot and the top two candidates go on to the general election. Very similar in nature to what we see in like the Boston mayoral primary this year, where they had four candidates, top two go on. Now the fact that Michelle Wu won by such a large margin that Josh Kraft decided not to pursue, that's a separate issue. But it would allow this so that instead of any one party being guaranteed a slot in the general election, you actually have to go out and all candidates have to reach out to all voters. You would open that primary truly to all voters. And it would allow a voter to say, all right, I for race X, I want to vote for the Democratic candidate. But here in race Y, I'm going to vote for Republican. And maybe in race Z, I'll vote for an independent. Those are not options that are available in our current primary process. And so that would change and hopefully make it so that we have better races at the general election time, but giving people choices that are more closely aligned to the electorate as a whole. 

Jim: 29:08

So that's the one question. The second question, same client, which would be petition B, would make the public records law of the state applicable to the legislature and the governor's office. So currently there's a statutory exemption for the legislature. And this question would just pretty simply just get rid of that statutory exemption. The hope is that it will open up the processes for the legislature so that we, the electorate, we the people of the state, can know more about the legislature, which is one of the most opaque legislatures in the entire country. And so that's what that question would do. A third question would create a new fiscal fund funded by already existing collected taxes, sales taxes, so that it doesn't create a new tax, but one that would specifically create a fund to fund conservation projects, nature conservation projects. And then the fourth question, which was primarily sponsored by former state representative Jonathan Hecht, would radically change how stipends are paid to legislators. So members of the legislature get a base compensation that's built into the state constitution. So everyone gets paid something, but there is this process by which additional funds are payable to members of various committees. I think it's seen as a way for the leaders of the parties to reward their friends in the legislature, and by extension, sort of punish those who don't play by the rules of the leadership. And the changes being proposed in this other ballot question would make that additional compensation more responsive to the actual work of the legislature, not just, hey, you've got yourself at committee chairpersonship, you get paid extra money. It would be you'd be a chairperson and you've done your work and then you get some extra money. 

Jim: 31:03

And so those are the questions which I have a hand in. But again, it was exciting to have my name out there. And again, as a solo attorney, I mean, there are attorneys who've done this for many years, attorneys who work for bigger law firms who do this sort of work and to have little old me be able to have a hand in these things, and we'll see what happens between now and next November. But with any luck, all four get on the ballot and all four win. At which point I'm definitely celebrating that night. So but just being able to help and be part of that process and to try to make some good change in the world is satisfying.

Matt: 31:36

Yeah. So in the process of doing that, I mean, you already explained a little bit like the cycle of it of getting signatures, but what are some other pieces of that process that you know the general public might not know about that might be interesting to hear about? Like yeah, just something. 

Jim: 31:49

Yeah, yeah. So again, people generally know about the signature gathering because again, they will likely be accosted at some grocery store between now and November to sign some sort of petition. So people see that. It's the work that leads up to that, which is a little bit behind the scenes, and you might see one or two quick news articles about it, but which is really interesting. So the very first part is the process of actually drafting a question. And what you are in essence doing is drafting legislation, because what you draft, if it succeeds, becomes a law. And so you have to understand, or at least you should understand, how the statutes work generally. And certainly any statutes that would be impacted by what you do, you should understand those before you can actually draft a workable question. And the process is certainly open enough to anybody. You don't have to have a lawyer, you don't have to go through that background. But I've certainly seen questions that were inartfully drafted that they could have used some help if they really wanted to proceed. Anyway, but it's a fascinating process to go through and look at the current law and say, all right, what are we trying to change and how do we draft language to actually change that law? I mentioned the conservation fund. That's a completely new concept. That question, which I did not do the primary drafting on, but just advice, that's a whole new thing. And so it didn't really require the concept of changing anything out there. 

Jim: 33:11

But if you're trying to change the whole primary system in Massachusetts, you have to look through the whole swaths of the statutes to see, all right, what we're trying to do, what does it impact? And sort of figure out, all right, what language in this section do I have to change? What language in this section needs to stay the same? Or one of the dominoes that fall, if I change this, how does that impact something else? And so there's that background work that happens even before anyone sees anything. And because of the nature of the process, once you submit the question to the attorney general, and the deadline for that is the first Wednesday in August, an odd numbered year, you can't change it. And so you can't go back two weeks later saying, oh, darn, I left out that sentence. Can't change it. It's written in stone when you do that. And so you have to do all that very careful work ahead of time and anticipate whatever issues might come up. So that's the first thing that's sort of not visible to the general public. 

Jim: 34:08

What happens then once you submit to the attorney general is also a fascinating process because you're doing two different things in parallel with the attorney general. One, you're trying to make sure that they certify the question. The attorney general's job is to look at the ballot question, the proposed ballot question, and determine whether or not it satisfies a very specific section of the state constitution known as Article 48, which governs ballot questions. They don't look at sort of overarching, is this constitutional with the constitution in general, just whether it satisfies Article 48. But it's still a process because what the attorney general will do is they not only need to do their own review of it, but their charge is actually to go out and find opponents. They actually seek out contrary opinions. Sometimes they find them, sometimes they don't. Go back to the dental insurance question. You can be darn sure that the dental insurance companies were vociferous in their opposition on that question. So you're trying to convince the attorney general that the question that you've presented to them satisfies Article 48. 

Jim: 35:08

At the same time, you're also working with the Attorney General's office to draft what would be the summary of the question that appears on the signature sheets. And again, the Attorney General's job is to draft something that is neutral in nature. It's not an advocacy piece. It's a think dragnet, just the facts, ma'am. But there's still a little bit of politics going on because as a proponent, you would like language that is clear and it has a positive sense as to what you're writing. Opponents might want to come in and might want to muddy the works and ask for different language that casts a negative twist on the language. And so there's a little give and take with the attorney general's office on language. You can offer your own language, then they'll come back with a draft, and then you can offer changes. But because there's a very limited time, this year is only a four-week period between when you submitted and when they had released their decisions, there's a limited amount of feedback. And so you have to be organized and coordinating with your client, in my case, as counsel, to make sure that everyone's happy with the language. 

Jim: 36:14

As it turns out, for the first two questions I talked about, we actually ended up with very simple, relatively short summaries, which was great from my perspective. I think it makes the questions pretty straightforward. By comparison, the dental insurance question back four years ago was a very complex and very challenging question to write a summary of. And so that summary was not quite so short. But there was not much we could do about it. Because again the nature of the question, it was a complex, it really didn't boil down to a really very basic concept. Now, so the people who did the collection for that question, the dental insurance, they were trying to get people to sign this question with a very long summary on it. But they told me what their secret weapon was. They basically went to people to say, Do you hate insurance companies? And when people said yes, they said, then you want to sign this petition. And they got a lot of signatures based on that. So needless to say, the attorney general couldn't write do you hate insurance companies as part of their summary. But that drafting of the summary is really important because it appears on the signature sheets. It'll appear in the red book when that comes out in the fall of the election year, and it appears on the ballot itself. And so it's a really important how the sausage gets made, sort of thing. It happens in the background that I find fascinating because there's a little bit of law, there's a little bit of politics going on to get the attorney general to agree to something that certainly is neutral and might even be positive for your client. So that's that background thing, which I find a lot of fun to be part of.

Matt: 37:42

Yeah. What about in the beginning? Like, why would someone even be approaching you with a ballot crash in the first place rather than, you know, like going through other legislation? What is the reasoning behind it?

Jim: 37:52

The reasoning, I think, behind that is that I think there's a lot of frustration with the legislature in how quickly or not so quickly it takes up legislation of great interest. So last year, I think it was last year, the legislature passed a really important maternal health law. There are aspects of that law that I helped draft back in 1998. Do the math.

Matt: 38:16

Yeah.

Jim: 38:16

It's over 25 years. And so I think the reason people go the ballot question route is that they see the legislature not acting in response to whatever issues that are out there, or even with legislation and it's being presented before them, we'll just not act on it. I mean, it happens in so many cases. And just citizens, we have that right here in the Commonwealth to go through that process and say, well, listen, if the legislature is not going to take this up, at least let me try it. And then I think there are topics that the legislature are simply not going to touch. I mean, ranked choice voting was not something the legislature was going to take up by itself. Changing our party primary process is not something the legislature was going to take up by itself. And so I think there are topics out there where there's enough interest amongst the citizens that they go through that process. 

Jim: 39:07

And so I think without knowing this sort of empirically, I suspect that a lot of people will say, I'm going to give it a shot. So I'm going to reach out to my state representative or my state senator, please promote this bill. Give it a shot in the legislature and see what happens. So I don't think there are a lot of cases where people have not at least tried going through the legislative route, but having failed, or having failed not because it got voted down, but because the legislature put up roadblocks, then here's this other path. And you would like to think and hope that the legislators would, I mean, writ large, would see this process and say, we'd rather have a hand in this rather than leaving it solely to the voters. The process of getting the ballot is extraordinarily expensive and time-consuming and all that. And so the barriers to entry are high enough that it probably doesn't impact the legislators all that much because in order to succeed, you need to be able to invest somewhere between five and ten million dollars, if not more, depending on how controversial the topic is. And that's a barrier to entry. So even if people have good ideas. Again, go back two years ago. The person who actually submitted the proposal to get rid of the MCAS requirement for high school graduation, was actually a college classmate of mine. And I saw her name on it. I said, Congratulations. Great, good for you. What's your plan? Again, I mean, I'm very supportive of it and go back to my homeschooling decision. But I think she would have been hard-pressed to pursue it herself. I mean, she saw the need, but didn't have the means by which to do that. However, the Mass Teachers Association, whoever it was, I think it was Mass Teachers Association, sort of picked up the gauntlet, as it were, and pursued it. So it's still hard.

Matt: 40:44

You need some type of powerful support somewhere.

Jim: 40:47

You need somewhere. Again, the dental question, what's fascinating about that is that guy who was a primary sponsor, he was completely prepared and had the means to self-fund it. The dentists around the state and around the nation, they had opportunities to support him early and didn't. They were basically a wait and see. It wasn't until we actually got on the ballot that people sort of went, oh, it's actually there. Now we can come out and support it. Which is fantastic. Yeah. If you don't have that support, it's hard. Not impossible, but hard.

Matt: 41:17

That's why there's not a hundred questions every year.

Jim: 41:19

That's why you're right, exactly. California, they might have their 100 questions. Their barriers of century are probably too low. Ours are pretty high. Right. If we get a couple every year, then that's or every two years, it's not so bad.

Matt: 41:31

Anything else to like wrap up this topic of ballot questions? Anything else from a person who's just a general voter going into looking at a ballot question? Anything interesting there?

Jim: 41:40

I mean, there were actually roughly 40 that got approved this year. So there are a lot of questions that could be out there collecting signatures. I mean, I like the idea of this aspect of direct democracy. I would be generally open to signing petitions. I would encourage people to read, read about them. Again, the summaries are on each signature sheet by law. And so if someone does come up to you and asks for your signature on petition, read it. Don't sign anything blind. But at this early stage, I think it's good to, if you can agree with the general concept, support it. There are questions out there that might be collecting signatures that I would not support philosophically. And I might not sign those signature sheets, and no one should sign something they don't believe in. But at this early stage, take a read. And if you can be generally supportive of the idea, you'll have an opportunity to learn more about it later on if they get past that point. Again, support direct democracy.

Matt: 42:31

Yeah, cool. Well, that's all interesting to hear how that all works and some of the background on that. Is there anything else that you want to talk about with your work or your journey before we get towards the end here?

Jim: 42:42

Well, yeah, there are a couple more things, especially things I've teased. So I want to go back to the music stuff a little bit. People who know me, I've referred to this professional networking group. And people know me in that group because they like to think they know me as a good lawyer. But I have not been shy about sharing my other activities with them, some of the political, but certainly the music aspect. And it's a bit a way for people to remember who I am. I have on more than one occasion, but this is not my own description of me, but people have come up to me in a very positive way, sort of describe me as a renaissance man because my interests aren't just in my work. And I often describe to people that I enjoy the practice, I enjoy the law work I do, but I'm able to enjoy it because there are times I can put it aside and I have something completely different that I absolutely love doing or to clear my head. And so I mentioned I sort of came back to singing after having kids and having done the master's degree. It was just an epiphany for myself to say, I really do like this. It gives me a different way to think and a different way to put myself out there. And then sort of discovering it and being able to participate in the Revels, again, allowed me to identify with a community of people who I liked an awful lot, were very supportive in lots of ways. And through the Revels, it allowed me to, I helped form a small theater group that was based in Waltham for a number of years. And we were doing, I thought, really good work. And then COVID came, and that really hampered us a lot. 

Jim: 44:09

But out of both Revels and that theater group came this a cappella group that I'm part of, which again has allowed me to continue doing my music and have a little bit more of a sort of direct influence on the music we do. So for the sake of the shout out to my own group, the group's called Crooked Mowth. For those of you looking up online, Mouth is spelled M-O-W-T-H. So we're not confused with all the orthodontists out there. But a lot of the music that we have chosen to do with Crooked Mowth has a message to it. We started off with a bunch of songs that had a sense of social justice to it. And they come from different eras and different artists. Then we've added some more songs that had more of a climate awareness aspect to it, one of which I wrote with a collaboration with uh local composer Andres Ballesteros. And again, it's fun to sing my own music with my three cohorts who are dear dear friends. As you know, Matt, we actually were able to sing this year on my porch here at Porch Fest. But it's for me, I call it that Renaissance aspect of having multiple things that one can enjoy doing and do well and have them complement each other in one's life. 

Jim: 45:15

Again I think it's important for everybody to find their sort of thing. Many times in the context of either introductions or people I've met through the networking group or other places. Tell me what you enjoy you do? People sort of, I like spending time with my family and kids. Nothing wrong with that. But what else are you doing? What else brings you joy or satisfaction? And I think that's I think that's a really important thing to have in one's life. And so I found that through this music. And I will offer that as an expansion, sort of in the context of us talking in this thing, is that when we moved to Watertown, one of the things that we really wanted to be is we wanted to be part of a community. I mean, when we, as homeschooling parents, our communities were never our school systems. And so we had friends and our kids' friends were sort of all over the place, but we never had maybe a little bit in Wellesley, but really not so much in Stowe. We weren't really connected to the community because the things we were connected to sort of were had a much broader geography. Kids don't live at the home anymore. And so by moving to Watertown, it really gives an opportunity for us to look at this community as a place to more actively participate than we've had before. 

Jim: 46:22

And so I look at the idea of my law practice and say I have clients all over the place, which is great. But the idea of be able to not just finding clients, but be able to find ways to help contribute to this community that where we expect to be for a long time. So in terms of Crooked Mowth, come hear us sing at some point. But so hopefully I'll have a chance to meet more folks here in Watertown as I begin to get involved in different activities here. 

Jim: 46:44

All right, one last thing. And just because it's a cool story, because I already teased it. And so you asked about sort of getting into the law and sort of a connection of that to my dad. And I mean, having grown up here in Boston. So, all right, where does the love of the music come from? Because my parents weren't particularly musical. Not that it really bothered me, but even as a young kid, I had an interest in music that sort of it's just here. So 14 years ago, I got a phone call out of the blue. And I was in my home office and it was from an organization here in Boston, and they say, are you the son of my parents? I said, Yes. And the next statement was, your birth father would like to connect with you. I had known I'd been adopted. This was not a surprise I'd been adopted, but I had never had sought out my birth parents. And so the fact that he was sort of seeking me out was fascinating. At the time, I was 46 years old. I felt I'm comfortable enough in who I am as an adult that this is not gonna rock my world, but let's find out more. Well, making a long story comparatively short. I have spent time with my birth father and actually my half siblings, half siblings who actually turned out happened to be born in Boston as well, unrelated to the fact that I was born in Boston. My birth father and his family were extraordinarily, are extraordinarily musical. So it was fascinating to have that come in. 

Jim: 48:03

I also mentioned earlier, I'm a geek. My parents were not particularly technology based. My birth father, who's in his early 80s, still does computer programming. So again, sort of, all right, where'd this all come from? I think I now know. One of the wildest connections that we discovered shortly after we connected in 2011, again, when he made the initial contact, my son was actually dancing in the Christmas Revels that year. And he was doing a form of international dance, an Eastern European dance known as the Kala Shari. Came to find out that my birth father, again, unrelated to the fact I was born in Boston, actually had moved to Boston eight, nine years after I was born, as it turns out, had joined an international dance group in Boston called Mandala. And a couple of things about Mandala. One, there are a number of people he danced with in Mandala who had become friends with me subsequently with whom I had performed before I knew about it. So wild. But it turns out that my birth father had himself in the mid-70s, in the early days of Revels, danced in the Revels. And in fact, had danced the Kalashari in the same outfits as my son was wearing in 2011. And so it was just one of those wild stories of some nature, nurture, all that. But in some ways, again, not that it needs to complete a story, but it helped provide these other connections with him and his family that would have otherwise been unbeknownst to me. But knowing them, I think made me understand a little bit more about who I am.

Matt: 49:38

Yeah.

Jim: 49:39

In a larger context. And so it it's cool. My birth father has been in slightly in ill health. I actually had a chance to visit with him a couple of weeks ago. He lives in Europe, as do my two half siblings. So I actually had to fly over and see them, but it is good to connect with all of them.

Matt: 49:53

Yeah.

Jim: 49:53

But it's a bonus family, as it were.

Matt: 49:56

Yeah. That's yeah, that's a whole other interesting story, I'm sure. 

Jim: 50:00

Most definitely. Yeah. So that's my story and I’m sticking to it.

Matt: 50:03

Yeah, well, I mean, we got a lot of your story there, and I'm sure there's a lot more to go, as with all these conversations. I could always talk for many more hours, but I think we got a good picture of who is Jim Henderson, and I'll put links to your law stuff, but your music stuff too, and anything else you want me to put links to in the show notes. Any last thoughts before we just close it off for the listeners here? 

Jim: 50:28

And again, I'll repeat myself. I love the fact that you're doing this podcast to support people in Watertown. And we have discovered how vibrant a community Watertown is. And I hope that for your sake, Matt, that your work continues to be embraced because I think particularly in these challenging days around us, having strong connections to the people in your neighborhood, in your community, are of paramount importance. And I'm happy and honored to be here in Watertown. So thank you for giving me a chance to chat with you, Matt.

Matt: 50:59

Yeah. Thanks for taking the time to share your thoughts and stories. And yeah, thanks.

Jim: 51:04

You're welcome. 

Matt: 51:05

So that's it for my conversation with Jim. I'll have links in the show notes for you to find out more about his work and his music. If you like these conversations and you want to hear more of them, head on over to Little Local Conversations.com. You can find all the episodes, find out events coming up, such as next Creative Chats with a documentary filmmaker, or next Watertown's Open on the state of real estate development here in Watertown. You can also sign up for my weekly newsletter, stay up to date on all these things. And again, I want to mention the Little Local holiday giveaway. Anyone who signs up to become a Little Local friend and support the podcast before November 26th, will have a chance to win some really cool gift cards and gifts from local businesses and organizations. Like I said, over a thousand dollars worth of stuff to give away. So I’m really excited, some really great stuff. Really thankful to the businesses and organizations involved. So I'll give a quick rundown of that. You can win stuff from Arsenal yards, including Buttermilk and Bourbon, Codesa, Medium Rare, Mighty Squirrel, Tori Jiro, and also the Boston Gold Kings, Campolongo Cookie Company, Cass School of Floral Design, Farina’s, Gore Place, Mosesian Center for the Arts, Mount Auburn Cemetery, Revival Cafe and Kitchen, and Ritcey East. Again, LittleLocalConversations.com slash friend. Or just head to the website and click on the top bar where it says Little Local Holiday Giveaway. Alright, I want to give a few shout-outs here to wrap things up. First one goes to podcast sponsor, Arsenal Financial. They're our financial planning business here in Watertown that's owned by Doug Orifice, who's a very committed community member, and his business helps busy families, small businesses, and people close to retirement. So if you need help in any of those areas, reach out to Doug and his team at arsenalfinancial.com. I also want to give a thank you to the Watertown Cultural Council, who have given me a grant this year to help support the podcast. So I want to give them the appropriate credit, which is, this program is supported in part by a grant from the Watertown Cultural Council, a local agency, which is supported by the Mass Cultural Council, a state agency. You can find out more about them at Watertown Cultural Council.org and Mass Cultural Council.org. And a couple more shout outs to promotional partners. First one goes to the Watertown Business Coalition. They're a nonprofit organization here in Watertown that's bringing businesses and people together to help strengthen the community. Find out more about them at Watertown Business Coalition.com. And lastly, Promotional Partner Watertown News, which is an online newspaper focused purely on Watertown. It's run here by Charlie Breitrose. It’s a great resource. Go check that out at WatertownMANews.com. So that's it. Until next time, take care.