John Himmelstein

Trial Lawyer

John Himmelstein is a criminal defense attorney based out of Boston, Massachusetts. With over thirty years of professional experience, he cares passionately about the law, his clients, and his country. Growing up in the North Shore area of Boston, he describes himself as a late bloomer who was “never really good at anything except running his big mouth.” Destined to be a lawyer, he attended college in his home state before establishing his practice in 1988. Despite building a solid reputation in his community, his career has not come without its challenges. After navigating several low points in his life, he now plans to relocate to the Carolinas, where he intends to start a new practice. As a self-motivated individual, he hopes to offer sound advice to those looking for legal help.

Where did the idea for your career come from?

I think I’m congenitally incapable of working for other people. I’ve got to work for myself and I’d like to think most successful people are like that. I think you go through history and look at who the successful people are and they are usually people who work for themselves and control their own destiny.

What does your typical day look like and how do you make it productive?

Ordinarily, I get up about five o’clock in the morning, and I get prepared for whatever I need to do. Every day, I list the ten most important things that I have to do that day. I always go back and review my calendar. I look seven days previous and seven days ahead just to make sure I’m not missing anything that should be covered during that 14-day window.

The typical day in court is not trying a case or doing something really dramatic. It can be a lot more mundane than that. I would say that most days in court are like “the regular season.” You’re just going in there and filing some motions, or you’re getting a court date or some discovery materials from the district attorney. But some days are “the playoffs.” The playoffs will be a trial, filing motions to suppress where you’re trying to keep evidence out, a probation hearing where your clients might go to jail if he violated, or making a motion to dismiss. Those are the kinds of things that are postseason caliber. Those are the big games that decide championships.

During the pandemic, it has been a little bit different because we don’t go to court as much. A lot of the court is done by Zoom, and Massachusetts isn’t doing jury trials yet. We’re doing some bench trials, and those are always in person. Arraignments are always in person. Probation violation hearings are often in person. Restraining orders are usually in person. But the routine stuff is by Zoom now until we get back to normal life, which I hope is sooner rather than later.

How do you bring ideas to life?

I don’t know if I’m a creative person. I don’t think of myself that way. I just think of what kind of lawyer I want to be and what kind of person I want to be. I think of myself as just a guy who pounds the pavement, and the guy who’s a fighter for his clients.

What’s one trend that excites you?

Zoom has really taken hold in law during the pandemic. I think it’s good for certain things, like if I’m representing you for a traffic ticket violation. Let’s say you live in Brookline, but you got a traffic ticket in Boston. Why should you have to come all the way from Brookline to Boston to appear in person before the magistrate or the judge to dispute a traffic ticket? It’s the kind of thing that can be done by Zoom, and it’s not really necessary for the people to be there in person. Zoom serves a purpose for cases that can be handled virtually. Even though I’m not a big fan of the whole virtual thing, I think the pluses outweigh the minuses.

What I don’t like about Zoom is how it minimizes the interaction between attorneys and courthouse personnel and colleagues. Those are the things that can make being a lawyer fun and exciting. There are also practical matters in law that are best served by doing things in person and in court. All that goes out the window through Zoom.

What is one habit of yours that makes you more productive as an entrepreneur?

Everything I do is scheduled. For everything I need to do, I make sure to reference my calendar and find a time when I can do it. If I’m going to court on Tuesday at three o’clock, or if I’m meeting a client on Thursday at nine o’clock, it goes immediately on the calendar, and I stick to it. I’m not that way in my social life, but in my professional life, everything is scheduled.

What advice would you give your younger self?

I would have done something differently when I was younger. I would have done some kind of national service, either joining the Army or the National Guard or the reserves. I’d do that for a year or two and get some maturity and get some discipline. I would have meant a lot to me to be able to say I had served my country, though I am also appreciative of the fact that I never had to serve in the military because of the people who came before me.

Another piece of advice I would have given to myself is to be grateful for what you have. Don’t always think the grass is greener on the other side. I didn’t fully appreciate how fortunate I was when I was young, and I think that might have contributed to me being a little reckless. I wasn’t as appreciative of the positive things and that’s what got me in trouble a number of years ago. I know a judge that is a good friend of mine and he took me into his office at the courthouse, and he said to me, “You know, whatever doesn’t kill you makes you stronger. You’ll get through this and you’ll be a better person because of it.” And he was right.

Tell us something that’s true that almost nobody agrees with you on.

He’s what scares me, and I think it should scare everybody. This cancel culture going on is very un-American, and I applaud attorneys like Alan Dershowitz and Jonathan Turley, who I don’t always agree with, but I give them credit because they are very outspoken against the cancel culture and against suppressing people. I’m very worried about the direction the country is going in and the idea that it is somehow okay to just cancel someone.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Being an entrepreneur, it’s like pounding a rock. You keep pounding the rock until it breaks. You just keep pounding it and pounding it. You keep pounding the pavement and never let yourself be outworked. I realized early on that if you want to leave the office early, you have to realize that someone else is still working and that’s your competition. I know people have a life and want to leave the office early sometimes; I leave the office early sometimes. But there’s no substitute for hard work. People in today’s society want to find every excuse there is to not compete at something. There’s no excuse for avoiding hard work. It’s corny, it’s cliché, but it’s true.

What is one strategy that has helped you grow your business?

Attorneys like me, we live on reasonable doubt. If I’m presented with a case and my client is charged with a crime, I’d look for reasonable doubt. Because if there’s any reasonable doubt, I don’t concern myself with whether my client did it. I take my citizen hat off and I put my criminal lawyer hat on and I do everything I can to make that pitch to the jury or the judge. Now you can’t do that 100% of the time. Sometimes a DA will offer you a plea deal that’s probably in the client’s best interest. If it’s in your client’s best interest, you should advise your client to do it.

What is one failure you had as an entrepreneur, and how did you overcome it?

I wasn’t good with money. I didn’t know how to invest in property. I didn’t know how to save. I was very undisciplined. What I did to overcome it takes me back to my suspension, because during the suspension, I found out who my true friends were. Anyone can be your friend when you’re riding high. It’s when you’re at your lowest ebb in life, that’s when you find out who your true friends are. It turned out I was really lucky, because not only do I know who my true friends are, but some of these friends are pretty good with money. I have a friend who’s helping me invest in some real estate and the stock market, and though I’m getting started a little later in life than I should have, I’m starting to build some assets for myself and to get better with money than I used to be.

What is one business idea that you’re willing to give away to our readers?

I think I would find someone who knows what they’re doing and get into real estate. I wouldn’t do it by myself because I don’t know enough about it, but I would find someone who knows real estate and partner up with that person. Real estate is a changing dynamic, and it’s an interesting dynamic.

What is the best $100 you recently spent? What and why?

My friends got me involved with this law firm that cleans up people’s credit and they put you on a payment plan. I made a relatively small deposit to get started with them, and they’ve been very, very helpful.

What is one piece of software or a web service that helps you be productive?

I’m probably the wrong person to ask as I am not very technologically savvy. I try my best, but I still have a lot to learn.

What is the one book that you recommend our community should read and why?

I recommend William Manchester’s The Last Lion, Winston Spencer Churchill. It is a trilogy of biographies on Winston Churchill. This was a man who had a difficult upbringing. He did not have a happy childhood, and he had a lot of failures both in politics and in the military. He was 64 years old when World War II started. He shows that a man can achieve greatness at an advanced age because he became maybe the most influential person of the 20th century. I would say Winston Churchill, Martin Luther King, Jr., and Jackie Robinson were the three greatest men of the 20th century. Churchill saw the threat of fascism early on. He never wavered. He never surrendered. He was courageous. I think any person can benefit from reading Manchester’s biography.

What is your favorite quote?

“The price of freedom is eternal vigilance.” Thomas Jefferson

Key Learnings:

• Be a fighter.
• Strive for fairness in all your dealings.
• Don’t give up.