James Irving: Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life

Pirie Jones Grossman
Authority Magazine
Published in
9 min readJun 11, 2021


You’re going to make mistakes. An intolerance of mistakes lies at the root of the American success story. And while the hunt for perfection is a worthy goal, if we become frustrated or discouraged by the mistakes we inevitably make along the road, our ability to grow will be stifled. I went through a phase where obsessing over a loss led to another loss, and then a third. Then I realized I was repeating the same error because I’d failed to focus on leaning from the first. Mistakes are part of the process. Handled correctly, they can lead to advantage.

Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50's.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing James Irving.

James V. Irving was born and raised in Gloucester, Massachusetts. He is a graduate of the University of Virginia (UVA), where he majored in English. He holds a law degree from the College of William and Mary and is a member of the bars of Virginia, Maryland, the District of Columbia and Massachusetts.

After completing his undergraduate studies at UVA, Mr. Irving spent two years employed as a private detective in Northern Virginia, where he pursued wayward spouses, located skips, investigated insurance claims and handled criminal investigations. In his early years as a lawyer, he practiced criminal law, which along with his investigative experience and trial work, informs this fictional account of Joth Proctor.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I grew up in Gloucester, an old and colorful fishing port in northeastern Massachusetts. My father was a doctor with a patient base in the fishing community. I played team sports, engaged in water sports and bicycling throughout my youth. I also became an avid reader at a young age.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Deep in the woods of my hometown is a ghost town called Dogtown Common. During the Depression, a local philanthropist commissioned out-of-work quarrymen to carve mottoes on some of the large boulders that characterize this place. I stumbled upon one of these as a kid exploring the area: “Never Try, Never Win”. I took that message to heart immediately and it’s been a touchstone in my life ever since. You can’t accomplish anything by dreaming about it. I’ve tried to take the bull by the horns in life and I tackled the transition to novelist the same way.

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

Imagination, perseverance, patience. While imagination is the critical component of fiction writing, it’s worthless without the perseverance required to establish a disciplined approach and stick to it. Patience is required because the process takes a long time with many bumps in the road.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

I’ve been a lawyer throughout my adult life and I’ve enjoyed it. I began — as many lawyers do — by trying cases. Mostly, these were personal injury and criminal cases, because those are the cases that most commonly go to trial. About halfway through my career I transitioned to become a business lawyer — meaning I handle various transactions and draft business documents. This includes the purchase and sale of businesses and the preparation of various employment and corporate documents. I went from getting my clients out of trouble to keeping them from getting into trouble.

And how did you “reinvent yourself” in your Second Chapter?

In becoming a novelist, I tapped a skill set I have been developing since college, but the ability to write well and persuasively is critical to the practice of law. Additionally, by grounding my fiction in the world of law and lawyers, and in a physical environment I’m familiar with, I’ve used my first career as a jumping off point for my second. I’ve made liberal use of my experiences as a lawyer in developing the plot ideas and characters that have been the genesis of the Joth Proctor stories.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

I’ve always been interested in writing fiction and I suppose I came to a “now or never” moment. I did not want to get to the end of my life and regret that I failed to accomplish — or really try to pursue — the thing I’ve always most wanted to do.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

I’ve always felt I had the skillset, because I’ve been writing fiction since college and because I’ve used and honed much of that skillset on a day-to-day basis in my professional life. There are only so many hours in the day, so I knew I’d have to make a real effort to transition to fiction writing. With my daughter fully fledged and on her own in life, it’s been easier to find the time.

How are things going with this new initiative? We would love to hear some specific examples or stories.

Things are going well and better than expected. Friends Like These and Friend of a Friend are out and Friend of the Court is in the oven (due out in late fall). My friends have been both excited and supportive, but I’ve also received excellent reviews and positive feedback from total strangers. It’s a fun genre and people seem to be both enjoying the stories and investing themselves in the characters.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

That would be the person I live with: my wife, Cindy. She knows how important this is to me and she’s given me the space, time, and encouragement necessary to succeed. The old saying is, behind every successful man there is a strong woman. I’m not sure I buy that, but I know I couldn’t have been successful in either job without her.

Can you share the most interesting story that happened to you since you started in this new direction?

The novels take place in my home community of Arlington County, Virginia, right across the river from DC. I had anticipated friends and acquaintances assuming they were the model for a given character, and I had a standard rebuttal for that. What I didn’t expect is how these people would see parts of the Arlington community from a new point of view. With imaginations fired by my use of local settings, I’ve had number of lively conversations about the place I live, its history and its possibilities.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

The question is how you measure success. Like most young people, I measured myself for a long time through other’s estimation of how I was doing. It takes a long time and a lot of self-refection to know yourself and to accept that you have both strengths and shortcomings and that they are both part of who you are. I’m fully comfortable with that. If you have a group of supporters — in my case and in most cases, family members and lifelong friends — it’s a lot easier to reach this point.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

No, I didn’t. I just rolled up my sleeves, developed a plan, and got to work.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

Time is a finite resource, and most people keep their lives pretty busy. So, if you are going to develop a new career, something has to go to make room for it. I gave that a lot of thought as I stepped into my new world. It can’t be family, and you can’t shortchange your current job, so I chose to cut back on a number of social activities. I rarely watch television, I don’t play golf, and I skipped a lot of parties. I think most people could discover a lot of re-purposeable time if they dropped less productive activities. The question is, whether the trade-off is worth it.

Fantastic. Here is the main question of our interview. What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a story or example for each.

You’re going to make mistakes. An intolerance of mistakes lies at the root of the American success story. And while the hunt for perfection is a worthy goal, if we become frustrated or discouraged by the mistakes we inevitably make along the road, our ability to grow will be stifled. I went through a phase where obsessing over a loss led to another loss, and then a third. Then I realized I was repeating the same error because I’d failed to focus on leaning from the first. Mistakes are part of the process. Handled correctly, they can lead to advantage.

Don’t let the ideal be the enemy of the good. This lesson comes from my wife, an avowed perfectionist. I undertook the construction of a stone wall in my yard. I worked at it and worked at it, but it never seemed right. So I’d take it down and start again — until the dog — the reason I was building the wall — took advantage of the opportunity and ran away. Pippi came back and I learned to match the standard of acceptance with the importance of the project.

Accept criticism productively. I had a partner who was as very successful lawyer — but he never improved. He never improved because he took even mild criticism as a personal affront. Some say it’s the secure person who can handle criticism, but perhaps it’s the willingness to accept criticism that makes a person secure.

Trust your instincts. A mentor of mine imparted this lesson when I was a young lawyer trying to develop a winning argument in a difficult case. Not: “do this” or “do that” but “trust your instincts”. Instead, I made the argument another member of the firm insisted I should make — and lost. The compelling argument is the one you can make with conviction. Your instincts will identify that for you.

Everyone has something to teach you. It’s logical to confront life’s daily challenges by adhering to time-tested attitudes and well-developed life philosophy. To do otherwise is to invite self-doubt. But that makes it all too easy to discount opinions and points of view that are alien to our own. This can be a simple as trying new things. Following someone into unfamiliar territory opens up new ways of seeing and understanding things.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

Tolerance seems to be in short supply in this world. Nobody’s right all the time and almost everyone has something to teach us. Most adults hold unshakeable social views that are unlikely to change. Rather than trying to convert others to our views, we might achieve a better result by learning to exist gracefully with those who disagree with us.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them. :-)

Jeffrey Brown of the PBS News Hour. Mr. Brown has shown a remarkable ability to place art in context within society while identifying the cultural significance of artist effort. He also shares my Massachusetts roots. I feel he’s a guy with a lot to offer any writer seeking contemporary relevance.

How can our readers further follow your work online?

My website is www.jamesvirving.com.



Pirie Jones Grossman
Authority Magazine

TedX Speaker, Influencer, Bestselling Author and former TV host for E! Entertainment Television, Fox Television, NBC, CBS and ABC.