My Story

Who knew?

While, throughout my life, I’ve helped and nurtured friends, family, and—yes—even some practical strangers, I never realized quite how much of an impact I’d had. That is, until I started telling close friends about how I planned to become a certified coach—and they surprised me with responses like:

You’ve really been like a mentor to me. Wait—strike the “like”—you’ve really been a mentor to me.

Am I going to have to start paying you—because you’ve been like an unpaid coach to me and many others. I’ve seen how you help people get clarity regardless of your own personal opinions.

You’ve opened my eyes to possibilities that I never knew existed; and been someone I can depend on to talk to without being judged.

That got me thinking about how I’ve played the role of coach from the time I was on my high school track and soccer teams—and in my Boy Scout troop. People flocked to me for help solving their dilemmas. In many cases, I could’ve just given them an answer—and, most of the time, it probably would’ve been right. But, instinctively, I knew it’d be more effective in the long run to talk about and strategize on how best to resolves those issues.

As I realized that these people had trusted me to help them to clear up emotional baggage and get down to essentials—without my being an official coach—I became happier and happier. Helping others—family, friends, clients—get clarity on career and life decisions has always been intrinsically rewarding. It turns out, all the time I have spent being a technology and business consultant, as well as an advisor, was a great training ground for becoming a certified coach.

My path towards starting a coaching practice began with technology consulting. While in college, I started L&D Computer Consulting; and I spent the next decade designing systems and applications for clients in finance, law, healthcare, manufacturing, and other industries. Specializing in remote access technology, building networks for music festivals, corporate training programs, and power plants, among others, I became a recognized expert. That led to my being interviewed for publications such as Inc., Newsday, and Computer Reseller News. In addition, I co-founded WebHostNY, a boutique web hosting provider.

And, yet, earning a good living solving problems for others – meeting society’s definition of “success” – left me unfulfilled. It wasn’t feeding my soul – and that was a problem I’d need to solve for myself.

Over time, I realized that, by just giving clients tools to solve their technology problems, I wasn’t serving them as well as I could. In fact, I recognized a much bigger underlying business problem while leading seminars and team-building exercises for organizations such as The New School, the American Management Association, and the Spain-U.S. Chamber of Commerce: American businesses were primarily focused on fixing what they think is broken—instead of innovating to provide what their employees and customers really need.

My work as an expert witness for state and federal courts allowed me to get better at focusing in on what really matters and to see how often people just don’t see what is right in front of them. I’ve seen so many companies—from mom and pop stores all the way to the Fortune 500—throw money, technology, time, and all sorts of things at problems that could easily be solved instead by opening their eyes to what the actual problem is or finding the root of the behavior that’s causing it. As a result, I work with my clients to uncover those root problems—most of the time, solving them is more of a mindset change than a money change.

Realizing that I was more often helping clients with overall business issues than strictly technology ones, I sold my tech firm and started Box of Rain LLC as a business consulting firm to:

guide entrepreneurs and growing businesses make their dreams become realities, often through making better decisions, and empower them to achieve success and maintain a balanced life; and

help several musical artists build their performing careers.

At the same time that I was building my own businesses, I always made time for my wonderful family and all kinds of live music, performances, art, and travel. Moreover, I was and, in many cases, continue to be involved in youth and adult soccer, PTA and community events, and Boy Scouting. It was a truly a heartwarming honor to volunteer as a staff member when my son attended the 2013 National Jamboree—which launched the Summit Bechtel Reserve, the BSA’s newest high-adventure facility.

Lenny Posing with Brock

Throughout my life, I’ve felt—and answered—a calling to educate and help out, whether it was: teaching at Queens College; running ice-breaker sessions for incoming graduate students at NYU Stern College of Business; running fund-raising events; coaching soccer; or leading kids on camping trips.

A life-changing experience…

On New Year’s Day 2016, I experienced having my body painted for the very first time. It was a life-changing experience. As I stood there naked on the street, it made me realize who I really was and what really made me happy in life. It flipped a switch in my mind, where I saw that certain things were going to be more important than money or having people like me. I realized that I was okay with myself and who I fundamentally was. Looking back on all of my past self-development, I saw that they’re all connected to authentic happiness.

I started thinking more and more about how the technology or business consulting projects that I did were giving people the ability to live a fuller life by leveraging technology—yet I never helped them to uncover the root of the issue. When I think about the projects and work that made me happiest and were the least stressful, it was when I was working on the root of the issue, not just the solution, and working toward what I want rather than what I didn’t want. It was about allowing people to be who they wanted to be by using technology.

Now, I focus on working with my clients to change their underlying constructs and thoughts rather than just using a “Band-Aid” solution. My true calling is to help people be their true selves—instead of sheepishly following society’s rules, constructs, and expectations. When I realized that the best way I can help people is with life coaching, I devoted the past few years researching and taking multiple life coaching seminars, podcasts, and trainings.
Doing something well isn’t enough for me. Getting myself to the point where I’m comfortable working with people to help them achieve the same enlightenment and quality-of-life improvement that has been possible for me.

If you want to explore how I can help you,
please contact me buy clicking on my picture below: