The Unexpected Rewards of a Circuitous Career Path

On trusting my gut, and taking leaps of faith

Ron Diamond
5 min readMay 4, 2022

Roughly each decade or so, I’ve gotten a little bored with my career, and pivoted to something different.

So what have I learned from all that …?

“Two roads diverged in a wood, and I —
I took the one less traveled by,
And that has made all the difference.”
— Robert Frost

It was exactly 40 years ago today that I got one of my early big career breaks: My first day as a “summer replacement technician” in the Engineering department at WNAC-TV, Channel 7 — Boston’s CBS television station.

Which is a fancy way of saying I’d end up working behind the scenes for the summer, in various capacities … doing technical direction, audio engineering, studio camera, lighting, videotape, video shading, master control, and more … to help create television seen by hundreds of thousands of people.

Quite a step up for an aspiring engineer/producer just trying to make a living in Boston radio.

Before I started the TV job, though, the station’s chief engineer warned me that — because the station was about to change ownership to another company — he couldn’t actually guarantee me more than 3 weeks’ worth of work.

Despite the uncertainty, I took the job anyway … and ended up staying nearly 10 years.

In the facility’s first stereo audio control room, designed & built in 1986.

From New England, I took another leap of faith, and moved across the country to pursue a new dream of working in post-production, in Los Angeles.

Armed with stubbornness, determination and dumb luck … after a while, I found myself as a picture editor working on television and video productions seen by millions of people, around the country (and even around the world).

I became part of dozens of projects, airing on many of the major broadcast & cable TV channels … including network primetime specials, documentaries, news, reality, magazine, promos, game shows, poker shows, plus DVD supplemental features, and more.

As a freelancer, a single phone call could mean a gig that’d last anywhere from an afternoon … to a couple of years. Which was an ongoing routine that made me decidedly more agile.

And in working all over Burbank and Hollywood, I continually appreciated being surrounded by the most talented population of creative people on the planet.

Besides collaborating with a number of established directors, producers, and other personnel … along the way, I got to work with up-and-coming talent like Anderson Cooper, Lisa Ling and others — before most people even knew who they were.

Being in the entertainment industry also yielded some unexpected opportunities:

  • Co-authoring one of the preeminent textbooks on digital Nonlinear video/film post-production;
  • Getting a private tour of the West Wing of the White House;
  • Visiting other cool places: backstage at Saturday Night LiveThe Tonight Show with Johnny CarsonLate Night with David Letterman … and even a full day on the set of Star Trek: The Next Generation.

And a lot more — whenever I allowed my world to open up, to look outside it.

After about fifteen years of living the dream in Los Angeles, I took another leap of faith, and pivoted into … software development, for mobile apps.

And with some single-minded persistence, things ultimately worked out pretty well.

There’ve been Fortune 500 companies, and small startups, and places in-between … fascinating projects and cutting-edge work … and amazing teams I was privileged to learn from, and be a part of.

Eventually, I was able to mentor others in turn. And occasionally, when I had something particularly useful to share, I was even fortunate enough to offer it to audiences at conferences.

More recently, I’ve focused on mobile software architecture … helping to develop and inspire best practices for software development teams as a whole.

So it’s been a great run. But why recount all of this now?

On this — for me, a somewhat momentous anniversary …
I can’t help looking back, and marveling at the variety of endeavors I’ve been honored to be a part of.

I’ve been extraordinarily lucky to have a dizzying number of great collaborators and mentors — including people who took me under their wing, patiently showed me the ropes, and gave me the encouragement and latitude to succeed.

It’s been an exciting journey.

… And my biggest takeaway?

Each time I felt compelled to make another leap and follow my muse — and was able to set aside preconceptions about what I was “supposed” to be doing — it freed me up to explore things I might not have considered.

In Radio … Television … Post-production … Software …
For about 100 companies in 30+ years …

The irony is that by NOT planning out a career too far ahead … giving myself permission to explore different areas along the way that struck me as interesting … and being open to change when it seemed like the right thing to do … I found myself rewarded with a career path more fulfilling than anything I could have mapped out in advance.

So I hope this story inspires you, just a little:

Not to be afraid to reinvent yourself occasionally, and try something new.

Even a dream you dared not hope might come true … may be out there, waiting for you right now.

With a bit of curiosity and openness — all kinds of things become possible.



Ron Diamond

Personal blog (from a guy who’s made software, and video, and other stuff too).