Make The Best Decisions You Can Make

Lessons from the stage of two defining shows

The dawn of 2016 brought a whole new sense of purpose into my creative world. I got to headline two big venues in a row on opposite coasts — one in Burlington, VT and one in San Francisco, CA — and performing hasn’t been the same for me since.

The first show was at the Flynn Center mainstage in Burlington, Vermont the evening of December 31, 2015 for a headlining performance at First Night Burlington. It was a big, celebratory night to help promote my latest album My Hero, The Enemy — my ninth (9) studio album to date — and I had a fiercely talented six (6)-piece band backing me throughout the evening. It was an unforgettable performance from everyone in the Gregory Douglass Band (all names below!), an incredible light show, had pristine sound (both off stage and on), and an enthusiastic audience. I had a line of people waiting to talk with me and get their CDs signed after the show — many of whom have been strong supporters of my music over the years, yet for some reason I received more gratitude and encouragement than ever before at this show. Every aspect of this performance seemed to make all of the difference for my fans, friends and bandmates — and it made all of the difference for me too.

Headlining the Flynn main stage was quite literally a dream come true for me because I grew up attending so many concerts there. I was born and raised in rural Vermont, so seeing shows at the Flynn was a serious night out in the thriving metropolis of Burlington. The Flynn has been a pillar of the arts community in Vermont for over 80 years, and it introduced me to some of the most influential artists of my formative years. I remember seeing Tori Amos at the Flynn on her Under The Pink tour when I was in middle school. It was just her and her piano, and seeing such a raw and masterful one-woman show helped me understand what I wanted to do with my life. Her songs felt like diary entries and her piano-playing was beautifully hypnotic. I was listening mostly to mainstream pop music of the 80’s and late 90’s up until then, so I became obsessed with the idea of an artist writing and performing their own music so vulnerably after seeing Tori Amos live.

Over time, Tori’s recordings taught me how to play the piano and how to craft songs that take the listener on an emotional journey. Her songwriting introduced me to the profound importance of conviction and truth in song. I even had the opportunity to meet her briefly backstage after that first show at the Flynn. She was still relatively unknown enough to meet and greet her adoring fans after performances back then. Her encouragement gave me license to follow my own dreams that night. I didn’t know it at the time, but her music may have saved my life throughout my youth. I know my music has done the same for others over the years as well, so it’s humbling to honor where it all began.

I’ve seen so many of my musical heroes come through the Flynn — Shawn Colvin, Patty Griffin, Alison Krauss, Kronos Quartet, Neko Case, October Project, and so many others. October Project was an emerging band I was introduced to by my late stepmother, Shari, when I was 13. She owned the local video store in town and always got advance screeners of new movies and albums, so she often brought them home for my sister and me. I think she judged a book by its cover, and her instinct told her I might like the new October Project album. I wish she were alive today to see what an influential band they became for me. I’ve even had the chance to share the stage with them and their former lead singer Mary Fahl time and again. I know Shari would be so proud.

October Project at the Flynn was one of the most memorable shows I’ve ever seen. They had such a distinct sound, and a unique configuration to support it live — Mary Fahl on lead vocals, a female and male backing vocalist, two keyboardists, two percussionists, a violist and cellist, a guitar player and a bass player. Mary’s voice commanded the stage like no other — deep, haunting and powerfully resonant. She was like a priestess of truth leading a sermon with an evocative choir supporting her. I felt like they were casting a spell of enchantment throughout the evening, and the collected nature of their sound consumed me. That performance made a lasting impact and solidified them as one of the most definitive bands to shape my own future of songwriting.

Needless to say, the Flynn has always been a benchmark for my musical aspirations, so it was a true honor to finally perform on the same stage that so many distinguished artists played on before me — particularly those who inspired me to pursue music in the first place.

Throughout my 15+ years touring independently, I have mostly performed as a solo acoustic act or within a duo/trio configuration. It has always been more financially feasible to tour this way than to tour with a band. This decision was always a blessing and a curse. On one hand, I’ve built a long career of performing in wonderful, intimate “listening rooms” — meeting and sharing the stage with some incredible fellow singer/songwriters, and performing my songs in their original, stripped-down form. On the other hand, most of these singer/songwriters were a lot more folk, Americana, and bluegrass than my music has ever been. I’ve been something of a “black sheep” in the singer/songwriter community because these listening rooms were coveted by a strongly protective folk community, and I simply didn’t “belong” in the folk community by many of their standards. Concert promoters never really knew what to do with me, and I was often paired with artists I wasn’t a good match for.

I was also recording studio albums that featured a full band and big productions. Most of my albums are a wall of sound from a production standpoint — each song more layered and diverse than the next, so it was a shame not to have a designated band to showcase my music on the road outside of the occasional album release show.

The money just wasn’t there to sustain it all; I was swimming upstream.

I continued fighting against the current for sustainability’s sake. There wasn’t much enticing me to make a band a priority from an economical standpoint, so I wasn’t willing to acknowledge how much that decision might be limiting my creative expression overall. It wasn’t until these two defining shows of early 2016 that I began to realize the gravity of these limitations.

The New Year’s Eve show at the Flynn was followed by another unforgettable album release show at The Chapel in San Francisco on January 10, 2016. I chose to present each of these shows as a “live album” performance, so the Gregory Douglass Band performed each song in the same order as it appears on the album. I wanted these shows to be extra-special and highly memorable for folks to experience, so with the help of team support, I went all-out for them. We assembled a four-camera video crew for The Chapel show in San Francisco, a multi-channel audio engineer and a lighting designer specifically to capture a top-notch video and audio recording of the night. The goal was to eventually release it all as a live album and “rockumentary,” and make use of select content for various ongoing promotion of My Hero, The Enemy — a project that many supportive patrons are currently helping me to produce.

We promoted each show as “official” East Coast and West Coast pre-release shows for My Hero, The Enemy because they were it — just two (2) shows. This was a departure from every other album I’d previously released because there was always a release tour that followed. As an indie musician, touring has been the only way to pay my bills, so I’ve always followed the same rules — write, record, release, tour to promote the release, rinse and repeat.

But this album felt different. The production on My Hero, The Enemy was so epic that I wanted to honor each song by presenting it the way it was recorded. So I opted to forgo any big album release tour and instead pour all of my time, money, resources and heart into two BIG release shows — BIG by indie standards at least :)

There were no corners cut in the planning process, and this decision changed everything.

The decision allowed me to take a “quality over quantity” approach to these shows. The outcome laughed in the face of my 15+ years spent as a tour hound — always trying to conquer the world with ambitious goals like “25 shows in 30 days,” and harboring a semi-masochistic sense of pride by attaining such lofty goals. Presenting two quality album release shows instead of a large quantity of album release shows was all I needed to celebrate the new album in style.

Taking a quality over quantity approach proved to be an astonishing way to present myself as the complete artist I have become while making each event the best it could possibly be.

I was able to put all of my energy, resources, promotional efforts and heart towards two (2) shows instead of stretching myself thin to semi-promote a string of 25 shows in a row. The experience was far more rewarding from execution to completion, and each audience got to experience a Gregory Douglass performance that was more fully realized than ever before.

This quality over quantity approach is something I’d like to apply to my work and my life moving forward.

I still love performing solo as much as I do with a band, but there’s no doubt in my mind now that every performance has to be the best it can be moving forward. This will call for a big shift in my touring plans from what they once were — and touring will likely happen less often, but any future show should offer the most memorable experience it can for everyone involved because that’s the best decision I can make for my live performances.

The most important lesson from these defining shows is this: every decision you make in life should be the best decision you can possibly make for yourself.

We try to cut corners far too often in life, and we half-ass things in the process of poor decisions or limiting beliefs. I believed I could only afford so much for many years instead of thinking outside of the box, and it stifled my creativity. I cut corners instead of being more thorough, and it limited my exposure. I half-assed my promotional efforts to cover a larger quantity of tour dates instead of giving every booking the promotion it deserved, and many of my shows were poorly attended as a result. I made poor decisions that lead to disappointing outcomes instead of making the best decisions I could for the best possible outcomes. I lost track of who I was in the process and what I’m truly capable of as an artist instead of honoring the artist I have become and making the best decisions I can to support that.

Every creative decision I make brings a sense of purpose to my life. It reminds me of who I am, why I’m here, and where I belong. But every time I make the best creative decision I can possibly make for myself at any given time, I feel a radical sense of inner purpose — like I’m fully awake, alive, aligned — absolute.

So honor who you have become, and make the absolute best decisions you can to support your beautiful self. Aim for radical inner purpose.

Here’s my mission

I want to change the dialogue on inner purpose. We all want a “life worth living for” before we die, so I think we need to start “living a life worth dying for” while we’re still alive. Too many people look back on their lives with heavy hearts full of regret when they could be living with radical inner purpose. So what are you dying to live for? Go ahead, get creative…

RIP (Radical Inner Purpose),

-Gregory Douglass

“Point of View” is a sneak-peek of the Live From The Chapel project. Live From The Chapel is a “rockumentary” film & live album in the making. My Patreon members are helping to make this project possible and already have access to tons of content from this project and more… Click here if you’d like to help me sustain all this creativity too.

The Gregory Douglass Band members in San Francisco included: Monique Citro on cello, Lisa Piccirillo​ on vocals, Seth Thomas Barbiero​ on bass, TJ Piccirillo on guitar, Ben Cassorla on guitar, Matt Bogdanow on drums, Jane Boxall on marimba & Glory Douglass Reinstein​ on clarinet.

The show was presented by EBH Presents & sponsored by Magnify. Eric Hanson was the Executive Producer. The show was filmed by Lash Music Media and is currently being edited by yours truly. The audio was recorded by Nic Pope at Different Fur Studios and mixed by Mike Tuccillo.

Special thanks to everyone involved with making this project possible: the band members, everyone behind the scenes, everyone who attended the show, and all my current patrons at Patreon.

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