I’ve kept a frequent presence at rock concerts ever since I was a kid. Back in the day, live rock and roll shows were reasonably affordable—even if you did have to sleep on the street to get tickets—because bands toured in support of the latest record they had produced. Live shows were a catalyst for selling singles and albums, pushed local radio play, sold t-shirts and memorabilia, and paid for the road antics of the bands who could live and party on “permanent vacation.”

The concert world today is obviously different because the ecosystem is so drastically different. There are still monster arena tours like U2, Springsteen, or the Rolling Stones 50th (gasp!) corporate sponsored anniversary. There are small gatherings of devoted fans at venues around 5000 seats for tireless road warriors like Cheap Trick or Chicago. There are nostalgia plays in casino showrooms or destination bars with one or two surviving members of one-hit wonder acts. And there are tremendous new stars like Adele who play the old game a new way and can still fill amphitheaters at top prices, sell plenty of music downloads, and inspire faith that the CD has a tiny bit of life left for the bygone tribe.

What I have noticed over the course of this music evolution is the underlying key to longevity and not moving down the food chain hasn’t much changed—the survivors tend to deliver a healthy balance of old and new material. This is no small problem, as the fans who come out to concerts are no doubt screaming for an artist to play their big hits. It’s natural. It’s satisfying. It’s a trap.

A few weeks ago my wife and I went to see one of our favorite groups, the still somewhat niche band Trans-Siberian Orchestra, best known for their annual Christmas shows and the ever-present holiday single, Christmas in Sarajevo. TSO blends heavy metal power chords with classical music and electric violins, usually with an interspersed layer of spoken storytelling. Several years ago they started branching out from Christmas themes, recording and touring a fantasy tale called Beethoven’s Last Night. This was the first time we had seen the show performed live, and while it was familiar to us, it was not well-known to much of the devoted audience. That was pretty brave, I thought, to tour a concept album that was not necessarily top of mind with their audience, but then they did something I found even more courageous. Toward the end of the show, when they had finished playing Beethoven and the audience expected they would play some oldies, they instead played several entirely new songs that had not even been released online. No one had heard these songs except those who had seen the tour, and the applause following was as you might suspect a bit tentative. The nervous quiet during these songs was not because they were bad, it was because they were new. If you are a regular on the live music scene, you know that awkwardness—but without it, there are no new hits.

New music has to be debuted at some point, that’s why it’s called a debut. Audiences can be very tough on new songs, they pay good money to hear hits and the survival of any act is contingent on meeting the expectations of fans. Yet long-term success is equally contingent on innovating, and facing an audience with the unknown or unfamiliar is always a daunting prospect. Who would willingly trade thunderous applause for quiet, polite clapping? The greatest acts know they have no choice.

Most of the hot Top 40 bands in the 1970s and 1980s would periodically release Greatest Hits albums, mechanical collections of their charting singles, usually pushed by their record labels for bankable cash acceleration. Some of these became all time bestsellers, notably The Eagles and Elton John. The question I always used to wonder when I handed over my cash for a dozen song vinyl collection was whether this was the end of the band or the beginning of a new chapter. For too many, we know how that played out, and we know where those bands are playing today, if at all. A Greatest Hits or “Best of…” album was easy money, the equivalent of predictable thunderous applause. Pushing out new work would remain the heart of risk, and the genesis of going to the next level.

Nothing about this cycle is unique to music. Business is the same, especially technology wrapped as consumer products. You need to play to your familiar success, the current incarnation of your brand, but the moment that catalogue is fixed, you’re doing dinner theater rather than headlining at Carnegie Hall. Think RIM with the standing ovation worthy Blackberry, Kodak and Polaroid with endless scrapbooks of silver snapshots, perhaps now Best Buy longing for a different curtain call than their former contender Circuit City. They all climbed the charts, but staying there remains a different story.

Steve Jobs liked to say that he never believed in focus groups, because it was not the job of customers to tell you what they wanted—how could they know what they wanted when it hadn’t yet been invented? No civilian could concretely describe iTunes, the iPod, the iPhone, or the iPad prior to their release. You can only imagine how many pundits prior to the success of these inventions could tell you of their impending doom solely on the basis of unfamiliarity. Of course Apple never stopped marketing its core line of computers during this unbelievable expansion of reach, they were still playing hits while composing new material and seeding it to the faithful, those with whom they had established profound affinity and could ask to trust them further with the unknown.

I also don’t think it is a coincidence that Steve Jobs was a huge fan of The Beatles, who in an active career that spanned all of about eight years never stopped putting out new material, took themselves off the road to focus on composition and the creative process, then reinvented their sound with almost every album, including a few radical pivots like Sgt. Pepper. Is it counter intuitive that the actual career of The Beatles was so short despite all that new material and no Greatest Hits collection until after their break-up? Possibly, but if impact is the name of the game, it is hard to dispute that The Beatles succeeded most of all at avoiding that most dreaded of dead-ends, The Greatest Hits Graveyard. Their incomparable legacy remains vibrant because they pushed themselves so hard to be innovating all the time while crowd pleasing.

Celebrated descriptors like “Built to Last” and “Good to Great” are hard-won praise tied to nimble companies for navigating the same difficult balance for so many years of reinvention. It’s a lesson in courage and vision that is as difficult to learn as it is to replicate, but it is that very bravery that can guide any individual career from ordinary to enviable. Facing the anxious reception of the untried might not be pleasant when a clear alternative is available, but it’s the only trail that bypasses the one-hit wonders.