During the recent Yountville Live weekend, I had a chance to catch up with musician, singer and songwriter, John Ondrasik, who performs under the stage name Five for Fighting. I have long admired Ondrasik, not only because he really knows his way around a song as a wordsmith, but also because he’s somewhat unconventional. He’s given Ted Talks, follows hockey probably closer than he does the music business (he’s a devout L.A. Kings fan), and is a relentless supporter of our troops and first responders. 

At 52 years old, Ondrasik has managed to remain relevant as a musician, singer and songwriter for decades now. And “relevant” is a tricky word. When a critic or writer describes a musician as “relevant”—well, I always wonder, relevant to whom? To strangers, their fan base, the Billboard charts or radio stations? To the test of time, critics or the Great American songbook? 

The artists I’m most interested in learning from—whether they’re musicians, songwriters, winemakers or chefs—are those who remain relevant, above all else, to themselves. They still manage—despite all the noise, rejection, critique and judgment—to embrace their own unrelenting, stubborn originality. Even if half the time, they privately wonder if they suck, they still keep creating. Because they have to. To stay awake. To feel alive. Because to be unapologetically inventive is to keep fighting. 

John Ondrasik: I was really fortunate to come up during the last wave of the music industry. I still remember the days of record stores—I used to go and play there…you know, I’d play at Tower Records. Three hundred people would show up. Then, all of a sudden, Napster came. iTunes came. Downloading came. And the entire industry changed overnight. Radio used to be so diversified. There were hundreds of independent radio stations playing what they wanted, and over the years, it’s been consolidated to mostly a handful of big conglomerates, so I was really blessed to catch the last wave. My songs sold some records.

But it’s a completely different universe now for artists. I’m 52 years old, and radio doesn’t necessarily want to play songs by artists my age, so you find yourself thinking; what else can I do to be creative? How can I keep writing songs? How can I get people to still show up and listen? I started to do keynotes, Ted Talks, symphony shows, quartet tours… And, you know, I’d rather do these things, too. You have to be able to adjust and change the field of play to survive, but these challenges make it fun for me, too. 

It keeps things new. I don’t mean to sound jaded, but if you’re lucky enough to have a hit song, you end up playing it 10,000 times, so you have to think of ways to keep it fresh. At every show, there’ll be someone that will only see you that one time in their life, so you need to give them something that has that special energy and integrity. For me, discovering all these different career permutations just keeps it fun.

JO: It’s a double-edged sword. Technology has kind of lead to this generic type of music. In one way, we’re much shallower than we’ve ever been. On the other hand, you can now make a record in your living room. Kids at the grocery store might hear one of my songs, Shazam it, and then they own it—just like that. There are some beautiful things about technology, too; it’s allowed us to consume music more easily than ever. The question becomes, Is there a way for musicians to make a living at music nowadays? That’s what I worry about as a music fan: will the next generation of artists be able to make a living at making art? You just have to be creative and still do the work, still build relationships, but without a doubt, what worked for musicians 15 years ago doesn’t work now. 

I tell these young kids all the time, the ones that want to be famous, be rock stars, have a number one single…I tell them: You know what you really want? You want the kind of career that lasts, so that when you’re 50 years old, people will still show up and buy tickets. That’ what you really want. Because that means you’ll be able to practice your craft for your whole life. That’s the dream come true. 

JO: That’s an hour-long answer, because you can define success as “commercial success”—sales, chart positions, how many tickets you sell—or you can measure success this way: am I getting better as songwriter? It’s kind of like comparing Justin Bieber to Leonard Cohen. Both very successful, but those are different definitions of success. Certainly you want to have some commercial success so that you can at least make a living. That’s very hard. It’s just like trying to be a successful winemaker in the Napa Valley. There are probably millions of people who dream of doing it, but only a few thousand are actually going to make it. Same with singer-songwriters—millions want to make it, but many don’t. It’s very hard to make it, actually.  The problem that I see with our culture is that younger artists measure success as just commercial success. That path doesn’t necessarily lead to fulfillment. For me, success is being able to feel good about an experience, whether it’s giving a live performance or a keynote speech, writing a song with someone, writing a musical or a song for a television show. Whether it takes off or not isn’t really what matters. What matters to me is whether or not it was a good experience. 

JO: After 9/11, I started to get emails from our troops in Iraq, basically saying they were listening to my music—sometimes before going on a mission, sometimes before returning home. That showed me how much music can help our troops with morale. And then I met troops that were suffering from PTSD and learned that music can be a healing factor for them, so I became very honored to perform for them. I also think we take our freedom for granted in this country. As artists—people who make wine, food, music—that’s something that in a lot of countries you can’t do. We sort of take all that for granted here. Troops protect these freedoms. Troops allow artists to play in our sandboxes. For me, it’s an obligation to recognize them and thank then, not only for our security and for protecting our families and freedoms, but for allowing me to do what I do. We have a VA hospital show coming up, and USO shows, too. I mean, I can’t drive a tank, but I can write a song.