Chatting with Stephen Kellogg ahead of his album release was a total pleasure. I caught him live a few years ago and he was so engaging and joyful as a performer. Stephen will be at City Winery in Boston on Wednesday as he starts a national tour in support of his latest record, Objects in the Mirror. The album is rock-solid–great lyrics and a nice balance of songs to turn up and songs to lean in closer. We got the chance to talk about the process and unlocking some of these new songs, the rules that seem to govern songwriting, and why they should be ignored.

RLR: There’s a real sense of reflection and taking stock on this record–how do you think about the songs in conversation with each other?

SK: I’m glad it’s coming across that way. For the last ten years, I’ve been looking at my albums as letters, or as documents of my legacy. It’s come in and out of focus at various points and I’ve been clearer about what I needed to write about and one thing that happened really nicely on Objects in the Mirror is I don’t have any reservations about what I’m saying. There were times on other albums where I’d delve into a topic or insight where I was thinking, “I’m going to try this out and see how it feels,” or “I think I might believe this.” With this album, and with the help of my co-writers and the people who helped me shape the songs, I feel really comfortable standing behind what’s being said and it feels really important to me.

RLR: So as you write a song and have a certain stance, how do you think about that negotiation with a co-writer, or an instrumentalist and what s/he will lend emotionally to a song?

SK: Maybe it’s a product of being 41 years old, as opposed to being 25 or 35, but when I’m writing for me and once it became clear these songs were going to be on my record, my feeling is that I’ll have the conversation as much as is necessary, but ultimately it’s going to be what I want it to be.

With the lyrics in particular, there were suggestions that were made, especially by Eric Donnelly, who’s a co-writer on a lot of them. We’d finish a song, and then he’s call me at midnight, and say, “Hey. I was thinking you should use this preposition.” And I’d be like, “Eric! We’re done with this one, let’s move on,” and then I’d hang up the phone and sit there and think, “Damn it, he’s right. We gotta change it.”

And my feeling is: tell me why, defend your position, and if you can make a strong case, I’m willing to get behind it. And I just know from experience at this point that if you don’t do that, you regret it. Because I have to stand up and sing it every night. So if it’s going to be me as an artist, I want to feel good about it.

RLR: It’s interesting to think about that shift in age. Do you think it was about confidence for you?

SK: There’s a shift that happens, and it can happen earlier for other people, where you move into a different mode of thinking. When I go back to that old way of thinking, I guess it was really a case that I felt someone else knows better than I do. You haven’t tested as many things and you haven’t had as much experience, so you think, “the record label knows,” or you’re trying to please a bandmate. But I think the singer has to believe what they’re singing. It sort of reads as confidence, but I don’t walk around with a Tom Brady level of confidence.

RLR: Yeah, you need a healthy level of self-doubt to be a songwriter.

SK: Yes, and once you get someone you trust to let into this process, you can share my self-doubts. You know that piano song, “Prayers,” I knew that I wanted that on the album, but I worked that one over in the most subtle ways for about ten months, well-past people saying, “No, no, no, it’s good.” But I had to keep tweaking it, because I felt like the message is good, but I was worried that I would say it the wrong way.

You get into songs because they invite you in. “So life did not work out the way you wanted, join the club.” That line hit my radar and I wrote it down, and then you’re following the song down the line and seeing where it takes you. And then at the end, you find this line, “Say your prayers, get off your ass, and get back to work.” And I thought “Who am I to say that to someone who’s been dejected?” Well, I’m someone who has felt that way and I just need to convey that. And this is the kind of thing I’d call Eric about. In the end, I gave him a writing credit, not because of chords or words, but because he just was a beautiful sounding board. He listened non-judgmentally, which if you’re going to write with someone, is kind of the whole dance.

RLR: There’s a line in “Love of My Life,” where you sing, “Saying it simple doesn’t make it mean less.” I’ve talked with a lot of songwriters over the years who would argue that saying things simply is often the goal. Can you talk about that a bit?

RLR: I also love, “Song for Daughters,” and I’m wondering how you think about walking that line between making a song specific enough so that it’s meaningful and broad enough so that it will connect with many people.

SK: I have been told at times that what I’ve written is too specific. You know, like: “Could you write songs with less dates and names in them? You’ll reach more people.” The thing is, I’ve tried. Once in a while I succeed that way. But some of the biggest songs are very very specific. People make rules for their purposes, like: “You can’t have a hit song with a name in it.” And then “Hey There Delilah” is the biggest song for three years. I know enough to know these rules don’t really apply and I am a very specific artist. People aren’t coming to see me to necessarily hear me sing or play guitar; that’s part of what I’m doing, but it’s not the main part, and the audience knows that now and I know that now. So if you try to make me into something other than what I am, I do it poorly. Can you imagine if they said to Josh Ritter, “Hey Josh, can you use less words and not be so educated?” Then what are you left with?

So where I am at is let’s see what happens when we just completely embrace who I was going to be anyway. And I think this record is that. We didn’t worry about genre or think “is this too country?” or something.

You take a song like “Song For Daughters,” that’s a pretty wide song. It’s really a song for women; as I started getting into it, I realized, this is a song for my sister, who’s going through a divorce; this is a song for my mother who’s finding herself a widow; and for my grandmother, and realizing that there’s a story there and the story began because we started simple and small and little. You get something wide, but if I’d started out trying to write the grand opus for all women, that’s a pretty daunting way to approach it. My dream is that girls to hear it and have it resonate and I want men to hear it and say this is the message we want to convey. And I hope these songs find their way to as many people as possible.

You can hear these new songs live on Wednesday, November 21 at City Winery. Get out there, folks!