There’s no question Broadway mainstay Sierra Boggess is one of the most beloved Main Stem actresses of our generation. Whether she’s an inquisitive young mermaid looking for legs, or a stern school principal without a leg to stand on, audiences can agree she meets every role with a warmth and tenacity all her own. Now, after a worldwide tour that brought her to London, Paris, Australia, and Japan, she’s back in the States, primed to unveil her latest solo act in a five-night stint at New York hotspot Feinstein’s/54 Below. A revamped edition of her 2012 Awakening, which she also premiered at the intimate venue, the evening promises an eclectic array of stories and songs that heal the heart and enlighten the mind, all delivered, of course, in signature Sierra style.

In anticipation of the big New York homecoming, we sat down with Boggess to discuss career revelations, set list surprises, her undying love of Barbra, and much, much more. Have a look at her answers below, and always remember, as she’d want you to know, “you are enough. You are so enough. It’s unbelievable how enough you are.”

Can you give a quick overview of your concert? What can audiences expect? 

The bones of this concert are based around my first Feinstein’s/54 Below show called Awakening, which I created back in 2012, and that was an amalgamation of different pieces that inspire me. But it’s not the same show, no. It’s morphed and evolved since. This year, I’ve have been concerting all over the world — I was just in Australia and Japan doing this concert — so, one of the things I’ve added is a whole section talking and singing about Australia and the inspiration I’ve drawn from that [experience].

On the whole, the show is mainly just about connecting with what is going on in our world right now, and understanding how important it is for us to recharge. I think we’re all light workers…. so, I want this concert to be something where people can come and relax, recharge, and feel inspired to then go out and continue putting good energy into the world, trying to heal our planet… things like that. That’s my aim.

What I don’t ever want my concert to be is just me singing my résumé at you. But that said, there will be some fan favorites in there. (laughs) It’ll be a little bit of everything… and more.

Can you describe your process in choosing the set list for this show? Knowing your theme, were there any specific songs you knew you had to include? 

Well, I plan, again, the songs that I know people are going to expect from me knowing what I’ve done throughout my career. So, you’ll get your Little Mermaid and your Phantom of the Opera… But then, I also plan what I want to talk about, in terms of inspiration and things like that, and then I pick songs that express those ideas, and go from there.

And let me tell you…. there’s a lot of really good stuff to talk about right now in terms of what’s going on in our country and in our world, even without being on one side or the other — although, I mean, for me, there’s obviously a right and a wrong (laughs). But regardless, it’s great to be able to use this art form as a way to sing out our issues, and to hopefully encourage people to live in their truths.

And on that note, I’ll say that we’ve added a new bit to the show. For the first time in a concert setting, I’m going to be singing the song that my character sang in It Shoulda Been You. [It’s] called “A Little Bit Less Than,” and it’s a really awesome theme song for living your truth and being who you are.

That song was really powerful and special to me, especially at the time when we were doing the show, as that was the year the Supreme Court passed the law in favor of gay marriage in all 50 states. I just feel compelled to say, with everything that’s going on in the world right now, that’s it’s the right time to bring that song back and sing it in my concert. So, that’s what we’re going to do.

How does your approach to cabaret differ from that of a Broadway show? 

For me, it’s a totally different animal in the sense that I get to be completely 100% myself. Even though I may be singing songs from shows that I’ve been in, I’m not completely in the character as I was when I did the show I’m singing the number from. I guess, in that way, it’s a little bit of both [me and the character], but it’s also reimagining the song and presenting it in a new way. I get the chance to explore within and speak from the heart. That’s why I love concerting so much. You get the real me.

In addition to your eclectic setlist and songs of inspiration, your show will also feature your sister Summer, on cello. Can you speak a little bit about your relationship with her and how you bolster each other as performers? 

Well, let me say, too, that my musical director, Brian Hertz, is actually my brother-in-law — he’s married to Summer — so it’s really been the three of us on this whirlwind journey across the country. We’re just a very tight-knit group. Obviously, we know each other so well, and we understand the whole intention behind why we’re doing these concerts.

And Summer and I…you know, she’s my sister. We’ve been best friends since childhood, and we grew up playing music together with our little sister, Allegra. The three of us used to play together all the time.

As a musician, I just love the way that she plays. I love her sound, and I think she’s one of the most extraordinary cellists out there. And then, as my sister… she just means everything to me.

We have the ultimate trust in each other, and again, we know each other so well. It’s just really special to get to travel the world with each other, and with Brian. You know, if you get to choose who you’re traveling with and where you’re going and who you get to make music with, this is, like… the ultimate group for me.

Moving toward your theatrical work, you’ve had quite the varied career as a performer, both on Broadway and abroad. Which of your Broadway characters would you say has taught you the most about yourself?

Oh, wow! What a question! (laughs) I mean, it sounds like such a cop-out to say all of them, but when you look at the range of characters… how could you pick just one of them?! Even just thinking about my last role on Broadway, which was Rosalie Mullins in School of Rock… that brought out a whole other side of me. I actually based the role around my sister Summer. (laughs)

But the qualities of Rosalie I just loved so much. She’s really somebody who has forgotten her inner child and forgotten who she really is…but that reminded me to stay in [a state of] childlike wonder. Of course, Ariel — and I talk about this in my show as well — she’s the one that represents that kid, male or female, who feels like they were born in the wrong body, the wrong place, the wrong time. It’s, like, really deep stuff.

Christine is the person that loves the unlovable, and I feel like I’ve always been like that — much to the detriment of myself in my relationships — but I think that’s why I respond so deeply to somebody like Christine, and I think that’s why audiences do as well.

Obviously, Rebecca in It Shoulda Been You, just by the fact that she’s choosing to be who she is and knowing that she’s enough — a lot of people know me now for my quote, “You are enough. You are so enough. It’s unbelievable how enough you are” — and the fact that I got to do that role and live and embody somebody who had to learn to just be their “enough” was gratifying in itself.

Sharon Graham in Master Class, which I also did with Tyne Daly… she, too, goes through a similar journey. She’s the girl who is singing a song she really should not be singing, but she’s so adamant about doing what she wants to do for a living, that she learns to push herself that far anyway. That taught me a lot.

There’s just so many things I’ve learned, I tell you! They’ve all just affected me so much. So, that’s why I have to give you, like, the longest answer ever (laughs).

In addition to your celebrated Broadway résumé, you’re also known, as you mentioned earlier, for your mantra, “You are enough. You are so enough. It’s unbelievable how enough you are.” Although you’re clearly a firm believer in this statement, has there ever been a time when you felt you weren't enough? What did you do about it? Do you have any advice for someone who may be stuck in a similar position? 

Oh, sure, all the time. Actually, when I first heard those words said to me, it was just as an off-the-cuff remark in a masterclass, and I wrote it down ‘cause I thought it was hilarious. But as the years have gone by, it’s actually come to take on quite a meaning for me, and resonate, to the point where I realized, “Oh my God. Wait a minute. This is actually a war cry.” And it’s helped me a lot in deep, dark situations.

But what I also want to say to people is that with this quote and with all the other ones I try to live by and put out in the world, I’m also putting them out there because they’re what I need to hear for myself. It’s such a misconception that once you say, “You are enough, etc.” that you just never feel less than. It just isn’t true.

[Repeating the mantra] is always a constant practice. It’s like anything — yoga, meditation, or even singing or painting or what have you — it’s a daily practice of choosing a mindset to come from a place as “enough.”

We live in a world and in a community where people are always striving for perfection, and things like that are just so unhealthy. It’s really important to take that “perfection status” out of the equation. Stop striving for that — that’s not a thing.

As for resources, I love Brené Brown. You can check out her books or listen to her TED Talks. That’s some really good stuff I would offer up to anyone who needs it.

And I just think once [those ideas] get articulated well, you get to decide. You get to actively make a choice and co-create your day based around being enough, or coming from a place where you’re just not. Which one feels better to you? Do you want to live in a world of your own “enough-ness” or do you not? The decision is up to you.

You’ve had quite the array of experiences as a Broadway leading lady. With all you’ve done and all you’ve learned about the business since your debut, what’s the best piece of advice you could’ve bestowed upon pre-Broadway Sierra? 

I would encourage myself to recognize and to make sure that what I’m doing for a living is not my only identity. Does that make sense? ‘Cause if you’re only identifying with being a performer on Broadway, and then things aren’t going well, then what actually are you? What is your identity? And if things are going really well, again, what are you? Are you just that? Or are you anything else?

We think, especially as performers, “Oh, when I get to Broadway, then I will have arrived.” But it’s not just about arriving. In fact, the arrival is actually this living, breathing entity that continues to be its own form of journey.

So, I’d tell pre-Broadway Sierra not to get too caught up in the “arrival” of it all. Just continue the journey, keep on doing the work, and enjoy the ride.

Shifting gears a little bit, let’s pretend you’ve won the chance to duet with one person, male or female, living or dead. Who would it be, and what would you sing? 

Barbra Streisand. Everybody who knows me knows I’m going to say that. (laughs). And what would we sing? I’d have to ask her what she’d want to do. (laughs). I wouldn’t dare to tell her what to sing. Whatever she’d want to do, I’ll do. I mean, she’s Barbra. Why not?

Along with your mantras, you’re also known within the community for your routine of picking angel cards before any given show. Can you speak about why it’s important to you to be connected with each of these words during a performance? Why is that ritual so essential to your daily life? 

I don’t remember exactly when it became a ritual… I think it happened while I was in London doing Love Never Dies. The idea is just that as you’re doing eight shows a week of the same thing over and over and over, sometimes your brain can get a little bit unfocused, you know? So, I started pulling a word each day, just to focus myself for each performance. It’s been a really awesome thing to do, and I’ve passed the practice on to a lot of other people through the years.

When I left School of Rock, I gave all the kids their own box of angel cards, ‘cause they’d always come into my room and pull words for themselves. And then, when I went to Paris to do Phantom over there, I bought the angel cards in French, so I could pick a word in French. It was so awesome, and then of course, the show didn’t happen. But still… (laughs). 

And when I’m not in a show, I’ll just pick a word for the day. I mean, I don’t pick a word every day, because I also don’t like the idea of getting too locked into something, but I do enjoy the ritual of picking a word and having it center me. It changes my day for the better, in ways I could never expect.

In that same vein, if you could pick an angel card to describe your Feinstein’s/54 Below show as a whole, which one would you choose? 

Ooh… cool question! Okay. I’ll say…. (pause) “Inspiration.” Yeah, that’s a good word. I think I’ll go with that.

Boggess’ self-titled solo show plays Feinstein’s/54 Below (254 W. 54th Street) September 4th & 6th-9th. For tickets and more information, please visit www.54below.com.