Rob and Jackie Wolf: “Don’t spend too much time inside your own head”

Jackie — Don’t spend too much time inside your own head: I am an overthinker by nature, but spending too much time stirring around in my thoughts never ends well. Rob — Expect it to be a long and bumpy journey, when moving to Nashville it came to be a quick realization that this is a city full of people […]

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Jackie — Don’t spend too much time inside your own head: I am an overthinker by nature, but spending too much time stirring around in my thoughts never ends well.

Rob — Expect it to be a long and bumpy journey, when moving to Nashville it came to be a quick realization that this is a city full of people with the same dream.

As a part of our series about rising music stars, I had the distinct pleasure of interviewing Rob and Jackie Wolf.

Rob and Jackie Wolf are relatively new to the Nashville Country music scene, a brother and sister duo based in Nashville, TN. hailing from Southern Montana, near Bozemen. Jackie is a graduate of Belmont University with a degree in Music Business and Rob started playing at age 15 in coffee shops and recently moved to Nashville. The duo is currently playing smaller, quaint venues in Nashville together, such as Alley Taps and similar venues to build their fan base. Jackie was about 7 years old when she fell in love with music and Rob was first bitten by the music bug in school productions in the 5th grade, but really dug in deep his freshman year of high school when he learned to play a few chords on the guitar. Although he always thought he wanted to be a pilot or pursue baseball. Rob’s music career was born while he worked as a dishwasher at Sage Lodge in Paradise Valley, MT where he eventually performed every Friday night. Jackie discovered some old videos of Elvis on YouTube and at that moment that she realized what it means to be an entertainer and how deeply that can move people. Together, they write their own songs from personal experiences, books and stories heard from friends and strangers. “Montana” is a song Jackie wrote when she first got to Nashville and pursuing a solo career in music. She was living alone and incredibly homesick and this is what came out at that moment. It is an ode to the place that made her who she is, and always well-received when played live. “Hallelujah” by Leonard Cohen also is a fan favorite they perform live and seems to get the best reactions from the crowd. Another song they co-wrote is a deeply personal song about the pain and struggle of addiction called “Mama, Don’t Give Up” that many people seem to relate too. The up and coming duo is writing and soon hope to be in the recording studio to put together their debut EP project.

Thank you so much for joining us in this interview series! Can you tell us the story of how you grew up?

Jackie: Thanks for having us! I was born in Maryland and spent a lot of my childhood running around with my sister and brother in the Appalachian Mountains or on the Chesapeake Bay. Eventually my parents grew tired of the fast-paced approach to life on the East Coast, so in 2010 we moved to Montana. There I spent a lot of time skiing, fly-fishing on the rivers, and riding horses. It was wild and rugged and beautiful. To many, Montana is regarded as “the last best place” and I would have to agree.

Rob: Growing up I was always outside doing something I probably should not have been doing. Whether it was playing in the mud in my church clothes, shooting out my dad’s truck window with a BB gun, or getting into trouble with my friends.

Can you share a story with us about what brought you to this specific career path?

Jackie: I don’t think there is any one thing in particula Rob I have wanted to do this for as long as I can remember, so I never really considered a different career path. But there have definitely been moments throughout my life which have confirmed to me that this is what I should be doing. I’ll never forget discovering Elvis for the first time at 7 years old. I found some old videos of his 1968 comeback special on YouTube, then ran and told my parents “this is what I want to be when I grow up”

Rob: I’ve always enjoyed singing while growing up, but there was one particular day when I decided I wanted to dedicate my life to singing. I had my eyes set on playing college baseball for a very long time. But one afternoon after I got done pitching in a tournament in Denver, my buddy decided he really wanted to go to a karaoke bar Rob We finally found one that we could go to since we were only 18. We went and had a great time. I sang two of my favorite songs, and then we went home. My dad then asked me if I had more fun singing or throwing a baseball. I thought about it for a second and came to a realization that I had more fun singing. So from then on I have had my eyes set out on only music.

Can you tell us the most interesting story that happened to you since you began your career?

Jackie: I once ran into Charlie Daniels in an elevator, and he passed away shortly after, but he gave me some wise words of wisdom in that elevator that I’ll never forget.

Rob: After one of our sets someone in the audience came up to me and said she wanted me to sing at her funeral. I said absolutely, and then I was like wait, I hope it’s not soon.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Jackie: Back when we were first starting, we were playing a show at a dive bar in Montana. There was a woman there who was completely gone three sheets to the wind. I have a hard time saying no to people, so when she asked to come up onstage and dance with us, I happily obliged much to my brother’s objection. In the middle of one of our songs people started cheering like crazy — I thought “dang we must be sounding wonderful tonight!” But then I looked back only to find that the woman had taken off her top and was completely nude from the waist up. It was pretty funny, but now we don’t let drunk people onstage anymore.

Rob: Although it’s not really music related, I was fishing with my friend one summer at a lake that we always used to go to. When I was pulling the boat out of the water my truck’s parking brake broke. My nice guitar along with my brand-new truck sunk to the bottom of the lake.

What are some of the most interesting or exciting projects you are working on now?

Jackie: We’re currently writing for our debut EP and are getting ready to record and release our first single. I’ve also got a bunch of cool surfing trips planned this year — thinking about maybe starting a travel vlog.

Rob: Getting into the studio has been a challenge with Covid and just recently moving to Nashville. We are trying to get into the studio as much as we can now. It is so exciting to see our songs come to life.

We are very interested in diversity in the entertainment industry. Can you share three reasons with our readers about why you think it’s important to have diversity represented in film and television? How can that potentially affect our culture?

Jackie: It’s important for all stories to be shared and for everyone to have a voice. Not only is it important for everyone to be represented accurately onscreen, but it’s also crucial that diversity extends to the writers room as well. That’s where the stories are created — stories that deserve the most honest and authentic hands to put pen to paper and bring to life. I also think it’s important for the entertainment industry to mirror our society in the sense that it shouldn’t be afraid to shy away from hard truths and painful realities because I know there are many in this country that still suffer because of the color of their skin or who they love. If more of these stories are brought to the surface and told through the art of film and television, then there is no excuse for ignorance.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.


1) Don’t spend too much time inside your own head: I am an overthinker by nature, but spending too much time stirring around in my thoughts never ends well.

2) Don’t compare yourself to others: I honestly can’t stress this one enough. Comparison truly is the thief of joy.

3) Sleep is important!: Coming from a chronic insomniac, never underestimate the importance of a good night’s rest.

4) Be kind to yourself — it’s a lot easier said than done: I still struggle with this one on the daily. I genuinely believe those mean, intrusive thoughts are the devil disguising himself as our own self-doubt. So if you don’t listen to him, then you won’t give him any power over you.

5) Beware of perfectionism: I’ve learned that what I once thought was an admirable trait, can quickly turn into a curse. It held me back from releasing so much music over the years because nothing was ever “good enough”. At some point you just gotta say release the damn song! There is beauty in imperfection.


1) Expect it to be a long and bumpy journey, when moving to Nashville it came to be a quick realization that this is a city full of people with the same dream.

2) Capitalize on each life experience as an opportunity to write, although you think life might not always be exciting or something worthy of being written about that could give you inspiration to write one of the most relatable songs.

3) Don’t compare your journey to someone else’s, social media allows you to get wrapped up in everyone else’s lives and it can cause you to get wrapped up in their successes vs your own.

4) Quality over Quantity — it doesn’t matter how many shows you perform as long as you are making the most of the ones you do perform and playing them to the best of your abilities.

5) Don’t look at others on the same journey as you as competitors but as colleagues, everyone you meet in this industry will have the same goals as you so if you used that outlook you would never build these amazing connections that we have. Being surrounded by other people doing the same things as us gives us more drive and more opportunities.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Jackie: Learn how to surf, go fishing, travel, meditate, do some yoga, get a good night’s sleep. If you’re experiencing writer’s block, travel somewhere you’ve never been. For me, this usually sparks new inspiration I couldn’t ignore even if I tried. If this doesn’t work or isn’t feasible, then sometimes you simply have to write yourself out of it. Force yourself to write for the sake of writing. Write in a journal, write a short story, work on an unrelated writing project. Write anything, no matter how bad or stupid.

Rob: Take advantage of the days that you can to enjoy family and friends. We all have seen what this last year has been like and how important it is to enjoy the little things in life.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger

Jackie: I really like Harry Style’s “treat people with kindness” mantra. It’s such a simple and fundamental concept, yet so often it goes ignored. It’s something every single one of us can do right here and right now, no matter who you are or how much money you make. If the world was just a little more kind, could you imagine how much could be accomplished? Because kindness leads to understanding, understanding leads to compromise, and compromise leads to change.

Rob: If it were up to me, I would love to turn off or disable all social media for a week or even just a day. Social media can be so toxic and part of the reason is because it is constant — it never shuts off. People only post about the best things in life and it is so easy to fall down the rabbit hole and compare your life to theirs. I think everyone could benefit from a break.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Jackie: I 100% would not be where I am today without the love and sacrifice of my parents. They have always encouraged me, my brother, and my sister to go after our dreams and have supported us every step of the way. I don’t know what I would do without them.

Rob: My parents have never had a doubt about me not wanting to pursue a traditional career. They have always been my number one supporters and have helped me build my confidence from day one. They have made it possible for me to move to Nashville and have the tools we need to create our music. I would not be where I am without them.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Jackie: “Get busy living or get busy dying” — from one of my all time favorite movies, Shawshank Redemption. That quote just gets right to the point and I love it.

Rob: My favorite quote is “Don’t let yesterday take up too much of today” -Will Rogers. Being in the industry that quote has a lot of depth and meaning. There will be nights where not a lot of people will show up to your shows, and it is not anything that you can take personally especially in the world that we live in today. So whatever happened yesterday you need to take it with a grain of salt and make the most of the next day.

Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. 🙂

Jackie: Stevie Nicks, without a doubt. She is by far my biggest musical inspiration and I hope someday I get the chance to tell her just how much she means to me. The impact she has had on me as an artist is immeasurable. As a child I sang with the old men in the tenor section of my church choir. I used to be really self-conscious about my low, raspy voice. But then I discovered Stevie Nicks. I just think she’s the coolest person in the world.

Rob: Luke Combs. He is one of my favorite artists. He is very relatable to me. We share a lot of common interests in the outdoors such as hunting and fishing. For being a big name he has always kept himself humble and down to earth. I hope to have the same grace and maturity that he does when I make a reputation for myself.

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