31 Songs About Leaving – Work, Home, Or The Past Behind

Sometimes you just want to leave it all behind. Whether it’s things that have happened in your past, leaving home, or something as simple as leaving work for the day.

If you’re in the mood to hear songs about one of the above situations, or many other such ‘leave’ scenarios, here are some of the best songs above leaving things behind. Just don’t leave this list too soon. 😉

“Never Going Back Again” by Fleetwood Mac

Song Year: 1977

One of the shortest songs from a hugely successful band, Fleetwood Mac, this song is about feeling pain from your past and trying to leave it behind. The song, albeit short, talks about a girl from the past and the mutually toxic relationship she and the vocalist shared. He sings about depression and trying to move on and leave the past in the past.

It is rumored that this song was actually written about the messy breakup between Lindsey Buckingham and Stevie Nicks, both artists in Fleetwood Mac. Whether or not that is true, this song is quick, catchy, and gives you all the feels.

“Breakaway” by Kelly Clarkson

Song Year: 2004

After her exciting win in the popular singing show, “American Idol,” Kelly Clarkson released this moving song about leaving home and the past behind. In it, she talks about never feeling at home in her small town and always wanting to belong somewhere. She learned that in order to be happy, she needed to let the past go.

This song is powerful and is easy to relate to. Kelly Clarkson wanted to make her own way in the world and she did. The song comes full circle as she ends with humbly singing that she will not forget her roots, even as she learns to soar.

“Changes” by David Bowie

Song Year: 1971

Bowie never fails to produce a chart-topper, and “Changes” is no exception. This tune is about facing the future and the unfamiliar and not being afraid to make waves. It may also have a double meaning about being unsatisfied with the world the previous generation left and a general distaste for “the man.” No argument here.

This song has an upbeat melody and tone, but the lyrics are also highly motivational. This is a great song to listen to as you go off to college, take a job in a new city, or when you are making any changes of your own.

“Movin’ Out (Anthony’s Song)” by Billy Joel

Song Year: 1977

Billy Joel is famous for his songs about the average Joe, living in America, earning him the nickname, “The Storyteller.” His music always has a way of transporting you into the song and making you feel like you know the people and the places he is singing about. “Movin’ Out” is about a young man that becomes dissatisfied with his home situation.

In the song, this young man, presumably Anthony, feels that he will not ever get where he wants to be in his small town, and therefore decides to leave home and “move out.” This is a great song to listen to when you have finally saved up enough to escape your oppressively small hometown and parents, assuming you have such burdens.

“Mexico” by Cake

Song Year: 1998

Cake is an alternative rock band from the 90s that never really got the recognition it deserved. Honestly, who does not love a band with a trumpet? “Mexico” is a song from one of their earliest albums about a relationship the lead singer had with a girl that was just a little too good for him.

He sings about comparing the two of them and how he always felt he stood in the shadow of her successes. He felt there was nothing to do but cross the border. The song ends there, so one can only hope he found what he was looking for south of the border.

Both Sides Now- Joni Mitchell

Song Year: 1969

Joni Mitchell wrote this song decades ago and yet this particular tune paints a beautiful and relatable picture for the listener today. This is a great song to give you perspective about leaving different situations after the fact.

Mitchell sings about the highs and lows of life with multiple metaphors and how moving on in your life and learning from the past can help shape you into the person you want to be.

“Go Your Own Way” by Fleetwood Mac

Song Year: 1977

Fleetwood Mac has a particular talent for writing songs with upbeat tunes and heartbreaking lyrics. “Go Your Own Way” is a perfect example of this, and was such a fan favorite that it appeared on multiple albums for Fleetwood Mac.

This song talks about how it is impossible to keep someone from leaving you when they have already made up their mind. It is a good reminder to let both things and people go, and that hanging on to the past will only hurt you in the long run.

“Good Riddance (Time of Your Life)” by Greenday

Song Year: 1997

One of the slower, more in your feels, songs from Greenday, “Good Riddance” is a song that divided their fan base. Written more as a ballad than a punk anthem, this song tells of the trouble with growing up and leaving the past to die.

When you are feeling nostalgic about your hometown or your college days, this song is a deeply cathartic way to release some of the melancholy feelings you may have. At the end of your life, it does not pay to live in the past, so this song preaches learning from your wins and losses and moving forward.

“Send Me On My Way” by Rusted Root

Song Year: 1992

This song first appeared on a Rusted Root album in 1992, but has since then appeared over a dozen times in movies, TV shows, and commercials. The vocalist can be hard to understand so feel free to look up the lyrics, but the artists themselves have said that many phrases are not real words in this song.

Interpretations of this song include happiness to be going on a journey and even the joy that can come with leaving behind a situation that you are done with. Whether you are leaving a bad relationship, a toxic job, or a situation that was not making you happy, this song is sure to put you in a bright and cheery mood.

Leaving On a Jet Plane- John Denver

Song Year: 1966

John Denver was actually a test plane pilot by hobby, and was killed when one such test resulted in a devastating crash. This fact alone gives a whole new, heartbreaking meaning to this song.

This song is about the sorrow one feels when leaving a loved one or their home behind. If you are leaving people you love and want a good cry, this is the perfect song to help release the pain.

The Anthem- Good Charlotte

Song Year: 2002

This is the ultimate rebel song about leaving the status quo and being your own person. It is up to interpretation if the singer is talking about an oppressive home life or some jerk teacher, but he very clearly does not want to be associated with them anymore.

Aptly named, this is truly “The Anthem” for when you need to leave behind something, or someone, that is holding you back.

Goodbye Stranger- Supertramp

Song Year: 1979

“Goodbye Stranger” is a very upbeat and catchy song about not wanting to be tied down or controlled by your past. The singer tells his lover that he needs to push forward but that he enjoyed the time they spent together.

This is a pretty great mentality to have when it comes to moving on in your life. You can recognize the need to leave and move forward and still look back on the past fondly.

Goodbye Yellow Brick Road- Elton John

Song Year: 1973

This song by Elton John is about a young man rejecting a job in show business and the finer things in life that come with it. Leaving something behind can be very difficult, especially when it was something you have worked so hard for and once you thought you wanted.

Elton John seems to have based this song on his own experience somewhat and shows that not all that glitters is gold.

Move Along- The All-American Rejects

Song Year: 2005

The lyrics in this song are touching and empowering. The All-American Rejects paint a relatable picture for the listener of the daily struggles we all face and how sometimes all we can do is leave the past in the past and try again tomorrow.

Shake It Off- Taylor Swift

Song Year: 2014

Taylor Swift is known for two things: writing songs about guys she has dated and writing hits that get stuck in your head. “Shake It Off” applies more to the latter and is a cheeky nod to all the things people say about her.

In this chart-topper, Swift recognizes her humanity and ability to make mistakes but also chooses to leave the negative comments behind and focus on her own future.

Cast No Stones- Cody Jinks

Song Year: 2015

This is a good country song to listen to if you feel that someone has mistreated you but you want to take the high ground. “Cast No Stones” is about how a man chooses to leave his past encounters with people without holding a grudge against those that have hurt or offended him.

Suds in the Bucket- Sara Evans

Song Year: 2003

This is a cute country song about a young girl leaving her home behind to run off with a boy she likes. She feels that 18 is old enough to make her own decisions so she drops everything and just leaves.

If you decide to leave home for a love interest like the girl in this song does, maybe say goodbye to your family first and not merely leave a note on the door like she did.

Wide Open Spaces- The Dixie Chicks

Song Year: 1998

This is the perfect song for when you feel too confined by your home and just need to get away and find yourself. The Chicks never fail to create relatable content and this song is one you can sing your heart out to.

“Hell No” by Ingrid Michaelson

Song Year: 2016

This song relates how Ingrid Michaelson was cheated on and she will not stay with an unfaithful man. She says that there is nothing this guy could do or say to get her back, as she is long gone. Leaving someone you love is always hard, but leaving a painful past is also cathartic.

Bye Bye Bye- NSYNC

Song Year: 2000

As the song title suggests, this song is about bidding farewell, particularly to a toxic ex or negative past. In this song, NSYNC talks about how you can not love someone enough to play both parts in a relationship.

This song is every bit as empathetic as it was when it rocketed to fame in the early 2000s. Not to mention, the music video with the boys as puppets certainly strikes the metaphor perfectly.

Free Bird- Lynyrd Skynyrd

Song Year: 1973

This ballad by Skynyrd has one of the most popular guitar solos of the early 70s, and includes truthful lyrics about why some people can not stay in a relationship when it feels like living in the past.

For the singer of this song, feeling free and leaving people and things behind are one and the same, and both feel necessary.

The Sign- Ace of Base

Song Year: 1992

Ace of Base came out with a few hits during their time, but “The Sign” is certainly on a different level. When you leave a bad situation behind, or finally choose to allow a terrible ex to stay in the past, the best revenge is being happy in spite of it.

This song is about just that; a girl that left someone who hurt her and is now showing them that she is happy and better off. Plus, this song is a great one to belt in the car with your girls!

Landslide- Fleetwood Mac

Song Year: 1975

This song is about changing and moving on, but it is also about growing pains. Growing up and experiencing new things can hurt, but it is never a good idea to put all your eggs in one basket.

Stevie Nicks has such original and haunting vocals, when you miss home and wonder if you made the right decision, this is a great song to sing along with while hoping you did the best you could.

Wild World- Cat Stevens

Song Year: 1970

Cat Stevens wrote some pretty hippy-dippy music in his day, but this song was a total smash for its relatability. This song could be about a man speaking to a leaving woman he continues to love, but it could also be written about a dad telling his daughter to be safe as she leaves home for the first time.

There are a lot of loving warnings in this song, and a lot of best wishes for the person leaving. Just as it hurts to leave home, it hurts to be left behind, especially when you still love that person.

Ramble On- Led Zepplin

Song Year: 1969

The year of 1969 is one of the best for awesome music, and this hit from Led Zepplin is no exception. This song is such a great pump up song for when you have had enough and you have made up your mind.

Whether you are leaving a job for good or are merely done with a bad day, “Ramble On” is a great tune to blast in your car as you throw obscenities out the window and peel out. It says the perfect amount of “Screw this!” and “Up yours!”

Separate Ways- Journey

Song Year: 1983

Journey wrote some power ballads in their time, and “Seperate Ways” is an incomparable song about letting someone move on when you know that it is not right. Steve Perry tells his love that he will always feel for her, but if she needs to leave, he will support her.

Breaking up sucks, even when both parties are mature enough to show each other that they truly want what is best for one another, even if the breakup is not perfectly mutual.

Midnight Train to Georgia- Gladys Knight and the Pips

Song Year: 1973

Gladys Knight has the voice of a smoky angel, and this song tells a soulful story of a man that could not make his dream happen in California. He leaves the job he is passionate about to go back to live a simpler, less glamorous life. The queen that she is, Knight sings that she will go with him wherever he leads.

I Will Always Love You- Dolly Parton (Whitney Housten)

Song Year: 1974

Although this song was written by Dolly Parton as a goodbye present to her manager, it was made popular by the powerhouse voice of Whitney Housten. It tells of a bittersweet story of leaving someone that you will always love, because you believe it to be the right thing to do for them.

Even if you may not have the incomparable vocals of Whitney, you should still sing along to this one, especially that perfect drop in the song before the chorus (you know the one).

(Sittin’ On) The Dock of the Bay- Otis Redding

Song Year: 1968

This song is about sticking to your guns and doing what you want to do, even if others do not agree. In the lyrics, a man leaves his home behind to head out west and live his life by the shore.

He says that he can not make everyone happy, but he can do what is right by him, so at least one person will be satisfied. Hopefully you can see the truth in this song, and stop caring what others think about you.

Birmingham- Shovels and Rope

Song Year: 2013

This band is not well known, but this song (one of their first) tells the story of the two lead singers and how they traveled across the country before they came together to make music. They traveled separately and had to find themselves to be better together.

Sometimes leaving home can hurt, but if you can hear this song and remember that one day you will be with the love of your life, happy and stable, hopefully it will encourage you to move forward and live for you.

Hide and Seek- Imogen Heap

Song Year: 2005

This haunting melody is one that will stay with you, even when you can not quite understand the lyrics being sung by Imogen Heap. The general story is of a woman feeling completely taken off guard by her partner. He is either making an executive decision that she does not agree with, or he seriously hurt her in some way.

In the end she seems to cut ties and accepts that he is not living with her best interests at heart and decides to leave him behind. This song, once you look up the lyrics and learn it (you really should look up the lyrics) is the perfect amount of light, sweet melody and a pain-ridden belting chorus.

Songs About Leaving, Final Thoughts

Whether you are leaving home for the first time, or are finally making the career move you have always wanted, these songs will give you the perfect playlist to make your move. With a perfect blend of happy, sad, and bittersweet songs, you can be sure that you are not alone in the way you feel: moving on is hard for everyone.