A Message For My 20 Year Old, Entry-Level Self

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The other day I was listening to a random Spotify playlist and a song from Kelly Clarkson’s 2011 album Stronger came on. I was doing something else on the computer while listening to music (as I do constantly) and this song made me pause because I literally listened to this album on repeat in 2011 – at the very start of my career.

I listened to it while I was crying in my crappy NYC apartment about my toxic boss. I listened to it on repeat during an entire 11 hour flight from NYC to Hawaii (it was the first non-stop flight between those locations on Hawaiian Air and I paid cash for a first class seat because I hadn’t discovered travel hacking yet…oops).

Proof of my obsession with this album…

I listened to it during the week my Mom and I spent in Maui where I literally jumped up every time my phone rang. I even leaped out of bed while I was sleeping once to frantically respond to a confused telemarketer. I was waiting for a call about a job offer from a new company I had interviewed with.

I was doing my best to try and leave the toxic environment at my first ever corporate job. Despite being told by an internal recruiter that the main company I had interviewed with wanted to hire me and having my phone glued to my hand my entire vacation, I never did get a call back. I returned to work after that week of vacation, defeated, but still listening to that album.

Still listening…

Here are some of the words I was listening to on repeat:

What doesn’t kill you makes you stronger
Stand a little taller…

What doesn’t kill you makes a fighter
Footsteps even lighter…

Obviously these are not the most groundbreaking lyrics, but upon reflection, I think listening to this album hundreds of times might have infected my brain because a month after that vacation I returned to work and quit without another job lined up.

I was terrified and almost broke. I had $1,500 of Manhattan rent due in a month…and then the month after that…and the month after that. Without factoring in the human body’s need to eat that amount of rent alone would quickly obliterate the relatively small amount of savings I had ($5,000).

I had no idea what the fuck I was doing…but it all worked out. I got a call about a new job that offered me a promotion and a 37% raise at a more prestigious agency literally my first hour of funemployment on my first Monday without work.

And now it’s 9 years later and I’m listening to this album while preparing to quit my career entirely. Listening to these lyrics again after all this time made me reflect on how much has changed in the last (almost) decade and what I wish I could tell my former self. So let’s get into it!

Now you may be wondering: Is this a post where we read through silly Kelly Clarkson lyrics? Hell yeah it is! You’re welcome 😉 .

You didn’t let me down,
You didn’t tear me apart
You just opened my eyes,
While breaking my heart

You didn’t do it for me
I’m not as dumb as you think
You just made me cry
While claiming that you love me
You love me, you love me

You said you loved me but that
I’m not good enough
I’m not good enough

Instead of a lover saying these things, I felt like the job was saying them to me – sometimes literally. It was my boss telling me that I needed to dress “fancier” to be considered for a promotion while he sat across from me wearing cargo shorts…It was my toxic SVP saying that I’m not good enough for a promotion despite accomplishing every challenge she had set in front of me after she had claimed that’s how I would reach the next level.

Didn’t get it the first time
But don’t think I’ve been so blind
And I may not be Einstein
But I know
Dumb plus dumb equals you

I wish I could tell the scared young woman I was that it’s going to be alright. I wish I could tell her that trying (and failing) to hold in tears while sitting in her cubicle after being yelled at by her SVP is not normal. I wish I could tell her to hang in there – that it will get better.

I wish I could tell her: You’re stronger than you know and you’re going to do amazing things. The perfect job doesn’t exist, but there are ones you won’t dread going to. The perfect boss doesn’t exist, but a few will get very close.

The perfect partner doesn’t exist, but yours is pretty phenomenal (and you’ll become an even better person and partner yourself, I promise 😉 ). Keep working on you. Don’t give up, keep your chin up and as cliché as it sounds: Follow your dreams. You’ll get there.

And now I’ll leave you with (of course) more lyrics from that album. This song is dedicated to corporate work! 

All I have to say is you don’t deserve me
You don’t deserve me
I’m finally walking away
’cause you don’t deserve me
And you’re not worthy

And I won’t let you pull me in
Because I know you’re gonna win
And I won’t fight you anymore
I’ve never been so sure
The war is over…

Yeah you owned me
Now you wish you had really known me…

This is not my surrender
I’m not running for cover
I’m right here, I know you see me
But your words no longer defeat me…

You can try a million times
You’ll get the same answer
All I have to say is you don’t deserve me

I can now confirm that the tough times I went through at work were indeed worth it because:

The war is over.
The war is over.
The war is over.

*MIC DROP*

What do you wish you could tell yourself a decade ago?

22 thoughts on “A Message For My 20 Year Old, Entry-Level Self

  1. Haha, we have so much in common! Kelly Clarkson’s ‘Stronger’ is one of my favorite songs to push myself during tough workouts and I guess it has applicability in many situations 🙂 It was very brave to quit that toxic job back then, it’s so great to see how things turned out for you. A great example of listening to our heart and trusting that we’ll figure it out. Congrats on being 3 months and 3 days from retiring!

  2. “This song is dedicated to corporate work!” Haha I feel that! I connected a lot with your story in this post, I felt really similarly about finally getting ready to quit my job.

  3. 10 years ago i should have told myself to buy a motley fool stock advisor subscription. we would be filthy rich by now and worrying about anything even less than necessary.

    i remember getting yelled at by a bad boss person at work. she was screaming like a little schoolkid brat throwing a tantrum. i gave her my best deadpan low key “why are you screaming at me? i don’t talk to you that way.” then i quit a month later because of confidence.

    1. I haven’t heard of a motley fool stock advisor subscription – I assume their predictions correct? And if only I had the confidence of a Smidlap back in the day – that’s a great response.

  4. Going through a tough time at work right now and counting down when the war will be “over” for me. I can relate to this post. Thanks again for sharing.

    and your pictures on the plane just makes me miss flying and vacation so much right now….lol

    1. I’m sorry your work is tough right now and hope it improves! And oops sorry to give you the travel bug. My bad! One day we can travel again. Hang in there.

  5. I need to go back 15 years and slap my 20 year old self 🙂

    This is what I would say:

    1. Don’t cut that trip to South East Asia short! Stay there for at least 2 years!
    2. Start a business and either make it big time or fail miserably.
    3. For crying out loud, stop wasting $500 a month on alcohol.
    4. Keep the long hair. I think it looks badass 🙂

    1. Well you just made me laugh out loud 🙂 . That is all some wonderful advice. And DAMN how did you spend that much on alcohol?? What were you buying? So fancy! Also I totally agree with the long hair – love it!

  6. Thinking of my 20-year old self takes me back almost 30 years (yes, I’m pushing 50), and much has changed since then. I worried too much back then, and I tried to have it all figured out instead of living more in the present. I’m much better about focusing on the now, right now, and being more decisive. These song lyrics capture how I try to live currently:
    We got just one shot of life, let’s take it while we’re still not afraid.
    Because life is so brief and time is a thief when you’re undecided.
    And like a fistful of sand, it can slip right through your hands.
    – Rod Stewart from Young Turks

    1. Those are some amazing lyrics! Thank you so much for sharing. It sounds like you’ve grown in wonderful ways!

  7. My 20 Year Old self would have told me to ‘**** off’ in no uncertain terms.
    You couldn’t tell me anything cos I knew it all !!!
    Not even Kelly’s lyrics would have got through

    1. Hahaha – well I’m sorry to hear that. Maybe some more hardcore music was needed to break through 😉 .

  8. Life’s wild twists and turns have gotten me to a good place, so I don’t think I’d change much…but I’d like to say to my 20 year-old self:

    – You’re even less conventional than you thought you were. It’s ok to follow paths less trodden.
    – Don’t bend over backwards trying to follow a partner who knows what they want already. Follow your own curiosities fearlessly and celebrate any friends or loved ones who are happy to ride with you.
    – You’re good at standing up for yourself against those who are mean, but learn to stand up for yourself against those who “mean well” but don’t get it.

    1. …Are you a writer? Because all of these are extremely poignant and could have their own throw pillows. Absolutely lovely insights and I’m so happy you wouldn’t change much 🙂 .

      1. Apart from entries in my private journal, not really! But thanks, I really appreciate hearing that from someone who’s written a lot. 🙂

  9. Definitely needed this! I’ll be 27 this year..still in my boring entry level job going on year 3. I like my new boss (he’s the 3rd one now) but have not received a promotion while everyone I started with in different teams have. Raises are degrading.. 1-2%. I started my new job search but then pandemic hit but I am still hopeful!

    1. YAY! I’m so happy it helped 🙂 . And ugh yep sounds familiar – I’m sorry about that situation, but it’s awesome you’re looking! Definitely keep that hope. I don’t know what industry you’re in, but availability in remote marketing jobs for example is booming. A few other sectors as well (tech, IT, healthcare etc). Not everything has dried up 🙂 . I hope you find something you enjoy that pays you what you deserve soon.

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