Taylor Swift + Leadership

leadership lessons from TTPD

These are my favorite TTPD songs, and what you can learn from them.

Imagine Taylor is writing about business relationships (she’s not, honestly we’re stretching pretty hard here again, but having fun).

  1. imgonnagetyouback - Picture Taylor as a cofounder of a startup that’s reached an interesting inflection point. “Whether I’m gonna be your wife or… gonna smash up your bike, I… haven’t decided yet, but I’m gonna get you back” depicts a moment where Taylor has to decide whether or not she’s going to stick it out with her business partner. Things have been tumultuous, but the startup has unicorn level potential.

    Tough decision, Taylor - I DON’T envy you here.

  2. TTPD - Here’s the thing, Taylor - moving on is okay. Who can decode you like me? Who’s gonna hold you like me? Who’s gonna know you like me?

    Maybe no one, Taylor, but business is business. People move on, and though it may hurt, it’s important to let the bird fly. When there’s a ton of turbulence, maybe it’s okay to go separate ways.

  3. fresh out the slammer - sorry the chorus in this song is just fire. Taylor’s got a go-to guy. A comfort place to run back to in times of chaos and trouble. I’m picturing an old family business you have to fall back on (nothing wrong with this, LOVE family businesses), that you don’t necessarily want to work at, but you can always go back to because it’s safe and easy.

    While it’s nice to feel like you have a comfortable place to call home after experimenting with other endeavors, it’s not always all it’s cracked up to be - and there’s likely a reason it didn’t work out the first time. (I’m still talking about business guys, come on).

  4. but daddy I love him - Sometime’s you gotta do you. Despite the expectations from family, friends, coworkers, you have to do what is best for you and for your family.

    If it’s starting a business, it’s starting a business. If it’s NOT starting a business (by the way, it’s actually OKAY if you don’t start your own business), it’s not starting a business. If it’s moving to a different city, state, country, then DO IT! Gotta do you.

  5. loml - sad. relatable. good. Taylor’s employer promises her the world - a fancy OTE, maybe a big salary and a hefty bonus. Things don’t quite shape up to be as good as they seemed.


    Don’t overpromise. Whether it’s an interview process or real on the job communication, don’t lead your people on - it’ll only create distrust and conflict due to misaligned expectations.

Ranking the rest of the 26 songs (based on my taste only - this list changes the more I listen tbh). I’m sorry, I just don’t love Florida.

  1. down bad

  2. the bolter

  3. I can do it with a broken heart

  4. thanK you aIMee

  5. clara bow

  6. Guilty as Sin

  7. fortnight (w posty)

  8. I look in peoples windows

  9. Who’s afraid of little old me?

  10. albatross

  11. black dog

  12. so high school

  13. I hate it here

  14. peter

  15. so long, london

  16. chloe or sam or sophia or marcus

  17. the alchemy

  18. I can fix him (no really I can)

  19. My boy only breaks his favorite toys

  20. the manuscript

  21. robin

  22. cassandra

  23. how did it end?

  24. the prophecy

  25. the smallest man who ever lived

  26. Florida

love taylor, great album, lots to learn. feel free to send me your heated takes about why I’m so wrong about which songs are better/worse than I said.

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