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10 Taylor Swift lyrics that double as advice for entrepreneurs

Editorial Team

6 min read
Woman listening to music with headphones in her living room.

Taylor Swift is many things to many people. The singer/songwriter is equal parts pop and country superstar, folklorist, and breakup guru. Her songs have been rocketing to the top of music charts since she was a teenager, and her emotionally drenched lyrics have touched millions worldwide.


Whatever tough situation you’re going through, there always seems to be a Taylor Swift song, or even a single lyric, that can help guide you through it.

She’s also an entrepreneur in her own right. Like other musicians at her level, she’s the face of what is, ultimately, a big profitable business. Taylor Swift is the name of a brand as much as it’s the name of a bestselling musician. In fact, she publicly contended with one of her old record labels to retain control and ownership of that brand. She’s the co-producer of most of her music, and has an orbit of endorsement deals, features, and collaborations with other artists.

Which is why we’ve poured through her catalog and pulled out the best Taylor Swift lyrics that also double as advice for entrepreneurs. After all, going through a breakup is one thing. Starting a business? That’s where you really find out what you’re made of. So, dim the lights, put on an “old cardigan”, and maybe take some notes — because these are the 10 best Taylor Swift lyrics that double as business advice for entrepreneurs.

1. “I’ve never been a natural, all I do is try, try, try.” – mirrorball (Folklore)

Here’s a not-so-secret secret: natural talent doesn’t get anyone very far. Even if you are born with some sort of natural talent or proficiency, it’s no substitute for hard work and practice. Entrepreneurs should know that almost nothing about running a business will come naturally. You can only find your stride through patience, dedication, hard work, and try, try, trying.

2. “We never painted by the numbers, baby. But we were making it count.” – the 1 (Folklore)

As an entrepreneur, you go against the grain. You don’t paint by the numbers, you don’t follow any pre-ordained script, and you refuse to be put in a box. Those are the qualities that make you powerful, as long as you make it count.

3. “I like shiny things, but I’d marry you with paper rings.” – Paper Rings (Lover)

Naturally, you want your business to be financially successful. That said, if shiny things are your only goal, it’s eventually going to be difficult to find the motivation to keep going when things get tough. At the end of the day, only a true passion for running your business, regardless of financial success, will keep you going.

4. “We’re happy, free, confused, and lonely in the best way.” – 22 (Red, Taylor’s version)

Yes, entering the world of entrepreneurship can feel a bit like being 22. To survive it, you have stay calm, stay focused, make the best decisions you possibly can, and try not to freak out when things inevitably get difficult and emotional. Just like Taylor, you’ll be happy, free, confused, and lonely, all in equal measure, and all in the best way.

5. “The road not taken looks real good now.” – ​’tis the damn season (evermore)

Becoming an entrepreneur means striking out on your own and taking a path not traveled by many. Deciding to work for yourself and carve out your own destiny is indeed a bit of a rebellious act. If you’ve ever been struck by the feeling of wanting to travel down the road not taken, know that you’re not alone. That instinct is what makes you a leader instead of a follower, and it’s what made you an entrepreneur.

6. “I tried to pick my battles ’til the battle picked me.” – long story short (evermore)

This one is pretty straightforward. In business, as in life, you can try as hard as you want to pick your battles. Eventually, though, a battle is going to pick you. The sooner you expect that that’s going to happen, the better. Expecting the unexpected is a big part of the job, and you never really know what fire you’ll be putting out before the day is over.

7. “Fighting with him was like trying to solve a crossword and realizing there’s no right answer.” – Red (Red, Taylor’s version)

It’s true, running a business can be a little bit like fighting with someone you’re close to. It’s a haze of confusion and mixed signals, wrought with emotion and blanketed in mind-numbing frustration. The solution, therefore, is usually similar as well. It will require compromise, and letting go of the things that don’t really matter.

8. “There’ll be happiness after you, but there was happiness because of you. Both of these things can be true.” – happiness (evermore)

You can really apply this line to any day in entrepreneurship. When the day ends, you’ll be happy to have it out of the way, and when a new day begins, you’ll also be happy to be pursuing your passions and dreams. There’s happiness in entrepreneurship, and there’s also happiness in stepping away from it. Both things can be true.

9. “Only 20 minutes to sleep, but you dream of some epiphany.” – epiphany (Folklore)

As an entrepreneur you’ll probably be familiar with the feeling of only having 20 minutes to sleep before the next workday. You may also be familiar with the feeling of suddenly having a game-changing epiphany the minute you decide to step away and wind-down. It’s important to remember that taking breaks from your business isn’t only about your mental and physical health, it can also provide clarity and make you a better business leader.

10. “And it’s 2 a.m. and I’m cursing your name.” – The Way I Loved You (Fearless)

Just… yeah. At some point, you may be up at two in the morning, cursing the name of your business. That’s normal. It’ll be okay

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