In October 2012, Taylor Swift released her fourth studio album, Red.

During its first week, the album sold 1.2 million copies. That made Red the fastest-selling country music album ever.

Red then spent 16 weeks at number one on Billboard’s “Top Country Albums” chart. And the following December, the album was nominated for “Best Country Album” ahead of the 56th Grammy Awards.

But one common critique of Red made Swift wince.

The album, which ventured into pop music territory at times, was criticized for not being “sonically cohesive.” Swift was increasingly interested in exploring elements of pop. But she was stuck trying to live up to other people’s expectations – mainly those of country music executives.

The response to Red helped Swift arrive at a new realization: she needed to part ways with country music.

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Taylor Swift’s Nashville-based music label was not thrilled to hear about her interest in pop music.

In Swift’s telling, the president of Big Machine Records “went into a state of semi-panic and…through all the stages of grief — the pleading, the denial.” Chuck Klosterman writes in GQ:

“[Swift] claims everyone at her label tried to persuade her not to make a straightforward pop album. She recounts a litany of arguments with various label executives over every possible detail.”

“‘Even [the title of the record] was a risk,’ she says. ‘I had so many intense conversations where my label really tried to step in. I could tell they’d all gotten together and decided, ‘We gotta talk some sense into her.'”

“I’d go into the label office, and they were like, ‘Can we talk about putting a fiddle and a steel-guitar solo on ‘Shake It Off’ to service country radio?’ I was trying to make the most honest record I could possibly make, and they were kind of asking me to be a little disingenuous about it: ‘let’s capitalize on both markets.’”

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But Swift possessed a characteristic that many artists (and many of us) lack: a significant level of self-awareness. And that self-awareness propelled her departure from country music. It gave her the confidence to make choices that seemed risky to others.

“I used to watch Behind the Music every day,” she says. …And I would see these bands that were doing so well, and I’d wonder what went wrong. I thought about this a lot. And what I established in my brain was that a lack of self-awareness was always the downfall. That was always the catalyst for the loss of relevance and the loss of ambition and the loss of great art.”

So when Big Machine Records asked her to add three country songs to her next album, Swift declined. “No, let’s pick a lane,” she insisted.

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We often get stuck with money in a way that mirrors Swift’s relationship with country music.

We may excel at saving money, or contributing to our 401(k), or minimizing our tax bill. And those are tremendous accomplishments. But is that all we’re trying to do?

Probably not. Yet, considering more personal uses for our money feels daunting. It’s like we’re sitting across a table from powerful record company executives.

We may know the particular interest(s) that we want to pursue. And, ultimately, we may not really care to factor in anyone else’s opinion. But a desire to make the “right” decisions exerts real pressure on how we think and act.

We don’t want to disappoint our family. We don’t want to make a mistake that’s visible to our peers. So we’re tempted to just stick with those basic rules of thumb that we so often hear. It feels safer, more prudent.

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Looking back, Swift believes that self-awareness showed her that “the safest thing [she] could do was take the biggest risk.”

And it’s self-awareness that can help us to reach similar conclusions with our financial decisions. We need to understand which financial choices can help us feel content, help us relax, help us save time. We also need to recognize how stress, fatigue, or general uncertainty about the future can impact how we use our money.

When we stop trying to please others, we become more empowered to:

• Prioritize all-purpose investment accounts over retirement accounts
• Invest in early childhood education opportunities, rather than just college
• Spend money on an expensive service that clearly improves our quality of life

At certain points in our financial lives, we need to be willing to “part ways” with the consensus for what we’re “supposed to do” with our money.

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Taylor Swift’s fifth album, 1989, “was made completely and solely on [her] terms, with no one else’s opinion factoring in, no one else’s agenda factoring in.”

And at the 58th annual Grammys, 1989 won the award for (overall) “Album of the Year” and “Best Pop Vocal Album.” Perhaps more impressively, by the end of 2019, 1989 was the third best-selling album of the entire decade in the U.S.

Swift’s record company had argued that she already “had an established, astronomically successful career in country music. [And] to shake that up would be the biggest mistake she ever makes.”

But, as we should say more often about our own financial choices, Swift’s response was, “Guys, don’t you understand? This is what I’m dying to do.”

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About the author: Kevin Mahoney, CFP®

Hi, I’m Kevin. I’m a financial advisor in Washington, DC. I’m also the founder of Illumint, an independent financial planning company in the District that specializes in financial planning for Millennials like you. I empower our generation with the confidence to invest an inheritance, financial gift, or extra savings. If you’re new to Financially Well, welcome – you now have access to the leading finance podcast for Millennials. I encourage you to read, watch, or listen to the ideas I’ve shared about making your money work for you. And then when you’re ready, please send me your thoughts & questions!