Last weekend, I had the incredible experience of attending Taylor Swift's Eras Tour in Toronto with my 78-year-old father, a proud "Elder Swiftie." Beyond the stunning performances and breathtaking production, what struck me most was the deep sense of connection and community among Swifties. It reminded me that, whether at a concert or in life, the bonds we form and the intentional acts of giving and receiving shape our legacy. Surprisingly, these same lessons tie back to estate planning. Here are thirteen valuable lessons to be learned from the unforgettable Eras Tour, and Taylor Swift’s career, one ‘era’ at a time:
1. Debut – Define Your Legacy
Song: “Our Song”
Lyrics: “Our song is a slamming screen door.”
From her very first, self-titled, album Swift began shaping the legacy she would leave on the world: not only did she defy expectations, but she has also since became the most famous artist in the world and, arguably, the best songwriter of this generation.
Whether you know it or not, you are actively building a legacy in this very moment. Maybe it is the start of a new “song” for you: a new career, a new journey, or maybe even a new location. Preserving the legacy that you are actively building is an important aspect of life. What do you want “your song” be? An estate plan is a customized tool that allows you to secure the legacy you have or will build. It is designed to secure what “your song” is and will be.
2. Fearless – Celebrate Milestones
Song: “The Best Day”
Lyrics: “I hear your laugh
And look up smiling at you”
Taylor Swift’s “Fearless” era was a defining moment in her career, and she even won a Grammy for “Album of The Year”. At the Eras Tour, it seemed like every person in the stadium had been waiting to sing these songs with her for over a decade. The happiness, joy, and excitement that echoed from the crowd while scream-singing “Love Story” spanned across all generations- from little kids to grown adults, it was a shared experience that will never be forgotten.
The “best days” we share with are family members are things that we hope are remembered for generations to come. Crafting an estate plan that protects those memories and values ensure that your accomplishments and milestones are celebrated and secured.
3. Speak Now – Your Legacy Matters
Song: "Long Live"
Lyrics: "Long live all the mountains we moved... I had the time of my life, fighting dragons with you."
My dad’s favorite Taylor Swift Song is “Long Live”. While Taylor did not sing it at the concert, her words ring true. Taylor’s Eras Tour is a celebration of her career, showing how important it is to curate and preserve what you’ve built over time.
Watching Taylor perform with my father highlighted how music bridges generations. Estate planning does the same—it's about creating a legacy that connects generations, passing down assets and values, stories, and traditions that strengthen family bonds over time. Your legacy is what you make it and who you make it with. It’s the mountains you have moved. It is the dragons you have fought and those who fought them with you.
4. Red – Prepare for the Unexpected
Song: "All Too Well" (The 10 Minute Version)
Lyrics: “Time won't fly, it's like I'm paralyzed by it
I'd like to be my old self again
But I'm still trying to find it”
One of the most moving moments in the concert is Taylor’s performance of “All Too Well” and the entire crowd of 70,000 belts out all 10 minutes of her iconic song. The love song gives you one clear message: life is unexpected, and change is certain and often uncomfortable. Life will almost never play out how you expect it to. From marriage and divorce to career changes and new chapters, it is important to be prepared.
I am fairly certain that each of us have had moments in our lifetimes where we sit back and think “this is definitely not how I expected life to play out,” and if you haven’t experienced that, it is highly likely that time will come. An estate plan goes far beyond planning for your death- it also is an instrument used to plan for life’s curveballs. What will happen if you get sick, or have an accident, and you cannot make decisions for yourself? What will happen if you find yourself needing long-term-care, but cannot afford the extremely high costs? An estate plan offers an answer to those solutions. With a carefully crafted plan- you get to determine how your affairs are managed and who will manage them for you if you cannot for yourself.
5. 1989 – Change is Inevitable
Song: “Welcome to New York”
Lyrics: “Like any real love, it's ever-changing”
1989 represents a whole new era in Taylor’s Career. It was her first album that separated her from country music and boosted it her career into new heights she had never experienced before. One of the most influential and impactful albums of modern times, this album represents change and shattering the barriers that have been built around us. Before Taylor even sang the first note of this set, the entire dynamics of the stage and production changed. We went from a cabin in the woods, to downtown New York City in the matter of minutes.
Building upon the Red era, life is unexpected and full of change. You may find yourself in a whole new city surrounded by strangers and unfamiliar landscape. When change comes, it is important to revisit your plans and adapt for what is to come. Estate planning is something that grows with you and that can adapt to each season, or in this case- “Era”, of your life. It is important to plan for the unexpected while also adapting to change.
6. Reputation – Guard What’s Yours
Song: "Look What You Made Me Do"
Lyrics: “I got smarter, I got harder in the nick of time…”
The Reputation era was probably the most electric and badass part of the show. It showed a side of Taylor Swift that was unapologetically bold. This era was about reclaiming her narrative and protecting what mattered most. This lesson applies perfectly to estate planning: safeguarding your assets and ensuring they go to the people or causes you care about.
In life, there may be “snakes” that threaten your legacy—unexpected claims, disputes, or challenges to your wishes. An estate plan acts as a shield, giving you control and peace of mind. Be like Taylor: anticipate the risks, take proactive steps, and ensure your story is told on your terms.
7. Lover – Building a Home and Community
Song: "You Need to Calm Down"
Lyrics: “Why are you mad when you could be GLAAD?”
Before the show even started, the friendship bracelet exchange is a simple yet profound act. You spend time crafting something meaningful, and then you share it with others, knowing they’ll appreciate it. These bracelets, small tokens of love and effort, were handed out freely—given with no strings attached, only the joy of connection.
Taylor opened the show in the “Lover” era. The pure joy and excitement that roared throughout the stadium when seeing an icon pop out of the stage was the most joyful thing I have ever experienced. Behind her was the “Lover House” where each room reflected a different era in her life- showcasing the art of building a home, or a community, and protecting it at all costs.
This era captures the sentiment of deep connection and enduring love, much like the bonds strengthened through both giving bracelets and creating a thoughtful estate plan. Just like giving or receiving a bracelet, estate planning is an act of love. Whether it's passing down treasured belongings, financial security, or even a legacy of shared values, it’s a way of telling loved ones: You matter to me.
8. Folklore – Craft Your Story
Song: "The Last Great American Dynasty"
Lyrics: “There goes the last great American dynasty,
Who knows, if she never showed up, what could've been”
During the Folklore Era, a cabin and trees, quite literally, grew out of the stage and transported us into Taylor’s world of storytelling, love, loss, and resilience. This entire era is about telling stories and similarly, estate planning is about telling your story—the story of who you are, what you’ve achieved, and the legacy you want to leave behind.
Think of your estate plan as your personal folklore. Whether it’s preserving family heirlooms, sharing your values, or creating a trust to benefit future generations, every detail contributes to the narrative that will outlive you.
9. Evermore – Navigating the Twists and Turns
Song: “Willow”
Lyrics: “Life was a willow, and it bent right to your wind…”
The "Evermore" era transports us into a world of quiet reflection and resilience, where life’s winding paths and unexpected turns become a thing of beauty. Taylor's introspective lyrics and visuals remind us that flexibility and intentionality can guide us through even the most turbulent times. Estate planning mirrors this sentiment: it’s about bending to life’s winds without breaking, ensuring your loved ones are taken care of no matter what challenges arise. Whether it’s addressing changing family dynamics, preparing for health care needs, or updating plans after a life-altering event, the key is adaptability.
Just as "Willow" shows how life can flourish with resilience and growth, an estate plan ensures your intentions remain strong and clear, even in times of uncertainty. With tools like revocable living trusts, you can adjust your plans as life evolves, maintaining control while preparing for life’s ever-changing seasons.
10. Midnights – What keeps you up at night?
Song: "Anti-Hero"
Lyrics: “I had a dream my daughter-in-law kills me for the money. She thinks I left them in the will.”
Taylor has stated that the concept of her Midnights album is what keeps her up at night. Like many, there are many nights where I have lied awake wondering what could happen in the future- and many nights I have lost sleep. What would happen to my dogs in the event of an emergency? Would my loved ones be taken care of? Would there be a huge fight over my estate? Many thoughts keep us up at night. What an estate plan offers is peace of mind. Peace of mind in knowing that your loved ones are protected, even your animals. Did you know that you can have a plan in place for your pets incase something were to happen to you?
11. The Tortured Poets Department – Finding Peace in the Midst of Heartbreak
Song: “The Manuscript”
Lyrics: “The only thing that's left is the manuscript,
One last souvenir from my trip to your shores”
Taylor’s latest album, The Tortured Poets Department, was added to the setlist after the album's release in April of this year and was probably my favorite “Era” of the tour. From the setlist to the stage design, it was a remarkable performance. The “TTPD” era is a reflection of what was and what is to come. It highlights the challenges of love lost and the joy of love gained.
Much like the stories told in this era, leaving a loved one behind is never easy. A tailored estate plan allows you to leave behind some comfort to those who will be grieving. Whether it is a trust to keep your family out of probate court, or a personal property directive outlining the distributions of your personal items: an estate plan allows your loved ones to focus on your legacy and your story rather than the stress of resolving your estate.
12. Estate Planning (Taylor’s Version)
Taylor Swift's journey of re-recording her earlier albums stands as one of the most empowering and calculated moves in the music industry. By reclaiming ownership of her masters, Taylor transformed a moment of loss into a narrative of control and legacy. Each re-recorded album reasserts her creative rights and preserves her artistic footprint for generations to come. It's a masterclass in recognizing the value of intellectual property and ensuring one's hard work is not only celebrated but also protected.
From an estate planning perspective, Taylor’s re-records are a metaphor for securing your legacy and retaining control over what matters most. Just as Taylor meticulously planned her re-recordings to safeguard her life's work, individuals can craft wills, trusts, and other estate planning tools to ensure their personal and financial assets are distributed according to their wishes. Estate planning, much like Taylor’s journey, is about proactive decision-making to protect what you’ve built during your lifetime and to leave behind a legacy that reflects your values and vision. Whether it’s songwriting royalties or family heirlooms, ownership and foresight are the keys to empowerment.
13. Conclusion Part 2: Be A “Mastermind” of Your Estate Plan
Song: “Mastermind”
Lyrics: “If you fail to plan, you plan to fail. Strategy sets the scene for the tale…”
In theory, this could’ve been added to the takeaways from the “Midnights” Era, but as a conclusion it pretty much writes itself. Taylor Swift’s "Mastermind" epitomizes strategic thinking and intentionality.
At the concert, it became clear that nothing about Taylor Swift’s performance was accidental—every detail, from the setlist to the lighting, was meticulously planned. Similarly, estate planning is about being a "mastermind," intentionally shaping the future for those you care about. By crafting a detailed plan, you orchestrate your legacy, ensuring that every asset, responsibility, and memory is handled according to your wishes.
Without a plan, you risk leaving your loved ones in a chaotic and uncertain situation. But as a "mastermind" of your estate, you control the narrative, setting the stage for a future that reflects your values and priorities. Whether it’s creating a will, establishing a trust, or designating powers of attorney, estate planning is your opportunity to write the final chapter of your story—on your terms. And just like Taylor, you can ensure that your legacy is one of intentionality, care, and empowerment.
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