Legal Priorities for Each Era in Your Biz

Thanks to the Eras tour, we’re having a moment in pop culture. Whether you’re a Swiftie or not, Taylor Swift’s Eras tour is shaping how millions define live entertainment. Let’s embrace the moment, shall we, and talk about how this concept of “eras” applies not only to massively successful recording artists like TSwift but also to your business. 

To stand the test of time, you must be like Taylor, who has managed to navigate the winds of time to stay relevant in an industry that is always changing. Your business too is always changing! And as your business grows and evolves, your legal needs change too.

Before you can determine your legal needs, though, let’s figure out what era of business you are in! ⤵️

Eras You Go through in Business

From a country singer fresh on the scene to a confident trendsetter and icon, Taylor’s been through some eras, that’s for sure. If you’ve been in business for a while, you can probably also think back through all the lessons you’ve learned and how you’ve grown and adapted along the way. 


Let’s round up the eras you go through in business, TSwift style. As you read through, think about where you’re at, so you can make the most of the legal advice that follows.

Debut

You’re in the Debut era when you’re just starting out in business. Like Taylor when she released her debut album, you’re innocent, inexperienced, and probably a little naive about what it will truly take to turn your business dreams into reality.

Fearless

If you’re in the Fearless era, you may sometimes be distracted by “shiny objects”. This is because you’re still honing in on who you are as an entrepreneur, where your business value truly lies, and maybe refining who your ideal audience is. (This is the era where your freebie and online course graveyard tends to grow. 😬) 

Speak Now

Once you hit the Speak Now era, you’re growing a brand and not just a business. This is where you start to hit your stride; you’re getting comfortable sharing parts of your story, you’re infusing everyday life into your content, and you’re voicing your opinions.

RED

In the RED era, you’re really going THROUGH it. You’re dealing with tough business issues, possibly issues that have never come up before. It’s possible you’ve made some bad investments or investments that, in hindsight, were badly timed. Maybe you’ve gotten into some sticky client situations, got caught up in the online comparison trap, or even had some copycats emerge from the woodwork. 

1989

Once you hit the 1989 era, you’re ready to start the next chapter in your business. You’re changing directions and embracing the fact that sometimes you have to pivot. A pivot is a risk, and sometimes it works, and sometimes it doesn’t. This era forces you out of your comfort zone. 

Reputation

If you’re here in the Reputation era, you’re focused on expansion, evolution, and doing business your way. You’ve got enough experience under your belt to know that you don’t have to fit inside someone else’s box. You feel free to run your business, build your brand, hire, fire, and generally act in a way that’s true to who you’ve become as an entrepreneur. With this confidence often comes stronger boundaries.

Lover

If you’ve reached the Lover era, it’s time for a breather. You’ve come through the other side of a period of intense formation and reformation. In this era, you experience a renewed sense of appreciation for your business. You’re focused on finding more work/life balance and having fun again.

Folklore

In this reflective season of business, you consider where you’ve started and how far you’ve come. In the Folklore era, you focus on understanding what has worked, what hasn’t worked, and the lessons you’ve learned along the way. Here, you feel empowered to pursue what works and cut out what doesn’t. You’re pruning the garden to make way for future growth.

Evermore

If you’re feeling like it’s time to experiment, play, and be bold, you might be in the Evermore era of business. You know what works, but how can you tweak what works to make it work even better? Growth means trying new things (maybe it’s running ads, hiring new employees, adding new revenue streams, investing in upgrades, etc.). Maybe you spend more to make more. Maybe you lean into innovation.

Midnights

You’ve made it. In the Midnights era, you’re confident and authentic. You’re more than a solopreneur; you’re leading a team, you’re a thought leader in your industry, and you’re not afraid to share the highs, lows, and in-betweens of entrepreneurship with others who look up to you. 


Now that you have an idea which TSwift-inspired era of business you’re in, let’s make sure your legal is in order.

Legal Considerations for Every Era

Here’s what you should have in place for each era of business, according to a lawyer! Keep in mind that different types of businesses have different legal needs and priorities. View all advice (including ours) through a critical lens, and reach out if you need individual help. 

Debut, Speak Now, Fearless

If you’re in one of these three eras, we recommend focusing on contracts, establishing your entity, and getting your trademarks, depending on the type of business you have. For online service-based businesses, check out our Contracts Starter Kit. Product-based and brick-and-mortar businesses should get their entity figured out and their trademarks in motion. 

Red, 1989, Reputation

Find yourself in the Red, 1989, or Reputation eras of biz? Online service-based businesses should have contract templates for EVERYTHING by now—this includes contracts for not just clients but also guest speakers in your program, guests on your podcast, digital products, and contractors. All business types should really start the trademark process here if they haven’t already. 

Lover, Folklore, Evermore, Midnights

Once you’re in one of these eras, it’s high time to have a lawyer on your team. You’re ready for a legal subscription that gives you access to answers when questions come up, quarterly trademark searchers, quarterly contract reviews, and more.



There is no one-size-fits-all legal plan for businesses. It depends on what type of business you have and what era of business you’re in. If you’re country Taylor, we suggest a legal consult to discuss where your particular priorities should be. If you’re post-Lover Taylor (especially if you’re in the six-figure range), you need all the bells and whistles that come with a legal subscription that gives you access to a lawyer when needed. 


Ready to seize your era and get your legal in order? Pick my legal brain to set up your legal roadmap, cover yourself with contracts, or reach out to us directly if you’re ready for the legal subscription!

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