Looking For a Mastermind in 2026? Here Are 10 Questions to Ask Yourself First

You've probably heard the buzz. Masterminds are everywhere right now—and for good reason. They promise community, accountability, fresh perspectives, and that elusive "next level" energy we're all craving.

But here's the thing: not every mastermind is right for every person. And not every moment in your business is the right time to join one.

Before you hand over your credit card and clear your calendar, let's pump the brakes for a second. Joining a mastermind can absolutely be transformative—but only if you're truly ready for it. So how do you know if you are?

That's exactly what we're diving into today. Whether you're a coach, creative, or service-based entrepreneur who's been scaling solo for a while now, these 10 reflection questions will help you figure out if 2026 is your year to invest in a mastermind—and which one might actually be right for you.

Grab your journal (or your Notes app: no judgment here) and let's get into it.

Why Reflection Matters Before You Invest

Let's face it: a mastermind is a significant investment. We're talking time, money, and emotional energy. Some programs run a few hundred dollars annually, while others can cost tens of thousands. The professional networking advantages alone can be worth it—but only if you show up ready to engage.

The entrepreneurs who get the most out of masterminds? They're the ones who've done the inner work first. They know what they need, what they're willing to give, and what success actually looks like for them.

So before you browse another sales page or hop on another discovery call, ask yourself these questions.

The 10 Questions to Ask Yourself Before Joining a Mastermind

1. What specific challenge am I trying to solve right now?

Are you struggling with lead generation? Feeling isolated? Or maybe you just need fresh eyes on your strategy? Get specific. The clearer you are, the easier it'll be to find a mastermind that actually addresses your needs.

2. Am I ready to shift from solopreneur to CEO?

Many women join masterminds when they're ready to stop doing all the things and start thinking like a leader. If you're ready to step into your CEO era, a mastermind is the perfect container for that shift.

3. What kind of support do I actually need?

Is it accountability, creative brainstorming, or pure networking? Knowing what's missing in your business right now will point you toward the right group dynamic.

4. What's my budget—and what ROI would make this worth it?

Define what success looks like in numbers or milestones before you commit. Whether it's one dream client or a full offer launch, know your ROI targets.

5. Am I willing to be vulnerable and share openly?

The magic happens when you show up authentically—wins, struggles, and all. If you're ready to let your guard down, you're ready for the breakthrough.

6. Do I have the time and energy to fully participate?

Masterminds require consistent engagement. Be honest: Can you carve out the time to show up fully right now?

7. What kind of group dynamic would serve me best?

Do you thrive in intimate groups or larger communities? Virtual or in-person? Industry-specific or diverse perspectives? Choose the environment where you flourish.

8. Who is facilitating, and do I trust their expertise?

A great facilitator sets the tone. Look for someone whose values align with yours and who has a track record as a business coach for female entrepreneurs.

9. What am I willing to contribute to the group?

Masterminds are a two-way street. Think about the unique perspective or skill you bring to the table for others.

10. Does this mastermind align with my values and vision?

Trust your gut. You're investing in a community, so make sure it feels like home.

Ready to Take the Next Step?

At Second Degree Society, we believe women are stronger together. Our masterminds are designed for the "disruptors" ready to build something bigger with real community.

Curious about what that looks like? Check out our upcoming events or explore more on the journal.

Because here's the truth: you don't have to figure it all out alone. And honestly? You weren't meant to.