Why You Should Join A Mastermind, Even If You Think It’s Not For You

Micah Shilanski, CFP®, shares advisors’ most common excuses for not joining a mastermind and why you should make the investment anyway.

3.8 min read

Micah Shilanski
Micah Shilanski
Financial Planner, CFP®

I don’t talk about my parenting fears with my attorney. My accountant doesn’t know what I’m worried about in my business. And my wife may not understand the impacts of my profit and loss reports on business growth.

But the guys in my mastermind group know about it, and then some. They’ve seen my profits and loss reports. They know what’s on my tax return and understand the struggles I’m up against as I scale my business.

Working with a mastermind group will be different than any other relationship you have, and as cliche as it sounds, having a solid mastermind group has changed my life.

I know many programs promise to be “life-changing,” but getting into a mastermind group and forging trust truly delivers in ways few other relationships can.

You see, the guys in my group understand the context of the problems and struggles in my life, so they can give me better life and business advice than any other group of professionals I work with. 

Advisory practices are primarily solo endeavors, so finding a sense of camaraderie through a mastermind can be a lifeline for many.

Unfortunately, too many advisors would rather continue their solitary struggle than reach out and forge these meaningful connections, balking at the price of enrollment. But my good friend Aaron Walker insists that’s just part of the cost of doing business.

What’s keeping you from joining a mastermind to become your best self? 

1. You’re afraid of the unknown

You may not like where you are now, but there’s a certain familiarity in the “known discomfort.” You know what to expect here, and, for the most part, you’ve figured out a way to at least manage it.

So, you continue to keep yourself small. You’re not reaching out or growing too much. You’re steady in your business or at least coasting. You keep telling yourself you’ll join a mastermind when you make x amount of money.

But your fears aren’t going away—they’re compounding because any growth you experience means you have much more to lose.

Even if you find the courage to finally scale your business, you won’t know the challenges ahead. You’ve never experienced this before.

When you don’t have anyone to talk you off the ledge or help you push through your upper limits, it’ll be tough to understand that you’ll be okay despite all the changes you’ll face as you level up.

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2. You don’t know who to trust

When you’re approached by a coach or a friend to enroll in a mastermind, it can feel like these guys are just part of some MLM scheme, hoping to cash in on your insecurity. But that couldn’t be farther from the truth.

The people you meet in your mastermind want you to be successful. They want you to be the best version of yourself. 

You may feel like a wallflower during your first few meetings, and that’s okay. But eventually, you’ll get drawn in and be comfortable sharing the issues in your business and life holding you back.

I used to struggle in my mastermind groups. I felt they were another opportunity for a bunch of successful guys to pat each other on the back—until I dared to ask an extremely personal question about my finances.

Because I dared to ask that financial undressing question, other group members opened up about their challenges. By asking that one question, I completely changed my mastermind group’s trajectory and everyone who attended’s success.

Unlike other professional relationships, your mastermind peers know your life’s context and can give you tailored advice.

Your attorney doesn’t know what in your business is keeping you up at night. Your accountant can’t advise you on managing your work/life balance. But your mastermind group can give you targeted advice on those things because they know you and they’ve faced similar challenges.

3. You’re a private person

I know it’s hard to spread your private, personal information on a table for seeming strangers to dig through. Many advisors have never shared documents such as their profit and loss reports, tax returns, and net worth statements with another breathing soul (aside from the preparer).

It can be intimidating to hand those pages over. You may be thinking that you can’t give that information out. But I want to encourage you—no matter who you are—that you need people who can give you unbiased advice and throw a red flag on your BS.

We all tell ourselves little lies and believe our excuses for not bringing in as much revenue as we wanted or holding on to clients that drag down our bottom line. You may not realize you’re drinking your Kool-Aid until someone else sees the evidence and calls it out.

There aren’t very many spaces you can visit as a successful person to talk about the struggles you have in your business and receive genuine feedback. You need a sounding board. We’re not here complaining about how hard it is to get our work done; we’re here solving problems and fostering growth.


Action Items

Let’s take a minute for a Tim Ferriss fear-setting exercise. Pull out a pen and a piece of paper to write down all the things that scare you about doing a mastermind.

Next, on a separate page, list everything you want to change in your practice but are dragging your feet. Maybe you’ve punted raising your fees for years—or there are clients you know you should graduate but haven’t.

Compare these two lists and answer honestly: would having support from a group of other successful advisors be worth the investment if you could make those changes you’ve put off?

In my practice, my masterminds’ impact on my bottom line has far exceeded any fee I paid.


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