5 Lessons I Learned from Leading a Mastermind

Jenna Kutcher 

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April 18, 2018


This year started with a bang as I hosted my first retreat with the Jenna Kutcher Mastermind group. 25 incredible women from all over the country (and Canada) gathered together in Waco, Texas where we spent 3 days diving into their lives, digging into their businesses, and helping them establish the dreams and set the goals they will achieve over the next year.

Throughout the year we will meet up in person 3 times at different locations where we will come together, troubleshoot things in our businesses, learn new techniques and strategies, and commune as a whole. Hosting a mastermind is probably the BEST thing I’ve ever done as an entrepreneur and I am so thankful that I get to lead these women through their best year yet. I’ve talked about why I don’t offer one-on-one coaching in an episode on the show and so toda I want to break down the 5 big lessons I learned from leading  a mastermind and share a little about our experience.

1.The power of community

The best part of leading a mastermind is the power of coming together with other people who “get it.” So often we are working with our heads down, in total isolation, even our families don’t necessarily understand what it is we do to make a living. When we can come together and be among others who are striving to improve, reaching for more, and driven to make it happen, it’s contagious. A mastermind facilitates conversations that go deep and fosters relationships that go beyond small talk. That paired with accountability create this energy that is palpable and hard to describe!

2. We’re all struggling

When you show up and you can admit that you don’t have it all together but acknowledge that you are gifted, dang, it’s the secret sauce. One irreplaceable part of a mastermind is that those that join are brave enough to admit that they need help figuring things out and putting the pieces of the confusing entrepreneurial puzzle together. Many tears were shed, many revelations discovered, but at the heart of it was a group of women not afraid to be vulnerable, admit that at times they flail, and ask for help. Far too often we show up with our guards up and we believe people expect perfect from us but showing up in the struggle is one of the most courageous ways to ensure that you will grow and learn.

3. It’s hard to see our genius

When something comes easily to us, it’s tempting to explain it away as not difficult or not important, but the truth is – those things don’t come easily to others. I chose the group of women specifically because of what their goals were, where they were at, and their mission for greater impact in the world. I noticed the women sharing about things they excelled at and light bulbs going off for others in the group. It’s far easier to recognize someone elses gifts than to look within and spot the things that set us apart. We’ve all got something to share and don’t minimize these things just because they come easily to you. It was beautiful watching people speak truth into one another’s lives and to help each other understand what their genius gifts were and how they can benefit, impact, and serve the world in bigger ways.

4. We forget how to dream

Let’s be honest, we’re so busy working with our heads down most days we’re praying we can get through the inbox and eat dinner before 8PM. A lot of times we get so caught up in the monotony, the minutia of everyday life that we simply forget how to dream bigger or what it looks like to get out of the grind and hustle and pursue something bigger. Achievers usually are list makers and sometimes we put ourselves in the tasks that we need not be in just to feel like we are “doing” but when we have no margin in our lives we don’t have space to dream bigger and to really ask ourselves, “What is it I want with this life?” One of the biggest things I want to instill in my mastermind women is how to create margin and space so that they have room to dream and grow.

5. It’s important to step out of your industry

When I joined my first mastermind, it was important to me to step outside of the photography industry and learn how other people were running their businesses. Sure, its tempting to jump into one with your best friends that do what you do, but for me, I wanted to see what was working in other industries and figure out how they would apply to what I was doing. Huge lessons can be learned by looking outside of your industry and applying what’s working for them to your business or which direction you want to go. I truly believe this also helps with the comparison game and creates a culture of being more open and giving because you aren’t as fearful of giving away your secrets to someone doing something completely different than you. I chose a diverse group of women so that they could sincerely grow from one another and teach each other and goodness gracious, it’s amazing.

(Bonus!) 6. We’re all cooler than we are online.

This is my favorite! I thought I knew the ladies in my mastermind before meeting them in real life. I mean, let’s be honest, some of them have hundreds of thousands of followers and the most impressive feeds. I spent months following them on social media, I had survey’s with very detailed information collected about them and their business, I did calls with them to learn about what they needed. But I was still blown away with how different it was to actually get to know them in real life. And what I found? They were so much cooler, funnier, smart, kind (the list goes on) than what they were presenting online.  I know everyone looks perfect online but let me tell you, little squares can’t show humor, heart, and hustle the way hugging it out in real life can.

The lesson here? Don’t be afraid to get real, show up for your audience and let them get to know you. Hiding behind a curated online presence is not helping you or your business. People need to fall in love with YOU first, your offer second.

So there you have it, the 5 main things I learned leading my mastermind and goodness gracious, I can’t wait to see what the rest of this year holds for this incredible group of dreamers, shakers, empire makers. If you’re curious about the mastermind or wanting to join for next year, jump on my waitlist at: jennakutcher.com/mastermind (make sure this link works!)


Want to know 3 MAJOR takeaways from my $100k a day biz coach? Click here.

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  1. Elizabeth Denniston says:

    I love this! Thank you for encouraging each of us in our own brand of beautiful. I couldn’t get your secret sauce quiz to open for me though. I tried in 3 browsers…any tips? Would love to walk through that!

  2. Jen Scherr says:

    I absolutely <3 this episode! My eyes were watering up because I think about all of things I'd love to be doing but psych myself out every time. I'm a "Dream Weaver" according to your secret sauce quiz, which I think is completely true. What stops me is the unknown, having no idea what I'm doing or who to go to for help. Listening to this podcast is definitely a confidence booster and reminder that I have to stop listening to the skepticism and know that I have what it takes.


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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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