3 Crucial Takeaways From My Secret Mastermind (That Every Woman Needs to Hear)

Jenna Kutcher 

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January 29, 2020


Jenna Kutcher shares the 3 crucial takeaways from her secret mastermind in Fiji.

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A few months ago, I flew 14 hours around the world with Drew and Conley and landed in the stunning lush country that you’ve seen on water bottles, Fiji. It was the most memorable trip I’ve ever been on because I got to bring my family with and we spent magical days in Fiji skinny dipping in our private pool, eating the incredible food, learning about the Fijian culture, and digging into biz.

I’d been invited to a mastermind led by my business coach Dean Graziosi and Tony Robbins, and was secretly pretty excited to be the only woman who’d made the cut among the 10 people invited. It’s not that I didn’t want other women there — that would’ve been awesome and probably way more comfortable for me.

But I was more so just anticipating watching what these men with big personalities and successful, multi million-dollar companies talk about business. I wanted to pay attention to how everyone interacted, if they’d lift one another up or jump straight into the competitive mode. I got to be a fly on the wall and an active participant for a few days, and even though it was slightly intimidating, I somehow felt mostly, really at ease going in, especially because my favorite humans got to come along with me.

This whole year for me has been about leaning into presence, and not pushing to chase down my next massive goal. I wanted to set up my business to sort of coast this year, so I could be invested in this transition into motherhood, and I was ready to talk about that with these dudes who I was pretty sure wouldn’t totally relate but I was ready to bring my feminine vibes and maternal energy to the party.

Here are the 3 most impactful lessons I walked away from Fiji with, and also the most common questions I got from the dudes in attendance — some of them might just surprise you.

How it Started

On the opening night at our gathering, we were invited to introduce ourselves and share a bit about what we do, where we’re stuck and what’s next for us. And we were also asked to share one big question we wanted answered at the mastermind. Lo and behold, I ended up being picked to go first. I explained a little about what I do, this current season that I’m in, and I told them that I really don’t totally know what’s next for me but that I’m good with that right now.

Truthfully, it’s the first time that I can think of that I’ve ever felt this way and it feels really, really good. All eyes were on me, and then Dean followed up with asking me: So Jenna, what’s your big question you have for the group this weekend? I answered that I didn’t have one.

It’s not that I didn’t want to learn from these guys or engage in the conversation. But I just truly did not have any burning, unanswered questions that I needed their insight on specifically. I didn’t go to Fiji with this one code to crack or with the motivation to leave with an action plan – in fact, it was quite the opposite. Fiji was just the start of a 3-week vacation with my family and I was protecting myself from getting so many ideas that I wouldn’t be fully present with my fam when we were in once-in-a-lifetime locations.

I’m in a place in my business that I never could’ve imagined 10 years ago. I mean, 10 years ago I was still wearing red and khaki as an intern for Target, to give you a little more perspective. I’ve experienced more growth than I could have ever anticipated this year, and I honestly account it to taking some of the pressure off and just allowing myself to relax a bit, for once. I’ve taken more time off, traveled more than ever this year, essentially worked part time and yet my business has never been better.

I’ve been a part of masterminds for the past few years and I’ve learned that usually the best value I get is in listening to other people’s questions and taking what serves me while discerning what advice just isn’t a fit for me. This was my plan for Fiji.

Needless to say, that night was the kickoff to a very interesting, and very educational few days. The highlight for me? Honestly, watching the hotel staff at an adults-only resort completely love on and adore Conley. I know that sounds strange, but I learned just as much about joy and kindness and contentedness and heart from them as I did from the brilliant humans at the mastermind. By the way, we were breaking the golden rule by bringing an infant to an adults only hotel. Thankfully they were able to accommodate my request and it worked out so well.

Our Ego Gets In the Way

I was the first to intro myself and share my non-question with the room, and man, in hindsight, I’m so glad I went first. What I experienced next, and in a few more of our meetings, was a lot of ego showing up and I think a lot of it was out of insecurity. I mean, have you ever been in a room that you feel like you don’t belong in? Imposter syndrome? We all have it and I was quickly reminded and no matter what stage of the game you’re in, you’ll likely still battle it. New levels, new problems, right?

Now, before I go too far, I want to say I 100 percent respect and admire every single person in that room. They are brilliant, kind, impact driven men who have all built incredible, impactful businesses and are leaving beautiful legacies for their families. These are top notch beings that I am blessed to know and love.

But as I sat back and watched as more of a spectator, it became super interesting, and super clear that a room of powerful men can quickly turn into a huge contest. Who can one-up the best? Who has the best questions? Who knows the most powerful people? Whose story is most moving or shocking? It was like a ping pong match that I’ll be honest, I wasn’t NOT into observing.

I mean let’s be real, it was utterly fascinating. And honestly, I get it. We ALL feel this pressure to prove ourselves throughout our lives. For a long time, I thought it was just women who had it bad. But holy cow, men have just as many insecurities that they try to mask with their egos. Where women many times measure their worth by body image, or influence, or relationship status, or income… men measure theirs just as stringently by money, success, and impact. They hold themselves to impossible standards, just like we do.

And these men at the mastermind HAVE all of that — money, success, power — yet I could still see this straining effort from so many to prove themselves. Isn’t it true that our ego can totally screw with our worth and get in the way of who we truly are?

I was so not judging those guys because I could see this truth and recognized it in myself: we have this desire to feel important. This year has been good for me in that way, because motherhood has actually forced me to drop the expectation to prove myself. I KNOW I can’t do everything and be the best mom and live a perfect life and scale a business. I don’t want to either. It’s why the phrase “imperfectly empowering women” has sorta become my mission and my slogan.

I want to lead by showing it’s okay to be messy and make mistakes and learn as you go, something that I think our egos HATE for us to do. They want us to stay stuck in insecurity. EGO is everywhere.

One of my fears in going was that I would hear about all the things I COULD do and not having people understand that they don’t really appeal to me, because I don’t necessarily care to make money money or speak on stages in front of thousands, that endorphin rush of feeling important or more valued doesn’t trump having more freedom and more time for me.

If we SERIOUSLY look at time as our currency, then the idea of doing these big things that will take months, even years, just doesn’t appeal to me. I could easily commit to writing a book or going on a podcast tour or running a live event or hosting a giant mastermind, but when I look at the time it would take away from my family, it quickly loses its luster for me and that definitely set me apart in a unique way!

Your intuition is your guru

Along the lines with ego, I saw a lot of people interested to get their big question answered and to me, I saw these brilliant humans who had already built massively successful businesses and I wanted to shake them and say, “You already know what you need to do, you don’t need anyone’s permission to go out and do it.”

I probably had one of the lower earning businesses at the mastermind, but I can tell you I had the highest level of contentedness and connection. I felt grounded, I didn’t feel frantic, I felt free to disconnect and be present, and the greatest lesson I’ve learned this past year and that I can really trust myself. That’s been such a process, and an empowering one at that.

I’ve had my own amazing mentors and teachers and voices, from entrepreneur friends who just had their own babies, too, to my mom, to women ahead of me in business who encourage me to embrace this special time even if slowing down doesn’t feel natural or come easy to me. Seeing how fast Conley’s first year of life went really made me grateful that I chose to black out my calendar for the year to give myself that time to be a mom first and an entrepreneur second.

This past year, I’ve learned to lean into my intuition. And as a woman, I feel like we tend more in touch with our intuition naturally. I mean, I’m the kind of girl who hires based on feelings, knows the second I walk into a space if it “feels” right and while my methods might not be textbook, I’ve learned to really listen to my gut and trust it.

As women, I feel like we often disregard our gut feelings or write off what our intuition is telling us to opt for more “head strong” ways – systems, logic, blueprints – those are all powerful tools but they should never replace what you know and believe to be true for you, especially in business.

A lot of the men at the mastermind brought their incredible wives along and I found myself dialoguing with these women more then the men! One of our conversations was just about how we as women innately know and feel things and it’s part of our superpowers. We have these instincts and when we tap into them, we are generally more successful.

I was constantly listening and learning, allowing my intuition to guide what advice and ideas I wanted to take with me – the ones that resonated and were in alignment and made sense and I felt free to leave the rest at the door.

One of the gifts I discovered this past year when I was more stretched juggling motherhood and business and working limited hours was getting really honest quickly about what would serve me in this season, and I was able to consciously let the stuff go that didn’t feel right without dwelling or questioning or trying to make something fit that didn’t make sense for me right now.

We talked about all different kinds of things that COULD work for my brand from joining the speaking circuit and speaking at large events to starting another mastermind to writing a book or creating more products – trust me, I know there are a million things I COULD do that would be successful but I’m really honoring not adding more work to my plate and focusing on how I define success which was which I’ll talk about in just a minute.

I know my enough

I have a whole episode about defining your enough as an entrepreneur and how it can literally change the course of your business and even your life. It’s a goodie if you’ve been feeling maxed out or you’re wondering where that threshold exists – or if it even does.

It’s been so important to me because once you know your enough, you know where to draw boundaries and say no so much more clearly and with confidence. When you’re pursuing more and more and more, there’s always something else to do, and strive for, and work toward. Entrepreneurs are the worst about setting goals, crushing them and being on to the next thing without pausing.

I mean, it’s a good thing sometimes. We want goals and measurable markers to aspire to, but when the goal is always just “more,” then where do we stop? When does it ever end? Where is the line drawn? Knowing what the number, or the achievement, or the amount of work is that YOU feel is truly enough for your contentment and peace will allow you to create a structure to get there, but not burn yourself into the ground.

Constantly going for more means you’re never done, and people at this level seem to tend to withhold joy from themselves. It’s like the “I’ll be happy when…” mentality, and then when they reach whatever milestone they’ve set, there’s another level they’re already pursuing. There’s no time for gratitude and joy, no space to take it all in.

During the mastermind, I was doodling… is anyone else a doodler? I need to keep moving while listening and I was listening so intently but I couldn’t get this vision out of my head. I was thinking about how I define success and it was so clear to me: I drew a picture of our log-lake house and the words I wrote: I want to feel peace and freedom. That is my goal. It’s a feeling, sure, but I wasn’t writing down email subscribers or profit numbers or Instagram followers, I define success as feeling peace and freedom and to me, that looks like time at the lake with my family, not adding more to my plate.

I saw the return on defining my enough so clearly this year. The simple economic principle of supply and demand reared its head when I blacked out my entire calendar for a year, making no commitments to events or launches. Literally NOTHING work related lived on my calendar for the entire year. Little did I know that when I did that, I inadvertently made my demand increase.

So instead of wishing I was on stages and feeling FOMO and seeing my friends doing these big events or book launches or conferences, I got to be home experiencing JOMO – the joy of missing out – because the moments that were unfolding right in front of me trumped any 15 second clip on an Instagram Story!

Literally anything you saw me do this year from launching courses to affiliate sales to small, intimate events, even recording this podcast – it was because I WANTED to, not because I had to. I didn’t HAVE to do a dang thing, I was committed to trusting my gut and my gut alone and so this was easily the most passionate fun year of business for me because it was fueled by my best “yeses” and honored by way more nos.

Heck, I can open my phone and reach more people than I could being on stage. So if I really have a message for the masses and can deliver it from home on my couch with Coco nearby, why would I not do that? My enough is way more about quality of life this year and giving myself blank space to choose what I want to participate in as I go.

The biggest questions people asked me

One of the biggest joys I had at the mastermind was teaching — go figure! It’s actually so funny — I didn’t go in thinking I’d have much to offer these successful men. These guys are well versed in business and marketing, what were they gonna ask me?

But the two biggest questions I was asked were: how to better connect with their audiences, and how to create a true brand with content that impacts, connects with, AND appeals to their people.

So full disclosure: the whole reason I was at this mastermind was because I won a launch that I was an affiliate for, The Knowledge Business Blueprint, such a crazy awesome course. And I beat out all these dudes — plus over 1,000 others. They have these insane email lists and followings and majorly successful businesses. And I truly believe it’s because I know how to meet my people (YOU!) exactly where you’re at. They were asking how I did it, what magic I was working over here. And I’m just like, “Umm, I post pictures of my baby and talk about how I mess up and ask questions so I can understand and serve people where they are already at.”

But really! I don’t try to pretend like I know everything or like I’m the authority on all the things. I share the strategies that I’ve seen work really well again and again, and I also share pieces of my life that make me an imperfect human and relatable. To me, it’s not rocket science. It’s just honesty. I don’t focus on trying to win over the masses and get the world rallying behind me — my mentality is much more a one-by-one, let’s do this together kind of thing.

Some people get so big that they forget they’re speaking to real people who are just trying to live their lives or run their businesses a little better, I realized it’s a gift to not be SO removed from the beginning that I’ve forgotten what it’s like to scrape together $100 to hire a designer on Etsy for a logo or to have your goal to simply be to pay for your gas… I have never forgotten what it’s like to bootstrap a business while simultaneously questioning if you can make it. I’ve never shied away from sharing the good, the bad, and the ugly of entrepreneurship.

Now the branding question made me chuckle a bit because dang, these guys’ brands are SO masculine. The work they do can serve men and women a like but simply in how they are showing up they are repelling half of the audience without even knowing it. I had a few choice words for my fellow attendees about that, and let me tell you, they were taking notes.

A lot of times our ego tells us to share the showy stuff, that that is the selling point and what people want to see. We can end up posting stuff that people can’t even relate to or don’t even desire, and I think that’s where I’ve figured out a different way. While you might not be able to relate to every aspect of my life, you sure as heck have bedhead some days, live in your coziest sweatpants, have kids that do the darnedest things, and have days where you’re hustling so hard your top knot goes awry.

I try to lead with imperfection. I’m like, here are my flaws, here’s what I’m working on, here’s my heart and I’m letting you into my messy middle, I’m not waiting to share when I have it all figured out (because if that were the case, we’d be waiting forever, right?) That sort of humility is what I think has kept me as a human relatable even when my business has grown.

The Big Picture

I learned so much in Fiji. Did you like getting a bit of an insider peek to my mastermind I attended last year? It was truly a trip, and I found myself feeling so affirmed in the stage I’m in right now. At one point during one of the meetings, it was running hours later than expected and I needed to feed Conley, so I grabbed a nursing cover, Drew discreetly snuck her in and I fed her while I was learning from the others who were still masterminding.

Later, some of the girls from Tony’s team came up to me and were like, “That was awesome! How empowering to see a working mom in action. Nobody’s ever done that at one of these.” And I just smiled, because that’s this season of life for me right now. It’s a juggle and it’s imperfect and it’s this mix of life happening and business evolving and it’s spur of the moment changing hats from boss to mom. I didn’t want to miss out on the content, my baby needed to eat, and that was reality.

That’s sort of my whole approach to life right now, this delicate dance of embracing being a mama and embracing my still growing business. I don’t need to perform or prove myself to anyone, and my peace is my ultimate measure of success. That’s all I could really ask for right now and I’m thankful you get to watch it all unfold. Thank you so much for being a part of this journey.


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  1. […] and Wednesdays. One of my favorite recent episodes was about her experience at a conference as the only female entrepreneur where she totally breastfed mid keynote speaker like a […]


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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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