What Jenna Kutcher's Mastermind is REALLY Like

Christina Scalera in high ponytail smiling big in nature

What Jenna Kutcher's Mastermind is REALLY Like

Spoiler alert: amazing.

Second spoiler alert: Out of respect for my Mastermind group (and Team JK!) I’m not going to cover what anyone else talked about or shared or the activities we experienced together except from my first-person experience. Regardless, hopefully this will give you some insight into what it was like!

mastermind with jenna kutcher

Before I joined the Jenna's Mastermind

In the past few years, one thing has been consistently true: I am invested in my own growth and development as an entrepreneur. There is no (legitimate) class or program you can take at a formal university that teaches you this stuff. And, even if that exists where you are, it’s never something I recommend because by the time there’s a textbook full of case studies written, it’s already three years behind.

My entrepreneurial journey began in 2014. The year before was a time of severe changes, both professionally and personally. It was when I started to dip my toe into the waters of what this online-biz-thing was. Like many of you, I bought all the courses I could. Once you pop ya just can’t stop.

Luckily, in those days, there weren’t very many courses for me to binge on. I remember I had a folder on my browser and would collect every course sales page I could find and put it in my purchasing queue. Yeah, that’s how few there were.

Online courses worked for awhile, and they were great. They’re even better now, as back then, the bar was set really low and there was no competition. I feel lucky I invested in some great courses—Webinars that Convert with Amy Porterfield, the Modern Calligraphy Summit, and oh yeah, what is now The Photo Lab™ with Jenna Kutcher (back then it was ‘Marketing for Photographers’... I bought it even though I didn’t know how to use a DSLR because I figured if these methods work for photographers they could work for lawyers!! Two super-saturated industries…)

For those of you who are just starting off and wishing you could be more advanced, please enjoy this learning time. It’s the honeymoon of your business, and <3 I miss those days.

The Big Shift

As The Contract Shop® began to take off, I had less time to learn and less resources to devote to learning. My time and money began to be consumed by business tasks and launches, including hiring contractors to help me with the increased needs within the business. Around this time, I also was getting asked to speak a lot at workshops and conferences I previously would have saved up for.

I remember having a fight with my family, trying to get them all to chip in to send me to Trouvaille during one particularly tight time, telling them it would have a great ROI because I’d make great friends with the other gals there and then they’d all hire me and then I could totally pay them back. Ohhhhh me. I have to laugh at myself. Less than a year later, I was invited to speak there, which was kind of surreal and there must be some cosmic lesson there that I don’t have time to parse out yet.

With a lack of new education and support for myself, combined with a feeling (I’m not proud to admit) of, “oh, now I speak at these things so I’m not going to pay for them” I was reallllllly feeling the pinch of no momentum.

I felt so tired serving everyone else while my own education and interests were neglected. I began to look for a way out of this funk. I landed on a full-year mastermind, which ended some good, some bad, but ultimately left me feeling like I didn’t want to join another one anytime soon.

mastermind with jenna kutcher

Enter Jenna's Mastermind.

Jenna and I had met in 2015 at Bonnie Bakhtiari’s Illume Retreat. Many of you remember that review because it went kinda viral. I went into more detail there, but suffice it to say, I started the week with no clue who Jenna was, and left it feeling really intrigued by this warm human being.

That was pretty much it for our interactions for awhile. Shortly after Illume, Jenna launched (and I joined) The Photo Lab™, which was an incredible experience that laid the foundation for the marketing I still do today. She was sweet enough to reach back out to me a few times via Facebook messenger, but I really figured that was it. She was/is a busy gal, and I’m just a tiny pipsqueak in my little corner over here.

But what I love so much about her is that she didn’t give up, she kept me (and the conversation we had at Illume) in mind. And she reached back out to me about her mastermind at the worst possible time (for me! She has no idea of this—and I’m glad!).

What Was Going On Behind the Scenes

I’d made some changes in 2017 that put me in a spot with my business I wasn’t happy about. I had been following too many people for too long and tried too many different things. My audience was SO. CONFUSED.

As a result, by August last year, I was desperate to regain any sense of traction and forward momentum. I hired many not cheap contractors (like, several $1000s each) to help me grow. And it was just at this time, after I’d made some really scary investments, that Jenna reached out to me with the opportunity to join her Mastermind.

Guys, I was so freakin’ scared.

For four reasons:

  1. Dude, this is Jenna Kutcher. The Contract Shop™ is not as successful as her business. How could I ever live up to her shop? She would see the inside of my business… could I ever live up to her expectations??
  2. Holy stromboli, how was I going to afford this? I was still in a very high-priced mastermind that I wasn’t getting much out of, and now I was going to layer another one on top? AFTER I had just made all those scary investments “they” (<<the collective internet ‘they’) told me to make to get to the next level?
  3. What if I was disappointed? I had invested in influencers before and felt like their offerings fell flat. Would I have unrealistic expectations? Would I get everything I invested back out of it?
  4. Some of the stuff she mentioned we’d be learning about was stuff I already had going in my business—like building a team. Would I be too advanced and feel held back?

Here’s how these things turned out, one by one:

  • I still don’t think Jenna has expectations of me as long as I’m living my mission by supporting others and impacting as many people in a positive way. In fact, before her Mastermind, I had gotten so singularly focused on creating products that sold that I forgot about my mission, and forgot about how I might be impacting someone’s life for the better. I’m so thankful for her ability to not judge where I was at, and seamlessly move me back to the channel of service instead of selling.
  • I did have to cut back. I wish I could be some ethereal law-of-attraction chick who is like, “OMG, I needed $1,000 and guess what?? I magically got a $1,000 check from the IRS for my tax refund!!” Buttttt that didn’t happen. I had to make some cuts, which included team members, marketing expenses and launch tools, which was extra scary as I made these cuts going into Black Friday. So far, though, it’s turned out for the best because they were things I probably needed to move on from for awhile, and this finally forced my hand.
  • What’s the most polar opposite of ‘disappointed?’ That’s what I am! I’ll explain more below in the retreat experience portion.
  • I remember specifically telling Jenna I was worried about joining because some of the things she had mentioned (specifically email marketing and building a team) were things I felt like I was already really good at. I’m so glad I joined, for so many reasons, but especially for the aspect of getting to see how Jenna’s business runs. I naively thought I was great at email marketing (despite a lack of funnels), and also thought I had a great team set up. Of course, shortly before our first retreat, my team kinda fell apart. I’m sure I’ll talk about that soon in another post, but suffice it to say, it was humbling to stand up there on the first day of our retreat in Waco and tell the group I needed help with… (waiiiiiiit forrrr ittttt….) email marketing and team building. Sometimes we need to trust other people when they see we need help, and instead of getting defensive, wonder if they’re right.

While some of this is doubtless applicable to you, you’re probably wondering what it’s been like so far. Shall we?

mastermind with jenna kutcher waco

Our Trip to Waco

If you read my review about Illume, which took place almost two years earlier than Jenna’s Mastermind and about 90 miles south, you know how inadequate I felt showing up there. I wish I could say that I have grown sooOOOoo much in the past two years and my confidence is just absolutely killer, but that’s not the case. Pretty much the only time I feel super confident is when I’m riding horses or skiing super-Gs. You life coaches out there can dissect why that is, because I can’t figure it out.

Anyway… guys. This is SO embarrassing. The other Mastermind gals and I were all in a Facebook group together before our first retreat. I stopped checking them out when each one seemed to be more beautiful and accomplished than the woman before her. It was nuts.

“I am lucky enough to be in this group?!” I kept asking myself...

I flew into Dallas the weekend before to see + stay with my parents. When I feel inadequate, I have a bad habit of trying to fix up my appearance. I spent the weekend getting eyelash extensions and had my hair re-dyed from its brassy, faded look (unfortunately, new color also never looks good when it’s brand-spankin’ new, a fact I conveniently forgot). And if you want to know how desperate I was, I had my hair dyed Monday morning on the way down to Waco. Yes. I’m that desperate apparently.

Nervous, full of anticipation, and armed with a killer blowout thanks to my insecurities, I made it to Waco early that afternoon. I was met by Jenna’s mom, who became one of the most influential women I’d interact with over the next few days.

The retreat center was gorgeous, and right across the street from Chip & Joanna’s house! An added perk that truth be told, we couldn’t really take advantage of since it’s a heavily patrolled area by the cops. Either way, it was fun to see it on our way in and out.

After getting settled and hiding in my room until the last possible moment, I emerged as one of the few remaining cars was pulling away for our evening meetup. After all, I didn’t want to bother anyone, so I was just going to drive myself and it didn’t matter if people left without me. This stems in part from...


I gotta put a break in the action to tell y’all something. One of the things she’s never talked about but that I’ve always admired and watched is how well Jenna holds herself. The biggest thing I struggle with is feeling like I’m bothering someone, all day every day. As in...

...Oh you offered me a piece of toast you weren’t going to eat anyway? Here, let me go buy you a Starbucks gift card.

...Thanks for that ride, I’m so sorry for the inconvenience, even though you offered and seem really happy to do a favor for me. Let me take you out to dinner now.

...You commented on my blog?! I need to sign up for your newsletter right away and forward it to 10 people!

Yeah. It’s a problem, and one I want to get over in 2018.

It’s one of the things I admire most about Jenna—she doesn’t second guess her decisions or worry endlessly about problems that don’t actually exist just because people are nice to her.

I want to be better at putting stuff out there for the world and unapologetically letting it be, confident in the work I do.

Sometimes our mentors and the people we choose to follow as leaders don’t have to tell us how to do something—we can learn from watching and simply being around them.

magnolia studios

Okay, back to the car thing. There was one car left and it had one seat, so I sucked up my hesitations and sandwiched in with these beautiful strangers from the internet.

When we arrived to our destination, everyone was there... Jenna, her sister ,and team had arrived (they were staying in the Bardominium—if you don’t know what that is shame on you!! Kidding). I was practically sitting in Julie Paisley’s lap by this point, since she was one of the only people I knew. But with a simple hug and turn to the group to address us, Jenna conveyed, “You are here, you belong, and we are a community."

I hate to give the lame cop out of, “we had a great night!” but we DID! It was the first time in a long time I didn’t think about work, I let my guard down and I forgot (for most of the night) that my eyebrows were kinda out of control.

And to top it all off, one of the women I’d grown up reading the column of in my favorite fitness magazine drove me home (which I still totally owe her dinner for in my mind).

Getting to Work

The next morning was full of the requisite intros and deeper dives into what we really needed below the surface of Instagram, our perfectly crafted email opt-ins and the numbers we used to measure ourselves.

Throughout the morning, one theme kept coming up. It’s something I even mentioned myself. We’re tired. We’re tired as entrepreneurs with all the hustle. We see people “making it” online and feel like we’re keeping up with them, but why does it feel so hard for us while it looks so easy for them?

Part of it is our “mindset,” which I’ve never been readily available to accept. I’m such a logical, empirically-based person that if there’s not a textbook with scientific evidence to back something up, I am largely skeptical.

However, throughout the retreat in Waco, any negative thoughts I had did seem a little bit louder... where they’re usually so quiet I just accept them and move on, in this safe environment they felt rude and intrusive. They were hard to miss, which was a good thing. It made me realize just how often I let them creep in and ruin my happiness, my good work and my ability to feel like I’m actually moving forward.

The safe environment has dissipated but I’m happy to say that filter I put up in Waco is still going strong. It’s easier than ever to see when I’m doubting myself or my work.

The other reason we’re all so tired (myself included) is because we’re focusing on too much. Ironically (maybe?) right before I left for the retreat my Facebook ads manager sent us our Christmas client gifts—she gave us the book The One Thing, and its message couldn’t have been any more clear coming from Jenna’s Mastermind.

To watch how Jenna seamlessly moves from product launch to product launch, it’s clear that her unrelenting focus is something most of us could stand to emulate sooner rather than later.

After a morning of digging deep, the afternoon was full of collaborative opportunities. I was able to get insight into how others perceived my business, and was forced to take a look at why I was doing some of the things I felt like I had to do.

With a perfect balance of work and play, we met up with Waco Tours to finish off the afternoon, touring the Fixer Upper homes and learning about Waco’s history. Of course I had to hassle the Baylor Boys driving us around (I went to Texas A&M, a school that is sometimes to never good at football).

Like any good retreat, there were tears, but not where I thought or expected them to come. At dinner that night, sandwiched in between Sue, Jenna’s mom, and Emily, a photographer from Boston, I felt myself doing something I never do, and certainly not in public—crying. Without going into details, it was cathartic and the result of a big epiphany.

mastermind with jenna kutcher

Wrapping Up the Retreat

Unlike other in-person workshops or retreats, this one didn’t feel rushed. Sometimes it feels like it’s over in a blur, but Jenna paced it nicely mixing the fun stuff with the serious stuff.

I left with a clear action plan surrounding ONE thing to move my business forward... not just a notebook full of scribbles I’d never look at again.

If you’ve never experienced an in-person learning opportunity, it’s hard to convey just how special an experience like this is. Your business can always make more money. You can always pivot and serve in new ways. You can retire (or crash into the ocean) old offerings and develop new ones.

But moments spent together in a carefully curated group by someone you trust?

Those are irreplaceable.

Every day (and with the new gratitude journal I decided to start keeping after this retreat), I thank the entire JK Team for the experience they curated for us. I know it wasn’t easy for them to give up their work weeks leading up to this, and I know for Jenna (or anyone leading a group of 25) that it’s not easy to hold that much space for others.

If you’re thinking about attending a mastermind or an in-person experience, here’s what I would ask yourself before you make the commitment:

  • What is this going to help me with?
  • Can I do this otherwise?
  • What value can I contribute to this group?
  • Will I be able to be open to suggestions I don’t like, or suggestions that don’t feel possible to imagine right now?
  • Am I open to change?
  • Can I get over my own insecurities to show up for my peers?
  • Am I ready to level-up in my business, or is there something I’m doing to secretly sabotage myself?
  • What kind of support can I expect?
  • What kind of impact can I make with this experience?

Photos graciously provided by Jenna Kutcher's team.

1 Response

Chelsey Nelson
Chelsey Nelson

March 14, 2018

I’ve been anticipating this post ever since I accidentally put two and two together and saw you in instastories from other attendees during the trip haha. Thanks for giving us an inside look and for being honest. It’s one of my favorite qualities about you and why I feel so loyal to your journey.


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