GOAL DIGGER

Are You Living in Alignment? A Conversation on the Almost 30 Podcast

Jenna Kutcher 

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August 22, 2022

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When a conversation as GREAT as this one comes around, I know it’s something I have to snatch up and bring over here to my Goal Diggers! I got to sit down with the incomparable Lindsey and Krista, creators and hosts of the Almost 30 Podcast to lay it allllll out on the table as we discussed one of my favorite, most-treasured practices in the last few years —- integration. 

Living in alignment with all of the beautiful parts of who we are is SO important for creating a life we really love. This conversation of ours originally aired on their podcast and I loved it *so* much that I asked them if I could share it with you here, too. And while you’re probably already an avid listener to Almost 30, if this is your first intro into the brilliance and humor that are Lindsey and Krista, I invite you to tune in and subscribe to Almost 30 wherever you get your podcasts! 

Evolving into New Versions of Myself

Krista and Lindsey always get down to the real and deep topics and waste no time with small talk. They asked how I felt meeting new versions of myself and the change that comes with new life experiences and goals.

I welcome evolution now. I used to resist change, and I think so many people can relate to that because change means uncertainty. But we just survived two years of utter uncertainty and hopefully we’re coming out of it different people than we were when it started.

Change to me is like an invitation of challenge and being stretched and evolution and contradiction. I often think about how Drew and I have been married for almost 11 years and we are totally different people than when we said those vows, yet we’ve both come home to ourselves over and over and over again and reestablish what that means, but we’ve also come back to each other every time. 

We all resist and avoid change, but change is where we grow and I’d rather be evolving than standing still.

Woo Meets the Work

This conversation followed a lot of the themes that I cover in my book How Are You, Really? including the topic of hustle culture. If you know anything about my business, you know I’ve developed it to a point where hustle is most often a dusty word in the corner… But it wasn’t always that way, and there are times when hustle aka “work” becomes necessary. 

I feel like female entrepreneurs are facing two camps. There’s the manifestation side, the woo side, and there’s the hustle side, the work side. When my editor chose my book I asked her why this book, why me?

She told me that she felt like there are only two camps that are being displayed in entrepreneurship and I represented where the woo meets the work. I like to exist in a space where I hold visions and cast visions but I’m also willing to work towards them. I hope that my example is proof that you don’t have to pick one side or the other in your life or business – you can do both.

Why Defining Success is Important

We talked about a concept that is so important to me and I teach repeatedly on this show and inside my book, and that’s the idea of defining your own version of success. Krista talked about seeing so many women working towards something but not enough of them know why they’re working towards that end point. 

For me, I worry that those same women will arrive at quote-unquote success and it won’t feel good, then they’re going to lose their ability to trust themselves to make the next decision. 

How many times are we out there in pursuit to prove ourselves wrong? It’s like, I thought I wanted the corner office and the high heels and the power suits, but I really like sweatpants and my feet don’t fit into high heels, but I’ve already invested this much, or I’ve already said this, or I’ve already told people this is what I’m gonna go after so if I don’t do it, I’m going to be a failure. 

If you don’t define your own version of success, you’re working off of other people’s maps.

More from this Conversation

I always feel SO full of motivation, inspiration, and just that soul-quenching friendship-feeling whenever I get the chance to spend time unfolding a little bit of life with Krista and Lindsey. I hope you felt some of that, too! 

It’s humans like this that make it even easier to dig into the deeper parts of life without the post-oversharing headache. And I know we could’ve talked for another handful of hours without even batting an eye, which just means I’m going to have to talk to them more often! 

In the meantime, there’s an expansive timeline of over 500 episodes of the Almost 30 podcast to tide you and I over. Search Almost 30 in your favorite podcast listening app, hit that subscribe button, and jump in! 


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  1. YES! As an entrepreneur of multiple businesses and mom, I’ve struggled with the you have to be this OR that, do this OR that, believe this OR that- I’m always somewhere in the middle. Aligned. Hustle hard then live. Not be fully one way OR the other. This was such a refreshing episode.

  2. Samantha Ray says:

    Hey JK! I am such a fan and have been encouraged by your podcast and content over the years. I’m a former empire-building lady entrepreneur, and I have many close family members are girl friends who are killer lady bosses, have huge followings, and have had lots of biz success. I felt like this episode (particularly the beginning) was a little off. I’m the friend that doesn’t always ask about my friends’ business success, and there are A LOT of reasons why. I wrote an open letter to you about it, because it meant a lot to me to express the other side… the family members and close friends who don’t always seem as supportive, impressed, or vocal about your biz as you might hope for. I hope my love comes across and that it can be a good addition to the conversation. Maybe others can relate?
    Here’s my open letter in response to this podcast,
    https://www.samantharaywriting.com/blog/2022/8/23/an-open-letter-to-the-jenna-kutchers-of-the-world

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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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