GOAL DIGGER

What’s Changed and What Hasn’t 400 Episodes and 4 Years Later

Jenna Kutcher 

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October 12, 2020

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Episode 400. FOUR HUNDRED. How is that number possible? The Goal Digger Podcast launched as a labor of love mixed with lots of hard work, topped off with the magic and kindness of each and every guest who volunteered their time to be part of my big podcasting dream. I truly have to pinch myself reflecting back on the guests I’ve had the pleasure of sharing this platform with, and the topics I’ve had the opportunity to dig into with you and for you.

When Kylie suggested revisiting episode one of the podcast and updating it for Episode 400, I honestly cringed. Not because I don’t stand behind the content (because I definitely do!), but rather, no matter how many episodes I have under my belt, I still get all sweaty and anxious when I have to listen to my own voice.

But, I agreed, because I think it’ll be not only fun to look back on how this whole show started, but I’m also excited to share how my view of some of the biggest topics I teach on have shifted since I launched as a 28-year old entrepreneur, a few years into her online business, with bright eyes on the future. My views and teachings on topics like legacy, social media, privacy, authenticity and more have evolved in the last four years, and I want to share that all with you in this episode. So, ready to hop in a time machine to November 18, 2016? Hit play to hear the clips along with my reaction to them all!

What I’ve Learned About Podcasting

I laugh when I think of recording these first episodes. Let’s just say you 100% do NOT need a studio or even a professional microphone to simply begin. All I had was iPhone headphones and a lot of nerves. Since episode 1, I’ve learned so much about podcasting — I mean, I made a course on the topic, because whew, I made a lot of mistakes but I can hands down say that starting my podcast changed the trajectory of my business and helped me to extend my brand in a way that I couldn’t with social media alone.

It’s generally now with how I lead and explain what I do and how I serve the world and it’s allowed me to not only show up each and every week teaching and sharing what I’m learning or what I’ve learned but my FAVORITE part is getting to interview incredible women that I admire and love and can learn from — like having an excuse to reach out to your heroes and getting the chance to connect and have a conversation that thousand of people get to listen in on — it’s THE best.

About 2 years into the show, I switched to having more scripted solo shows, mainly to keep me on track but so that I could live up to the mission of sharing tactical, applicable information without the fluff, and lemme tell ya, mom brain played a huge part in that decision because I just wanted to make sure I didn’t go off on weird tangents or tell the same stories over and over again.

I think we’re still trying to find the perfect balance of bullet points and delivery on the tips and tricks and while I sincerely hope it feels like you’re just hanging out with your girl, Jenna, I can definitely see and feel the growth and change that has happened since this show launched!

Social Media and Legacy

Legacy fits into my business today in different ways, when I think about our lives when I hit record on that first episode, we were in such a different stage. We hadn’t experienced our two miscarriages, birthed my daughter, moved back to Minnesota — life was just so different and I feel a greater charge to make sure I am not just documenting but living my legacy out loud. It’s more than just a pretty photo album and a few key stories, it’s the day to day moments.

When I was a wedding photographer, I always talked about how I want my couples to plan a marriage more beautiful than their wedding and now as a digital marketer, I want to encourage my students and peers to live a life even more beautiful offline than the pretty, shiny squares you share online. For me, I’ve been focusing on documenting the everyday life more, the unstaged, uncurated, non-styled stuff… I can 100% admit that it’s easy to lose yourself in the minimal, beautiful, styled stuff that you see online but I don’t want to remember standing by a wall in an outfit that I only wore once, I want to remember those moments that just naturally unfold.

I also have written letters to Coco from the day I found out I was pregnant, I started a word doc and every month I just add a little note to it. It’s like 40 pages now but I love reading back through my journey to meeting her and what life has been like since she arrived and I hope she will cherish it someday. Those are the things I hold close to my heart, no one else sees them, they aren’t shared publicly, and I plan to keep it that way.

I feel like the word “legacy” has also transformed for me in the sense of what I hope to bring to the world. I want women to see that they can be both an amazing mom and have a successful career, I want them to see that they can live a life that is enriched by their passions and that they can make a living while having a life — I feel like THAT is the legacy I want my work to be.

Social Media for Business

It’s so interesting thinking of how different the internet was even just a few years ago. I still wholeheartedly agree that social media is the best free form of advertising and that it’s an important piece of the marketing puzzle, but I don’t necessarily think it’s the best place to make a sale. Social media should be the introduction, the handshake, the place that you show up and let people know what they can expect from you and feel connected to you. It’s the place where you catch their interest and allow them the chance to get to know you, but I don’t totally think it’s the best place to sell your product or push your service.

Social media is a huge part of your business and your strategy but if it’s your only plan for selling, I’d highly encourage you to focus some attention and energy on building something you DO have control over whether it’s a website or a blog and you know I can’t end this thought without talking about email lists — but that’s where I think you get the best results for your efforts. Instagram is powerful, 100% but it’s just one spoke on your wheel of marketing. Too many people are putting so much time and effort into social media and using vanity metrics to track their progress without really understanding what is driving real results for them or what’s moving the needle closer to their bigger goals.

If I had to choose between my email list or my social following — even though my email list is like ¼ of the size of my social following, I’d hands down choose it over and over again. In fact, the other day I was exploring what it would look like to pull back on social media and how it could impact my business and I asked one of my dearest friends who runs a successful online business who has posted far less frequently this year if it’s impacted her business and she said, “Nope, we’re still hitting our numbers, if we weren’t, I’d be posting more, but right now email is fueling my business and I feel like I’m serving my clients and subscribers well in that way.”

The climate of it this year has been challenging online and at a time where there are so many important social issues, a presidential election, and a lot of universal hardship, it’s hard to know how to show up well and where social media plays a role in all of it! It has definitely been used for good to spread messages and awareness and to educate and it’s also put a lot of things into perspective.

I’m still navigating how I feel about it all and what the shift will look like for myself but I think we are entering a season of life where we need to get super honest with ourselves about our user habits, how social media is making us feel, how we’re contributing, and what really matters. For me, right now, I want to focus on living my life offline in the most full way and only sharing when I feel inspired or excited too, not because I feel obligated to.

What I’ve Learned About Privacy

I’m a little surprised that even when I started this, I admitted that I am more private than people assume, and years later, even more so. I think motherhood really made me think more critically about what I’m sharing and how my daughter is being shared on the internet and trust me when I say I’ve grappled with how to share our joy and our miracle with the world while respecting her and her own story.

I don’t have answers there, I’ve certainly overshared at times and regretted it, and I feel like the older I get, the more private I become. That isn’t to say that I don’t share “real” things, I just don’t share everything. I think you can connect with people without seeing their entire lives being lived out and my hope for connection is still so strong, especially in an era where we’re so disconnected from others, but finding that balance between sharing enough and keeping it real, while also being mindful of the fact that the internet doesn’t need to see everything, it’s complex and tricky!

The biggest thing I feel like I’ve always done, since day one, is shared stories that matter. I don’t’ share every aspect of our lives, in fact I feel like the internet sees maybe 2% of our world, but I do share stories that matter to me, moments that made me pause, experiences where I gleaned something or felt alive. I learn through stories and I teach through stories and so that’s something that definitely hasn’t changed and it’s allowed me to connect with people like you through our shared experiences or the places we want to go together.

Now, is mac and cheese still important to me as it was when I recorded this first episode? I’m literally laughing because I seldom eat it — but I still thoroughly enjoy it. I mean, it’s definitely one of my favorite foods. 3 years ago I went gluten free during our pregnancy struggles and so that changed my love of cheesy carbs and while I’ve found some great gluten free alternatives, I’m definitely more of a once a month mac and cheese girl vs. once a week, though Coco does love it and I always sneak a noodle or two of her Annies!

The funny thing about mac and cheese is it’s still a valuable teaching tool! The thing I did early on without even realizing it, was I connected myself with memorable things outside of the services I offered. Therefore, people wouldn’t only think of me when someone would say, “I need a wedding photographer in Wisconsin” they would think of me when they were strolling down the aisle at the grocery store or cooking up some Kraft. Looking back, it was super smart to share those other aspects of my life, things I could have easily written off as boring or basic because they helped connect me with others and gave me something other than what I do to be remembered by.

What Authenticity Means Now

I still want to be your permission granter, I want you to define success for you and I want to enrich your life in a way that makes you pursue your wildest dreams to live a life that feels like peace and freedom. I also want to encourage you to really ask yourself those hard questions that will allow you to determine what success looks like for you — not that I be a mirror for what you should want but that I reflect just a touch of what is possible for you or what is waiting for you.

Since that first episode, I’ve been on a crusade, this journey of defining and redefining success. It’s looked different in different seasons, from aiming for 6 figures to transitioning out of wedding photography, starting a family to actually taking time away, the 7-figure mark to wanting a seat at certain tables… It’s evolved as I have evolved and continues to shift as I continue to ask myself those hard questions and pursue different priorities in different seasons.

When I think of the word “authentic”, I think of how that word has shifted for me over the years. To me, it’s showing up truthfully, it always has been and always will be that, but in terms of trends on the internet and the way the word has held different meanings over time, I feel like I just want to show up as my true self. We often put the words authentic and relatable together and I can say without hesitation that I was far more relatable at the beginning of this show, perhaps my life now is aspirational to you or maybe it’s an example of something you’d never want — remember, we define success for ourselves.

Authentic doesn’t mean we air our dirty laundry on the internet or show up in every second of both good and bad, it also doesn’t mean that we need to always try to keep it real and relatable, it just needs to be a true reflection of who we are, where we are. I will always speak my truth and do my best to show up just as I am, when I have the answers and when I don’t, when I’ve arrived at an explanation and when I’m in my messy middle, to me that’s what authenticity is.

Two lessons are still important to me: Living out your “why” every single day and the fact that you are more than your followers. The internet era we live in can make us think our worth is wrapped up in numbers, but let’s tie our efforts online to real, honest connections and real results, while we boldly live our our legacies, define success for us, show up authentically, and as our “why” evolves as life gives us new experiences, new dreams, new purposes, and new hopes.

The Big Picture

There you have it, episode number one, updated to fit the episode 400 version of myself and The Goal Digger Podcast. So much of what I teach has stayed the same at its core, but it’s not surprising that my view of legacy, social media, privacy, and authenticity has evolved as my life and business has changed, too.

And I have to say, despite the audio being a little less clear than it is now, I am so proud to look back on that starting line. If there’s anything you take away from episode 400 of the Goal Digger Podcast, it’s that starting before every detail is perfect is the only way you can build something to look back and reflect on. You can only reach episode 400, whatever that means for you, if you start with episode one. So Goal Diggers, this is your permission to show up as your imperfect, authentic self and without any more hesitation, start digging your biggest goals…


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  1. Hi Jenna. You are AMAZING. I’ve recently discovered your voice, your authenticity, your vulnerability and what you stand for, and I can’t stop listening to your podcasts: when I go fo a walk, when I take my bike, when I garden, when I prepare the dinner for the family… you’re with me, just like a Life Force or a second “little voice” within and around me. Thank you for all your advice and the good work you’ve already done. I’ll definitely buy some of your courses as I can’t wait to be inspired by such a wonderful woman! Keep rock’in!

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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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