What Worked, What Totally Sucked: A Review of 2018

Jenna Kutcher 

posted by:

Previous Post




January 2, 2019


THIS ROCKED, THIS SUCKED. C’mon, time travel with me for a minute.

We’re two days into 2019. First of all, HOW? Second of all, you should know that when I recorded this episode I was still rubbing my baby bump awaiting sweet Baby Kutcher’s arrival into the world. When I prepped for maternity leave and recorded almost three months of the podcast in advance, I still had a little time in 2018 to close out the year strong… And man, did I.

Today I’m recapping what rocked in 2018, and in the interest of full disclosure, what totally sucked. This year is going to look a LOT different for me, for Team Jenna Kutcher, and for The Goal Digger Podcast, and I’m letting you in on the never shared, behind the scenes of what we’ve got planned at GDP HQ.

2018 was a chart topping year for me in so many ways. We nearly doubled our sales, doubled my following, doubled my email list, and hung at the top of the charts each week with this very show. There were so many highlights and epic failures that happened in the last 365 days and selfishly, I want to break them down so that someday I can come back and remember this year that felt like a total blur.


Let’s talk about the #1 highlight though: When this episode airs, hopefully baby Kutch is safely in our arms and into the world. Being able to not just get pregnant but to stay pregnant this year and finally start our family has been the #1 blessing that 2018 brought to us. As I write this episode, I’m on a plane with my baby kicking my ribs and not a day goes by that I don’t thank God for the opportunity to meet this sweet baby and become a mom. As I try to even imagine what life will look like when this airs, I get a little teary eyed because I know our world is about to be rocked. I know I’ll likely be sleep deprived and happy. This thing we’ve been wanting for SO long is finally here and if you’re in a season of uncertainty or waiting, I pray that our baby can give you some hope. This pregnancy journey has impacted a LOT of this year, so with that first highlight, comes the first thing that totally sucked…

Now, if you’re struggling with fertility or growing your family, you might just want to skip ahead, because there was a season that I wanted to punch anyone who said what I’m about to tell you. Okay? One of the first things that totally caught me off guard and wasn’t really on my annual plans was dealing with all that pregnancy brought me – beyond the actual baby. I found out I was pregnant on April 1st, it was the day after we moved to Minnesota. Our home was in boxes and there I was peeing on a test to find out that our biggest wish had come true but I wasn’t prepared for what happened next.

With my last two pregnancies that ended in loss, I had a little bit of sickness, but not much. Overall, I had felt pretty normal. Not this time: I was wicked sick for the first 17 weeks of pregnancy… and when I say sick, I mean, I wasn’t functioning like a human being. There were many days I just laid in bed and stared at the wall: TV made me sick, my phone made me sick, forget about sending an email. And so while I was so thankful to be pregnant, the sickness that struck mixed with the unnerving anxiety that we could lose this baby, too, was crippling. I had heard of post-partum depression but I had never really heard many people talk about depression that can hit in the first trimester and for the first time in my life I was on a teeter totter of knowing that my greatest prayer had been answered but that I also wasn’t in control of the outcome or what the journey would look like.

I would sit in a chair and just cry because I didn’t want to do ANYTHING. I felt totally gray, like a shell of myself, I couldn’t work out, I could barely go on walks, and no food sounded good… nothing. Nothing made me happy and for the first time as an entrepreneur I had a lot of trouble even caring about my business. Needless to say I was entirely freaked out if that’s what I had to look forward to for the next 9 months. During this season of pregnancy, I also had a lot of travel from speaking engagements to weddings to photoshoots and masterminds and so I was throwing up on planes, in taxis, and hotel bathrooms. All I wanted to do was be home and in bed.

After I got through week 17, mostly thanks to acupuncture and “turning that corner” that people kept referring to, I felt a lot better and trimester two wasn’t so bad. That isn’t to say I didn’t still struggle but I was finally able to lead my team, to dream big, to work hard, and to start preparing. I do want to be honest, pregnancy didn’t feel natural to me. I feel like when you see pregnant people who “have the glow” it paints this picture of this miracle in action and while it is a total miracle, there’s also a lot happening inside of you.

My body ached a lot, I had wicked heartburn, and my anxiety kept sneaking in. I had been raised with a mother who LOVED pregnancy (like she actually wanted to be a surrogate for others) and so I believed that that would rub off on me, but my journey was a lot bumpier than hers. While there were aspects I did love about being pregnant like the little kicks and moves and seeing the ultrasounds, most of the time I just didn’t feel like myself.


Enough body talk, ya hear? It’s safe to say that pregnancy and preparing for baby totally changed my business and the plans we made both for how we would navigate this calendar year and what the next year would look like, so let’s dig into that!

At the beginning of the year I mapped out every quarter with big goals of launches, a new course, and a few other projects. When April hit and the morning sickness came, I started to watch the plans I had drafted slip through the cracks. The things that I was so excited by at the beginning of the year now felt like mountains to climb and so we had to really look at where my time and energy would be best spent. Instead of building out the new course I had dreamed of, we did a major pivot and instead focused on updating all the courses I already had that were doing well.

To be honest, I think that this pivot was one of the smartest things I’ve ever done as an entrepreneur because not only did I get to work and focus on what was already working for me, but I got to go into maternity leave knowing that all of my courses were current, awesome, and up to date. It was such a good lesson for me to remember that more isn’t always more and while I hope that course that I dreamed up WILL come into fruition in the next year, I also think that sometimes we need to focus our energy on what’s already working instead of being “on to the next thing!”

Finding out I was pregnant also gave us a BIG deadline to wrap things up and a huge need to batchwork. The longest I’ve ever taken off of my business at one time was a month and so to be planning for 3 months away and unplugged threw a wrench at my team – and let me just say – my team is INCREDIBLE and stepped up to the plate because they want me to really enjoy maternity leave. We started looking at what needed to happen and since I wasn’t able to work much during my first trimester, I felt like I had a solid few months to work double time in order to get us ahead.

There were a lot of big things we tackled as a team. We had to record almost 60 episodes of this podcast in a 2 month time span… like can you even believe that? In September we were already 4 months ahead and by October we were almost 6 months recorded out. That’s a LOT of content and interviews and outlines to create and record in a short amount of time. There were a few weeks where I felt like all I did was sit behind my microphone in order to pull this off but I knew if I really wanted to rest, I had to have peace of mind that you guys wouldn’t even know I was gone.

We also had to plan our email marketing strategy for the next 6 months, our blog content, our Pinterest strategy, I had to work with my sponsored partners to get our campaigns photographed and events done before I wasn’t able to travel – not to mention, we decided to buy another condo on Hawaii that needed renovations. So ya know, things got a little crazy there. I recorded an entire episode about how to prepare for a break from your business and let’s just say my methods felt a little insane but we got it done thanks to this exceptional team!


Speaking of team, this is something that went INCREDIBLE this year. I honestly can’t speak more highly of the women I get to work with every single day. Team was a huge win and so I want to share a little bit about what I learned this year. First and foremost, it might shock you to learn that I only had 3 salaried team members for the 2018 year, 2 of which were my mom and sister. The rest of my small team were contractors, but I work with about 5 women on a day to day basis.

This year I learned the importance of having support in such a new way when I was sidelined due to morning sickness and trying to prepare for leave. These women stepped up in BIG ways so that the world didn’t even know I was confined to my bed for a solid 3 months. In case you’re wondering, here’s the make up of my team and how things have shifted a big this year!

Inbox and Support: this position used to be handled by Caitlyn but is now handled by an amazing woman, Stephanie. Steph jumped on my team to cover a maternity leave and I never let her go. She went from simply managing our support inbox to playing a much bigger role on the team managing both of my inboxes and helping us manage the Jenna Kutcher course community and she’s been an invaluable piece during launches and keeping the day-to-day operations met. It’s been so much fun having her on in a more full-time capacity and we love our Steph! If you’ve emailed me recently, you’ve likely heard from her. She’s incredible.

Content Creation: Since we now have Stephanie, we moved Caitlyn’s position from being more of a VA role to stepping up as a content creator. Caitlyn has been with me the longest and has gotten to watch me create courses and content for years and now it’s like she can live inside of my head. So we pulled Caitlyn out of the inbox and now she helps me create and develop courses, she runs my Pinterest strategy, she helps create content for blog posts, and she also helps write outlines for my solo shows for the podcast. This pivot has been huge in having help creating, since we pump out so much content each and every week.

Tech and Strategy Guru: Oh Danielle, how do I even begin with this mastermind. She’s been with me almost as long as Caitlyn and started simply as my support inbox gal but now she’s my main strategy girl who helps me take my big ideas and make them a reality. We work together daily on how we can automate things, build campaigns, and launch our products and Danielle is a literal genius when it comes to this stuff! I couldn’t do half the things I do without her and I am so thankful to have her making all the crazy things that comes with online marketing less intimidating or scary.

Podcast Producer: You probably know that my sister Kate works on this show but with a twist of plans, she’s heading back to school to get her masters in nursing and so while we are SO sad to see her go, I’m excited to get back to just being sisters too! With that said, we had to make a hire. I did ONE Facebook post and ONE Instagram story about the podcast producer role and we had over 500 applications in a 24 hour time period. Being in my 3rd trimester with a ticking time bomb of a baby on the way and with my sister having a set end date, I had to make a quick decision which totally freaked me out since all past hires were made strictly on referrals. But while the process felt daunting, it ended up working out great. I used LinkedIn to hire which was amazing and was able to quickly find people who had tangible experience, which is how I found Kylie. Kylie flew to Minnesota for 2 days of training with Kate and I and now she’s the leading lady of the Goal Digger Podcast. She has experience in the radio world, blogging, and social media management, so she was a shoe in for the position. Since I didn’t have much time to train, I really needed someone who had a background in this world!

Lastly, I ended up making ONE additional hire that I’m super excited about. Her name is Brooklyn and she applied for the podcast position but from one click to her website, I knew that I wanted her on my team for something entirely different. Her copy was quippy and captivating, the way she spoke totally enamored me and since we have SO much copy coming out of this team, I knew we could use one more person. I was brushing my teeth and telling Drew about my favorite candidates for the new job when I had the idea: what if I made TWO hires? Now Brooklyn is on the team to help take some of the work off my plate and to help me continue to dream on how I can serve you all better. So pumped about this extra hire!

Beyond my day-to-day team, I also have Kerry who does my Facebook ads (tune into episode #58 to hear “How to Make Facebook Ads WORK For You”), Jen Olmstead from Tonic Site Shop on web design, Renee from payment savers, Rebecca who runs the shop, Olivia Herrick who does my graphic design, Matt who does my podcast editing, my ad agent Maddy, and so many more people making this all happen.

As I think about being on leave and what went into preparing it, I am so thankful to have these powerhouse women on my team and making things happen while I am away snuggling babe! It’s crazy to think just a little over two years ago, I was totally flying solo. It’s because of this team that I was able to have a chart topping year in SO many ways.


Well, we had a record-breaking year! This year we had over $2.5 million in education sales, we had nearly 10,500,000 total downloads on the podcast in 2018 alone, made 200k in sponsorships and sponsored content, 175k in sales in our Shopify Store and over 150k with affiliate marketing. I went up over 600k followers on Instagram in 2018 alone, we quadrupled the number of reviews on the podcast, and we stayed towards the top of the business charts almost the entire year. We also purchased our second condo in Hawaii, moved states to Minnesota, and traveled a ton. I don’t say all of these numbers to brag but I also want you to be able to see how I’ve created a multi-million dollar business that allows for us to live the lives we’ve dreamed of.

I am not just proud of our chart topping year in terms of income but more so how we really took back our time and created systems and protected our best yeses. In 2018 we spent THREE whole months in Hawaii and 90% of that island time was dedicated to resting, we took vacations just because, protected our weekends together, and said more “nos” than ever before. I always laugh because I almost always fly coach and I walk through that first cabin of people in first class.

I try not to generalize but most of them happen to be men of importance in business suits who are frantically taking that last call, writing a quick email, or punching in texts before the plane takes off. I always wonder if they ever lift their eyes or really enjoy that experience that a lot of people will never get in their lifetime. As I walk back to coach, I think to myself: I likely make more than all of those men and here I am with my eyes open and with nothing urgent pulling at me and for that, I am the luckiest.

Along with our chart topping results left a lot of learning moments for me, I think the biggest lesson I learned this year – that took me a little while – was in figuring out WHERE and HOW I serve best. You know that I am a HUGE fan of outsourcing and I think that this year taught me that I can do it even more and that I should be doing it. Drew and I are HUGE financial savers, like I’m a money hoarder and I love the security that having savings offers. I went to my mastermind and asked my mentor Brendon where I should be investing my money because a lot was sitting in our bank account not really doing much of anything and he came back to me with: TEAM.

Part of me wants to keep a super, super lean team. I kept thinking: I don’t even know who else I could hire but once we really started preparing for maternity leave, I started to see ALL the little things I was doing day in and day out (and on those 14 hours days) where I was failing to hand over the reins or to ask for help. This didn’t totally suck but one of the biggest growing pains for me this year was really understanding my role in all of this: I am the face, I am the voice, and I am the visionary. I need to be able to cast a strong vision as a leader, get the right people in the right places, and then help them to do their jobs best. It’s not me creating collages in Canva because I can, it’s not me writing out detailed blog posts, but it is me in constantly pointing my team in the direction we are heading and making sure that the vision I am casting is being executed and that our people (ahem, YOU) are being served and being served well.

This discovery is actually super empowering to me because as I look ahead to 2019, I’m not afraid of hiring more if we need to, I’m not afraid at replacing myself in certain places or roles that I’ve been still doing, because I want my brain and energy to go towards the bigger picture, the bigger game plan, and I can only truly cast a vision if I create mental space to do so!

What a year… am I right? As I look ahead as to what next year will hold, I pray that as we settle in as a family of 3, I continue to follow my gut, trust my intuition, and chase my dreams. I am so excited about the way we used 2018 to be a launchpad for my most perfect year ever, which for me looks like rocking this podcast for you and teaching my courses. We’re planning to cut WAY down on travel, speaking arrangements, and partnerships to focus on what I do best: educating and inspiring. I’m really looking forward to an intentional year that isn’t about going full steam ahead but in being rest-filled, present, and strategic. If you’ve never really taken the time to review your year, I’d encourage you to do it! I did an episode like this for the last two years (if you really want to see growth, head back to episode 9 to hear about how different my life was just two short years ago and episode 113 to hear the difference a year can make!)

Taking time to really reflect, see your progress, acknowledge the growing pains, and look at how far you’ve come is incredible! I’d love to hear about your biggest WIN of this past year, so hop on over to @goaldiggerpodcast on Instagram and celebrate with me, because so much can happen in 365 days and I’d love to come together to celebrate at a community.

Happy New Year! Something tells me that 2019 is going to be YOUR year, Goal Digger!

We Love Our Goal Digger Sponsors

Slack: Where work happens — Go to slack.com to learn more

Get 2 Months of Skillshare for 99 Cents at skillshare.com/GOALDIGGER


Leave a Reply

Your email address will not be published. Required fields are marked *

  1. Melissa says:

    gosh Jenna thanks so much for sharing your maternity struggles. I was also hit with debilitating depression, nausea and dizziness the first trimester. It put a real hold on my business which is still quite in its embryonic stages and will have to wait until I’m back to more of myself after the baby, In the meantime I’m transitioning to other things that will begin to help make income instead. Thanks again, it feels so good to know I’m not the only one who had to let go of a few dreams for the time being.

  2. This article presents clear idea designed for the new viewers of blogging, that truly how to do running
    a blog.


The Latest From the Goal Digger Podcast

BINGE listens


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). 

hey there!


What do you want to read today?

Except instead of a video game, this is you IRL. Let’s get laser focused on setting your goals for this month, year, and beyond so I can hand over resources specific to how YOU want to grow!

Take The Quiz!



free downloads show


Free downloads to elevate your game.

FREE challenge



Screw the junk mail, I'm bringing "real" right to your inbox. Deep encouragement, tough questions, needle-moving challenges, and smart strategies to help you make your dream work. You in?

great idea alert!

Hey, Let's Be Pen Pals!

    © JENNA KUTCHER 2024


    |    SITE CREDIT

    |    GET IN TOUCH

    |    Legal