The 10 Biggest Mistakes I’ve Ever Made as an Entrepreneur

Jenna Kutcher 

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July 18, 2018


I’m a true believer that taking action in our businesses is one of the most important priorities we can make. I hear business owners agonize over what to do so much that they become stuck and don’t make any decision at all. I believe the worst thing that can happen is that we will make a mistake, learn from it, grow and move on. To prove this, today I’m going to talk about the 10 biggest mistakes in my business and how each has helped shape who I am and where my business is today.

Too many educators put their best foot forward, show their highlight reel and pretend to have it all together, and I’d rather be an open book in case it helps you guys learn from my experience as well. Without any further adieu, my top 10 WORST business mistakes… YIKES.

1. Doing what everyone else was doing when I was starting out

From my editing style to pricing to what my website looked like, I looked outward for inspiration on so many things I was doing in my business. But what does this accomplish? It makes you blend in instead of standing out and when you look like everyone else around you, the only differentiator people will have is the price. This causes you to be price shopped which is not fun. You want your clients choosing to work with you because of the things that make you different, your strengths, the experience you create. Stop looking outward and look inward for inspiration.

2. Waiting to start an email list

If you haven’t heard the story of why I think starting an email list is so important, check out episode 12. I spent way too many years focusing on the number of followers that people could see, instead of growing a list of dedicated fans wanting a consistent way to hear from me about anything and everything I was up to in my business. Today, growing our email list is the number one priority in my business because it drives the most profits. (Check out jkemaillist.com if you want to start a list today for my free resources on the topic!)

3. Caring too much about what people thought about me

This one is SO important… and so hard to summarize in a blog post. The emotions of what people thought kept me from posting, writing, and sharing what was really on my heart. It had me playing small when I was ready to play big. All because I was writing narratives in my head about what people thought. And, Goal Diggers, I do not want you to do the same, okay? Okay.

4. Scaling too big too fast and getting burnt out

I got in the habit of saying yes to all the things because at face value they were all really great opportunities. What ended up happening is I worked myself into the ground and when I had my first miscarriage, I just could not carry the burden anymore. You guys know the story that led me to outsource out of desperation, but my goal for you is to not reach that point. Protect your yeses and make sure they are your best ones. The ones that fill you up, drive the biggest profits and are aligned with your dreams and goals.

5. Waiting to invest in a team

Speaking of outsourcing, check out episodes 7 (Caitlyn), 98 (Kate) and 120 (Danielle) if you want to hear from my team and the backstory to how we got to where we are today. Let me tell you, it was a process. But one that has been worth every investment. Having the right people in the right roles makes this business run smoothly and we have a lot of fun doing it, too. Tune into the full episode for all the details on this!

6. Not creating a repeatable system and letting my inbox suck me in

Not too long ago, there were entire work days spent solely in my inbox getting absolutely nothing is done that moves the needle in terms of my goals or profits for the business. What did it accomplish? Getting to everyone else’s questions, tasks, and requests of me. Today I don’t login to the inbox until I’ve done a few more important things first. Like snuggle with Drew, some yoga, identify my top 3 things to accomplish for the day. Then, I set a timer and get to as much as I can and then I’m out again. Need more guidance on this topic? Check out episode 80 where Abby Grace talks about tips for getting out of the inbox.

7. Saying “yes” to too many things to build others businesses

Look, there are A LOT of really great opportunities in my inbox, and I’m sure you have them as well. But I have to look at each and every single one of them through the lens of my priorities for this year. Would that online summit teaching and sharing audiences with other great educators to my target market spread the word and be good for business? Sure. But, would my time be better spent in my genius zone, serving the audience I already have? Absolutely. I talk in episode 69 about how to graciously say no if you have a tough time with this one.

8. Not being willing to invest in education for myself

Guys, I am an EDUCATOR. I know the value of education… and yet, I had trouble committing to my own education. However, with time I have realized just how crucial it is to keep moving forward and evolving. This last year, I gave my entire team an education budget this year to make sure they could learn and grow in their individual areas and I was tempted to skip this part for myself, at first. And then it hit me! I just never, ever want to get comfortable! I always want to be growing, learning, and evolving (and pssst: I want the same things for you, too!)

9. Creating too much content and not sharing it well

We were content writing machines last year. This year? We’re working smarter and aiming at sharing that great content instead of constantly writing something new. Here’s what I’ve learned: that amazing content you created did not reach even close to all of your audience and sharing it in new and creative ways will continue to grow your audience without spending additional hours creating something new. Check out episode #163 “5 Ways To Promote an Opt-In”  for my best tips to accomplish this.

10. Not outsourcing things that I needed to get off of my plate

There are things in your business that only you can do. I promise you that list is much smaller than you think. Since growing my team, I outsource anything and everything I can think of and it has allowed me to dream and see the overall business and the direction we need to take when I’m not stuck in the day to day running of it.

Check out my outsourcing guide here!

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  1. ANGELA LYNCH says:

    Jenna, you truly rock! Thank you for being such an open book!

  2. Lauren Guido says:

    Hey, were can I find all your podcasts in order?

  3. Sheereen says:

    It’s funny, that alot of people say create tons and tons of content, but miss the mark on how to share it properly not just once but over and over agin. Thanks for the tips!

  4. Dan King says:

    Great post!
    So one thing I struggle with is outsourcing. How do you outsource when you believe that you are the best at what you do? Do you outsource tasks or whole projects and just manage it?

    Thanks for sharing.

  5. […] The 10 Biggest Mistakes I’ve Ever Made as an Entrepreneur- episode 171 […]


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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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