The 5 BIG Mistakes You’re Currently Making

Jenna Kutcher 

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April 3, 2019


business mistakes

There’s so much information out there, isn’t there? You’re constantly feeling like a chicken with your head cut off and wondering if anything you’re doing is RIGHT. Sound familiar? If you’re feeling that way today, I want for you to take a deep breath, pat yourself on the back, and remind yourself that doing ANYTHING is better than doing nothing. Today’s episode is dedicated to the top 5 business mistakes I currently see entrepreneurs making (and hey, they are mistakes I find myself making too, I’m not guiltless!) So let me walk you through the 5 biggies and then give you solutions on how to stop making these silly business mistakes with your time, your money, your words, and your beliefs. It’s time for you to get to work and I want for you to do it with confidence that you’re not messing up… Because you, my friend, are anything but a mess up!

Mistake 1: You’re waiting for permission or perfection

How many of you are waiting out there? You’re waiting for: the perfect time, the right amount of money, the updated website… You’re waiting for someone to affirm you, you’re waiting for validation, you’re waiting for the answer, or to have it all together. A lot of our lives are wasted simply waiting. I want you to stop making this mistake. Waiting is making you play small, waiting is making you miss out, waiting is delaying your dreams… Perfection is killing your pursuit and I hate it.

Now, let’s talk about the “other P” which is Permission. I feel like a lot of us have walked through life waiting for permission. We sought out permission from our parents, from our peers, from educators and instructors and coaches. Our lives have been spent waiting for permission and affirmation to do the things we love because those things give us the confidence to believe we can.

But now let’s talk about this whole dream chasing business, because last time I checked, there hasn’t been a “Dream Chasing 101” course in college. There aren’t people qualifying you, grading you, or cheering you on as you spend your nights Googling how to turn your passion into profits. There aren’t report cards that tell you you’re finally qualified to pursue that one thing you’ve been thinking about. It doesn’t work like and and that’s where you’re messing up right now, because you’re busy waiting for all those things and they aren’t coming, so you’re spending your life playing small.

I wish you could understand the amount of DM’s that slide into my inbox everyday of people simply wanting permission to pursue their dreams. They want me to look at their account or check out their blog or see if I like their product or they tell me about the dreams they have but they just aren’t chasing or aren’t sure they could chase. Trust me, I’m a words of affirmation girl myself, but every time I get these messages, I shake my head and think to myself, “If you’re waiting for me to tell you to go for it, that it’s time, you’re not going to get far.” The thing about this journey of dream chasing is that the ONLY person that can give you permission is YOU. You have to stand firm in the belief that you are capable and you have to have unwavering conviction that you’re going to prove the naysayers wrong… yeah, that’s right, you’re going to face more critics than cheerleaders but those people will become the ones that you’re excited to prove wrong and soon enough, you’ll totally forget about them. know this might sound harsh, but the truth is, there are no permission granters out there when it comes to chasing your dream… if that desire isn’t strong enough in your heart and that conviction isn’t running through your veins, then you’ll likely never truly succeed.

Mistake 2: You don’t know how to talk about what you do!

We were on a walk when we ran into a neighbor Bob. Bob hadn’t met us yet and so he stood at the foot of his driveway in his Dickies sweatshirt and told us about his sweet wife Mary Lou. We got to talking and of course the question came up about where we work. Now, let me first preface this and say, I hate this question… especially when I approach it with an assumption that the person asking simply will not understand “what I do.” So when we told Bob that we both work from home and then went down the gamut of explaining what a podcast was and how we can work from anywhere in the world and then we quickly changed the conversation.

But that night I was thinking about YOU and how you probably do this a lot too. It’s like we don’t really want to explain what we do and we aren’t quite sure how to tell people about it and it kind of doesn’t feel like a real thing or a real job so we glaze over it and move the conversation on to something else. Are you guilty of this too? Maybe you just assume people won’t understand so you say something like, “Well, it’s kind of confusing,” or maybe you downplay your success or perhaps you hide behind that 9-5 job title instead of sharing what you’re really working towards or crazy passionate about.

So what would it look like if you felt confident in your answer for the next time someone asks you, “What do you do?” What would it feel like to share that side hustle or passion or dream with confidence? What if you didn’t assume people wouldn’t understand and made sure you could explain it in a way that not only helped them understand but made them interested… because if we can’t even share what it is we do with people who are asking us, how the heck are we going to actually get out there and do it!

What if when Bob has asked me what I did, I told him, “I run an online business dedicated to empowering entrepreneurs to pursue profits and passions and I educate women through my podcast and online courses!” Now, even if Bob isn’t familiar with the world wide web, chances are he understands that I am an educator and I teach others online. Even if that conversation ends there, I at least expressed what it is I do and gave Bob a chance to be interested in it instead of glazing over it and changing the subject! These questions can help you craft the perfect response.

Who do you serve? (Ex: I serve female entrepreneurs)
How do you serve them? (Ex: Through my podcast and online courses)
What is their end result? (Ex: I empower them to pursue their passions and profits!)

It’s so important we get confident in verbally expressing our dreams and speaking them into existence, we have to stop hiding and start bolding allowing ourselves to step into these roles and feel worthy and competent in doing so! The more you say it, the more you believe it, the more you believe in yourself, the more others will believe in you!

Mistake 3: You’re not willing to start small

It’s funny because I’m so deep in this entrepreneur game that sometimes I forgot what it was like to just start… but when I start to really think about it, I am reminded at how small I started and how every little bit added up over time. It’s easy to compare yourselves to strangers on the internet, right? You see these people who seem like overnight successes but the truth is you jumped into their story in the middle of it… you missed those years of grinding, pinching pennies, and saying prayers that this whole thing would work out (speaking from experience here!)

One of the biggest mistakes I see people making is that they aren’t willing to start small – they don’t understand that sometimes in order to make those dreams into reality, you have to grind, you have to hustle, you have to do things you don’t necessarily love to afford you the ability to do what you love everyday. I’m all for inspirational quotes and posters and sayings but I feel like there’s this false narrative out there right now all about how everything we do in this life has to be passion forward and how it’s okay to abandon responsibility or to let go of certain gifts when we get sick of them but if I’ve learned anything about creating and building a successful business, it’s that most days looked like a lot of time spent doing things I wasn’t crazy about just so I could make money to fund those passion projects that were so deeply embedded in my bone marrow.

When I started my business, I was working 50+ hours a week at Target, I was training for a full marathon, running a wedding blog, and trying to learn how to use the camera that I planned to turn into a full fledged photography business. For an entire year, I did ALL the things in order to gain the stability it took to make a leap. I didn’t just abandon my 9-5, I used it to help fund this bigger dream. The same thing happened when I realized that maybe wedding photography wasn’t my true passion anymore, it could have been easy to just say, “Hey, I’m done, I’m not passionate…” And on to the next thing. But the truth was, I needed to stay in the game, serve my clients well, and show up because sometimes you have to do things you don’t totally love to get to a point where you can close one door and fully open the one you’ve been waiting for.

Don’t be afraid to start small, don’t be afraid to have a side hustle or to work slowly towards that bigger goal, don’t be afraid to sell one product or offer one service, don’t discount the power of one, and definitely don’t feel like you have to “follow your bliss” every single day in order to live a good life. There are so many people who are abandoning the things that got them started, who aren’t willing to do things they don’t totally love to gain the freedom to pursue their wildest passions, who feel like they are “too good” to keep doing some of the small stuff but in reality, it’s all those small things that lead you to bigger ones. I’ve met so many people who have this grander vision for their life and I LOVE that, I’m a dreamer, too, but I’m also a realist who knows that you climb up the ladder rung by rung and I’ve never lost that hustle that got me started all those years ago.

Mistake 4: Your “why” isn’t obvious or strong enough

If we were face to face and I asked you first: what do you do…. And then I asked you “why?” What would you say? Like could you look me in the eye and tell me exactly why you are a photographer or a designer or why you sell skin care products or became a social media influencer… like I really want to know, do you know and can you communicate your “why?” I know this whole topic can sound a little woo-ey or make you roll your eyes and think, well duh, I know my why but I don’t really know how to explain it… but it’s important.

One of the things I find in entrepreneurs is that they either:
A.) Didn’t have a strong enough “why” to begin with (and to be honest, I don’t think simply making money is a strong enough why to keep you successful.)
B.) They forgot their “why” along the way because it got buried under the to-do lists and the daily tasks and maybe when they turned their passion into a job it suddenly felt more job like and less passion drive.
C.) They haven’t pivoted or allowed their “why” to change as they’ve grown on the journey – and let me tell you, buckle up because entrepreneurship is a crazy roller coaster of a journey and you won’t be the same person you were when you started!

I still remember what my “about me” said on my website verbatim when I first started. It said something really woo-ey about my love of documenting love stories and how love stories are meant to be told and preserved and passed down as heirlooms… Now, is that true? Absolutely, but is that my “why?” No. Why did I love weddings? Because I’ve always been obsessed with them. Why did I become a wedding photographer? Because I wanted every bride who hired me to be able to live through their wedding day again through my eyes because my eyes wouldn’t miss a single moment that mattered, the ones that they didn’t even realize were happening.

Now, when you’re starting out, your why can sometimes be strongly crafted by what you’re consuming. When you follow all these people who are doing what do you do and you slowly start to talk like them and your captions sound like theirs and your images are inspired by theirs and you never really ask yourself, “Why am I doing this? What is my why?” Your “why” needs to be woven in everything you do. It needs to be clear, it needs to be communicated, it needs to be the thing you wake up to, dedicated to make it happen. My why? It’s to impact the masses with the BEST free education so that they feel empowered and worthy of chasing their wildest dreams and building businesses that support their lives and not the other way around. When I wake up and use that as my ground zero, I’m going to make sure that my time is best spent doing those things, that I am spending my precious times on the things that will move THAT needle the most and I’m not letting little distractions hold me back from that bigger mission. When you have a strong why, it can serve as a ruler that allows you to measure up every decision against it: is this in alignment with my why? Yes or no?

Mistake 5: You’re not willing to invest in your dreams

Now this is a biggie… maybe that’s why I saved it for last. Let me first set a scene to help you understand this a little bit deeper. Let’s say you wanted to go out and start a bakery. What kinds of things would you need to have before you could open your doors and make your first dollar? Well, first, you’d need doors, right? So you’d have to rent out a space. You’d need to invest in tools like an oven and baking items, you’d need to buy ingredients. You’d probably purchase a sign and maybe even get some advertising. Before you could make a single dollar, you’d have to be willing to invest in this dream of running a bakery and that dream wouldn’t happen without those investments, right?

So why are we afraid to invest in other businesses? Why are we hesitant to purchase tools that will help us get farther faster? Why do we question if we should buy a course that will teach us skills that we don’t know? Why won’t we invest in ourselves and yet we expect others to invest in us?

I remember the first investment I made when I started my photography business. I was using whatever dollars were left from my paycheck to hire a graphic design student to make me a logo, to purchase a domain, and to have a WordPress site… but the first time I really said, “I believe in myself and my dreams enough to put money down,” was when I had decided to purchase an ad. Now, let me tell you — it’s not something I’d advise NOW because I think you can run successful businesses without paying for ads but the market was way different 8 years ago.

I decided to purchase an ad for a few hundred dollars each month to try and reach brides that would hire me and while I felt sick to my stomach because purchasing that ad spot meant I was really going to do this whole thing, I also was smart enough to realize that if I booked ONE wedding off of that investment, it would pay for itself. That simple reasoning has been the exact way I have approached investments over the last 8 years and it’s still how I choose if something is worth investing it: Do I really believe it can get me a result and what would I have to do to simply break even in this investment?

You’ve Got This

So there you have it, the five big mistakes I keep seeing you make. I hope that today’s episode does all the things you’ve been waiting for. If you’ve been waiting for a sign, this is it. If you’ve been waiting for permission, you can grant it to yourself. If you’ve been wondering your why, you’re equipped to know it with conviction, and if you’ve doubted investing in yourself, know that I trust you’re a brilliant CEO and will choose the right thing for you! You don’t have to stay in this place forever, you are not a tree, so keep moving and never forget that imperfect action makes things happen. I am over here cheering you on and reminding you that you absolutely CAN!

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  1. Janina says:

    This was exactly what I needed to read today. I’ve been struggling with balancing the huge work week and the hustle it takes to do what I do and the very fact that you identify that was enough to rocket a sob straight from my face. The amount of times I’ve assessed and re-assessed my passion for what I do and why is almost daily, but to read it laid out like that gives me the encouragement that I’m on the right path. So in case no one tells you today – thank you for your help.

  2. How to Describe Your Business and Find Your ‘Why’ – Anchor ‹A› Digital Design Co. says:

    […] One of the best podcast episodes I’ve listened to recently was The Goal Digger Podcast episode #245: “The 5 BIG Mistakes You’re Currently Making.” If you’re struggling with how to describe your business or knowing what your ‘why’ is, absolutely take a listen to this episode. […]

  3. […] One of the best podcast episodes I’ve listened to recently was The Goal Digger Podcast episode #245: “The 5 BIG Mistakes You’re Currently Making.” If you’re struggling with how to describe your business or knowing what your ‘why’ is, absolutely take a listen to this episode. […]

  4. […] ne of the best podcast episodes I’ve listened to recently was The Goal Digger Podcast episode #245: “The 5 BIG Mistakes You’re Currently Making.” If you’re struggling with how to describe your business or knowing what your ‘why’ is, absolutely take a listen to this episode. […]


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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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