Dear Jenna: What was your biggest business mistake?

Jenna Kutcher 

posted by:

Previous Post




July 31, 2016



Dear Jenna, 

I feel like everywhere I look I’m seeing perfect business owners running perfect businesses and I’m over here thinking I’ll never make it. I feel like I’m just not cut out for this because around every corner seems to be another mistake just waiting for me to make it. Have you ever felt this way? Have you ever wanted to throw in the towel? PLEASE just tell me I’m not alone and that you weren’t perfect because right now I need a little dash of light and reassurance to know that I can make it in this crazy industry.


Feeling Like a Failure 


Oh, my sweet, sweet friend. Here I am pushing away feelings that I just want to throw up because as I read where you’re at, it takes me right back to a few very pivotal moments in my business (and trust me, they aren’t moments I like to dig back up to the surface.) So here’s what I first want you to know: no one likes to talk about their failures. Chances are, you won’t scroll through Facebook or Instagram and see people airing out their garbage or the moments in life that make them feel like a giant loser. Why? Because it sucks. There are moments in everyone’s lives where we would rather just stay in bed with the covers over our head that focus the things that life throws at us.

So let me tell you a little story about a girl in 2011 who had just left her corporate job to pursue this crazy dream (a dream that included a gig as a wedding photographer, something she had ZERO professional training in.) It was a beautiful fall day, I was spending it with one of my all time favorite couples on the planet. They had just finished their beautiful ceremony and we were heading out to a cornfield to get photos of them with their wedding party at sunset! The light was perfect, the group was beautiful, the stars were aligned. Everything was PERFECT.

Later that night they were dancing and my memory card flashed it was full, no biggie, I quick ran to my bag, grabbed another one, formatted it and shot away. That night I got home and was backing up my cards when I realized I was missing a chunk of the day. I freaked, went card by card, double checking but somehow those sunset images and portraits were no where to be found. I figured I had lost the card so I called the venue, called the maid of honor, called the limousine driver… tears in my eyes, a lump in my throat. The next day Drew and I went to the venue and scoured every inch from the parking lot to the nooks and crannies in the floor – nothing. 

It took me a full week to realize my mistake: I had reformatted over the wrong card and had shot over all of those portraits. Yes, I lost a few hundred precious, unrepeatable images. I was devastated, I threw up, I told myself I would never, ever shoot another wedding. I was so, so afraid of disappointing my clients. I knew in that moment I wasn’t cut out for this – the stress was too much. 

I drafted an email the next day (I would sob if I even tried to talk about it.) I shared the images I had (which included every single hour of the day except the one!) I cried, I promised them photos for life, I begged for forgiveness, and guess what? They gave it to me. By the grace of God my clients understood. Sure, they were disappointed, I’m sure a little mad, but they truly showed me the meaning of grace in a way that I still can’t comprehend. Since this incident, I’ve gotten to photograph them three more times, even meeting them on a beach in the Outer Banks last year to meet their sweet baby girl. That failure?

I still think of it often but it taught me three incredibly important things (if not a million more!) 

1.) Work with people who see the best in you, who believe you, who extend grace.

2.) Label your cards and NEVER, ever format a card on a wedding day or at a shoot.

3.) Have a second shooter, have a camera that has two card slots, and protect them with your life.

Just thinking of that time in my business hurts my heart but here I am, five years later, still shooting, still working with incredible couples. I’ve never publicly shared this story because I always feared that clients would see this and get nervous (trust me, y’all, I’ve come a LONG way since I started in 2011!) But what I do know is that when we share life: the success, the failures, we become more human, more real. Wherever you are at today, whatever failures you’ve encountered: they do not define. You need not live IN your story, you can live on top of it. I believe in you and as those failures come and go, so will the successes. It’s all a part of the journey and this journey is not always easy, but it is always worth it – always. 

Do you have a Dear Jenna question? 

Send an email to: hello@jennakutcher.com with the subject line: Dear Jenna! 


Leave a Reply

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

  1. Francoise says:

    Thanks Jenna! I needed to read this today 🙂

  2. Terri says:

    Wow! Thank you for being so brave and sharing your amazing story with us. You have no idea the impact you are making on people every day! Thanks friend! Terri Hinojosa

  3. Anna says:

    I needed to read this today, thank you.

  4. Patrice says:

    Jenna, thank you SO SO much for sharing this! There is nothing that will make me love a brand/person more than transparency. I think it allows your followers/fans a way to connect with you on a deeper level. We all have those cringe-worthy moments that are hard to recognize, let alone share with the world! Thank you for being an inspiration!

  5. Lucy says:

    THIS POST. I love it SO much. You encourage me every stinkin’ week. I want to share this 75 thousand times. I know at least ten business owners that need to hear this right now. Thank you for sharing your heart in a very real way. YOU ARE A POWERHOUSE.

  6. Ugh- we have a story that could be cousins with yours. And, yes, I thought we should just quit and go die in a hole. Thank you for being candid and sharing- failures don’t define us for sure, but without them there are SO MANY things I’d be without that make me better because of it. Wine has to ferment for a good while to be enjoyed and mistakes lend us the same quality. But, gosh, when I’m in the thick of it, that stomach drop is the worst feeling ever!

  7. Danielle says:

    Jenna, you continue to inspire me in more ways than I can count. Thank you for sharing your story. Failure is absolutely a part of this entrepreneurial rollercoaster and really appreciate the reminder that it’s how you handle your failures and what you learn from them that matters.

  8. mary says:

    that is definitely a barf moment. oh my gosh feel sick just thinking about it… but I’ve had my own! I thought I forgot to download one 32GB card (about half the wedding) only I can say by the grace of God I just saved it in the wrong place (my laptop). Now I have 3 hard drives that write to each other and a back up system to keep my brain from doing that again!

  9. Kira says:

    Thank you for sharing! We have all had those gut-wrenching moments, good to not be alone! Absolutely LOVE the new site too, by the way.

  10. Mary says:

    Living my oops moment right now: met with a large group of people to capture a family portrait for their mom’s 80th birthday…and not one of the images is tack sharp! Totally blew it, don’t even know what happened, because the next large group session a week later was perfect.

    I’m trying to make it up to them in every way, but feel terrible, because I know how hard it is to get everyone together again!

  11. Amanda says:

    Wow! My jaw dropped to the floor when I read that. I am a newborn photographer and have never deleted images or misplaced a SD card but just reading that made me feel sick!
    Thank you for reminding us that yes you will get knocked down but you have to get back up again. Thank you for sharing your story Jenna!

  12. Yazmin says:

    This was so inspiring! I love the part where you mentioned “work with people who see the best in you”

  13. Oh man! That would be the worst! I have one where we were eating at this local eatery for a sponsored post. We drove 30 minutes, had a reservation, a table by the window, all the food & drinks we wanted,all the staff greeting us and doting on us (which was already weird for this newer blogger) and I was going to document it all. I went to take a picture and NO SD card! I had no back ups (lesson learned) and I knew it was still sitting in my card reader at home. I almost burst into tears. I already felt like a poser but this just proved I was. My husband ran out to take the car and drove to the nearest place that sold SD cards. I confessed to our waiter the issue and 25 ish minutes later we were shooting with a brand new SD card. It all came together in the end and I totally learned a lesson! I’ve never not had my memory card (and I carry all kinds of back ups now!!)

  14. Kathryn says:

    Jenna, thank you so much for sharing this piece of your beautiful heart. I needed to hear this today 🙂

  15. Aura says:

    Thank you for reminding us rookies that we all start somewhere and that we all make mistakes! You’re awesome in all that you do!

  16. Amy says:

    I’m in tears. I have had such a rough time lately keeping my head above water. I feel like it’s hard to keep breathing. Reading this made me feel like I’m not alone. You hit it right on the head, no one shows negative things on social media. It’s always the pretty and glam part of the biz. Thank you for always being open and real. I wish I could give you a big hug and then eat some Mac and Cheese.

  17. Thank you so much for sharing this story — it take great courage to share failures and you did it with such, grace and honesty. Fear of failure or sharing my fears is soo scary to me and you gave me the strength to realize, my failures don’t define me, so thank you!

  18. Seriously, I think we all HATE making mistakes, but isn’t that the best wayto learn? It’s like “oh em gee, I never ever want to feel like that again, so let me not do that ever again.’

    It definitely is comforting to know we aren’t alone!

  19. Anna Oates says:

    Sometimes what we need to hear comes from where we aren’t looking for it- thank you for this post, it was what I needed today.

  20. Angela says:

    Wow, your story made me cry! Sounds like they were amazing people to be so gracious and hire you to photograph them again after that! Thank you for sharing such a vulnerable story!

  21. Dana says:

    So this made me tear up and I totally didn’t expect that.

    I could feel just how awful you must have felt because I would’ve felt the exact same way! I am so glad you didn’t toss the towel in then and there and continued to grow.

  22. Layla says:

    A very similar experience happened during my wedding, but honestly it wasn’t that big a deal, I knew my photographer is an incredible person and shot the most incredible pictures either way. Your work speaks for itself! I wish I lived near your pictures are magical!


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