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An Open Letter To The Girl Who's Afraid To Fail

Updated: Mar 10

If you're afraid to put yourself out there, this is for you.

Hey you, I see you.

You have dreams.

You feel them smack center in your chest, a little fire that sparks a vision, where you imagine yourself owning a photography business or earning your bachelor's degree or opening up your own bakery in the little building on main street. You think about it often, but it would never work, right?

What would people think?

What if it failed?

What if I told you that you might fail. . . the first time. What if I told you that failing is a very beautiful thing and the only way to success is through failure?

I know I usually blog about cookies, cakes, and baking supplies, but I also blog about more than baking.

In this letter to you I will share with you how many times I've failed and why (as embarrassing as they were) I could never wish away. Because those failures provided the stepping stones for me to learn, grow, and master many many skills.

For those of you who don't know me, I will introduce myself. I'm Cortney Winn. I'm a wife to my wonderful husband and mom to my two cute boys. I'm also the owner of Winn Cakes, a cake business I started from my home that is now one of the top-rated cake businesses in Utah.

I've even been featured in Rocky Mountain Bride Magazine!

Now that I told you the highlights about myself, I want to tell you about ALL the things I completely sucked at, failed at, or am still figuring out! Here we go.

First, I want to share one of my favorite quotes with you:

"The master has failed more times than the beginner has even tried." - Stephen McCraine

That quote has picked me off the ground more than once and I hope it will do the same for you. I hope it, and this letter, will give you the courage to fail.

All The Things I've Failed At:

Making Wedding Cakes:

You didn't see that one coming did ya? I've had, not one, but two epic wedding cake fails where the cake didn't make it to the wedding table.

I've had uneven cakes, unsupported cakes, cakes that melted and cakes that leaned. I've had cakes that were the wrong shade of blue and cakes that I just wasn't proud of. The first actual PAID wedding cake I ever did was a disaster and I'm so mad at myself for getting rid of the picture. Basically, only the top tier survived and that's what the couple used for the cutting ceremony. The bride was amazing and so gracious with me. Obviously, I didn't charge them and it took me over a year before I picked up a cake pan again. The second time (years later) the wedding cake didn't make it at all, there was no saving it. I had to bake a last-minute replacement on site and deliver it to the reception 30 minutes before it ended. This picture is the last-minute replacement. See how the frosting is drooping from the hot cake?

What I learned: I will never be amazing on my first or second or third try. Failure, when other people are watching is crushing, but it makes the achievement so much more rewarding when I do make a show-stopping cake because I put in A LOT of failures for it. And I still have so much more to learn and skills to develop. I think I will always feel a little novice at cakes no matter how many I make.


Yep, before Winn Cakes was Winn Photography. I know, I'm not that creative with names. And yes, I legit took a picture of a stick and felt the need to post it on Instagram. In fact, my epic failure still lives on Instagram for all to see. Maybe I was trying to capture a stick's struggle to stand out from other sticks. . .

Here's the link if you want more of my short-lived photography career: Show me the mediocracy!

What I learned: I learned how to adjust aperture, shutter speed, and iso. I learned a little bit about Photoshop and how to use natural light, which has helped in my cake business! loved editing pictures. I loved taking pictures (of sticks). But, I didn't love taking pictures of strangers. I wasn't very good at it and was so worried about whether or not my clients liked their images. I never got amazing feedback from anyone and that soon led me to move on and eventually sell my camera.


If you haven't noticed yet, I am a creative being. I like to make things. So, naturally at one point I tried my hand at becoming an artist! I never named this little side gig because it was so short-lived. . . Maybe I should name it so I can properly lay it to rest. . . how about Drawinn? Okay, Okay. I know I'm not that funny. . . I have no idea why I chose to draw feet. Maybe it was my subconscious telling me to walk away from my drawing career.

What I learned: I learned that I truly love to create. Drawing just wasn't the right outlet for a side-gig. (I never tried to sell a drawing, but I dreamed of being that good.) I still draw on occasion, like once a year, when I need a creative re-set and time away from my other projects. This is something I do just for myself.

Personal Training Business:

I worked at four different gyms throughout Utah. I spent $11,000 on tuition, so I really tried to run with it. . . pun intended.

Honestly, it just wasn't the right time in my life. I wasn't a big enough person in my own life to help others with theirs. I didn't have a good relationship with food or my body, so how could I teach other people to eat healthy and love their bodies?

I've seen immense personal growth in myself since then and I wouldn't trade my knowledge and experience in this field. . . even for the $11,000. I say this grudgingly because I never came close to earning that money back, but I became smarter financially from this experience.

What I learned: I learned where I needed to grow emotionally and that being a coach is not something to be taken lightly. When involving other people's lives and well-being you must have a foundation on which to lift people up! I also learned the valuable lesson of money and loans.

Clothing Boutique:

I did name this one! And. . . dove head first into the deep end. I registered Winn&Wear as an actual Utah business. I bought a business license from Cedar City, filed for a whole-sale account, set up a website, and bought a LOT of clothes to store in our one bedroom, newlywed apartment. Oh boy. This failure also lives on Instagram

What I learned: I don't have great fashion sense. I also learned that 103 units of clothes do not fit in a single bedroom apartment and why having that much inventory is a liability. I learned how to register a business, write a paragraph description of a white tee-shirt, set up a website (like the one you are looking at now), and the basic concept of profit and loss. Again, my little photography venture came in handy for Winn&Wear.

The Wedding Dress Shop:

One time, on a whim, I decided to post on Facebook that I was now going to sell wedding dresses. I still had my whole-sale ID and so I could order wedding dresses. I never ordered a dress because most brides want to actually try the dress on before they commit and even with my whole-sale discount, it was too much of a risk to order dresses for brides to try on.

What I learned: Um, common sense? I started to learn to really REALLY try to think things through. . . but I'll be honest, it took me a long time to really kick my urge to chase anything that sparkles. It's still hard for me. I just want to do everything and know it all.

A Mary Kay Consultant:

If you live in Utah, chances are you've heard of Mary Kay. I threw 3 parties in my career as a Mary Kay consultant and spent way too much money on make-up I didn't even wear. The only people who came were my mom, grandma, aunt and cousin. They are the best supporters I could ever ask for.

What I Learned: You gotta love and believe in what you are doing otherwise it won't work. Also, there are only two Mary Kay products that I actually did like. The make-up remover, and the mascara.

My First, Second, Third and FOURTH Attempt at My Bachelor's Degree:

I paid the application fee to four different colleges and got accepted before life shoved me in other directions. I couldn't ever seem to find the ideal living situation or right job to work with school. I ended up going to AmeriTech for my personal training cert. Later, after I was married and had kids, I took a few courses from WGU, but I (as I often do) had too much going on with cakes and writing for me to make the sacrifices I needed to in order to make school plausible. I am now, finally, finishing my second semester of college in pursuit of a bachelor's in Business Marketing and both semesters I've managed (somehow) to get straight A's! (This is one of many college acceptance letters that never turned into anything.)

What I learned: It obviously took me a long time, but I eventually learned how to put down the distractions, grow up, and take this goal seriously. Being a full-time student, mom and business owner, I have learned to move with purpose, cut-out the fluff in my day, wake up at 5 to get things done, and just show up. It has helped me in my writing, reading, and time management. It showed me that I can accomplish hard things . . . if I'm willing to do the hard things.

My First Attempt at a Blog:

My first blog attempt gained a whopping 15 views from all my posts added together.

Just yesterday, my Sugar Cookie Recipe reached 187! It's definitely not celebrity status, but that's not the point. The point is I've learned! My blog grew more than 12x what it was on my first attempt. The last thirty days have gained 451 views! This is a picture of my blog numbers from last month and there is growth and I've even made money from it!

What I've learned: Sometimes it's not me that's failing. It's my knowledge. I've been reading books, joining classes, and listening to podcasts. I didn't understand the how and why of blogging when I first tried, but now I do! I'm still learning, but I'm proud of the jumps I've made just by taking the time to LEARN.

Working As A CNA:

I could kick myself, because I just threw away my old CNA badge along with my purple stethoscope. It would have made a good picture for this. Oh, well. So, yeah I took college classes in high school to become a CNA. I did all the clinical hours, passed my classes, but when it came time to actually get certified, I didn't do it. After all that time and money invested, I discovered that being a CNA was not for me.

What I learned: You won't know what you like, or what your talents are if you don't try, but if you discover what you don't like, it will be easier to find what you DO like.

Learning Another Language:

I have been actively trying to learn Spanish since I can remember. When I was old enough to read, I remember checking a Spanish/English book out of the library and my cousin and I went through it, making vocabulary lists. I took all the Spanish classes through high school, I would try to talk to my co-workers who spoke Spanish, I'd listen to Spanish music and podcasts, and yes, I have Duolingo. Maybe one day I will be fluent!

What I learned: You can't just memorize words or practice here and there. You have to be active and persistent in this goal. Like brushing your teeth and showering, learning a language has to be integrated into your daily routine or it won't work. It's not like riding a bike. You will lose it if you don't use it. Also, practicing another language out loud with strangers is intimidating. So go easy on anyone who is trying to speak English. They are brave and incredibly smart to have learned another language.

Running a Marathon:

This is me at my first (and only) half marathon. I've had a goal to run a full marathon for years. I've gone in spurts of training followed by long intermissions of binge eating and laziness. Note that I did not train for this event AT ALL. I did not run a single mile before I did this race. Do not do that. Do not be like me. I literally, could not walk for two days after and the migraine I got from dehydration was the worst I've ever experienced in my life. The skin on my feet had rubbed off by mile 7 and I had blisters on blisters on blisters.

What I learned: Goals are not things you just wake up and achieve one day. They require thoughtful, purposeful preparation. They also require sacrifice. It showed me that running a full marathon is accomplished in the preparation, the runs leading up to the race. Not the race itself.

My First, Second, and Third Attempt At Publishing A Novel: