On Dreaming Big

Having diverse aspirations, what happens when it doesn't work out as you hoped, and advice for people with big creative dreams.

*Quick note: If you scroll to the end, I have some exciting updates about Feeling! Magazine, and what you can expect to be rolling out next. :) I included some questions for you, specifically! Thank you, dear wonderful readers!

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When I find someone doing work that interests me, I like to launch a full lifetime analysis on them. I love a biography. I want the gritty details. I’m searching online bios, and yes, even Wikipedia, to harvest the details of the dominoes in their life that fell just right to get them into whatever it is they’re currently doing. I’m figuring out where they went to elementary school, how their father spoke to them, the repercussions of their second divorce, and what their first job was.

I think we dig into the life events of those we perceive as successful because we’re trying to align our own dominoes in the perfect order to get the same results. We know that won’t work, but we still do the research.

I used to have a lot of beliefs about my creative career, and almost all of them have drastically changed in the last few years. I also used to put heaps of pressure on my pursuits to become everything I needed them to be, and then felt devastated when they weren’t. (I feel like that could apply to someone’s dating life too, no?)

This was especially true at age eighteen, when I was extra existential about what I would do with my life. I remember my high school friends and me eating crackers, sitting on the floor of a teacher’s storage closet next to a science skeleton, trying to problem-solve each other’s futures. At one point, I was going to start a surf and smoothie shop and be married to a surfer, naturally. Then maybe I’d be a writer. Or a teacher. Or own a horse farm.

Ladybird had a very similar experience.

I felt the pressure of choosing a major, a career field, and also a calling. What was I made to do? Eighteen-year-olds know a lot of things, but it’s impossible to know all of those things when you have so little life experience.

I used to think a career was a set-in-stone, long-term identity, but now I see it more as an unfolding storyline that weaves through the rest of my life.

I try not to be a prefacer, but I do feel like there are a few personal notes that will help you understand my perspective.

1. I have always loved to work. I started working as young as I possibly could. If I were born during the Industrial Revolution, I would have been the best child laborer on the floor, I kid you not. I swing so hard on the overworking pendulum that I will keep going until I make myself physically sick. This is not a badge of honor, but a confession. I like working so much that it can become an idol. Usually, hard work makes me feel better, and so I manipulate work to meet my spiritual and emotional deficits. At my best, I am ambitiously serving others and creating experiences and art that help people feel loved. I float a little when I get to do that. At my worst, I am “This is Me Trying” by Taylor Swift. I feel let down, immensely, that my achievements and efforts didn’t give me the emotional result I wanted, and so I see myself as a failure. *More on that later.

2. I have always had so many dreams. I am entrepreneurial to a fault, I’m drawn to a creative work style, and I deeply want my work to hold meaning in ways that help others. My current dream list (which I’ll share at the end) is very, very long. It’s been ongoing since I was in elementary school. I have not “picked a lane” or “niched down.” I have one life to live, and I’m thrilled by the diversity of work I’ll get to do as I grow older.

This silly graphic about work and life aspirations went viral recently on both TikTok and Substack, and if you relate to it, consider everything I write from here on out like a big hug.

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This was from a reader in my comments section, which inspired me to write this post:

“Small shop owner, school teacher, and now creative director and designer? My hero! I'd love an article on your path and how you've managed to string together such an inspirational career. As someone with similarly diverse aspirations, I've sort of been on a kick of looking to others who have taken those more unconventional paths through their lives and careers -- all without sacrificing depth or quality for superficial 'jumping' between fields. Just a thought. Loved the article and loved the glimpse into your philosophy on positivity! ”

To answer your question, I am essentially making my own Wikipedia page for myself.

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The Origins:

I present to you a page of one of my most prized possessions, my Smashbook from 6th Grade. You can tell I was really into daytime television — just a visit to Carlos Bakery from TLC lands at number 10 on my overall life aspirations. And yes, I was in a movie. I was an extra with a backpack on for a small Christian film that used my middle school for some scenes. We drove to a theater about an hour away to see it, and the scene where I was standing in the background was cut. But it still technically counts, right?

I also find it worth noting to you that I have indeed taken an iPad to Starbucks, achieving that super-specific aspiration for my past self.

You can tell that I am a dreamer, specifically where it says “(Part of) Bucket List,” clearly indicating that 10 items were simply not enough.

The Early Years:

Third Grade:

I began circulating my wildly popular publication, “Kids Weekly News,” in Mrs. Wheeldon’s class. Getting the papers over to Mrs. Peters’ was difficult, but it did happen on occasion. Each edition was made by hand until I discovered WordArt. Another student, Victor, made an opposing paper, and there was a publication war briefly in the spring. Mine won out until I ultimately became bored.

Photos courtesy of Mom, who had the hindsight to eep these treasures.

Fourth Grade:

I got my first video camera, and my best friend Hannah and I made a web show we called Hanner-Nanner and J-Dog. We had a theme song (not in the show, just one we sang out loud), and then I learned Weebly in computer class “free-time Fridays” and made a website for us. I added a view counter, firework effects, and music started blaring when you opened it.

Middle School:

I started my first business when I was 11. I had started babysitting, but decided it was not lucrative enough. I asked my mom if I could host summer camps in our home so I could have 10-12 kids come at a time and be paid hourly. Somehow, she agreed. So I, a child, became the director of smaller children, developing camp themes, crafts, and activities. Moms, who in hindsight must have been quite desperate to have 3 hours of quiet, would drop their kids off at the house for a few hours and go run errands. Notable mention: I was really into TLC, and began vehemently baking elaborate cupcakes during this time as well. I don’t think I ever booked a paid gig, though.

Late Middle School:

I decided to become a photographer. iCarly was at its prime, and I had already filmed everything in my life on my Flip camera and edited it for hours. So I saved up babysitting money to buy a “real camera,” and then my photo obsession exploded. At this point, I was taking a hundred photos, editing them to smithereens on PicMonkey, and then uploading them in their entirety to Facebook. Some moms that I babysat for saw the artistic vision and asked me to photograph their kids’ birthday parties. This became my full-time summer gig for a few years! I had business cards and everything. I would take photos in bounce houses, first birthday cake smashes, and like clockwork, another mom at the party would see me in action, and ask me to attend their kids’ party next week.

Early High School:

I continued to photograph everything. I took a Journalism class and expressed myself through writing, photography, and video editing — I also met the love of my life. During the school day, I was learning Adobe programs and skipping study hall to play on them more, and after hours, I was taking family photos.

More High School:

I got my first job at the YMCA as a summer camp counselor. I was 16 and in charge of keeping thirty 7 and 8-year-olds from drowning, and also thoroughly entertained for 8 hours. It was like Lord of the Flies. Naturally, I loved this job and cried big tears at the end of summer when I said bye to the kids.

The summer between High School and College, I landed a marketing Internship at a local agency and learned more about copywriting, Squarespace, and how long a lunch break is supposed to be. Mostly, they had me paint walls in their office, though.

College:

Over college summers, I nannied, became a barista, and interned twice as a social media marketer. (One quick note: I probably learned the most college life skills from being a barista. Everyone should have a service job when they are young. You will learn so much from those interactions with angry people, cleaning dishes, and sweating in a coffee trailer with people who are different from you.)

During college, I was struggling with a lot of big feelings. A tidal wave of circumstances and hormones collided, and I found myself in the trenches of real, tangible depression. I wasn’t healthy. I took to painting the side margins of my Bible as a sort of balm for nighttime anxieties. The thin pages got quite sticky, and I ran out of space—so canvases and cardstock were next. I painted anything that felt hopeful. Flowers. Suns. Words. Blobs. Colors.

I started hanging them on my dorm walls. Then I ran out of space to store all the art supplies next to my bunk bed and began learning to draw on my iPad, which quickly became my favorite way to illustrate. Something in my work struck a chord with other college girls who visited our room. Probably also dealing with their own tidal wave of emotions, the hopeful words I painted spoke to them. Soon, people were asking to buy art prints.

I listened. I launched a business almost instinctively, as if it had to come out of me. I started an Instagram and a blog where I wrote about hope and shared illustrated reminders. From my dorm room, people were buying prints every day. I called the business Twenty Seven, named after the Psalm that started all the nighttime painting. I stored my art in my Volkswagen and did markets every other weekend. Twenty Seven developed a bit of a cult following. I rented a physical booth in a local shop where I sold my products, and a loyal base of joy-seekers and color lovers began to show up.

My Instagram hit a big growth spurt from a series of “color dots” I made, and suddenly I was being asked to paint murals, design packaging, and sell my work online.

I graduated college on a Thursday, got married that Saturday, and after our honeymoon, I signed a lease on my storefront in our historic downtown.

Ages 20-23:

My storefront dream came to a beautiful, complete fruition. It was better than anything I could have imagined, with a thoughtful team of joy-makers and a beautiful space that marked the city. It ended painfully. I wrote, really vulnerably, about that experience here.

I opened in the fall of 2019, and it was incredible. The store was full of curated goods, seasonal displays, a greeting card bar with confetti, and a signature candle scent called “Indoor Sunshine.” The best part of owning that store was how much it meant to other people. I think, in its colors and light, it was a safe space for weary people. And that is all I could have asked!

In 2020, I used the closure time to revamp and add a tea bar. Loose leaf tea has been a hobby for years, so I worked with a team to develop Twenty Seven’s own tea line and physical tea bar — the first in Lakeland. We had the best matcha lattes, London Fogs, and crazy good summer iced teas. Our teas were being wholesaled across the country and served in other coffee bars and grocery stores, too.

I made the decision to close in 2021, and the loss affected me for years. I don’t really want to hash out the sad parts again, but I did in this article if you are curious. Quoting myself,

“My store couldn't survive the extended closure and I was unable to get rent relief, so l had to close down my dream almost as soon as I got it up and running. I sold everything could. I had to call every employee that I so deeply loved and tell them how sorry I was. I had to throw any ounce, confetti piece, relic of the store I couldn't sell into a dumpster behind a Panera Bread myself.

To decide to close my store was the hardest thing I’ve had to do for myself. I was mortified and embarrassed. I truly thought my storefront would forever change the landscape of my city. I imagined myself running it into my forties. It was my dream come true. There were a lot of older, negative voices who made me feel like I couldn’t do it — did I just prove them right? I had so much to prove, and yet I had failed.

It was a really hard way to start adulthood and it's been really hard to shape a vision of hope for the future when it felt like more loss would be inevitable. I grieved violently. A palette of smeared hues. Every day I was unsure what color of grief would bubble up.

I think even harder than going through all of that was the other side of it. I think it all re-wired my nervous system. I went through phases of emotional Olympics. I started having physical pain. I started having nightmares. I, truthfully, still really struggle with the beliefs this time period of loss wove into me. I often get really frustrated with myself for not being over it.

I was massively ashamed and felt like I failed so young that there wasn't a future for me.”

A few really random crazy things happened in the midst of closing up my big dream.

I ended up teaching middle school and high school.

Mrs. O’Brien:

I ended up, somehow, guest-speaking at a middle school Entrepreneurship class in 2021. And then I just never wanted to leave, because I loved it so much.

Fast forward to 2025, and I’m now directing that very Entrepreneurship program. Every day, I get to build things that are good for kids.

Turns out, I love a whiteboard. I love grading papers. I love school, and creating precious, safe spots on campus for tired and confused adolescents. I was made for holding prom drama and catching high school tears in the girls’ bathroom. I can command an army of bouncing-off-the-wall middle school boys and lead them to do great things. I love the classroom.

I get to teach them all the things about small business I wish I had known. It feels redemptive in deeply emotional ways, often.

A few years back, a group of high school students—most of them unfamiliar with my past and the story of closing my store—pitched me on building a coffee shop and retail store on campus. I asked what they wanted to name it, and they said, “Restore.”

I think I cried that night. Because they had no idea they were literally going to restore something in me when we built it together. And we did. I got to make another store—this time with a precious community.

I was an in-the-classroom teacher for four years. Now, I work in a hybrid role as a curriculum writer and program director.

During my time teaching, I’ve always maintained contract design work too. I have had soe awesome experiences working on murals and interiors for small businesses and non-profits. I’ve done packaging, event, brand, and product graphics, and even got to design a coffee table art book in 2023.

Color Theory Tea:

Twenty Seven Teas got to live on as a rebrand. I worked with another business owner to build out more tea blends and a fresh brand for the loose leaf concept. I sold Color Theory Tea to them last fall (which was a really cool entrepreneurial experience), and now the only association I have is the packaging design.

New York, New Jenna:

I’m 26 now! And I have a lot of questions! And a lot of hope!

I did some major healing from the 2020/2021 losses, and we’ve also landed in a city that could not be more different than where I grew up.

Right now, I have a full-time role in education and am also doing contract design work, content creation, and writing. I love all of it very much, so I am saying yes a lot for a season!

Moving here has made new dreams pop up and resurrected old dreams, too. Can I tell you a secret? I really want to make art prints again. I want to create new art and make a branded print shop. Which, given my story, is essentially like going back to the dragon that burned me and slaying it. I am scared, still. But amazed the desire has come back, and curious if it’s time to go for it. (???!!!)

I also recently started taking writing more seriously. I am tapping into the dream of writing a magazine and going full force after it here, on Substack. I shifted from years of “no one will even care,” to “what would it look like if I really, really went for it?!” Like…what if I made my DREAM publication?! What if I made the thing I wish existed? I’m going for it!

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Now that you are caught up to speed, here is some general advice for anyone in the twisty-exhausting throes of pursuing creativity as work. You probably know all this already, but you may need a reminder (and a hug):

1. You have more time than you think. Careers generally do not peak when you are young, despite how Disney Channel framed it (peaking around 15 years old, HA).

2. Anything can happen! Make that dream list! And also hold them loosely, because dreams will change as you do, and that is a good thing! (I no longer want to dye my hair red like I did in middle school, for example)

3. “Success” is a moving target, and you will define it differently in different seasons. Stop holding yourself to a standard you set years ago that is no longer applicable. Focus on a new target for where you are now.

4. Open those fists!! I used to grasp my future plans with white knuckles. Having a pandemic come out of nowhere and take everything out of control reminded me how little control I actually have. That stressed me out for a while, but I’ve found freedom in the lack of control now. I believe God has plans for me, knows me, and loves me, so that makes me view the future bubbling with hope.

5. Every job teaches you something really valuable. Camp counseling, barista-ing, teaching — all of those opportunities refined me and helped me learn what I love to do.

6. It’s okay to operate in seasons. Seasons of life change and shift, not every job is a “forever job,” like not every home is a “forever home.” How freeing that you could experience so many different types of work you love in your one, precious life!

7. Get really good at your craft. I have had to remind myself often not to focus on the metrics and made-up numbers of success, and actually get good at designing. Remember to read books about your craft, take classes, and immerse yourself silently in the hard work.

8. Be diligently avoidant of social media. Protect your heart. As a creative person, I notice that the more time I spend on social media looking at other people in my field, the worse I feel about myself and my work. I lie to myself that I am “behind,” when there is actually not a race we are all competing in.

9. Be serious about contracts and payment terms. I shrugged stuff off when I trusted people, and I should have sought more radical clarity from the get-go. Do not assume someone will behave the way you think they will — always get it in writing!

10. Do more of the work you really loved as a child as often as you can!

11. 9-5’s are lovely and hard. Self-employment is lovely and hard.

12. People remember how you made them feel. Try to make them feel safe, welcome, and celebrated.

13. You have time. You are capable. You are unique. Your voice and contributions will be different than anyone else’s. You, without a trophy or gold star, are inherently valuable and precious. Rest.

As Connor often says to me, “If you could see all that God has in store for your future, you would not fathom how good it is!”

Let your dreams ebb & flow. Everything is going to be okay. You have time.

*Feeling! Magazine Updates/Housekeeping:

I am still utterly blown away that Feeling! Magazine is a Substack Bestseller! Thank you, thank you!

I am so encouraged and would love your help & feedback (since this has always been a group project) on some new ideas I am rolling out:

1. I am revamping the Friday Whimsy Dispatches to include new themes and printable recipe cards. In order to make it the best it can possibly be, I am taking this Friday off to get my ducks in a row. I think the following Friday will be the best recipe round-up I’ve ever done! I am culinarily way out of my league — but it is exciting!

As part of the ongoing “Making my Kitchen my Favorite Restaurant” concept, I am going to start to base weekly menus loosely on restaurants I am really inspired by! The first one will be GEM Home in NY! Do you have a spectacular, favorite, unique restaurant that could potentially inspire home menus? I’d love to know.

2. Substack chat. I have yet to utilize the chat room feature for subscribers, but would like to use it as a place to directly interact with each other. I was thinking of sharing weekly “joy boosts” with challenges, hopeful reframes, and inspiration. Almost like I’m just sending you a little text in the middle of your day. What kind of creative prompts or challenges would make it useful and inspiring to you, personally? Would love your feedback.

3. Finally…calling all the BIG feelers! An introduction of a new segment! The “Dear Jenna” advice column!

   

   Ever since listening to Delilah as a kid in my mom’s backseat, I have wanted to take calls and hear other people’s stories. I have had the itch to write more about feelings, and especially the intersection of feelings and design. I thought tapping back into my favorite radio host would be a great way to do it. (Her voice comforted generations, people!!)
   

   Do you want kind, hopeful advice about big feelings, creativity, entrepreneurship, creative entrepreneurship, joyful practices, how to find your signature scent, what colors you need more of, or what lamp would look best in your living room!?

   Write me! Similar to the rhythm of this article, write a question, and I will do my very best to honestly answer it as helpfully as I can here on Substack for paid subscribers. Let me be a cheerleader for our dreams and ideas! I am excited for the conversations to come!

   ✉️ 💌Send your messages to jennaisfeeling@gmail.com ✉️💌 I will be looking for them!

As a final bonus, a few things that are on my current dream bucket list: publishing a book, writing children’s books (and then reading them to kids like at those Barnes & Noble events growing up), designing a t-shirt collection, starting a school, having a baby or two or three if I really like the first two, traveling to Copenhagen, revisitng Korea, going to culinary school (a short stint or semester kind of thing), get really good at writing, publish more books, learn to slow down, have a townhouse somewhere and design it all myself, be a florist when I’m retired, own a flower tea shop? Maybe! Let me know in the comments what is on your list!

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