Lindsey Roman: Preparing for Motherhood as an Entrepreneur

Lindsey Roman Photography

We’re in a fun season of featuring our inspirations on the Outside Fam blog…..and someone we LOVE to follow and learn from is photographer and educator Lindsey Roman.

I (Chelsie) had the privilege of meeting her way back when at an event I was speaking at. I’ve absolutely loved following her journey as she has taken the photography industry by storm! (I also may have happy cried a little when I found out she was pregnant too! Having babies has made my stoic heart way too emotional ;)

And, as a fellow working mama, I was so interested to hear how she is preparing for motherhood while still working hard at her dreams. Here’s a peek into her thoughts below….how she got where she is today and what her next season holds!

· Hey, girl, hey! In a nutshell, tell us a little bit about yourself + what you do?

My name is Lindsey Roman. I’m a destination elopement and intimate wedding photographer based out of Oahu, Hawaii. I’m also an online social media guru and business educator. I teach workshops, online courses, and co-run a business education company with my biz bestie. Okay, but all of that makes me sound way fancier than I actually am, and I’m all about keeping it 100%. Let’s get down to the nitty gritty. Here’s who I really am: I’m an imperfect wife forever trying to find that work life balance (HA!). I’m a mom to be (no literally - I’m sitting here at 39 weeks wearing no pants (don’t judge me) with a MEGA big belly about to pop any day/hour/minute). My friends say I’m a spitfire ball of energy who loves laughing, talking too loud, and being the life of the party. I’m a girl who always has her bags packed ready for the next trip or adventure, an unprofessional dancer (peep my insta stories for proof), and a 20-something girl with BIG dreams helping women and fellow business owners step into their God given calling. PHEW. That was a mouthful. 

Lindsey Roman's photos

· What was the journey like to become an entrepreneur + business owner?

My journey was definitely an unexpected one. I never ever in my wildest dreams imagined doing what I do as a career. I wanted to be an actress. I loved entertaining and using my talent as an art form to tell stories and evoke emotion in people. I grew up watching the Disney channel and would just look at Hilary Duff in Lizzie McGuire like, “One day I’m gonna be her.” I double majored in theatre and film in college fully expecting to head off to LA after graduation to try and “make it big.”

Well graduation came around, and for some reason I wasn’t ready to make that jump. So instead I took a year to do an internship with my church college ministry. I was on staff working with students, while simultaneously exploring some passions of mine I’d always loved. One of those was photography. I had had a DSLR camera for years, but only knew how to use the thing on auto. So one day I picked it up, and my husband (boyfriend at the time) Andrew taught me how to use it.

Simultaneously Instagram was starting to pick up as people were creating online platforms to market themselves or businesses in an aesthetic way. I was interested in online marketing and took an Instagram course and fell in love. I started using that platform to build a brand and a photography business.

Andrew + Lindsey in New Zealand

I began photographing friends and families in my church. My friends started getting engaged so I would take their engagement photos, which led to shooting their weddings. And that’s where I found my niche. I LOVED shooting couples and weddings. I knew that was the direction I wanted to go.

I lived in Kansas at the time, and wanted so desperately to dive into the adventurous elopement and intimate wedding scene that was happening in epic areas like National Parks, mountains, and unique places. So, I started traveling on my own dime with Andrew. We would make weekend trips to nearby states like Texas and Colorado, and I did couple calls on Instagram to try and get portfolio work in the National Parks we were visiting. From there, my photography business slowly started to snowball. I got one epic shoot in the Great Sand Dunes National Park in Colorado, and that led to something else, and that led to something else. At the time Andrew also had joined the coast guard and we got stationed in Oahu, Hawaii. Moving to Hawaii was the absolute perfect storm my business needed. Hawaii was the landscape for my business to take off. We moved here in the summer of 2017 and since then God has blessed my photography business SO much.

As my business and online platform grew, more and more people looked up to me as a photographer. Eventually I started offering mentor sessions which slowly led to starting a photography workshop with my best friend Evie Rupp. Our workshops took off more than we ever dreamed, that we decided to also offer an online version of them - so we created The Heart University where we offer both in person workshops and online courses for photographers and creative entrepreneurs. That’s pretty much where I’m at now, with so many more exciting plans for the future!

  • You’re now expecting your first baby while running a successful business. What kind of emotions have you experienced during this time of balancing both?

I’ve always wanted a career. I’ve always wanted to do big, important things for the world. I used to believe that you could either choose to do that - have the big, shiny, awesome career, or be a mother. I didn’t think you could do both. So that led me to the idea that I never wanted children. I’m also an only child and I never babysat other children growing up, so not being exposed to other kids played into it. I would look at other mothers almost with shame like, “Wow, they could have lived such a beautiful life if only they wouldn’t have had kids.” I honestly used to think like that, which makes me so sad thinking back on it.

Lindsey Roman Baby Announcement

My worldview of motherhood was SO limited and skewed. I think ultimately it was fear. Fear kept me thinking that I couldn’t be a mom and have a career. Yet every time someone asked me where I saw myself in 5-10 years, the image that always came to my mind was Andrew and I picking apples in an orchard in the fall. I’d be wearing braids and overalls, and our children would be running around us picking apples off the ground, with sticky messy faces. And every time I saw that image I just thought, “That. That’s what I want for my future.” I think there was just always a disconnect between where I was currently and that image in my mind. I wanted the beautiful family in 5 years, but didn’t want to take the steps to get there. To actually say, “Hey yes. Let’s do this. Let’s try to get pregnant.” Because choosing to take the active step required putting my faith and trust 100% in God. It required me to step back and not make my job my idol. Because I knew the second we got pregnant, there would have to be a change.

It wasn’t until last year that my heart started to truly move in this direction. We found out we were pregnant in October 2018, and my immediate reaction was, “Holy crap. This is it.” Over the last 9 months I’ve had to do a lot of heart work with God preparing me to balance both motherhood and running a business. But God has had such grace with me, and has taught me SO much during this pregnancy. I no longer believe you have to choose between motherhood or having a career. I’ve seen so many beautiful examples of woman who crush it at both, and those women inspire me.

· You’re planning on continuing your career while raising a little. What things are you doing to pivot your business to accommodate both?

I’m planning to outsource a TON. I’ve already had an editor, an associate photographer who shoots for me, and an assistant for about a year. Trusting and relying on them has been so helpful in the lead up to going on maternity leave. Once I’m back, we’re adding on an intern in the fall which I’m planning to outsource all the things I don’t need to do myself.

I take the photos. I create any writing content for blogs and social media posts. I teach. But other than that, everything else like putting blogs together, running Pinterest, handling my inbox, booking travel, managing my calendar, submitting work to publications, editing, etc… I don’t need to do any of that. Once I’m back from maternity leave, I envision a much stricter work life. I used to work whenever and wherever, but I know with an infant that’s not going to work. I’ve always been notoriously bad at balancing work and personal life, but I know having a baby is going to force me to make boundaries for both. When I’m working, I want to focus 100% on work. And when I’m not, I want to focus 100% on my family. I’m planning to create strict work hours to help balance both those things. I was already transitioning my business to head in the influencer/educator space anyway, so having a baby while scaling back on weddings has fit together nicely. 

Lindsey adventuring

· Having a child brings new perspectives to our lives. Do you have any new visions for your business that have been influenced by being an expectant mother?

I think the main thing I’ve learned through pregnancy is just how excited I am to do what I used to fear - balancing both motherhood and running a successful business. I’m so excited to teach my little girl how to follow her God given purpose and create a life that makes her so fulfilled. I see so many people go to a job they absolutely hate, come home, complain about it, and do it all again the next day. They never do anything to change it because they don’t believe they can. I’m so excited to teach her to use the gifting and talents God has put inside her to help make the world a better place while doing something she loves. I don’t believe you have to settle for a job you hate. I think the unconventional life of an entrepreneur is something I’m so excited for her to see me do as she grows!

Lindsey Roman Nursery

 ·  Speed Round!

Weirdest pregnancy craving? Frozen fruit

Favorite business tool? Honeybook

 Travel destination you can’t wait to visit with your babe? Iceland

 Three things you hope to teach your child? Confidence, Faith, and Trust

One quirky thing about you that you don’t tell most people? I used to work at Disney World as a character performer haha. I don’t know if that’s quirky or not. 

·  Best place to follow your adventures?

Instagram @mrslindseyroman and

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