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Get Gutsy With Caroline Winn: “I Quit My Job In Finance to Become a Full-Time Photographer”

Welcome to the Get Gutsy interview series! Each month, I interview people who are getting gutsy– stepping outside their comfort zones to reach their goals and live a life that makes them truly happy.

Click here to read past Get Gutsy interviews.

get gutsy with Caroline Winn- Jessica Lawlor

Today, I’m excited to introduce you to a woman who not only inspires me with her words, but also with her beautiful photos, photographer Caroline Winn.

Here’s a quick story about me and Caroline:

If you’ve been reading the Get Gutsy blog for awhile, you may recognize Caroline’s name. She was one of the winners of the first-ever Get Gutsy Essay Contest back in 2014. I’ve been following Caroline’s blog since 2013 and we’ve quickly bonded over a shared love of yoga, running, solopreneurship and more. If you aren’t already reading Caroline’s blog (and admiring her wonderful photography), what are you waiting for?! I know her story below will inspire you.

1. Hi Caroline! Thanks for being on the blog today. Could you please give us your best Twitter-style introduction? (140 characters or less!)

I’m a 26 year old wedding and fitness photographer from Boston, 2x marathoner and certified yoga teacher with a peanut butter addiction and country music obsession.

2. Tell us about how you are getting gutsy.

In April, I quit my day job in finance to pursue my photography business full time after growing it on the side for three years. While the move was well thought out and planned, it was still a huge leap of faith.

I no longer have the security of a steady paycheck, health insurance and a boss telling me when to show up or what to do. Every day feels like a new adventure with a new set of challenges, insecurities, and obstacles to overcome. I am constantly pushing my comfort zone and learning new things about myself and how to run a business.

Honestly, “getting gutsy” does not come naturally to me. Deep down I am a shy introvert who resists change with all her might. But I’ve come to learn growth – and even happiness – is found outside of my comfort zone.

get gutsy with Caroline Winn- Jessica Lawlor

3. How did you get into photography? What do you love about it?

My senior year of college, I registered for an introduction to film photography class somewhat on a whim. I was a marketing and finance major so up until this point most of my classes were taken to fulfill degree requirements, I had never just taken a class for fun. Growing up, I had always been “the girl with the camera” in my group of friends but I had never really pursued photography beyond that. That semester, I quickly fell in love with photography. I loved how it was a creative outlet but there were also a lot of technical aspects to it.

After college, I was working in a high-intensity marketing job (on what I had thought was the path to my “dream job”) and I wasn’t very happy. I started taking evening photography classes after work and spent my weekends playing around with my camera and reading photography blogs. My passion grew from there.

I love photographing people and capturing the fleeting moments that you might otherwise miss or forget. These days, as much as I love photography, I equally love everything that comes with running my own business, such as, branding, marketing, blogging…even bookkeeping 🙂

4. What is it like being a full-time photographer? Can you share a “day in the life? (Though I’m sure every day is different!)

Being a full time photographer has been a big adjustment!

I’m used to working a job with set hours Monday through Friday but with photography, every day really is completely different. Some days, I spend completely behind a computer either editing photos from a shoot, blogging or responding to emails. Where as some days, I’ll have client meetings at a local coffee shop, an evening shoot or an all day wedding!

Because I often work weekends, I try to take at least one full weekday off. I’ve found that in order to be successful I have to be really organized. I write everything down, set alarms for reminders, and usually have multiple to do lists going at one time.

A typical day starts at 5:30 a.m. I wake up, go to the gym and get right to work when I come back. I’m best in the mornings so I try tackle the biggest tasks then. In the afternoon, I’ll schedule meetings, phone calls and try to get outside for a walk or to take pictures for fun. I find when I step away from my computer is when I get the best ideas and inspiration. I’m still trying to figure out a routine that works for me, but it gets easier every day!

5. I’m sure there have been many challenges along the way in your journey. What’s your approach to tackling setbacks?

I have faced a lot of challenges on the road to being a full time photographer, and I’m sure I will face a lot more going forward! For example, I have dealt with resistance from friends and family toward my career change, clients not valuing my work, and internal battles of self-doubt.

I think the most helpful approach to tackling these setbacks and many others has been always coming back to the “why” behind what I’m doing. Why I want to be a photographer. Why I love doing what I do. Why I started this journey in the first place. Whenever I’m feeling down or begin to doubt myself, I always step back and ask myself, “would I regret it in five years if I quit right now?” The answer has always been yes.

6. Can you share a bit more about the resistance from family and friends? That doesn’t sound easy to handle at all. How did you deal with those interactions and feelings?

When I first quit my secure, well-paying corporate job to spend my summer working for another photographer for little pay, most people thought I was crazy. No one told me outright not to do it, but I think a lot of them thought I was making a huge mistake. In that first year or two, I got a lot of comments that I had to brush off. It’s hard when you’re already taking a huge leap and not sure even sure yourself where you will land to not take what other people say to heart though.

I was extremely lucky that my sister was always supportive of with my career transition. (As a kindergarten teacher, she similarly decided the corporate world wasn’t for her.) She was my sounding board during those first few years and talked me through hesitations and doubts. She helped me see everyone has different career aspirations and priorities, and what works for me might not work for someone else- and that’s okay! Now that I’ve been able to carve out a career for myself with photography, those who doubted me originally are more supportive and I don’t face the same resistance anymore.

get gutsy with Caroline Winn- Jessica Lawlor

7. You mentioned self-doubt. I think this is something we can all relate to. How do you pull yourself out of that mindset? Any tips or tricks?

I think having a support system is so important when it comes to self doubt (or just bad days!). I have a close photographer friend that I talk to constantly about everything from how to respond to an email and what culling software is best to what we should wear to our photo shoots that evening. We are always picking each other up and talking through self doubts. It’s so nice to not go through this alone and to have someone who can relate. Working for yourself can be lonely and isolating at times so I’ve been really working to build a network of other creative entrepreneurs. Don’t be afraid to put yourself out there, introduce yourself via email or ask someone to coffee- you never know where it may lead!

8. What one piece of advice would you give to someone who wants to follow your path?

Set small goals! Haha Jess did not tell me to say that 🙂 I just loved that post so much because it’s really true.

I am so impatient, I always want to jump ahead to the ending and so I constantly have to remind myself to do the little things well and the big things will follow in time. If you want to work for yourself, consider starting a side hustle first. Working two jobs will help you save money while you start up your business and show you whether or not you REALLY want it because it will be a lot of work!

9. What does your life look like five years from now? More importantly, how do you hope to feel?

Recently, I’ve been really trying to let go of the idea of a “five year plan.” Growing up and in college, I was such a planner. I held on SO tightly to what I thought I wanted for my future and I quickly realized after college how limiting that was. It’s kind of exciting to think the possibilities of where I could be in five years are endless. That being said, I hope I’m happy and healthy. I hope I’m continuing to push the boundaries of my comfort zone and take risks. I hope I’m surrounding myself with people that lift me up and prioritizing the things I love.

get gutsy with Caroline Winn- Jessica Lawlor

10. What does getting gutsy mean to you?

Getting gutsy means not letting the fear of failure stop you from doing something. I don’t want to look back on my life and wonder what I could have accomplished had I not been afraid to try.

Want to connect with Caroline?

Website // Blog // Instagram /Facebook // Twitter

(Photos courtesy of Caroline Winn Photography)

Know someone you think I should chat with for the Get Gutsy interview series? I’d love to hear about them! Let me know in the comments below!

Want more gutsy content delivered straight to your inbox twice a month? Be sure to sign up for my FREE #GetGutsy e-newsletter filled with inspiration, ideas and action items to get out of your comfort zone. When you sign up, you’ll also be sent a FREE copy of the Get Gutsy ebook, filled with 19 inspirational stories to help you get gutsy.


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Meet Jessica

I live by the saying “Life begins at the end of your comfort zone” and help others do the same to reach their biggest, brightest goals. Read my story here.

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