How I Quit My 9-5 and Started My Own Business

Prosecco & Plaid and Rescue Dog Nora-4The Backstory

Five years ago, working for myself was something I never thought about. Not only did it seem unrealistic, but I never even entertained the thought. What would I do? Where would I even start? For the most part, I’ve taken the safe route my entire life. My mission was always the same, get good grades, do well in sports, work hard and get a good job. I took courses full time in the summer so I could graduate from college early and start applying for jobs sooner. As a journalism major my dream was to work at a magazine. Lucky for me I graduated in December of 2008, when our entire economy went to hell in a handbasket. So the magazine dream was pushed aside and I was lucky enough to get a job with a small consulting firm in New York City. I started a few weeks after graduating. Two years later we were acquired by a much larger firm. A lot changed and it was a very rocky transition, but I managed to keep my job. I was moving up the ladder, getting promotions, doing the corporate thing. There was only one thing missing, my happiness. My general lack of enthusiasm for my career path was nagging at me.

Find What You Love

I moved around a few times during the time at my consulting job. In between our move from Los Angeles back to New York we lived in Newport for a few months while we looked for a new apartment in the city. During that time I took advantage of being home and seeing family. Once a week I would have dinner at my Great Aunt’s house (Aunnie). During one of our dinners we started chatting about my job, I generally tried not to discuss work, and I spent most of the night complaining about all the things I didn’t like. Aunnie said to me “you have to find what you love, and do that.” I sort of laughed it off, must be nice, I thought. To think that I could just do something I wanted or enjoyed. It’s not that easy, I wish.


Craig and I found a place in New York and moved back there in February. Neither of us were happy. We weren’t happy in New York and we weren’t happy at our jobs. It wasn’t the same anymore. When we first moved to Brooklyn four years prior we were on a high. Living in the city, it was like nothing we had ever experienced, coming from a small beach town in the smallest state in the country. If you can make it in New York City you can make it anywhere, there’s definitely truth to that. But now it just felt loud and claustrophobic and expensive. In March during the vacation my family makes every year to the Bahamas, Aunnie passed away suddenly and unexpectedly. Everything changed. I was devastated. I was so mad at myself that I had moved back to New York for a job I didn’t even like. I missed the last month of her life because I had to take the promotion, it was so much more money, I couldn’t say no. The only thing I realized was that the sentiment money doesn’t buy happiness couldn’t be more true. And what she had said just a month prior “Find what you love and do that” kept running through my mind. It seemed ridiculous and trivial that first time she said it, now it was real.


Aside from being in a general sad fog for a few months after Aunnie passed away, I spent a lot of time in reflection. Thinking about my life and what I was going to do with it. I felt a sense of urgency. I didn’t want to let my life pass by, staying on the hamster wheel. I thought about how I always wanted to work in fashion and my dreams of working at a magazine. I had heard of blogs and seen a few, so I thought if I started one and used it as a resume builder, it would be a good way to get a foot in the door somewhere. So I bought the domain and a camera and started a blog. How naive of me. It did absolutely nothing for my chances at getting a job in fashion, except maybe an unpaid internship, and even that was unlikely.

Jess Kirby Newport RI Craig Mackay Photograhy Prosecco and Plaid

The Leap

Starting the blog was exhilarating. It was all I could think about. Any free second I wasn’t working at my day job I spent working on it. It was creative and new and fun. Shortly after Aunnie’s death I told my boss I wanted to leave New York and move home. I figured I would have to find a new job and I was terrified. Turns out they needed me, and allowed me to work remotely and move back to Newport. We were so happy and relieved to finally be going home. Blogging back in Rhode Island felt amazing. It was a turning point. I realized what a unique opportunity I had to share the incredibly gorgeous place I call home with people around the world. There couldn’t be a better backdrop to my photos than the beautiful island where I grew up. After working from home and blogging for about a year I decided to quit. I don’t think I slept for two weeks. It was one of the most difficult and scary things I’ve ever done. Nothing prepares you for quitting a job and starting something on your own. But I did it. I quit.

The Aftermath

I anticipated quitting being harder than it was. That was the easy part. Figuring out what to do afterwards was not. I wasn’t prepared for the financial or emotional difficulty. I blew through the money I had saved in 6 months. I had only been blogging for about a year when I quit my job and was definitely not in a position to be living off of the money I was making from it. I started a small digital consulting business to help supplement my income. The first year was incredibly stressful. I was navigating unknown territory. There was no handbook, no step by step guide and being in Newport I wasn’t near other bloggers nor did I think to reach out to any and ask for advice or help. It was a rollercoaster but I was so happy. I couldn’t believe I was doing something I genuinely loved, every single day.

camel cardigan sweater denim shorts new balance sneakers prosecco and plaid-15

The Journey to Now

That first year (or really two years) there were a lot of growing pains. Craig was learning the ins and outs of photography and I was learning everything I could about blogging. I went to every event I could, sometimes taking the train into the city just for a brunch hosted by a brand. Meeting people, bloggers and brands, was invaluable. I learned about photo editing and Craig learned about lighting and lenses. We spent hours experimenting with angles and settings. During the coldest winter we’ve ever had, we shot photos outside almost every, single day. Now we are coming up on our third year this Fall. This blog has become our business. To think that we have our own company that is our vision, where we make the rules and we set the schedule is still crazy to me. We work our asses off. We work non-stop. I often get comments from people like “it must be nice” or “wow you guys have the life” and we do, we absolutely do. I wouldn’t change what we have and what we are doing for a second, but having your own business is so much more work than I ever imagined. We haven’t taken a real vacation since we started three years ago. I work most days from 8am-10pm. We work weekends and we work holidays. I’m never not thinking about our business, new ideas, new content, what we can do to make it better.  But I’ve never been happier. I love what I do. I love the people I get to work with and the friends I’ve made. I love that I can go walk my dog in the middle of the day or spend a weekday at the beach in the summer just because. I still can’t believe I collaborate with brands I’ve loved for years. Finding new places to shoot and coming up with new content ideas is so much fun. Every time I get an email from a brand or company I get excited, it never gets old.

 So what’s the lesson here? I think for me, the lesson is that life is short but it’s also long. And at the end of the day you have to find what you love and do it. Maybe it’s an art class, or learning how to knit. I’m not here to tell you to quit your job or switch careers, unless of course you want to. But do something for yourself that gives you joy and lights a fire inside of you. It’s amazing what can happen when you get out of your comfort zone. Life is messy and hard and complicated, but it’s also beautiful and fun and worth taking chances once in while. You might surprise yourself.

jean shorts and bikini on the cliff walk prosecco and plaid


Leave a Reply

  1. Joanne Rodino says:

    Thank you for that post and for exposing your private journey. I dream of the day when I can say “I quit”, not because I don’t like my day job, but to follow my true passion and hearts desire to sing full time. I worry about the $$$ and health insurance and then get paralyzed to make the jump. Thank you for being brave! Seeing your thoughts, fears and inspiration behind the blog is inspiring. ps. I live in Newport too. We met last year at Madewell and you helped me pick out a coat for my daughter for Christmas, which she loved! The best to you both.

    • Jessica says:

      Thank you Joanne! Yes of course I remember you, I am so glad your daughter liked the coat. Thank you for reading and following along. The good news is you have a day job that you don’t hate. I think the important thing is allowing yourself to explore your passions and you are doing that with singing so bravo! xx

  2. Jackie says:

    This entry is so inspiring and motivational! Perfect timing for me to read 🙂 I’m at a point in my life where I’m experiencing so much of the same you went through and I’m now finally figuring it out and on the path to my own career happiness. It’s scary, and exciting but I’m so happy. Congrats to you and thanks for sharing!

  3. Allie says:

    I love this so much! It’s everyone’s goal to find a job you absolutely love, so congratulations that you’ve accomplished that! Now, I need to be brave and do the same, haha!

    • Jessica says:

      Thank you Allie. I feel very lucky to have found something I love and to call it my “job.” It can be difficult to even figure out what that is, but exploring the things you like and figuring out how to incorporate those things into your life is the best way to find happiness!

  4. I loved reading this! I just started out my blog and this really gave me motivation to keep going and doing what I love. I’m living in Rhode Island too and I must say we are lucky to live in such a beautiful state. Your blog is such an inspiration to me. Thank you for doing what you do.

    xx Emily

    • Jessica says:

      Thank you so much Emily. Congrats on starting a blog. Thank you for reading and following along it means more to me than you know. xx Jess

  5. Debra says:

    I believe in signs and this article came out a day after I had a serious conversation with myself about my happiness at my 9-5 job. Deep down I know I should be working for myself but that leap had always scared me. Thank you sharing your own story with us because it gives some of us that faith and courage to take the leap ourselves.


    • Jessica says:

      Thank you Debra. It is so hard to know when and how to make the leap. It’s definitely not for everyone and I feel like there is no “right” time if you do decide to do it. Thank you for reading and following along it really means a lot. xx Jess

  6. Jen says:

    “life is short but it’s also long” — my dad says this all the time. Thanks for sharing your story, and congratulations on all that you have accomplished with your blog! I feel so fortunate to have a career doing what I love, but blogging has become a serious passion of mine as well, so the future should be interesting. 🙂 x

    Jen | affecionada

    • Jessica says:

      Haha it’s funny I know I didn’t come up with that one on my own and it was probably my Dad or grandfather that I heard that from but it’s so true. Congratulations on having a career path that you love that is so wonderful. Thanks for your comment and for following along I really appreciate it. xx

  7. Thuy says:

    Loved reading this post. Read like a story. What I love the most is that you didn’t tell anyone to quit their jobs, pursue a rocky career, and leave their 9-5. You just told them to do what they love and sometimes I think people forget that someone could love their 9-5 and that a life that isn’t filled with entrepreneurship can be equally as fulfilling. And also, sometimes people feel like their career HAS to be something that they love. I think you can have a fulfilling life with a job that you enjoy but a hobby that you love. I don’t think you necessarily need to turn your hobby into a business. Whatever works best for you. I want people to know these things!

    • Jessica says:

      I totally agree! I know a lot of people that love their 9-5 and that is amazing. I definitely don’t think entrepreneurship is for everyone, to each their own. But I do think whatever it is you do for work, finding happiness whether it’s through your job or a hobby is so important. You don’t have to LOVE your job but it’s important to find things you love to do and incorporate them into your life! Thank you for your comment! xx

  8. This is something that I need now. Your article is really inspiring & motivational! And really, just in time!

    Thank you sooo much, Jessica♥

    Olya, x

  9. Meghan says:

    Love this post! Having just gone through the process of leaving a job I hated to curate a job I would love – your words resonated with me! Here’s to having the courage to craft your dream job and working to make yourself happy!

  10. holly batton says:

    Thanks for writing! Right at this moment I am still in my 9-5 job and trying to plan to leave to follow my own passion. It is so hard to know when the right time is. Congratulations on all your hard work. I love the saying “do what you love and you will not work a day in your life”, works well in this situation.


    • Jessica says:

      I totally agree. I don’t know that there is a ‘right’ time but I hope you find happiness in following your passion! Thank you for reading. xx

  11. so cool to hear your story! it’s scary to take that leap, but totally worth it!

  12. Maggie says:

    I love this!! I like my job, and would love to be in a position to quit my job for my blog. Maybe someday!

  13. Deborah says:

    Great read! Thanks you for sharing. ❤️

  14. Jenna Tropea says:

    This speaks to me on so many levels! Thank you so much for sharing your story. I’ve moved around a lot over the past 2 years with jobs when all I’ve really wanted to do is take on my blog full-time. I’m not at the point financially where I can make it, but knowing that other women have taken the leap and survived makes me feel confident for when the time comes!

    xo Jenna

    • Jessica says:

      Thank you Jenna. Moving can be so hard and stressful, I feel your pain. Thanks for reading and following along it really means a lot to me. I wish you the best with your blog! xx Jess

  15. Story says:

    Loved reading this! About a year ago my boyfriend received a job offer in Newport and I discovered you while looking at #newport on Instagram. We’re from Dallas, TX and had zero knowledge of Newport or Rhode Island so your Instagram posts really inspired us. He officially got the job in April and has been living up there since. I have visited several times and have fallen in love! I will be calling Newport home in November 🙂
    I have a wholesale clothing showroom in Dallas and absolutely LOVE working for myself. It’s truly a blessing to be able to work (almost) anywhere and not be tied to an office. I can’t wait to start my new adventure in Newport!

    Thanks for the beautiful pictures and inspiring posts- Story

    • Jessica says:

      That is so awesome! Congrats on calling Newport home, I hope you are ready for a New England winter coming from Texas, haha! Congrats on being your own boss, I know how hard it is but also so rewarding. Excited for you and your new adventure in Rhode Island. xx Jess

  16. Laura says:

    Love this! Graduated college during the same time as you-awful job market! Stuck in a job that I hate. I always wanted to do something with fashion or a blog, but it’s intimidating! Love your blog and I’m a fellow Rhode Islander (born and raised).

    • Jessica says:

      Thank you Laura. I know the fashion industry is definitely intimidating, don’t know why that is, it’s just clothes after all! I’m sorry you’re in a job that you don’t love but I guess at least you have one! I hope you find a way to pursue your passion. xx Jess

  17. Tina says:

    I have been closer to going part time in my job and doing something on my own for the rest of the time than I am now as some things jobwise and privately have changed. I guess I would never quit a secure and a “not too bad” job completely, but your post is really encouraging my thoughts as I often feel like I am going to be missing something out at home with our five rescue dogs (a dog life is SO short)…
    Will be on a USA trip including a few days in New England soon, with road trips so I know my thoughts will spin 😉
    Tina in Germany

    • Jessica says:

      oh my gosh 5 rescue dogs that is amazing! I only have one and it’s so much work. I hope you have a wonderful time here in the US especially in New England! Thank you for reading Tina. xx

  18. I LOVE this post. Thank you for sharing your journey with us. It’s very inspiring and I agree with everything you said. At the end of the day. happiness is everything. Such a great post!

    • Jessica says:

      Thank you so much Adrianna. I really appreciate you reading and your feedback it means so much to me. Totally agree, finding happiness, whatever that means for you is so important. xx Jess

  19. Kela says:

    I really loved reading this post Jess. Thanks so much for sharing. It is especially inspiring for me since I have been tossing this idea of staring a blog back and forth for 2 years now, ugh! if it’s not the right camera, it’s the website, it’s the content, it’s the consistency, what have you. I am an over thinker by nature so reading this definitely an eye opener made me feel more at easy about starting something.

    While we’re on the subject, do you have a camera you’d recommend for stating a blog? Nothing that would break the bank please. Thanks so much!

    • Jessica says:

      Hi Kela,

      I totally understand, I am an over thinker myself but sometimes it can hold you back. It can be hard and scary but just taking the leap and doing it, even if it’s not perfect, is a good first step. As for camera recommendations, we started out with the Canon Rebel t3i which is definitely the most affordable. But the Canon 6D is in my opinion a much better camera, a bit more expensive but worth every penny. Also you need to consider a cropped frame vs a full frame camera, the rebel is cropped and the 6D is full frame. If you know how to shoot in manual mode the 6D is a no brainer in my opinion.

  20. I believe I came across this great article for a reason. I just recently left my 9-5 to continue my passion as a personal fashion stylist…full-time! I know what I need to do but wasn’t sure where to start. Thank you for your post. I can now get it

  21. Your post really spoke to me. After teaching special education and reading for almost 37 years, I’ve decided to launch a nonprofit! My golden retriever, Bree, & I will bring books to children who cannot afford them or whose libraries have closed. We’re in NJ , not too far from Rhode Island and near the beach as well. I’ve never worked for myself, but am very excited! We need to raise funds for the bus and the books so we’re creating storyboxes to sell. These will launch soon on Esty & Instagram so please follow us. We’d appreciate your support!

  22. Angeka says:

    Thanks for this amazing post! It stands out from the other “how I quit my day job” I usually find around the internet because this one seems honest and real and not so “business-y”. Good luck with the company, may there be many years ahead! 😀

  23. Airi says:

    I was inspired this article SO MUCH. I needed 30mins to read this because I’m not native English speaker. However your sentences are easy to understand. I felt familiar with the story you. I also choose safe way/route and I’ve never choose other side. Actually I quitted prior job last year because I had to work for 12hours in a day. There was not my own time. Quitting job was huge decision to me. It was scary thing. After that, moved to new city where my boyfriend living in and found new job at there. Sometimes, I think about “I screwed up my life?” Then, I met your blog. After read this, I can breathed easier. I’m happy to know that famous person like you are also feel nervous and do hard work till business is on track. Now I charged power to going ahead! Thank you for sharing your story very much. Your words encouraged me. Send huge appreciation from Japan xxxx

    P.S. I’m sorry for my bad English and long comments include negative story.

    • Jessica says:

      Hi Airi

      Thank you so much for your comment. I am so glad you found the post encouraging. Keep working towards your goals! Sending you love and positivity. xx Jess

  24. Anastasia M Arnold says:

    Ughhh…couldn’t be better time to read this post of yours. I’m right in the middle of switching jobs myself and pursuing what I am and what I love the most . I’ve lived in Newport for the past 11 years and have been getting bored with it. Your blog is a sweet and much needed reminder of all the things to still love and appreciate on the island. Cheers to the island life!

    • Jessica says:

      I totally understand Anastasia! I sometimes get the itch and need to get out of here for a bit. Travel is a great reminder of how special this place is. Congrats on pursuing your dreams. xx Jess

  25. Ella says:

    Just happen to have stumbled upon you blog. Great essay above. I feel like that is definitely one of truest statements ever! ““Find what you love and do that”. I currently work a 8:30 5:30 in the big apple and absolutely hate it. I do not have time for myself or to enjoy anything worthwhile or this chaotic and exciting city. Sometimes I just want to go to the museum in middle of the week……..Yeah right. Everyday is mundane, repetitive and lacks enthusiasm. Thank you for sharing your story, it has given me some hope in the possibility of changing my life around somewhat.

  26. This was so incredibly insipiring and just what I needed to read. Thank you! Quick question…how did you find out about blogger meet ups, get together’s, and events? I really want to connect but am struggling to figure out how! Thank you so much in advance ❤️

  27. Ariana V says:

    What a lovely post. I recently left my job and have been focusing on my blog and doing freelance makeup. This is so inspiring and it’s nice to connect to someone with a similar background story, I also went to school for journalism in hopes of pursuing a magazine editor job but shortly realized I wouldn’t want to leave CT for it. Family and happiness is so much more important at the end of the day. Xo Ariana V |

  28. Ali says:

    Hi Jess,
    What a great blog! I’m not surprised to see you doing something this wonderful. You always struck me as a beautiful, strong, old soul.
    Congrats to figuring it out early on in life! It took me a lot longer but I am happy to be following my own path as well. Having a great partner makes it a little less scary and very rewarding. It’s nice to see you with such a simpatico partner.
    I love what you do! You inspire me with your style and your passion. I look forward to keeping up with what you’re doing! Oh and a big congratulations on buying your first house!
    Cheers, Ali (Hodgson) Richards xo

  29. Lauren says:

    Thanks so much for sharing your life changing journey; I’m right there at the crossroads of should I or shouldn’t I ? I will be 56 in June and I feel like I’m still young enough to “Jump” what better time than the present..right? I sit at my desk at work so unfulfilled and unappreciated, I feel like a rusty robot! When I discuss the topic openly I hear the opinions of family members and friends with rational and valid points and think of being void of my health insurance and I freeze up. I do pray a lot and I have strong faith,I want to step out… God continues to show me signs that I should make this move; perfect example is stumbling upon your awesomely encouraging post!

    Continued blessings and happiness to you and yours-Lauren

    • Jessica says:

      Hi Lauren, Thank you so much for your comment. Just a little side note, my Mom actually started her own business in her 50s (somewhat inspired by my own leap into freelance). In her 40s she did a complete career change (she was an attorney for 20+ years) and now she owns her own business. So honestly anything is possible with hard work, passion and dedication. Wishing you the best of luck in this next chapter! xx

  30. Anjim Plays says:

    Great post and I am happy you are following your dreams on doing something your love. I am on my way to being a full-time gaming blogger and writer some day. Keep up the good works and enjoy your work-free life.

  31. Serene says:

    These are such inspiring words Jess! Thank you! I just started my blog almost a year ago and loving it. Do you have any specific tips for starting to earn money/collaborate with brands? I would love to learn from you 🙂

  32. Lauren says:

    What a beautifully written blog!
    I’m fairly new to reading blogs and only came across yours today.
    Easy to read, wonderfully honest and true – with much content that is very relatable – I will definitely be keeping update on your blog.
    Thank you! Xx