Small Business Blogger Spotlight: 10 Questions with Jess Oakes of Positively Oakes

Have you ever thought about starting a blog and making money from it? I gather that a lot of people have. I love to include a blogger spotlight in my small business series once in awhile, because blogging is and truly can be a fulfilling career choice.

It’s a great way to make money while being flexible with your schedule, especially if you have little ones at home like so many of us do. It’s also a creative outlet, as I’ve come to learn over the last year and a half. It’s incredibly fun, and brings all kinds of cool opportunities.

jess-positively-oakes-small-business-blogger-spotlight But you know what I really didn’t expect?

How HARD it was going to be.

Like any job, you get out entirely what you put in. So the more work you do, the more success you’ll have. And even still, you might work countless hours on it and not have the kind of success you dream of.

Cute mommy and me Where's Waldo Costume // Small Business Blogger Spotlight: Jess of Positively Oakes. Read her story and learn from her years of blogging experience! Read more at

Sometimes it’s a total crap shoot.

But my guest today has become incredibly successful monetizing her blog and growing a real, legit community. She’s managed to separate herself from the pack in a VERY crowded space, and when you read her interview below, you’ll get a look behind the scenes at what it takes and what motivates her to continue to develop her blog and her community.

And her success did NOT come from luck.

I’ve been a fan of Positively Oakes for quite some time. She’s done a great job of monetizing her blog and creating a real business from her blog, while maintain a truly authentic voice. I can’t wait to introduce you to Jess, the founder of Positively Oakes. Scroll down for the interview.

Small Business Blogger Spotlight: Jess of Positively Oakes. Read her story and learn from her years of blogging experience!

Small Business Blogger Spotlight: Jess Oakes of Positively Oakes

Glad to chat with you! First, tell us where we can find you online.

I’m Jess, founder of Positively Oakes. Find me online at

What inspired you to start your own business?

I wanted a place where Moms could come and feel heard, feel like they were reading real and raw stories/experiences, a place where we could be truthful. I wanted to be able to share my journey of life, into Motherhood — the good the bad and the ugly and be able to have fun while doing it.

What inspires your work and what sets you apart from everyone else?

My family, they inspire my every move–they push me to work harder and follow my dreams. I think what sets me apart is that I’m pretty open and honest, I keep things real, raw and truthful. I might post pretty pictures, but in each caption, in each blog post I don’t sugar coat anything or pretend like things are perfect, because they’re not.

What is your background and how did you develop the skills to start your business?

I have a background in marketing so I had somewhat of an idea how to market. 😉 However– I am pretty much self-made as a businesswoman and still learning each and everyday.

What has been your biggest success to date?

I am currently planning my third “A Positively Baby Shower” and I can’t believe it. It’s a baby shower for Moms that could use a little extra help during this special time, a pick me up. We spoil them with a day full of gifts, lunch, games and giveaways.!

What has been your biggest challenge?

The comparison game. In this industry especially it’s so hard not to feel defeated some days, not to compare yourself to others and feel like you’re losing. I am slowly but surely learning to overcome it.

Describe your typical work day.

I work from home most days, though I travel quite a bit for events, conferences and other things. I have two assistants (both very part time) that help me keep my sanity and then an amazing husband who helps more than he knows. Typically a work day starts right when I wake up, then I feed the babe breakfast and spend time with her, she usually goes to Grandmas after that until her nap time so I can work for 3-4 hours straight, then comes home and naps and I work some more. I work a LOT, I’m kind of a workaholic and it’s a work in progress still trying to balance it all out and be the very best Mom I can while still providing for my family.

Which small businesses are you inspired by?

Fawn Design (Jenny), seriously she’s super Mom and killin’ it and STILL is the most humble, kindest girl you will meet!

If you could go back to the beginning knowing what you know now, what would you have done differently?

Be happy with your little successes. I am constantly rushing right past each “little success” and wanting the next big thing. I wish I had taught myself from the beginning to celebrate each little victory.

What’s your best advice for someone who wants to start her own creative business?

Be patient, be yourself and work HARD.

Read more about Jess and follow her journey at Positively Oakes. Follow her on Instagram

Tell us YOUR small business success story for a chance to be featured in the small business spotlight! For a chance to be featured in one of our small business posts, email info {at} cuteheads [dot] com & tell us about your business.

Small Business Blogger Spotlight // Go behind the scenes with popular blogger Jess Oakes and find out what it takes to monetize your blog.

13 thoughts on “Small Business Blogger Spotlight: 10 Questions with Jess Oakes of Positively Oakes

  1. Awesome interview! It’s so nice to read about a successful blogger who keeps it real. I’m trying to balance motherhood and blogging, and it’s so hard. Blogging is also a lot more work than I ever thought, but it’s also more rewarding. I love her tip about remembering to celebrate the little things. I need to do that.

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The Cuteness: sharing daily inspiration, kids fashion, work/life balance + small business how to's from mom & business owner Esther Freedman