Why did you choose to freelance? How did you get started?

My parents have always been self-employed, so I grew up understanding the perks and challenges of this type of lifestyle.

I spent one year in a 9 to 5 job after grad school and immediately knew that I was my parent’s daughter and that the office life wasn’t for me. Not only did I feel constrained by sitting in the same chair all day, I also got tired of doing the same things over and over again.

Aside from the ability to set my own schedule and work at home with my dogs, something I love about freelancing is how I can dabble in all of my interests. My first freelance job was an ongoing project to run the website for a newspaper in California. This job showed me the potential of freelance work, which hooked me for life!

Who is your entrepreneurial inspiration? How did you find out about them?

I know this question is likely referring to a public figure but, when I think about my entrepreneurial inspiration, my mind keeps coming back to my parents.

In my household, the response to a goal was never, “you can’t do that.” Instead, I always heard, “that’s great! How are you going to make that happen?”

My parents have always been my cheerleaders, which has made all the difference.

diana fitts and family at christmas
Fitts family at Christmas time!

What’s your biggest pet peeve?

I asked my fiancé about my biggest pet peeve and got, “Ha, too many to count.”

Picking from what apparently is a very long list, one of my pet peeves is dog earring book pages instead of using a bookmark. I know that a well-read book should look well-loved, but I think we can do that without folding all of the corners of the pages.

What are you currently reading? OR most recent book you’ve read? what impression did it make on you?

I’m currently reading the new edition of I Will Teach You To Be Rich by Ramit Sethi. While even Sethi admits that the title sounds suspicious, this book completely changed my mindset about how I handle my finances and save for retirement.

Jumping into self-employment, I knew that my finances would get more complicated and that I needed a solid plan for ensuring my family’s financial stability in the future. Sethi’s book is not only the most comprehensive and easy to understand “beginner” financial book I’ve found, it’s well-written and actually entertaining to read.

ramit sethi finance book i will teach you to be rich

What’s your favorite holiday & why?

We go bonkers over Christmas in our family. If you walk into our house, it’s a constant stream of Christmas music and Hallmark movies. Both my fiancé and I grew up in families that had very strong holiday traditions. These traditions meant a lot to both of us and we really enjoy keeping the Christmas cheer alive each year.

Where do you live? Would you rather live elsewhere?

We currently live in Lake Oswego, Oregon, which is right outside of Portland. It’s absolutely beautiful and we feel really lucky to be so close to what Portland has to offer while only being steps away from the river. We love where we live, but would also like to explore other areas before we set down roots.

What’s the most useful/important thing you’ve learned so far about freelancing?

A huge part of success is having the confidence to reach out to new prospects everyday, no matter how many rejections come through. Thinking about my recent freelancing wins, it came down to sending that one email to someone who happened to need me at the right time.

My journey in freelancing has taught me that, while it can sometimes feel like a game of chance, the results I see are related to effort I put in and how committed I am to building my network.


Diana Fitts is a freelance writer based in Oregon. You can find her at dianafitts.com and hire her by becoming a GigLoft hiring partner!