Featured Freelancer: Jamie Ousterout

Written by Richelle Stewart on May 18, 2020

Meet May’s Featured Freelancer Jamie Ousterout, founder of Stabilimenta, an operational strategy consulting firm based in Raleigh.

Say hello this month’s Featured Freelancer: Jamie Ousterout, founder of Stabilimenta, an operational strategy consulting firm based in Raleigh. Stabilimenta’s mission is to help professional services organizations become more efficient and effective so that the quality of their operations matches the quality of their services.

How long have you been freelancing?
I started my business in mid-July 2018.

What is your “exit” story? Why did you decide to freelance?
During the spring of 2018, I was thinking about starting my own company. This had been a dream of mine for a while, but I felt like I needed to wait until I had a certain number of years of experience before I could break out on my own and be successful. I was talking to a good friend of mine who told me that I shouldn’t wait and encouraged me to start my company.

Following that conversation, I started thinking about three things: What am I good at? What do I enjoy doing? And what does the Triangle and greater North Carolina area need? I realized that I had always enjoyed establishing and optimizing processes, systems, and structures; that this was something I was good at; and that the growing entrepreneur scene in the Triangle could really benefit from my expertise. This became especially clear to me when I was casually chatting over beers with the founders of dash, a high-end animation and motion design studio located in Raleigh. As I was sharing my thoughts about starting my own company, they asked me a pointed question: “If you were to start your consultancy, what would you do for us?” I left our meeting promising to send them a proposal within the month. dash along with Lighthouse Films, a film production company based in Wilmington, signed proposals with me and I began work with both companies in July 2018. 

Share how freelancing has been great and/or how it has been hard.
I love the fact that I’ve crafted the perfect job for myself that utilizes all of my skills and experience. I enjoyed being an account manager because I love working with clients; however, I always had a creative side to me, and I feel like this got buried by being a project and account manager for so many years. Now I am the one working with my clients to write their mission, vision, values; I’m interviewing employees and customers to gather information; I’m creating strategies and documentation. My role as a consultant has allowed me to embrace the fact that I am a writer and strategist…along with a project and account manager. 

I also love that I am my own boss and can set my own schedule. For years, I struggled with work/life balance. As my own boss, I can choose who I work with and when. I also have a strict policy about only working with good people–and I’m very proud to say that all of the clients I’ve worked with to date have been incredible.  

The biggest thing I have been working on since I started my company is having patience and trusting that the good work I do for my clients will not only truly help them succeed but also will generate future work. 

What is some advice you would share with soon-to-be or wish-to-be freelancers?
The same advice that my friend gave me: Don’t wait to start your own business! However, at the same time, really think through what you are going to do, what your mission is, what your positioning in the market is (and how you’re different from your competitors). While I started my company in July 2018, I didn’t officially launch my website and start actively promoting it until November 2018. I took time to dedicate myself to doing the very best job I possibly could on my first two client engagements, build out my own internal processes, and create my company’s branding.  

What is some advice you would share with clients on how to best work with freelancers?
I actually worked with Uncompany to develop a Best Practices for Working with Freelancers document. A few key things to remember: 

-Freelancers are not your full-time employees so you can’t expect them to be available to you 24/7, and they may have different work schedules than the typical Monday-Friday from 8 AM-5 PM. 
-Set expectations upfront and be sure to share as much background information as possible. The more your freelancer knows upfront, the more successful he or she will be in working with you and creating excellent deliverables. 
-Communicate often and share feedback–just remember to be specific in your feedback and focus on facts rather than feelings (e.g., don’t ask them to change the color from blue just because you don’t like the color blue). 

What are your favorite tools/apps/platforms?
My newest obsession is Miro. It’s amazing for conducting virtual brainstorming sessions and creating quick flow charts as well as user journey maps.