Consultant Spotlight: Krista Gray of GoldSquare

Krista Gray started work as a small business owner and consultant a few years after spending nights and weekends creating content and producing websites for struggling friends, colleagues, and their referrals while building startup companies full-time in San Francisco. Inspired by clients' happiness when empowered to easily share their work with the world, she decided to leave her job to fully dedicate herself to helping people and companies shine online. Today, her business ( builds beautiful and affordable Squarespace websites while Krista serves as a consultant for people and companies that want to improve their presence online. She enjoys freelance writing in her free time, covering topics such as business, creativity, and travel for publishers which include Brit + Co, The Muse, and FabFitFun, among others.

The Upside: What did you do in your past life before going out on your own?

Krista: I worked in a handful of different roles at three Bay Area based startups; since startup companies require each team member to wear many hats, I got a great education about products, community, growth, and content during my six year span.

What's your current elevator pitch?

I help people and companies shine online.

You've been out on your own for 3 years now. What originally made you pull the trigger?

I saw that people and business had a real need for something I loved to do, and eventually couldn't resist my urge to make the leap to try life as my own boss. I've always been entrepreneurial and flourished while working independently, so the change felt like an exciting and natural next step.

What's been your biggest *win* as an independent contractor?

Banishing burnout. For the first time in my life, I feel like I have a truly healthy work/life balance that contributes to my ability to do my best work and inspires my creativity.

What's been your biggest challenge as an independent contractor?

My biggest challenge has been understanding my bandwidth and effectively scheduling work. In the beginning, I underestimated how much time a project might take or how much time clients might need to gather materials, assets, and provide feedback. Though my calendaring is much better two years later, I do occasionally run into some stressful overlap.

What was your biggest stumble and what did you learn from it?

My biggest stumble was probably on the accounting side of things. Though I have an amazing accountant I work with now, I moved so quickly to set myself up in the beginning that I missed a few key steps/failed to have a good process in place for tracking expenses, etc. Other things like buying health insurance, investing for the future, and making it a point to participate in my own continuing education also proved to be challenging. Being self-employed requires doing a lot of research and holding yourself accountable to take action!

What do you love most about being an independent contractor?

I love having the ability to fully design my days and pick projects that really resonate with me. My clients are amazing, and it's truly a pleasure and an honor to help them share their work with the world.

How did you land your first clients?

My first few clients were friends or contacts I made through friends and colleagues; my client base then quickly expanded as I connected with their networks.

Who helped you along the way and how did they help?

I have a wonderful friend who serves as a quasi-mentor to me, and her support and encouragement made me feel confident about trying something new. My family and friends were also wonderfully supportive and encouraged me to give my idea a solid shot. It was nice to have their support as validation. Today, I count a couple of networking groups as solid support. I especially love Dreamers//Doers, a community for women, as a space to ask questions, bounce ideas, and make offers.

What do you think is the biggest misconception about independent contractors and freelancers?

I think there's a misconception that freelancers are super young, inexperienced, or unreliable — and this isn't the case at all.

What steps do you think one should take when first starting a consulting career of their own?

Know what your niche is and where you can add real value for your clients.

What advice would you give someone who's interested in going out on their own?

Do your research. Understand where you can have an impact and streamline your abilities and offerings in a concise, presentable way. Set goals and execute. Measure your results so you can optimize your processes and workflow and know when it's time to stop working on something that doesn't work. Stay true to your passion, interests, and your gut. Most importantly, never be afraid to ask for help.

Where do you see yourself in 10 years? What's next for you?

I'm honestly not sure; I work hard to constantly iterate on my ideas and offerings while keeping my pulse on trends/what people and companies need. I hope my work is relevant and useful in 10 years, and that I'm still fortunate enough to wake up feeling inspired and excited to get to work everyday.

Alright Krista, now fill in the blanks...

Spotify is the one app I can't live without because music keeps me energized and inspired.

Venmo has been a life-changing timesaver because I never to deal with cash or cashing checks. The most unexpected item I carry in my bag is a pair of socks from The Bar Method. I always have them! I think the future of work will be about flexibility. I also think soft skills and creativity will be incredibly valuable.

Follow Krista Gray's journey:


Instagram: @wanderandlove

LinkedIn: @kristagray

Twitter: @thekristagray

#KristaGray #Goldsquare #consulting #flexibility #creativity #TheUpside #DreamersandDoers #TheMuse