Defining Success: Krista Gray


Krista Gray helps people and companies shine online. After five years building community and creating content for startups in San Francisco, she launched GoldSquare, a boutique web production studio that designs and develops beautiful and affordable Squarespace websites. Krista also freelance writes about lifestyle and travel topics for publications such as Brit + Co, Business Insider, INSIDER, and FabFitFun, to name a few.

Passionate about seeing the world, Krista has successfully grown her business while working in different parts of the globe. She's collaborated with international clients based in Hong Kong, Melbourne, and Peru so far this year.

How do you define success?

For me, success is two-fold. First, it’s helping my clients get to a place where sharing their work, passions or business online isn’t overwhelming or difficult anymore; instead, bringing what they care about or do into the digital space is exciting and full of comprehensible possibility for growth.

Second, success means that I can live the kind of life that makes me feel as healthy and happy as possible. Basically, I feel successful when I’m able to do work I love while maintaining a state of financial stability and well-being.

How do you measure your own success?

I measure success by my happiness, quality of life, and an exciting project queue. 

How does success feel?

Success feels like a new stepping stone for the next challenge. I basically see it as a big check mark before seeking out my next opportunity to learn, improve and grow.

When was the last time you felt successful? What happened?

I recently celebrated a year of being a business owner and in my reflection, realized I’ve accomplished a handful of things that I would have only dreamed about a short twelve months ago.

I’ve been so fortunate to work with clients I admire on projects that truly light me up inside. When I think of the work we’ve done/are doing together, I seriously have to stop and pinch myself. It’s pretty awesome.

How do you celebrate your success?

I haven’t celebrated it specifically to date. On a day to day basis, I try to take advantage of the opportunities I have because I’m self-employed.

In a small way, waking up without an alarm on most days, taking late morning walks through my neighborhood, working at coffee shops I love and calling it quits early on the occasional afternoon are all mini-celebrations of the life that I’ve worked so hard and have been so fortunate to build. 

I also travel and work from different places as much as I can, whether it's at a coffee shop that's a short walk away or another country on the other side of the globe.

What advice would you offer to someone who wants to be successful?

Figure out what sets you apart and how that skill or trait can be valuable to others.

Be open to the idea that something you think is a flaw right now could actual be a major strength in the right role or environment for YOU. For me, it was always being a generalist. It turns out that while my varied background across content and marketing roles left me feeling like I wasn’t outstanding in any single role on a  team, it’s actually what allows me to produce client projects from end-to-end because I understand enough about each aspect of the work.

Everyone has amazing talents and areas where they're skilled or can learn quickly. Figure out what yours are and get to work!


Twitter@thekristagray | Instagram@wanderandlove |