Anna Osgoodby

Anna Osgoodby

Social Media, Branding & Web Designer, Co-founder, Bold & Pop
$100/Session | 2 Reviews
  • Career Exploration
  • Industry Insight

About Me

When it comes to your career, I know firsthand that sometimes you need to take big risks to get to where you’d like to be. My name is Anna Osgoodby and I am a social media professional, designer and lifestyle blogger based in NYC. After graduating college and starting my career in the Pacific Northwest I found myself taking my first big risk a year later when I hopped on a plane to move to New York City. For the next 6 years I would lead the social media department at a boutique PR agency where I specialized in strategy and management. In 2015 I was ready for my next big risk and co-founded Bold & Pop -- a social media branding and web design collective. I was yearning for a career that allowed more flexibility to spend time back home (living so far from family is no joke!) and starting my own business was the ticket. At Bold & Pop, we work with fellow creative entrepreneurs and small business owners and specialize in creating colorful designs, campaigns and content. Helping other dream chasers reach their goals has always been at the heart of our work and I think it shows in all of our social media campaigns and design projects. While owning your own business is a ton of work, it’s work that I’m so thankful to be able to do. I love to mentor others thinking about doing the same. In addition to running Bold & Pop, I also have a New York City lifestyle blog. My blog has been one of the main platforms to develop my personal brand and even inspired me to further my experience in graphic and web design. Over the years I’ve been fortunate enough to work with a number of brands and be featured as an influencer and would love to share my advice with those looking to launch or expand their blogs. As a Career Contessa Mentor, I can offer guidance on a variety of topics including: - Learning more about working in social media - Standing out and moving up in the social media industry - Building your personal brand - Using social media to further your career - Insight into the culture of working at an agency - Leadership advice for management positions - Relocating to New York City for your career - Tips on building an online portfolio - Breaking into freelancing or starting a side hustle - Advice for launching a business - Launching and monetizing a blog - Working with brands as an influencer No matter what your goals are, I’m dedicated to sharing my experience and tips to help you with your next big risk! I can’t wait to answer your questions and put together an action plan to help you crush your goals.

Hustle and heart will set you apart.

Get to Know Me

Current Position
Social Media, Branding & Web Designer, Co-founder, Bold & Pop
Previous Positions
Lifestyle Blogger + Designer, Anna Osgoodby Life + Design September 2010 - January 2017
Social Media Director, Boutique PR Agency August 2009 - December 2015
BS, Journalism Public Relations - University of Oregon


"I had a great talk with Anna! She was clearly well prepared and offered some great insights from her experience. She also followed up with a very thorough recap of our conversation and a wealth of resources for me to utilize moving forward. I definitely came away from our conversation feeling as though I'd learned things that would have taken a few painful mistakes for me to discover on my own, so I'm a happy camper. "
- Michelle R. , 28 Nov. 18, 2016
"Anna is a class act. She is whip-smart, kind, fun and I could tell she really has a passion for helping people. I would highly recommend Anna as a mentor! "
- Anonymous, 39 Nov. 06, 2016