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330: What Happens When You Go Back - How To Quit Working
330: What Happens When You Go Back

330: What Happens When You Go Back

Listen to the interview here:


Anthony Chatfield started a successful business right out of college, but when his second child was on her way, he made a surprising decision — he got a job. Anthony tells his story of becoming an entrepreneur, getting a job and returning to entrepreneurship on this episode of the How to Quit Working Show.

About Anthony:

Anthony Chatfield has done a little bit of everything in the digital marketing space over the last 10 years. From early years as a freelance content writer, to running his own marketing agency in Seattle and New York, to overseeing Digital Strategy for a New York City inbound agency, he’s worked closely with clients to grow their businesses online.

Anthony started his career online in 2006, quitting his college job and working at home as a freelance content writer. From blog posts about Super Bowl commercials to 30,000 word eBooks about social networks (most of them new at the time), he built a business in Seattle that helped him stay independent, working from home.

In 2009, he founded a content marketing agency in New York City. He worked closely with small businesses to develop content plans with blog posts, social media content, eBooks, and more to generate new business online. He ran this business for more than four years before reentering the workforce in 2013.

After 7 years of working independently one-on-one with clients, Anthony took a job with an Inbound Marketing Agency, ThomasNet RPM, in New York City to ensure, among other things, good benefits for his family. The agency was relatively new at the time, and within his two years there, Anthony moved into the role of Director of Strategy, overseeing growth from 20 accounts to nearly 70.

Quitting a Job for the Second Time

Despite the initial necessity of a full time job, the freedom of working from home and spending time with his children was severely missed. So much so that in 2015, Anthony decided to leave his day job to work independently and spend more time his wife and two children.

Anthony currently runs a digital marketing consulting firm in Pittsburgh, PA working with other agencies, startups, and small businesses who are building out their marketing efforts online. In his spare time, he writes on his blog about productivity and marketing, and runs a podcast about board games with his friends in New York.

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About Jeff Steinmann

Jeff wants to help you Live More. He is the author of How to Quit Working, A Simple Plan to Quit Your Job for a Life of Freedom. He hosts a weekly show called The How to Quit Working Show that features lessons from Freedom Fanatics who quit their soul-sucking 9-5 job and created a business that lets them live a passionate life of freedom. Jeff also writes for several media outlets, including The Huffington Post, Lifehack and Elite Daily. Most of all, Jeff is a Freedom Fanatic, fiercely devoted to finding a better way to “do life”.

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