Convince Your Boss to Allow You to Work Remotely with the Co-Founder of Work Well Wherever, Maryellen Stockton - Episode 020


According to Upwork and Freelancers Union, the majority of the U.S. economy will be made up of freelancers by the year 2027.

But why? Why are we shifting towards a lifestyle of gigging it?

The “be your own boss” rhetoric is pervasive and persuasive. It promises freedom, flexibility, and meaning. The truth is that becoming your own boss comes with a slew of responsibilities like paying quarterly taxes, maintaining expenses, expensive health insurance, and finding clients. While in theory, you may not be spending time commuting, you may be trading the precious hours with family and friends on mundane administrative matters.

Meanwhile, large corporations are finding it more difficult to find and keep great talent. Many of them are simply unwilling to give their employees what they want - freedom, flexibility, and meaning. Yet, statistics show that “50% of the US workforce holds a job that is compatible with at least partial telework.”

So what’s the solution?

Remote work.

In episode 20 of The Daring Kind, Host Nicole Hernandez chats with Maryellen Stockton, the co-founder of Work Well Wherever. She and her partner help corporations successfully launch flexible work programs to lower the cost of employee attrition and create a more fulfilling and meaningful company culture.

If you’re someone who honestly knows entrepreneurship and freelancing is not for you, listen in. This episode is for you!

BTW, we have an announcement! Find us on Instagram to learn more!


  • Why even the best music doesn’t make up for the commute.

  • The top fears of management when considering remote work and how to combat their assumptions.

  • Tips for making remote work, work.


  • Pitch your boss on the idea of allowing you to work remotely. Make an offer that can’t be refused. (It might be helpful to share this episode with them.)


Maryellen is the co-founder of Work Well Wherever, a company that is focused on improving the way remote teams work. In 2014, she began working remotely in the staffing industry and became passionate about company culture, employee engagement, and building teams outside the traditional office.

Maryellen lives in Atlanta with her husband Matt and her two kids, George and Winnie.

Cole Hernandez