Corporate Gig to Freelancer: A Love Story


Richard Ellis currently runs his own freelance communications business called and is making more money than he did seven months ago, when he was working at a well-paying, conventional job as a management trainee for an industrial supply company. He went from being unhappy and depressed in that job, to loving life and his work, but it was not easy and he did not do it alone.  His relatively quick journey has many lessons for anyone who may want to leap out of a  cubicle into being their own boss.

Lesson #1: Lean into your community to get new ideas and support for new work.  Do not suffer in silence. If you are unhappy, tell the people you trust and solicit ideas for how you might change your current situation. In Richard’s case, his brother’s fiancée gave him the idea and his first lead that is now the foundation of his freelance writing business.  His girlfriend, Katie, was also instrumental in supporting the change, and he engaged a financial coach at Next Door Chicago who helped him plan and execute the leap from a regular paycheck to his own business.

Lesson #2: Use proven talents that are marketable. In addition to his entrepreneurial founding a business in high school, Richard knew he could write as evidenced by a writing award he won at his Ivy League school and an internship he had at a wine media company. Once he looked at sample press releases, which would be part of his offerings, he knew he could do comparable or better work for clients and save them money at the same time. 

Lesson #3: Stop researching and take action. Once he had a plan he did not waste time creating a complex business plan, but instead he pitched his first client, the CEO of a public relations  company. He provided samples of his work and offered to take on a high volume of assignments at a reduced rate. This has since led to many paid assignments from this company and others to a point where he can barely keep up with demand. 

Lesson #4: Follow your gut. Richard knew on his first day of his old job that he was not going down the right path and began planning his move out of a job within weeks of starting the job.

Richard works really hard and often has 12 hour days but he reports his happiness level to be “off the charts”.  In addition, he is set up to pursue his next dream which is to travel the world while making a living.

Laurel Donnellan


Founder and CEO


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