Yes, There Are 3 Really Good Reasons Why Your Boss Should Support Your Side Gig.

My boss was aware that I had my own company; it was my company who he made my checks out to twice a month when I worked as of-counsel for a real estate developer in New York (it was as an independent contractor). The job had all the markings of a typical full time job. I came into an office every day from 9:30am to 6:00 pm, I had an hour for lunch, and how and when I completed my tasks were dictated by someone else.

It was initially understood that, though I would spend the majority of my time in the office handling all of his matters, should there be any down time, I would be free to work on matters involving my other clients. Though we seemed to have this “understanding” that I would be working on other projects, his demanding of my time and attention became reminiscent of a jealous lover. It was as if whenever I was busy working for another client, some emergency would all of a sudden come up and I would have to immediately give my attention to him.

Additionally, he even expressed that he felt as if I were giving more attention to my other work than I was to his. This was the furthest thing from the truth, because his work comprised approximately 80 percent of my workload.
As I went on to work at other firms, and even interview for positions that were not related to the legal field, there was always one question that would come up: “So, how long will it take for you to wrap up your other matters and close the doors to your practice before coming on board with us?” I completely understand why a law firm would ask me that. Most law firms and even the legal industry shun attorneys who work at a firm and also utilize firm time and resources to handle outside matters. I get that.

However, I was always baffled when that question would come up for a position that was not legally related or when the position was not full time. At the time, most of my clients had their own 9 to 5 jobs as well, so any work I did for them, including our correspondence, took place either during lunch hours or after work hours to accommodate their schedules. I felt that whatever I did during my time and not during business hours was my business.
I do not believe in putting all of my eggs in one basket. If there are ways to collect from more than one source of income, I am seeking those opportunities. However, I have come to realize that not every working environment is conducive to those who have a desire to earn from many different sources, even though there are several benefits for employers to embrace the “outside endeavors” that their employees may be involved in.
These benefits employers have with employees who have side hustles include:
1) Acceptance, Transparency and Trust:

As an employer, if you are aware and accepting of the fact that an employee also has other interests and endeavors outside of your workplace, a level of respect will definitely become evident in your daily interactions. Being at a full time job will not stop a thriving entrepreneur from working on their other career goals.
It’s best that all parties are open and transparent with everything that they are involved in so, if necessary, boundaries and limits are set in re: expectations while on the job. It should be understood by the employee that no employer resources (including time) should be used for outside work, and trust should also be given from the employer that the employee will still be able to manage and maintain their workload without unjustified fears which may trickle down to unwarranted disdain for an employee who decides to do more with their free time.
2) No Resentment:
Let’s face it, we have all, at one point in time, had resentment towards our jobs or our bosses. It may be due to unnecessary work hours, failure to be promoted, difficult bosses, etc. If an employee is delivering the results you request and require for that position, there is no need to add any reasons for them to hold resentment towards a job or a boss that shuns them from pursuing other interests while still doing great work for their employer. Focus on the results they are giving to that job and do not seek to hold them back from other interests because it will definitely cause resentment towards the company and the work they do for the company.
3) Employee Retention:
Most entrepreneurs I know ultimately left their full time jobs for numerous reasons. Some decided that they needed to put their full energy into their “side gig” if they truly wanted to see it grow. Others left out of fear that they would be reprimanded by their jobs for having interests outside of company business, even when it was not in direct competition with what their full time jobs offered. Until an entrepreneur builds a business that is fully sustainable, they will attempt to hold on to all sources of income to maintain their lifestyle and fund their interests. If you have an employee who delivers and hits all work related marks as it pertains to their job requirements, why push them away?


I realize this article is severely skewed in favor of the entrepreneur. So, as a word of caution, if you are currently a full time employee, before you start your side gig, please refer to your employee manual to ensure you are not infringing upon any company policy by starting an outside business. It has taken me years to understand and accept my need for flexibility in all work opportunities. I am wise enough to know, now, that every employer will not be supportive of your side gigs. While you are building your entrepreneurial efforts, there are other options, outside of full time work, that may be able to assist in supplementing your income should your day job not be conducive to your new efforts.
Rashida Maples, Esq. is Founder and Managing Partner of J. Maples & Associates (www.jmaplesandassociates.com). She has practiced Entertainment, Real Estate and Small Business Law for 9 years, handling both transactional and litigation matters. Her clients include R&B Artists Bilal and Olivia, NFL Superstar Ray Lewis, Fashion Powerhouse Harlem’s Fashion Row and Hirschfeld Properties, LLC.