The Side Hustle

If you are looking to get your foot in the door, thinking about shifting jobs, (or industries) or simply looking for more, the art known as the Side Hustle is a great way to start. The author of Side Hustle: From Idea to Income in 27 Days, Chris Guillebeau, defines the side hustle “as an asset that works for you”. With respect to Guillebeau’s definition, it is assumed the goal of the side hustle is to develop a strategy and methodology to appreciate the asset. Within the prospect of every gain comes an inherent risk or liability, in this case scheduling constraints, late nights/early mornings, expending large amounts of energy, limited time for leisure activities, etc. To counterbalance the apparent risk, author and entrepreneur Damon Brown provides three foundational rules when starting your side hustle. One foundational rule is stating your “why.” It is important you clearly state your purpose to help align your priorities and stay the course to your end goal. Here are a couple recommendations:


  • Gain Experience and Grow Network: Lacking experience or a diverse network can put a constraint on job opportunities and hinder your career advancement. The side hustle provides an environment to edify your network and also close any experiential gaps that may exist between yourself and your aspiring profession.
  • Fulfillment: Your current occupation may not be in alignment with your interests but embarking on a side hustle provides a possible outlet to pursue an opportunity that aligns with your passions.
  • Additional Revenue: Not every opportunity will provide monetary compensation at the onset of your endeavors, but there are opportunities out there that will immediately provide additional income.

Now that you have stated the vision and purpose for your side hustle, the next step is to raise awareness of your pursuits. Identify individuals in your network who can assist you with connecting you to individuals or companies that fit your interests. Once the connection has been made, request to speak with the individual, conduct an informational interview to better understand the company’s vision, responsibilities and opportunities.

After conducting an informational interview and you deem this individual or company aligns with your goals and aspirations, clearly demonstrate you want to volunteer to help with a project or during a busy season. If the other party accepts your invitation, great! If not, revisit the previous steps mentioned in this paragraph and repeat until you land your side hustle.

Below are a few ways you can put these words into action for certain career paths...

  • Coaching: Inquire to see if there are any “special” or self-scouting projects you can assist with. Looking to help on a smaller scale, see if you can assist with scouting upcoming opponents and breaking down film.
  • Scouting: Provide your own personal write-ups on players. This is applicable to all levels: pro’s, collegiate and high school.
  • Administration: Demonstrate your willingness to participate in projects or brainstorming sessions that address the challenges and time demands facing the department.

The Trust is here to support you.
Ready to learn how?