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Things to Consider Before Moonlighting

Updated: Jan 8

by Chloe Lee. |


It is always a good idea to earn passive income, in fact, the use of smartphones and the internet has created a gig economy where we can all work part-time or engage in short-term projects periodically. Now, finding and obtaining a second job is only a few clicks away. The reality is that most of us do not earn enough to be able to afford a decent standard of living. Therefore, for those who have time to do so, we tend to rely on moonlighting to sustain ourselves financially.


What is moonlighting? It is simply the act of having a second job, usually after normal 9-5 hours. It used to refer to working when the moon is up (therefore, “moon”-lighting), but can also refer to other secondary work arrangements.


However, other than it being a huge juggling act, moonlighting is not necessarily straightforward or easy. But fret not, here are a few simple things for you to consider and prepare before you begin freelancing or picking up side jobs!


Check Your Contracts


Some companies have very strict and formal rules about moonlighting. Often times, these regulations are stated in your contract, or you might be told during your induction that there are steps to be taken to inform or declare your second or side jobs. Before you get into trouble for breaching your contract in any way, it might be a good idea to reach out to your HR Manager to clarify and get the green light to work elsewhere. Remember to obtain permission in a black-and-white statement and not just rely on word-of-mouth or verbal agreement – this might save you from problems in the future!


Informally, it might also be helpful to notify your Manager or team of what you do on the side. In such a way, you can be honest and transparent about your commitments and even obtain tips and advice where necessary. Although it is not a formal procedure, keeping your team in the loop is always a good way to build rapport.


Ready Your Materials


Now that you have formal procedures out of the way, you need to make sure to have everything you need to be able to provide good services or quality products. You never know when a business opportunity is going to come by, and need to make sure you have the materials ready to send out quick replies. When you have your portfolio, resume, and rate card ready, closing a business deal can be done during a five-minute snack break. As a freelancer, you often communicate on-the-go and reply whenever or wherever you are or can. As such, be prepared with all the information you need and have them stored in a folder that can be easily accessed. Examples of materials would include:

  • An introduction deck: this would explain who you are and your background

  • Portfolio: this is to showcase your previous projects and credentials

  • Resume: a short and sweet breakdown of your experiences

  • Products and/or services: details down what you have to offer

  • Rate cards: prices for your products and/or services

  • Quotation

  • Invoice

  • Receipt


If you are selling products, you need to make sure you have all your stock and packaging ready to go! Whereas if you intend to be a Grab driver, you need to make sure your car is always in a good condition. Whatever roles or jobs, having these materials ready allows you to think through your unique selling propositions and price-points. One of the benefits of viewing these as side jobs is the autonomy to reject projects that do not align with your values or prices. As such, if someone is offering an unrealistically low price for your services, you can kindly reject it because it is not your sole source of income. Detailing down the conditions in your invoice is also crucial to ease your workflow and make sure you get paid!


Work Out a Process


Be it writing, performing, photography, coding, website development or even babysitting, you need to create a system that helps you work efficiently. It doesn’t have to be a complicated or fancy dashboard, but can be a simple spreadsheet to help you keep track of your work and finances. I have a simple excel sheet to help me keep track of my engagements and more importantly, the payment! It includes:

  • Project name

  • Date of engagement (from [date] to [date])

  • Status (ongoing, delayed, postponed, completed)

  • Invoice (either the Invoice Number or the status of whether or not I have sent it out)

  • Payment status (delayed, paid)


I also have tabs to keep track of the quotations I sent out to interested or potential clients – this allows me to follow up with them accordingly.


As for my invoice tab, I have included:

  • Invoice Number

  • Name of Client

  • Date sent

  • Deposit (e.g. paid 30%)

  • Receipt number for deposit

  • Payment status (delayed, paid, etc)

  • Receipt number for full payment


Of course, this is a very simple tracking system and one that works for me. As you venture into different projects, it is important to have something ready so you can effectively manage your accounts well.


Manage Expectations


Other than managing your own time, you will need to learn to manage the expectations of your clients, too! As you are juggling between your main and side gig, you have times where you would need to prioritize one or the other (and still ensure good quality work). As such, as soon as you acquire a new client, you need to be honest about how full your plates are and your level of commitments. If you foresee yourself entering a busy period at work, you may have to communicate your unavailability to your clients (or stop taking/renewing projects at all); or even be transparent about expected delays.


By communicating your timelines as openly as possible, you are building a healthy rapport and creating a sense of trust. This is much better than overpromising and under-delivering. So, be clear about your availability, for example:

  • Setting fixed times for communication, such as weekends or after 6pm on weekdays

  • Turning on auto-replies to inform your availability

  • Do not bite off more than you can chew


Prepare to Make Sacrifices

Unfortunately, working on multiple jobs often suggests that you would then have less time for something. This could be sleep, personal me-time, or lesser social events. One way or another, in order to make time to complete your side projects, you would have to make sacrifices in other areas. So, choose how you want to manage your time wisely, and even be honest with your family or significant other about the struggles you are or will be experiencing.


Do remind yourself that your mental well-being should not be sacrificed, and if you find yourself struggling or burning out, make sure to recuperate and make time for yourself, too. Without a healthy mind and physical body, you cannot accomplish much or produce good quality work – so always prioritize your health!


File Your Income Tax

There are guides online that walk you through the process of filing income taxes for your side businesses or freelance work. Do note that there are different forms and procedures if you have a registered business, compared to merely working as a freelancer. Although this is a tedious process, it’s an important step to building your creditworthiness (which might be of good use in the future)!


Being able to work on a side gig you enjoy, that also acts as a source of extra income, can be a huge joy. It may require a lot of effort and sacrifices, but can be made easier when you have the right materials and processes in place. Take it one step and a time, and slowly work towards a balance or momentum that works for you. You got this!

You can find out more about the author on Instagram.


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