Lessons I Learned From My Moonlighting Days

by Yaritsa Arenas | Creative Business


There are salaried employees and there are business owners… but don’t forget about the salary employees who freelance in the evenings. The moonlighters, the side hustlers. It feels like these days there are many more people who want to (or have to) take on a second job to grow their passion business. I myself did it for many years and I made some notes of things I learned during that time.

Why moonlight?

People do work after hours for a variety of reasons, here are just a few examples:

You get the idea, there is really no right or wrong reason for moonlighting. It’s what works for you and your current needs. I did it for both to expand my portfolio and to earn a little extra money. I also found it helpful to expand my design skills by exposing myself to other projects that my “day job” didn’t cover.

My advice to moonlighters

There are a few lessons that everyone eventually learns when they take on a side hustle. Here are a few that I learned, some the hard way, some a little more easily.

1| Your day job comes first, but your night job is a very close second
Unless you’ve flat out told your freelance clients that your day job takes precedence and they’re ok with that, you still have to keep your deadlines with your freelance clients. Which might mean that you have to allow yourself a little wiggle room in your timelines. Something might take you 6hrs to do in your day job, but you might have to estimate 8-10hrs for freelance projects. Don’t forget there are more interruptions after hours. Anywhere from you had a long day at work, you have a family emergency, train delays etc. If you think it will take you 2 days to do, say it will take 3 or 4. This allows you to keep your word to your client and gives you some padding for any unforeseen issues. It’s best to underpromise and overdeliver than to do the reverse.

2| You need sleep!
No really, you need sleep. You can only run on fumes for so long before it starts affecting both your day job and your night job. And all other aspects of your life. You’re unfocused, irritable and you’re more likely to make mistakes. Not to mention it’s bad for your health. It’s a given that late nights are inevitable when you’re moonlighting, but be careful how you spread them out. You might have to schedule a “no work” day, that you can use to relax, catch up with your favorite shows, spend time with your friends or even get to bed early for a change! Self-care is especially important when you’re overworked.

3| Don’t take on more than you can handle
Remember that you’re accountable for everything you take on. You’re not a huge company where you can hand off overflow to your co-worker. It’s just you. And even if you do outsource a project, you’re still the liaison between the client and your freelancer. If you take on too much more than you can handle and dear old Murphy is paying close attention, know that anything that can go wrong, will go wrong. Putting out 1-3 fires is much easier than putting out 5-6. Particularly if those fires arise as you’re walking into a conference call in your day job.

4| It will take longer than you thought to finish
It bears repeating, there are interruptions spanning from sickness, to phone calls, to events, to just plain being too tired to work. Always pad your timeline. I don’t mean give yourself an extra week so you can catch up on your favorite, but a day or two here and there so you can put out any fires without having to miss a deadline.

5| You might have to take a day off from work
Is your day job moving on the slow side, but your evening projects are starting to pile up? If you have the vacation days, you might have to take a day off from work to catch up. Make sure of course that you give the appropriate amount of notice and that someone is briefed on the work you have in-house. Don’t just call in *cough cough* sick.

6| Try new things when you can
For a lot of people, freelance projects allow you to learn/practice new skills that your day job just doesn’t require. Take advantage of this. Learning is always a good thing. You might even learn something that can help you in your day job. Perhaps you can implement new techniques that your boss never really thought to. Hey, there may even be a promotion in it for you!

7| Surround yourself with a good network
In your day job, for the most part, you have other people you can talk to about your projects. Whether it’s critiquing your design, helping you out with copy or teaching you something that you can’t get the hang of. In the evenings, you’re generally on your own. It’s great to have a group of go-to people that you can show your work to. They can help you when you run into issues and likewise, you can help them when they have troubles. It’s easier to learn new things when you have someone to discuss them with than when you’re banging your head on the computer because you just don’t get it.

8| You can fire your problem clients
Weed out the clients that drain your time and energy so you can make room for the ones that remind you how much you love what you do. When you’re working a full-time job and then working extra hours on your side hustle, you want to be especially careful of who you take on as a client. Because your time is more limited, you want to make sure that you’re not working with someone you dread dealing with. It can take all the joy out of your freelance business and eventually you can start hating what you do. Your time spent with them, is not leaving you any room to work with the client that already loves the work you do and respects your experience.

9| But HOW do I fire my client?
There are several ways of doing that, from the very blunt to the subtle.

10| Do your best to end on a good note
Whether you’re closing out a project with a client you loved, firing a client that is no longer a good fit or even if you’re at a point where you’re leaving your day job and taking that side hustle full time, do your best to end on a good note. You never know if they can refer you to a future client down the line or if your paths cross again another way. Best to have friends than enemies.

What are your thoughts?

If you’re considering moonlighting in the near future or knee-deep in it now, I’d love to hear from you. What else have you learned?

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