I’ve been side-hustling as a freelance writer since before side hustles were a thing.

As I described in my post on working from home, I’ve written from pretty much every location possible. Often, those various locations were necessitated by the fact that writing wasn’t my full-time gig. For most of my 10+ years writing, it’s been a side project supporting my full-time income.

As anyone who’s ever managed multiple commitments knows, there’s a huge grey area when it comes to moonlighting. You’ve got downtime at your day job… do you sneak in a few minutes of writing? Do you respond to client emails when you’re on-the-clock?

Answering these questions isn’t easy. There’s no clear-cut, always-right solution to balancing an income job and a side hustle. I’m not going to give you that here, but I will give you a few strategies for finding the right approach to juggling both.

Know Your Situation

Let me give you two examples from my past that demonstrate why there’s no clear-cut answer here:

  • In my first job out of college – as a high school secretary – I was told that I’d have downtime to fill, and that I could fill it however I liked. Others before me read romance novels and watched the Panda Cam at the local zoo (needless to say, school secretaries aren’t typically 21…). I chose to learn web design and take on writing projects during that time.
  • Another position later in my career required so much effort that writing during my working hours wouldn’t have even been possible (whether or not my trust-issues-having boss would have signed off on it in the first place).

You have to know the people you work with, the culture of your company and the stakes you’re facing.

  • Do you work in a “results only work environment” where you’re effectively left to your own devices as long as you finish your work? Or do you work in a stricter workplace with a no-moonlighting policy? Check your employee handbook – if one exists – to confirm.
  • Does your company have a disciplinary program in place? If so, are you likely to be reprimanded if you’re caught working on the clock? Will you receive a warning or be put on a performance improvement plan? Or will you be fired straight out at the first offense?
  • How close are you to striking out on your own? Getting fired is rarely good, and I wouldn’t recommend burning any bridges you can leave intact. But getting caught on the clock is one thing when you’ve got one foot out the door already – it’s an entirely different situation if you still fully depend on your day job income.

Weight your own situation carefully before deciding on how you’ll split your time between your day job and your side hustle. Err on the side of caution when it comes to when you work (and who you tell about your dual incomes) until you’re 100% confident that revealing your moonlighting status won’t put you at risk of discipline.

Establish Firm Boundaries

Regardless of how you divvy up your time, setting clear boundaries is important – not just so that you don’t get caught, but for your mental health as well. Trust me. Switching back and forth all day – even if your day job employer is ok with you side hustling on the clock – is a recipe for quick burnout.

Some of the specific boundaries you might find helpful include:

  • How much time and energy you can dedicate to your side hustle in the first place. For instance, my available hours look very different now that I’m raising a family than they did when I was a young freelancer with no commitments. Don’t tell yourself you can find 10 free hours a week to freelance if five is more realistically your upper limit.
  • When specifically you’ll work on your day job vs your freelance writing, including when you won’t work on anything at all. Protect your health and well-being by scheduling downtime into your routine from the start.
  • Which computers and other resources you’ll use for your different commitments. If possible, keeping your side hustle on an entirely separate computer makes things neater (especially if you work in a place where moonlighting is frowned upon and your company-issued equipment is subject to search).
  • How you’ll manage emergencies that come up. Clients will have problems. Subcontractors you partner with will let you down. Set a policy for handling issues that arise (preferably, one that doesn’t involve hiding in the bathroom, pecking out quick responses on your smartphone).

The boundaries you need to stay sane while moonlighting will also vary by your circumstances. If you have a family at home, for example, setting clear expectations about when you will and won’t be working (and whether you can be interrupted when you are) can go a long ways towards minimizing conflict at home.

Tune Into Your Feelings

The way you figure out which boundaries you need to set comes from listening to your feelings.

Bear with me, because we’re going to get all touchy-feely up in here. When you’re pushing yourself by moonlighting with a side project, your logical and critical minds will tell you all kinds of things about the work you’re doing.

Maybe they’ll tap into logic and tell you how important it is for you to launch a new career or to have two incomes coming in. Maybe they’ll shame you by making you feel like you’re letting everybody down by juggling two projects or that you aren’t really good enough for your work (hello, imposter syndrome!).

Parsing out those voices is important, but there’s a third voice in there that’s just as critical – but often overlooked. My very, very talented therapist calls it the “inner child,” but you can think of it as your innermost feelings about what’s happening to you.

Take an inventory every so often. How do you feel? Do you feel exhilarated? Excited? Stressed? Anxious? Irritable? Depressed?

If your feelings aren’t good ones, there’s something about your moonlighting arrangement that isn’t working. And if you really dig into your feelings (journaling and meditation are both great for this), you may be able to identify a specific problem that’s in need of some boundary-setting.

Of course, not all negative feelings resolve nicely with cleanly-drawn boundaries. Moonlighting is hard, and it’s understandable that you’d feel negative emotions in the process. But even if you can’t solve problems right away, you may find that simply acknowledging them – and promising yourself you’ll handle them as soon as you can – makes a world of difference in how you feel.

Keep Your Health in Check

There was a period in 2012 when I was sick with bronchitis for six months straight.

In all fairness, I brought it on myself. I was working full-time as a marketing assistant, while also preparing to go solo as a freelance writer. Being in my carefree mid-20s, I wasn’t thinking about managing my health relative to my workload. I ate a lot of fast food (no time to cook), and I spent a lot of late nights out with friends, justifying them as necessary for blowing off steam.

I wouldn’t go back and trade the wonderful memories I have from that era, but I would like to go back, shake myself and gently suggest eating an orange or going to bed at a decent hour once in a while.

Don’t be like I was.

As a freelancer, your ability to work depends on your health. If you can’t think because you’re stuck in bed with yet another cold, you can’t work – and if you can’t work, you can’t get paid. You don’t have to be perfect, but you can’t treat your health like it’s guaranteed (at least, you can’t in the long term).

Find Options for Synergy

One final tip for managing moonlighting I want to touch on here is that, if you plan strategically, you may be able to leverage your day job for the benefit of your side hustle by looking for options for synergy.

Assuming you’re moonlighting because you want to go into your chosen side hustle full-time at some point, what can you do at your day job that’ll get you there faster?

I’m using the example of freelance writing because it’s basically all I know, but the following applies to any field or industry.

  • If you’re trying to establish yourself as a blog writer, could you contribute articles to the company blog at your day job to build your byline?
  • If you’re focusing on copywriting, could you work with the marketing department to run your copy in a live environment (and, hopefully, get those all-important proof numbers to back up your skill)?
  • If you want to work full-time as a business writer, could you help support your company’s annual reports, newsletters or other key documents?

Find opportunities for synergy where you can. Track them. Measure their performance as best you’re able to. Add them to your portfolio. You’ll get paid to do work that’ll ultimately help you land better-paying work in your chosen specialization.

What other tips would you add to this list on moonlighting while working a full-time day job? Leave me a note below sharing your experiences: