Almost every freelancer starts out side-gigging. Only the bravest, most well-prepared, or foolhardiest begin by freelancing full-time.

Side-gigging is a fantastic way to enter the field of freelancing, or even to supplement freelance income during lean times. It builds your portfolio, enables you to experience part of the freelance lifestyle, helps you develop new skills and pursue interests, and builds a financial/professional security net in this uncertain economy.

On the other hand, all of those benefits seem pretty abstract when you’re exhausted, overworked, and falling asleep at inopportune moments.

So how do you side-gig effectively – without losing your mind?

1. Set realistic limits

Don’t promise complete, I’m-wide-open-Boss availability to your freelance gig OR your main job – that just sets you up for conflict. That doesn’t mean that you have to inform your primary work that you’re exploring freelancing, or vice-versa. It just means that you need to set reasonable boundaries. Make sure that you’re realistically estimating the time it will take you to complete projects (handy dandy how-to here). That’s good not only for your freelance pricing, but also for your sanity.

Establish IN WRITING exactly what will be expected of you. Try to get schedules and deadlines as far in advance as possible. You, will need to be especially wary of scope creep since you’re already signing up to work a bit harder than the average bear.

Once you have a reasonably accurate estimate of how much time it’s going to take, sit down with your calendar. Sketch out how you’ll organize your days in order to be productive – this doesn’t have to be obsessive; you’re just deconstructing a Big Scary Project into digestible chunks.

Here’s the key to side-gigging sanely: set limits. Make time for things like eating, and sleeping, and seeing other humans, and staring into space blankly. Make time for doing nothing.

You are not a Work Robot, though side-gigging may temporarily tempt you to become one. Make time for the side-gig, yes, but also make time for leisure and rest and sloth, or you will burn out.

2. Make it worth your while – either in experience, or $

Do not side-gig unless the job in question is good for your career, your wallet, or your soul – try to fulfill two of those criteria.

Supplementing your primary work with work that doesn’t make you happy, teach you valuable new things, or pay you adequately is a recipe for dissatisfaction. Remember, you’ll be sacrificing some of your leisure time for this, so make it worth your while. If you’re side-gigging temporarily as a way of “dipping your toe” into freelancing, that’s great and laudable. But don’t settle for a side-gig that doesn’t fulfill you, put a notch in your professional belt, or help pay the bills.


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3. Expect a certain amount of lost time

You’ll work some nights and weekends. You’ll miss out on some leisure time.

Occasionally, you will have to be lame and stay home while your friends go vodka-bowling or tequila-dancing. Whenever I’ve been working on a side-gig that I enjoyed, I didn’t resent this– my sense of accomplishment made me happier overall! But go into side-gigging with your eyes open; for a while, you may get pretty busy.

QUICK BONUS TIP: the easiest way to create extra time and mitigate some of this loss of leisure? Stop watching TV and its higher-tech cousin, Netflix. You’ll miss out on season cliffhangers, but you’ll be surprised how much more productive you are.

4. Build a support system

Again, you don’t have to tell your primary work that you’re freelancing,but do tell friends and family. Telling loved ones about your plans may get you work via word of mouth, it inspires them to pursue their own interests, and most importantly, it gives you encouragement and a sense of community.

5. Make a date to reevaluate

Pull out your ol’ calendar again. Make a date FOR yourself, WITH yourself in 3 months – this is your “staff meeting.”

In 3 months, sit down and think about where you are, and where you’d like to be. Some questions to ask include:

  • Are you happy with your current side-gig?
  • Would you like to continue – or would you like to try something new?
  • Would you like to make your side-gig your permanent job, or shift more energy towards that passion – and how can you use your current experience to do that?

Giving yourself a concrete deadline for reevaluation allows you to relax during especially stressful side-gig periods by giving you a sense that you can always re-orient or change plans. It also gives you a chance to strategize when you want to improve your side-gigs, or make a side-gig your main gig.

I am by no means a perfect side-gigger; over the years, I frequently procrastinated, over-committed and over-scheduled myself, got overtired, wasted time on the aforementioned Netflix, and made many missteps. But by plugging away, I was able to turn my side projects into (dual!) main-gig careers that fulfill me and keep me financially stable – and that’s been worth many minor sacrifices. If I can do it, so can you; go and find the side-gig that nourishes you, and don’t worry about the nay-sayers. I promise, you can side-gig… and still stay sane!

Freelancers, do you find balancing your side-gig and other jobs difficult?