7 Hacks For Balancing A Job & A Side Hustle, According To People Who’ve Done It

by JR Thorpe
Lightfield Studios/Shutterstock

These days, having a single nine-to-five, secure job till the end of your working life is increasingly rare. CNN reported in 2017 that more than 44 million Americans now have a side hustle — a job, or several, alongside their main income-earner — and statistics from Bankrate in the same year showed that 28 percent of millennials between 18 and 26 have at least one. It's pretty common to be a double or triple threat, juggling more traditional employment with freelance work, commissions, artistic jobs and other passion projects. Millennials have a lot of debt, high goals, and big dreams, and multiple jobs and occupations are often the most sensible way to deal with all those elements at once.

I'm a typical millennial in that I have more than one side hustle: I combine content, copywriting, and a career as a librettist and lyricist, plus I write novels. However, figuring out how to prioritize your time, pursue the right side hustles at the right time, and organize your obligations can be tough. And that's without the added question: do you want to make the side hustle your main focus or stick with a more fragmented arrangement? Management is key for side hustling while remaining sane. Here are top expert tips on how to do it.


Be Prepared For The Side Hustle Journey To Get Weird

For some of us, side projects are easily chosen: they're what we've always wanted to do, usually something artistic that doesn't pay particularly well. However, whether you've dreamed of doing something your entire life or have just had an Amazing Idea, the path of the side hustle very rarely runs smooth.

Marketing expert Dorie Clark wrote for Harvard Business Review that your great start-up idea might not actually be all that. "Don’t fall in love with your first idea," she says, particularly if you don't have a clear idea of what you want it to do or the audience it's meant to be for. (Just 'make me lots of money' is not a clear mission picture.) "Don’t just come up with a clever notion; make sure people actually want it before you spend a lot of money developing it," she wrote — and that can take more than one try.

The fluidity of the side hustle is both a negative and a positive. While that fantastic idea you had in grad school might not pan out, new opportunities can also crop up unexpectedly. (I got into lyric writing out of pure chance.) Embrace the fact that your side hustle might not end up going the way you expect.


Expect To Find It Tough When You Start

The beginnings of a passion project may spark such inspiration that you want to work on it all the time — even in times when you're meant to be doing something else. The balancing act is rough, and you shouldn't expect to get it right first time, no matter how good you are at multi-tasking.

Songwriter Jess Godwin, who balances school outreach programs with custom music production, tells Bustle that sharing energy equally between your jobs can be impossible. "Balancing has definitely always been tough in the past. I used to try to make sure I tapped on everything in any given day, but that resulted in burnout and all around frustration. It killed my creativity," she says.


Use Organizational Tools Like A Pro

With multiple demands on your attention, different deadlines and priorities, and shifting circumstances for all angles of your work life, you're going to need to keep on top of it all. Calendar apps are your best friend, as are notes apps and voice recorders in case you need to record a memo on the run. Group them together with an app like Evernote.

If you're a visual thinker, use that to your advantage. Penelope, who manages her own business as a proofreader and indexer while also writing, tells Bustle, "I do it with a spreadsheet. A big, complicated, multi-colored spreadsheet." If you're more digitally inclined, MindMeister is a great mind-mapping app.


Know Your Money

Side hustle earning you money? Get on top of your tax situation, Jennifer Lowe, senior director at Wolters Kluwer Tax & Accounting, tells Bustle. "Gig work is typically touted as easy and flexible and a great way to make some extra money, but these are really self-employed individuals that have all the tax headaches of a sole proprietor. Combined with the “regular” tax implications of a 9-5, some of these individuals could face pretty complicated tax scenarios. A little tax planning could go a long way," she says.

So what's her advice? "Any income received from a side hustle or gig type of arrangement must be reported and is subject to income tax, along with income earned from a more traditional 9-5." Whether you're doing it as a self-employed worker or on a gig-to-gig basis, you still have to pay tax, she says — and record all your deductions. It's really important, she says, "to keep adequate records to substantiate any deductions — e.g., vehicle repairs, mileage logs, materials, business use of a cell phone, home office, etc. This tends to be one of the biggest challenges."

If your side hustle is paying dividends, you need to have an excellent money organizing system. Use the same invoice template each time, customized to your own system and needs, and keep them properly filed, on paper and in places like Dropbox. Investigate the best accounting software to help you balance your books as a self-employed side hustler.


Experiment With Time Management

What kind of time do you have to devote to your side hustle, and how can you organize your other job(s) around it? For some of us, this question is easily answered: compulsory hours at work, other time for side hustles. For people who are combining several or self-employed, though, things are a bit more complex.

Figuring out priorities can be highly individual. "This year, I’m trying a new system where I designate two weeks at the top of the month to get creative," Godwin tells Bustle. "Then for the remainder of the month, I can release and focus on seeking out workshops and gigs! So far so good! Even though my music and videos are not the biggest money maker of all of the gigs I do, I make sure to give most of my time to that, because in my mind, creating will always be my main gig." If your side hustle is earning you a bit of money, consider negotiating with your work to take one day a week to devote to it.


Recognize That Your Identity Might Feel Fractured

Balancing a full-time job with other pursuits can be tough for your identity, as Jennifer, who works both as an academic researcher and a member of successful bands, tells Bustle. "I do worry that colleagues might think I'm less 'serious' or committed to my 'proper' work, but the benefits of playing massively outweigh that fear. Overall I think I'm getting better at taking both sides of myself seriously, and also enjoying them more!" she says.

So how do you make the different parts of your life feel more connected? Simple signals can help a lot. "I've tried to align the two 'me's more by wearing the same clothes as much as possible for both activities, which helps me to feel more 'authentic' in both settings, actually," says Jennifer.


Beware Of Side Hustle Burnout

Working two or more jobs is hard. Stress levels can mount, and there are only so many hours in the day. If you've noticed that you're always tired, miserable, worried and on the verge of snapping, there's a strong chance you have side gig burnout.

If it does happen to you, it's a prompt to take action — but many side hustlers don't. CEO Jaimie Crooks told Forbes, "Instead of taking a step back and recognizing that something is wrong, [side hustlers] push themselves to work that much harder to land the next client or finish a big project. All that pressure and stress has a cumulative effect that can do much deeper damage than simply causing you to feel disinterested in your work."

Feeling burned out? Stephanie Weaver writing for Inc recommended that entrepreneurs whose side gigs are burdening them stop comparing themselves to others, don't overlap between gigs, and use their passion to propel them through tough times. Easier said than done — but admitting that you're finding it hard is the first step.


Balancing the obligations and needs of jobs and side hustles can be difficult. With these expert tips, though, be prepared for things to get progressively easier over time.