13 (Uncomfortably Probing) Questions to Help Moms Find the Perfect Side-Hustle

Are you doing it yet?

I do it sometimes.

And I’m pretty sure the woman next door to you does it All. The. Damn. Time.

Yes, these days we’re all side-hustling. Apparently.

And the sad truth is that in these difficult economic times sometimes a side-hustle is just plain old necessity. Sometimes a side-hustle is all that keeps a mamma at home with her kiddos. And, just as importantly, sometimes a side-hustle is all that keeps a mamma in touch with adult conversation. (And away from daytime drinking/ugly-crying in the shower.)

The internet is overrun with advice from gurus, ninjas and mavens about different ways to make extra money. So how are you supposed to find the perfect side-hustle for you? 

Here are 13 uncomfortably probing questions will help you choose the perfect side-hustle for you, your family and your season of life.

Shall we get started?

How to choose a side-hustle that works for you, your family and your season of life

1 | Why do you even want a side-hustle?

What's your motivation, darling?

What's going to keep you going when your sofa, and her slutty sister 'glass of Chardonnay', sing their siren call? What's going to fire you up at early o'clock in the morning when your mattress apparently has you in an Anaconda-style death grip? 

Why do you even want a side-hustle?

  • Is it purely for financial reasons?
  • Is it a creative outlet?
  • Is it a way interact with adults again? 

Your answer to this will help you narrow down your side-hustle options and help you stay on track when the going gets goopy.

So...I'm going to Zero Dark Thirty your cute ass and ask one last time: Why do you want a side hustle? 

2 | Is your to-do list a white knuckle ride?

Are your days calm and well-managed right now? Or do your days feel like a roller-coaster ride where you just cling to the safety bar trying to ride them out?

If your to-do list is overweight and bloated now, think how dreadful it's going to look when you’re side-hustling. How are you going to fit in a side hustle?

  • What are you going to stop doing or do more efficiently?
  • What household systems can you set up to save yourself time, effort and energy?

I have a helpful mini-training on making more efficient use of your time (and save up to an hour a day on all those household chores). If you think this would be helpful to you, click HERE to go take a look. 

3 | Where will you work?

Some side-hustles will undeniably take up some space. So where are you going to work? Do you have space to store supplies, inventory or paperwork?

Flipping ebay finds could be just your thing, but not if you lose or damage that valuable antique before you can ship it to the buyer. 

4 | What are your business hours?

The worst thing about side-hustling from home is that you’re technically always at work. It can be tempting to sneak a look at your emails or just pin that one article to read for later because, you know, it’s work related. But if you’ve got kids at home or if you’re in the middle of family night, all they’re seeing is a distracted mamma and wife. (Guilt trip alert - no apologies)

I know because I’ve been there and made that mistake.

I highly encourage you to set work time and non-work time. This division can also help keep you sane. 

5 | Does a side-hustle pass the family test?

In Lauren Greutman’s stunningly honest and helpful book ‘The Recovering Spender’, she talks about her heartbreak at not being able to put her children to bed for months because she had to work shifts at a local restaurant.

Of course, it depends what type of side hustle you choose. But I think it’s important to be clear from the start what you are willing to sacrifice: sleep, time with little ones, date nights. And to think what impact will this have on you and your family?

How can you combine the side-hustle with family life?. What you your non-negotiables?

Also, take a moment to think about how you’ll nurture yourself. Self-care is not a luxury, it’s a duty. If you’re struggling to tend to your own needs, take a look at this high-speed approach to self-care. 

6 | Do you want to build a business?

Some moms release their inner dominatrix and set up their own business for greater control and flexibility. Other moms would rather not deal with all the paperwork and stress that goes with owning that business.

So let me ask you...

Do you want to build your own business or help someone build theirs?

Your answer to this question really depends on why you want a side-hustle.

Either way don’t be swayed by all the ‘boss lady’ vibes out there in Internet land. Let’s remember that, sadly, most businesses fail (#partypooper)

7 | To blog or not to blog?

Hands up if you’ve seen any of these headlines:

‘Start a blog in 15 minutes’

‘How I started a blog and left my 9-5’

‘How I made £34,000000000 with my blog last month’

(OK, so that last one was made up but you know what I mean.)

Yes, sometimes it seems that all you have to do is start a blog and wait for the dolla’ bills (or the pound coins) to roll in. Let me be the voice of doom here and point out that monetizing a blog isn’t all puppies and rainbows. And the writing! God, there’s so much writing involved. 

So, here's the question for you...do you really want to write a blog?

If you don’t fancy starting a blog, don’t. Don’t follow the herd (they may be going to the abattoir).

If you do want to start a blog, here are the only resources I’m going to recommend (and they’re both FREE). There’s a lot of noise out there but these two moms are grounded, sticky-bun-sweet and super helpful. They’re the like the Property Brothers of blogging (just don’t ask them to open plan your kitchen.)

Elna Cain at Twinsmommy.com: How to Start a Mom Blog in 2017

Summer Tannhauser at ladybossleague.com: Pinterest Power 5 Day Free Course

8 | Do you have bills, bills, bills to pay now?

If you’re side-hustling for strictly financial reasons, ask yourself: when do you need the money?

This one is the ugly sister of question 6 above.

A dog walking gig can pay you tomorrow but monetizing a blog will take at least a few months if not a year or more.

9 | How much is your time worth?

Read any blog post on ways to make money from home and you’ll come across surveys. Companies that will pay you half-a-pittance to answer dull questions about all kinda shit.

But it’s not just surveys. There are many other hustles that pay mere pennies or cents or pesos.

And I’m not knocking these hustles as an idea. Consistency (and a high boredom threshold) will result in some decent pay outs. But calculate your hourly rate on this hustle and you’ll probably find it’s depressingly low. Like, way-below-minimum-wage-low.

On the one hand, these hustles can eat up your time and really take a toll on your feelings of self-worth. On the other hand, they might just be the perfect fit for your current season of life. You decide. 

What’s your time worth, mamma?

Don't undervalue yourself. But don't be a diva, either. 

10 | Do you need to earn more?

If you’re side-hustling because of money worries, remember that saving $100 is the same as earning $100.

Why not have a go at cutting your spending and setting up a budget? You may find that you won’t have to actually earn more money. And if you do still need to bring in extra money, a budget will help you spend that money wisely.

My personal recommendation would be to invest in You Need A Budget (YNAB) software. This is not an affiliate push. I’m just stunned at how much YNAB has helped me become a better budgeter.

If you’re looking for a paper-based system, why not take a look at this breath-takingly beautiful set of printables from the talented Abby at Just a Girl and Her Blog. 

11 | Do you need to spend money to make money?

Please exercise extreme wallet-clenching prejudice when choosing a side-hustle. There are many work at home scams that target moms.

But there is another, more pernicious way to lose your money while looking for a side-hustle which is called….drum roll, please ….courses.

If you’ve been living in a cave and haven’t noticed, everyone and her hamster seems to be selling a course these days. Whether it’s a blogging course, an Amazon FBA course, a transcription course, or a ‘how to find things to flip on Ebay’ course, they are all over the internet and they all cost your cold hard dinero.  

Yes, sometimes it will be necessary to learn some new skills in order to make your side hustle pay off. And I applaud those who are brave enough to keep learning.

But be careful, mamma.

Before you fork over hundreds of your local currency, (or your soul or your first born) to learn ‘the dark arts of blogging’ or the ‘alchemy of Ebay’ do some research. Then do some more research. Drink some coffee. Then do some more research. Basically, research the crap out of it, that's what I'm saying.

You see, there is a lot of free information on the internet. Yes, someone will package that information up in a convenient and pretty course for you. But there’s a lot you can figure out on your own first. That's why we have Google. 

So let me ask you, How much are you willing to invest to ‘learn your craft’?

if you intend to buy courses, books, or coaching, set yourself an ‘education’ budget and don’t be seduced by slick copywriting, sugary photos and botoxed testimonials (‘I made $34,000 in 27 minutes’).

If you’re wondering whether to invest in a specific course or not, take a look at this helpful list of questions to ask before you press 'buy now'. It could save you a small fortune. You can thank me in chocolate. 

12 | Where’s your wheelhouse?

I’d love to design beautiful quote graphics to sell on Etsy. Just make something once and sell it again and again. Sounds great. But the truth is I both suck and blow at  design (in case y’all hadn’t noticed).

There are plenty of things you could do to make money. So make a list of your strengths and interests and find a hustle that fits somewhere in the middle.

Side-note to the side-hustle seekers: Even if need money like yesterday, try to find some hustle that doesn’t make you want to stick a fork in your eye. Doing what you hate when you could be with your family or asleep = crap.

13 | Do you know when to quit?

If you’re setting up your own business as a side-hustle, I need to drop a stinky truth bomb here. And it’s a big one.

You see, there’s a lot of optimism surrounding the side-hustle. People are telling us: if you want something hard enough, you’ll make it. Just believe in yourself. Dreams do come true.

Well, I’d like to be a Disney Princess but that dream is never coming true. No matter how hard I wish upon a star.

If you're starting a business, you might not turn out to be the next Marie Forleo. You might fall flat on your sweet face. But that's OK. 

If you have the guts and guile to start a business, I'll be cheering you from the sidelines every step of the way, pom-poms and all. Just be realistic and know at exactly what point you’re going to pour the gas, light a match, and walk away bad-ass style from the burning wreckage of your side-hustle. 

A bonus question: Do you look good in orange?

Just a quick note to remind you that whatever you’re earning with your side-hustle, the taxman probably wants to know about it. Don’t do a Capone and get done for tax evasion. Orange is not the new black. And you’re too pretty to survive prison.


There you have it. 13 questions to help you find your Ryan Gosling level side-hustle without kissing a load of wart-ridden toads first.

Just remember to take care of yourself and don’t listen to bullies who tell you that you should be side-hustling 24/7. What the hell do they know about your life, anyway?

Good luck, mamma.