A Working Mom’s Guide to the Side Hustle

March 25, 2022

Gig economy, side hustle, the current economic climate is constantly evolving and ripe with opportunity and portals of entry.  To understand where we are today and how we got here, a quick (very quick) lesson.  The “Gig Economy” developed during the global financial crisis as a result of full-time employment opportunities being scarce. Workers, particularly those just entering the job market, were forced to take a series of part time jobs to make ends meet.  In the years since, the gig economy has evolved from being a response to market conditions to now being a choice of many, supported by the digital revolution. The benefits of working various gigs include freedom to explore different career interests, the ability to have a flexible lifestyle, and the notion of not being tied to a single employer (source: Korn Ferry).

But the downsides and criticisms of the gig economy do not run short.  For all the flexibility gigs offer, there is a risk of burnout and negative impact to work-life balance as workers are required to balance competing priorities, managing schedules, and responding to opportunities when they arise or risk losing them.  There is also a loss of compensable benefits – even though the gig worker is likely working full-time hours, there are no vacation days or sick days.  No work = no pay.  And forget about employer-sponsored retirement contributions.

So, what’s the answer?  For many workers, enter the side hustle.  The side hustle is a great way to explore interests outside of your day job, expand your skills, and earn extra money while still enjoying the stability and all the benefits of traditional employment.  If you are intrigued by this idea and have already identified what you plan to do in your own side hustle, here are some tips and a push to get started.

Identify your Goals. What do you want out of this side gig?  For some people, a side hustle is simply a short-term strategy in boosting one’s income.  I have a former colleague who had a personal creative hobby, which started as a means of decompressing after a stressful workday.  As her daily practice developed into a true talent, she began selling the product at weekend fine arts fairs.  From there, she created an Instagram profile to display her products and cultivate a following, so when she makes an appearance at a festival or fair, she is fairly confident she will sell out.  For her, her intention is to keep her day job, continue to hone her skills and enjoy making money from her hobby.  It’s no stress, no pressure.  She creates as much or as little as she wants to on her own terms.  I imagine if she ever gets too busy or simply feels like her hobby-turned-side-job is no longer bringing her joy, she’ll simply stop doing it.

For others, a side gig may be a starting point on the path to financial independence and eventually being able to give up full-time job for full on self-employment.  For a lot of the small business owners I know, their company started as a side hustle and grew with intention.

It is important to be clear with yourself at the onset what you want out of your side gig.  There’s a substantial investment in time, effort, and energy needed to make a business succeed.  Be clear with yourself what you want and what it is going to take to get there.

Try Before They Buy.  If you have an idea of what you want to offer but aren’t sure how to execute it exactly or how it will be received in the market, my recommendation is just try it! Start by offering your service as a courtesy, giving away a sample, etc. with the purpose of gathering feedback and practicing your execution.  This is your market research phase.  You want to answer the questions “Is my service/product desirable?”  “Would customers be willing to pay for it?”  “How much could I charge?”  “What does service delivery look like?”.

My very first “client” was a close friend who had lost his job at the beginning of the pandemic.  It was unexpected and very traumatic for him.  At the time I was on maternity leave, and I needed something productive to do with my brain during the long daytime naps.  An offer to overhaul his resume evolved into working together to clean up his online presence, fine tune his job search criteria, and prep and debrief for his interviews.  It was only then that I realized that I had a marketable skill that was going to be valuable as the pandemic economy looked bleak.

From that experience, I was able to build my initial service line and start designing a business model, which I then continued to test out on friends and family until I decided to formally launch.
I continue to do that as my clients’ needs evolve.  If you aren’t sure how to execute something or how it will be received in the market, don’t not do it.  Get out there and try it, solicit feedback, and keep adapting.

Start Small.  While you are trying things out and seeing what works, resist the temptation to be “all in” and invest amounts of money you can’t afford to lose.  Determine what is essential in getting started and what can come later when you start to bring in money to reinvest in the business.  For me, my first major consideration was advertising costs.  With the help of a marketing genius friend, I identified social media platforms I could utilize and free or low-cost networking opportunities I could utilize to get started building my client base.  Investment in a web site, purchasing a domain, and online advertising came later and only when I felt confident I could cover those costs and was comfortable with the possibility of risking them.

Get By with a Little Help From Your Friends.  I already mentioned relying on marketing insight from a friend.  I am not ashamed to say that marketing and business development is my least favorite part of managing a small business.  I asked A LOT of questions up front and someday I hope to happily pay someone to manage my marketing efforts.  The point is, know what you don’t know and seek out help.  Other small business owners are usually happy to share their knowledge and offer support.  Seek out subject matter experts and those who have come before you to help you get started and maybe avoid some of the mistakes they made along the way.

My last recommendation is to Manage Yourself Closely.  This goes back to my first tip on identifying your goals.  Whatever you decide you want out of your side hustle, you will need to outline your incremental targets and how you will dedicate your precious time outside of your full-time job to achieve them.  Life keeps on ticking by, and it is SO EASY to get swept up in the daily minutiae and 99 things trying to steal your focus.  Treat yourself like your boss and give yourself clear and measurable deliverables to stay on track.  Be as specific as possible when designing your goals, the acronym SMART can be useful here – Specific, Measurable, Achievable, Relevant, Timebound.

You’ve got this.

 Jessica Milewski is a human resources/recruitment professional, masters-level educated in management, and SHRM/HRCI-certified, currently being her own boss lady during COVID times as a resume writer/career coach.  As her seven-year-old daughter likes to explain “Her job is helping other people find jobs”.  For help with your own job search, you can find her at


Source cited: Korn Ferry. Motivation and Retention in the Age of the Gig Economy.


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