Adulting 101: Side Hustles

by Ashley Wirgau

The ever-popular side hustle. The obligatory free-time eater of millennials and stay-at-home-moms everywhere (and anyone else looking to earn some extra cash). With more and more opportunities making their way to the digital world and with previously company-claimed jobs becoming easier for individuals to pick up, we are entering an era where side hustles can sometimes become a primary means of income. So how do you know if it is finally time to move your side job front and center?

Ridesharing, blogging, dog walking, online tutoring – these are just a few of the countless ways people have found to supplement their income nowadays. With the great appeal of schedule flexibility and work-from-home convenience, these side hustles are quickly becoming more popular than traditional 9 to 5’s, which begs the question: How does your average accountant-by-day-turned-dog-walker-by-night know when it is time to let the canine career take a starring role? Start by asking yourself these three questions to see if you are ready to take the leap.

Does your side hustle make you happy?

…as in happier than your real job. If the answer is no, there’s no need to continue through Questions #2 and #3. They are irrelevant. Keep your day job, keep your sanity, and keep your side hustle within its current parameters. Whether you took it to build your bank account or to keep you distracted from your latest break-up, use it as a means to an end and do not allow it to take center stage. Side hustles come and go, but a career is forever (unlike your last relationship).

Can your side hustle support your current lifestyle?


…as in would you be able to still have a roof over your head, food on the table, and a Mercedes in the garage (if you are accustomed to that sort of thing). Seriously, though. Can your second job pay the bills if your first job took a hike?

Don’t leave this up to your best guess, either. Sit down, crunch the numbers and make sure they work for your budget. Remember to take into account the benefits that currently accompany your primary job, as well: medical insurance, life insurance, short-term disability benefits, retirement investments, and any other perks you might enjoy, including a company cell phone, unlimited coffee, an ergonomic office chair, and friendly co-workers.

While some of these benefits have a definitive monetary value and can be easily calculated into your decisions, others like the awesome officemates you now call friends are more difficult to quantify. Most side hustles leave you working independently, and you might end up missing the office environment more than you’d like to admit. Who is going to laugh at your jokes? Who is going to eat your leftover pizza from the break room fridge? More importantly, if no one is there to steal your lunch, what is your excuse to run out for a bag of tacos and a giant cherry coke which (let’s be honest) you’ve been envisioning all morning?  

How legitimate is this side hustle, really?

…as in what kind of fly-by-night, multi-level marketing, might-still-be-a-pyramid-scheme operation are you working for? If you’ve landed yourself somewhere in the ranks of Mary Kay or Tupperware sales, the likelihood of your employer going belly up is slim, but lots of start-ups promise the stars when what they deliver is closer to a flashlight. Don’t be fooled. Make sure you are working for a legitimate company. For starters, check out the rankings for top-performing MLM’s of 2019 and see if your business made the list.

Once you’ve confirmed that your side job is with a reputable company, give yourself some time (think months, not weeks) to make sure you can see yourself doing this work long-term. It might be entertaining to run drunk 20-somethings around in your Uber for a couple Saturday nights, but how many evenings does it take before the shine wears off and you are left with nothing but a couple extra dollars and the stale smell of vomit in your floor mats? Depending on your sense of smell, you might not make it to the end of the first week. A side hustle can’t be a legitimate option for the long haul if the newness and bonus money is clouding your rational thought, so make sure to put in at least six months before shooting that resignation email off to the boss.

With the rise of VRBO and Lyft, Beach Body, and essential oils, the opportunity for making money at your convenience is like never before. Add in the super-connectivity the internet and endless apps bring, and we might be saying farewell to traditional workdays altogether before most of us even reach retirement – and for those who’ve found the right side hustle, that time might already be here. 

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