If You Picked Up a Chill Job I Wouldn't Judge You
Being a Creator Getting Paid Means...
Before you read this post I do want to clarify an important point. If you’re dealing with unexpected job loss-you’re dealing with a different calculation. You’re just needing a job. I get that. I helped my mom out for 3 years as she went through a horrific job loss and job situation. You’re just trying to do what you need to do and in those moments any job is a good job.
Let’s Talk Chill Jobs
I first dipped my toe into the content creation space as a personal finance blogger. I had a lot, I mean, a lot of financial issues due to lack of financial skills, not earning enough money and a 3(ish) year experience being a financial caregiver after my mom lost her job. It would take years to clean up the financial mess and feel comfortable enough to take big risks again related to what I dreamed about and my goals. I was that person who always worked multiple jobs, kind of like that running joke on Martin or Living Color about Jamaicans having 9 jobs. That was me, but I just happened to be African-American.
To be honest, I’m still that girl.
So when earlier this year people jumped on Tabitha Brown for saying that it’s not a bad idea for people to work a job, side-hustle etc. while pursuing their dreams-I totally got it. She was like “I was driving with Uber/Lyft and working during my free-time as I made progress towards my end goal.” Now she has a business with multiple streams of income.
It was so weird to me to see people freak out about that comment given the financial climate that we’re living in.
A few days ago 42 million Americans lost access to supplemental food resources and access. African-American women are losing jobs in unprecedented numbers as a part of current Federal policy. Did you know that over 51% of African-American women will become a financial caregiver to a family member or friend during their lifetime?
What Does Getting a Chill Job Have to Do With Creators Getting Paid?
Quite a lot actually.
Building a business and brand takes a lot of work, focus and dedicated energy. It will likely take longer than people are telling you to hit the income metrics that you’re working towards.
Get a Chill Job That…
Meets the following criteria
Get a job that is easy to do and requires NO BRAIN ENERGY. You aren’t making decisions, you’re fulfilling a relatively simple task. Because building an online business requires so much brain energy that you want to avoid accidentally adding more decision creep into your life.
Ask yourself, are there side-hustles that lean into activities or interests that you enjoy while earning you paid time off (PTO)
What are the benefits that your state has passed that a chill part-time job will allow you to pay into as a solopreneur? Colorado has paid family leave that Solopreneurs can qualify for. Are you able to access medical insurance as a part of that part-time job? There’s a reason why so many people were working at Starbucks for such a long-time.
My friend Kara Perez runs a well-known personal finance brand called Bravely Go. She has thousands of subscribers, community members and followers. She’s been featured on NPR, Forbes and other media spaces and she also has a part-time job. Kara has also been chronicling how she and partner were preparing for his job loss and becoming a one-income family. I know of many other content creators with success brands who’ve also opted to keep their 9-5 and work both concurrently.
Some Fun Side-Hustle Examples
Now, the bigger the city you live in the easier it is to find many of these roles. I would discourage doing Uber Eats or anything that adds to wear and tear to your car or requires you to use a lot of energy if at all possible. The key to all of these chill side-hustles is that the companies will share what their needs are and then ask if you’re available to work. You only say “yes” to what makes sense for you and your personal and business schedule.
Convention Center Staff-If a city has a Convention Center they are typically constantly staffing for the following roles:
Registration
Wayfinding-Helping people move around the venue
ADA support
Session scanning
Special event prep-Conferences typically host fun events for their attendees
Security
Coffee Shop Barista
Love coffee
Like people
Leave after the shift is done
Day Care Staff
I almost didn’t add this to this list. But there are people who are truly gifted at working with children and actually like them. Must pass a background check.
Theater/Performing Arts Staff
Ushers-Help people to their seats
Scanners-Scan tickets (some venues are starting to shift to digital scanning)
Coat Check
ADA support
Wayfinders
Sporting Venues Support Staff (Football/Hockey/Soccer/Baseball/etc. Stadiums)
Staff the security scanners going into the venue
Ticket scanners
Customer Experience Staff
These venues need staffing in all specialty areas such as VIP lounges, Club Levels and Suites
Front desk support at your favorite spa-Then you get discounted or free access to the spa (make sure to ask about that)
Front desk support at your favorite dance or fitness studio-Then you get free access to dance classes) ask about this
Caution!!
Do not do the following at your chill job: become a supervisor or manager-You’re expensive and that’s not where your energy should be going. It needs to be focused on building your business. Do not be in any role that requires you to do deep emotional labor beyond being fabulous at the pleasant role that you’ve been hired to do.
Chill Jobs Are Not
Involving driving-Unless you’re obsessed with driving. Or, this is the only option available in your town.
Working at a warehouse especially if your work and productivity is timed
The only exception would be a benevolent small business owner who has a heart of gold and happens to own a warehouse. Or, you live in a town where this is the only job available right now. That’s totally ok.
Anything heavily customer service focused-Too many people yelling at you.
Pick your Chill Side-Hustle with precision and DON’T let it slip that your goal is to work a non-committal job at the highest capacity. People will love how amazing you are. You’ll love that you can come and go as you please and that you’re not in charge of anything except for showing up to work your shift. You’re going to be amazing at this because you’re NOT taking away from your dream.
What A Chill Side-Hustle Can Do
Besides the obvious which is pay your bills.
A chill side-hustle gives you space to experiment and test out different types of monetization approaches in your business.
Takes pressure off of you to make money in ways that might not be in alignment with your brand or ethos.
Provide some of the funding needed to pay for the cost of running a business. Especially if you were unexpectedly forced into starting a business before you planned on starting.
Give you access to fun activities or experiences that you’d like to experience but have cut back on.
What’s My Experience With Chill Side-Hustles
I Love Them!
Have you ever wondered how I’m attending so many fun events? I work for a company that staffs those events. I really like the people that I work with, that I’m not obligated to work other than what I feel like working and I’ve landed some cool opportunities as a result of my fun side-hustle.
That year I was a host on a local Colorado radio show-I landed that because of a casual conversation about podcasting with an attendee.
That City Cast Denver podcast episode-I met the producer of the show years ago at a fun short-lived side-hustle and we’ve become friends. It was easy to pitch myself as a guest because they were aware of my podcasting background.
Watching the Denver Broncos kick some team’s butt-That wasn’t me buying a ticket, I worked the game.
The American Economy
Sucks Right Now
You must think pragmatically about the steps you take moving forward. I joke about this but eggs are still expensive in Denver. The price of EVERYTHING has gone up. Don’t let pride get in your way.
Continue to build your dream business.
Prepare for all financial eventualities-I was completely unprepared to become a financial caregiver when it happened.
Don’t add to your emotional and energetic load with your chill side-hustle. There’s a reason why I didn’t add anything that was physically taxing, required driving or doing too much. Chill is an Energy and a Verb.
Adding a chill job doesn’t isn’t an indication that you’ve failed at what you’re trying to do as an online entrepreneur. It’s a signal to yourself that you’re paying attention to the economy.
My Home insurance has gone up.
My Health insurance has gone up
Food prices are increasing
Other people in my life are dealing with financial pressures too. I very likely will end up helping people out financially again.
I want to normalize making strategic financial moves while you’re working on and building your dreams. I’m really happy to see more conversations around building an online brand and business while still working a 9-5 and continuing to work a 9-5 once someone has built a successful brand and business (if they feel like it) I want to normalize in a not so normal time that it’s important to lean into common sense. Now is not the time to be under-employed for whatever reason (unless something has happened OUTSIDE OF YOUR CONTROL like an unexpected job loss)
Who are Working Chill Jobs
I think it’s also important to know who is saying “yes” to a chill job
Entrepreneurs
Students
Retirees
Parents
People working a 9-5
One Last Thing
A chill job can be phased out as you need or don’t need it. You can work it as your business and brand ebbs and flows, personal energy changes or your wallet tightens up. It’s up to you. Think of it as an insurance policy.
They are people with dreams just like you. These are people who ARE NOT giving up on their dreams. In fact, they’re doubling down on them. They aren’t failures. They’re focused and income problems won’t distract them as they continue working towards their end goal.
Let me know what you think,
Michelle
HR Kyle Services
Looking for a new job or up-leveling your career right now can feel really overwhelming especially if you’re also building an online and business. That’s why I’m so excited to share HRKyle with you, they are sponsoring Creators Getting Paid and here’s what I love about the services that they offer.
Emotional and Mindset support-I’ll never forget now stressful it was for my mom many years ago when she was looking for work and she had no resources to help her with the process. Emotional and mindset support would have been so helpful at that time.
LinkedIn Optimization and more
Or, you could try out HRKyle’s Career Accelerator Membership that provides members with a comprehensive career search approach. Either way there’s no reason to do this on your own. I love their people first approach.
Go to hrkyle.com to learn more. Make sure to tell him that Michelle Jackson sent you.



