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What Would I Do If I Wasn't Teaching? 7 Worthwhile Side Hustles to Build a Bridge to a New Career

I’ll start by sharing that the purpose of this post is not to convince teachers to leave the profession. As a former teacher and partner to a current teacher, my in-person and online circle is naturally made up of teachers -- most of whom are doing their best to stay healthy and positive in what I can only describe as a never-ending Mad Hatter’s tea party. They check their emotions at the door, attempt to put on a literal magic show several times a day in front of changing live and virtual audiences, and achieve minimal success at not carrying their stress home with them. At the same time, they delight in and share the treasures that come from their students’ daily contributions...poems, journal reflections, arguments, and thoughts shared aloud. Despite these little joys, some of the strongest people I know are barely holding themselves together.

Murmurs of What if I wasn’t teaching? have grown more urgent and frequent for many, whose collective sympathetic nervous systems have been in a near-constant state of high alert for months. Despite all the signs that point to unsustainability and burnout if they remain in the profession, many teachers I’ve spoken to feel trapped for a variety of reasons:

  • Loss of benefits -- namely, inability to afford health insurance

  • Prior investment -- time, money, and soul invested into degrees and certifications

  • Dependents -- partners, children, parents, animals, and other family members who rely on a stable, predictable income to survive

  • Fear and uncertainty -- many aren’t sure how to carry their skill set to another position

I can certainly empathize. In the months leading up to my resignation, my thoughts were consumed with these concerns. Could I afford an extra $265 per month, at the least? I am a perfectly healthy individual, and know that other teachers (many of whom have pre-existing conditions) would be faced with a much higher monthly premium. What about the thousands of dollars and hundreds of hours spent on my bachelors, masters, and doctoral degrees? I had completed 57 of 60 credit hours for my doctoral degree when I resigned from teaching. While I do not have children, I put pressure on myself to carry financial weight in my relationship -- we had just purchased our first home, the mortgage payment of which would take up almost 3/4 of my partner’s monthly income. What if I couldn’t get income quick enough after resigning? The ultimate barrier for me, and from what I’ve gathered, most teachers considering leaving, was fear and uncertainty. What can I do with this highly unique and equally undervalued skill set?

I was talking with one of my clients yesterday who reminded me of something so simple, yet empowering: our feelings are real, but not necessarily true. They are a manifestation of our thoughts, which are also real, but not necessarily true. We can choose to see our situation as a trap and feel resentment, hopelessness, and fatigue. Or we can get curious and look for the opportunity. For more on choice and such, see my previous post (So what do you do now?). But for now, what I’m trying to say is that, for most teachers, leaving the profession is going to be scary. And uncertain. And nerve wracking. And defeating. And so very heartbreaking, for those who love their children.

But it can also be empowering. And healthy. And lucrative. And fun. Just, maybe not at first. We (hopefully) don’t view our students and colleagues as either ‘all good’ or ‘all bad’ -- why should we view any challenge or opportunity in front of us as such?

I’ve been working for myself for nine months, and in that time, I’ve birthed a freelance writing career that makes me proud and excited for the future. I got there by using my ‘unique skill set,’ trying new things, trusting my instincts, and shelving notions of what I thought I should be making monetarily, compared to my peers. I took pay cuts. I took on pro bono projects for the sake of learning and growing. I made and continue to make many mistakes. And I’ve hit my stride. If there’s one thing I hope my teacher friends and peers will take from this post, it's that waiting for a career that will magically allow you to utilize all your skills is not a ticket out of teaching, or any job where you’re unhappy, unfulfilled, and unsafe. You have to give yourself the greenlight and be willing to take a risk. Below, I’ve listed seven side hustles, job platforms, and work-from-home gigs -- most of which I’ve done personally -- to help you build a bridge to your next career career, or possibly morph into your next career. A career where you believe you will feel safe, valued, and inspired to come to work every day (which in some cases just means getting out of bed, putting on your soft pants, and sitting down in a quiet, sunlit room of your home). #1 Freelance job platforms Freelance platforms like UpWork and Fiverr advertise literally thousands of positions daily for the following types of work: accounting and consulting, administrative support, customer service, data science and analytics, design and creative, engineering and architecture, IT and networking, legal, sales and marketing, translation, software development, and writing. Freelancers submit proposals with background experience and relevant work samples to compete for jobs, all of which can be performed from home. Pros: Choose your own projects and clients; set your own wages; build a portfolio before attempting to reach out to local clients; the fee removed from your earnings gets smaller as you complete more projects for individual clients Cons: 5 to 20% fee removed from your earnings; it can be challenging to make your first $1000; processing earnings can take several days to a few weeks, depending on your clients’ responsiveness; limited amount of ‘connects’ per month to apply to jobs; some projects require an NDA, so you wouldn’t be able to include them in your portfolio. Soft pants friendliness rating: 5/5 (no one I’ve worked with has had the privilege of even glancing at my bottom half) My experience: Using UpWork has been nothing short of a dream. It has enabled me to complete a variety of projects with highly reputable agencies and individuals, and I’ve learned new skills along the way. My first job on UpWork was a $10 task, and it took over a month to make my first $1000, but four months later, I have made almost $5000, and as of today (October 1), I have earned over $2500 for the month of October -- by far, my most lucrative month to date. One third of my clients are long-term, and I am excited to work on projects that are mostly writing-centered and focused on education. I achieved Top Rated status last month, which puts me in the top 10% of talent on UpWork, and I’m well on my way to achieving Top Rated Plus, which will grant me reduced fees on contracts and quicker payments. I’ve included some examples below of neat projects I’ve completed or are currently working on:

  • Content writer for multiple education websites

  • Editor-in-training for a highly successful and popular education website

  • Professional educator training scriptwriter, presentation designer, and narrator

  • Content writer for an attorney who specializes in prenuptial agreements

  • Project contributor for NYU’s Center for Data Science

  • Editor for a client that centers on exposing historically marginalized youth in urban areas to world-famous artists and their works, and that fosters ongoing mentorship to encourage students to pursue creative talents

  • Assistant application writer for a new charter school in a different state, whose curriculum and culture are founded on social emotional learning, project-based learning, mindfulness, culturally relevant pedagogy, and interdisciplinary learning

#2 Pet sitting

Must love dogs? For many, taking on pet services is almost too good to be true. There are a variety of reputable local companies, like Charleston Dog Walker, or apps like Rover, who are seeking reliable people to perform the following services: dog/cat boarding, dog/cat day care at your home or the pet owner’s home, dog/cat drop-ins at the pet owner’s home, and dog walking/running.

Pros: Get paid to socialize your own pets; get paid to exercise while taking dogs on walks and runs; flexible scheduling; choose which breeds for whom you’re comfortable caring; exposure to a variety of breeds to see which ones you’d love to have as a potential pet; increase your bookings by earning positive reviews; SNUGGLES.

Cons: Up to a 20% fee removed from your earnings; unpredictable pet (and pet owner) behavior; more dust and dirt in the home means more air filter replacements, vacuuming, and removing poop from the yard; potential for other animals not to get along with your pets or children; potential damage to personal belongings; if you board or care for multiple pets at once, it can be difficult to get other tasks accomplished.

Soft pants friendliness rating: 4/5, but only because dog hair and slobber means your soft pants will spend more time in the laundry.

My experience: I use Charleston Dog Walker when Ian and I go on vacation and we love their professionalism and great communication. I considered applying for a position, but decided it would be difficult to get most of my work done if I was spending a considerable amount of time driving to and from other people’s homes. I’m grateful that my brother told me about their experience with Rover, an app that allows you to set your own rates, choose your own services and animal preferences, and communicate directly with pet owners.

My dog loves having furry friends come over to the house, and we’ve noticed that he has become more calm and comfortable around people and other animals who visit our home. Additionally, you can make great money if you find a sweet spot with your rates, and if you join the app, you can see what others in your area are charging. I made almost $700 in my first month, and as I sit down to write this post on October 1, I already have $1,250 in bookings for the month of October (all of whom are clients with dogs I cared for in the previous month). I feel comfortable sharing how much I’ve earned so far because working through Rover has been such a positive experience, and because I know that so many others, like me, find joy, companionship, and strength through being around animals. I’ve posted some pictures below of dogs I’ve cared for in the last two months :)

#3 Ride-share/food and grocery delivery

Uber, UberEats, Lyft, Instacart, Postmates, GrubHub, DoorDash...the ride-share and food/grocery delivery market is looking pretty plentiful these days. I know teachers and students who are making up to $1000 per month by taking advantage of surge prices in cities like Charleston and Columbia.

Pros: Listen to music and podcasts; become more familiar with your own city; flexible scheduling; personal fulfillment in knowing that you are assisting people who cannot shop for themselves; great for extroverts, networkers, or people who like to make conversation with new people; option to receive payment instantly.

Cons: The more driving you do, the more miles you put on your vehicle, which means more frequent routine maintenance, potential for accidents/broken parts, and depreciation in value; potential damage from intoxicated riders; requirement to carry commercial rideshare insurance; terms of service change frequently; likelihood of hearing from and biting your tongue when you pick up talkative conspiracy theorists…

Soft pants friendliness rating: 5/5 -- because everybody else in Food Lion is already in soft pants, and if you’re just doing ride-share, your riders probably don’t care what you’re wearing.

My experience: I completed a background check for Uber/UberEats and received the sticker to put in my car months ago, but I have not yet completed my first ride. While I love driving in the car and listening to music/podcasts, I have some reservations about taking on strangers and adding additional wear and tear to my vehicle. I do, however, feel peace of mind knowing that if I needed to start earning additional income, I could do so at the drop of a hat.

#4 Remote online teaching/tutoring

Not much to say here, as most teachers have taught remotely at some point in the past year and a half. There are countless companies -- local and national -- who are actively recruiting for qualified teaching staff in a range of content areas and grade levels (check job boards like Indeed). Open positions also include ACT and SAT prep tutoring positions, writing coaches, literacy specialists, elective leaders, ESOL instructors, teacher assistants, and special education teachers.

Pros: Ease of transition from teaching in a school district; utilizes educators’ existing skills; potential for autonomy in designing and implementing curriculum; potential for flexible scheduling; some companies may offer opportunities for teachers to renew their certifications; high likelihood of getting hired during a growing nationwide teacher shortage.

Cons: Tutoring sessions and class times may need to take place at a fixed time each week, limiting flexibility; some companies may require teachers to use scripted or pre-designed curricula, which some teachers may find restrictive; compensation may be lower than a previous in-person teaching position; tutoring positions may be inconsistent and temporary.

Soft pants friendliness rating: 4/5, because it might feel weird at first to wear a blazer on top over your fuzziest PJ pants, but you’ll get used to it.

My experience: My only dance with online teaching was within the school system, and with leaving being so difficult, I wasn’t in a place to move quickly to another student or group of students. Plus, my style of teaching doesn’t involve sitting behind a computer for multiple hours of the day. It’s really a matter of personal preference.

#5 Professional/personal organization

I remember when ‘professional organizer’ was one of the top jobs of the contestants on the Bachelor, and thinking, this job was made for me. Don’t rule this one out, especially if you are a Type A teacher like I was. Professional organizing requires the long range planning and backwards design skills of educators.

Pros: Many positions are remote and offer ‘projects’ near your home address; potential to make several thousand dollars per month; flexibility in scheduling; great entry point into a sales position; many companies offer free or compensated sales and design training; potential to start your own business.

Cons: Some companies may require cold-calling, which is not for everybody; potential for dealing with difficult or high maintenance customers; depending on your area, there may be a low need for this type of service.

Soft pants friendliness rating: 2/5 -- depending on the agency you work for, you may have a dress code or be encouraged to wear certain attire.

My experience: I stress-organize and rearrange my entire house at least twice a year. I find it personally fulfilling despite the fact that I’m putting off larger tasks and receiving no compensation.

#6 Restaurant gigs

It’s no secret that Charleston is experiencing a significant staff shortage in its food and beverage industry. Our city, which relies on tourism and hospitality as one of its greatest sources of income, is more desperate than ever for reliable workers who are willing to learn and be team players.

Pros: Instant cash at the end of each shift; high likelihood of getting hired during a shortage of restaurant staff and (at least in Charleston) a high volume of restaurants and bars; opportunity to learn from the best in the industry and to try new foods and beverages (many restaurants serve a family meal each week or ask staff to try certain dishes on a daily basis so they can better explain them to customers.

Cons: While teachers are used to being on their feet, the fast-paced nature of food & bev can add extra strain; the most lucrative shifts are typically in the evening, with closing shifts ending anywhere from 9 PM to 2 AM; if you’re concerned about being around a high number of unmasked and/or unvaccinated people, this job may not be for you.

Soft pants friendliness rating

1/5 -- many restaurants have stipulations for what their FOH (front-of-house workers like servers, bartenders, hosts, and expeditors) and BOH staff (line cooks, dishwashers, bar backs) can wear, mostly due to DHEC protocol and safe food handling guidelines. A line cook or dishwasher could *possibly* pull off soft pants, but they are very likely to get dirty.

My experience: While I’ve been working food & bev since I was 8 years old (seriously), I’ve only spent a summer doing so in Charleston (not counting my time as a production worker at Callie’s Biscuits, since that was not a restaurant). Put simply, the higher a restaurant charges for food, the more FOH servers stand to make.

If you’re curious, try checking out an app called GigPro, developed by Charleston chefs. It allows you to book FOH or BOH shifts at any time. GigPro may be useful to ‘test the waters’ before deciding if food & bev is a long-term option for you. There are also an abundance of advertised positions that compensate workers at competitive wages for the industry.

#7 Research studies

This one is last for a reason -- as a researcher myself, I don’t advise applying to participate in study after study, particularly if you don’t meet the criteria. I am also painfully aware that many teachers already feel that they have been participating in an uncontrolled experiment for the past year and a half.

Pros: Financial compensation for little to no effort; potential for improved physical and or mental health outcomes; ability to opt out at any time; opportunity to learn more about important biological or neurological issues; personal fulfillment from assisting in a study that could improve the lives of others.

Cons: Potential adverse physical and/or mental effects from treatment in an experimental group; minimal to no biological or neurological benefit if assigned to a control group/placebo during treatment; potentially invasive screening processes; potential for your personal information to be sold to third parties (with your consent).

Soft pants friendliness rating: 5/5, though I have yet to encounter any studies testing the effects of soft pants on personal and professional contentment :)

My experience: I have no prior experience participating in long-term research studies; however, I am going through a lengthy screening process to take part in a study that could hopefully help me with a personal issue that I’ve struggled with for some time. I learned about the study from a Facebook advertisement (famous last words…). If selected, I will make close to $1000 over 3-4 months, which feels like a drop in the bucket, but from a more positive outlook, could cover a significant portion of home utility costs. For me, financial compensation is not the greatest benefit I stand to gain. For those living in Charleston interested in learning more, I suggest visiting the Coastal Carolina Research website, where they have listed information about the following active and recruiting studies:

Working for yourself is not for everyone, and the same goes for these side hustles. I hope and believe that life after teaching can feel more attainable and exciting after reading through the jobs I’ve described above. Each day, I have a moment where I am overwhelmed with pride and gratitude that I had the courage to venture into the unknown. Regarding money, I am well on track to meeting or exceeding the same amount I was netting while teaching. The only difference is that I am happier, healthier, more energetic, more inspired, more creative and rockin' the soft pants. Every. Damn. Day.

Please don’t hesitate to reach out if you want to learn more about my experience with some of these ventures -- if doing so can help at least one person reach a place where they are more personally and professionally fulfilled, that’s something I can feel great about.


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