Crazy Awesome Side Job Ideas that Earn Lots of Extra Money (and you’ve probably never heard of)

Crazy Awesome Side Job Ideas that Earn Lots of Extra Money (and you’ve probably never heard of)

Have you ever noticed that when you start looking at new cars, or maybe buy one, it seems as if that you notice that same make and model everywhere. Suddenly the roads and parking lots are filled with Camries, or Volvo station wagons, or Odysseys. You just can’t believe how many there are. There were never that many of them before, were there?

Actually, there were. This is explained by something psychologists call “selective attention.” It basically means that your brain filters out the majority of stimuli so it can focus on what is important. Once you’ve chosen a specific model of car, or you have recently bought one, that becomes “important” and your brain takes notice of it.

So what does that have to do with transitioning out of teaching or starting your own business? The possibilities for making money on the side – or creating a business to support you and your family – are limited by only one thing : your mind. As you start focusing more on moneymaking ideas, you will train your brain to see them, and train your brain to look at your skills from a new perspective. Things that you never would have considered before will make you think, “I wonder if…” And that ‘s a great thing, because people have made successful businesses by using an amazing range of skills and ideas. Let me give you a few examples that I never would have thought of, but that have been built into successful businesses. 

Karate Kids

Olivia Roney was putting herself through college when the karate school she worked for bounced a couple of her paychecks. Since she was paying her own way, she knew she had to fix the situation – and FAST. So she started contacting daycares and preschools and offering to teach on-site enrichment classes. She found one, and grew from there. Today, Couching Tigers is offering karate classes in almost 100 locations in Indiana, as well as licensing its curriculum. Her programs now include character development and have touched the lives of thousands of children. What’s more, her eyes light up when she talks about her company.

How you can make this side job work

So you don’t know karate and you don’t like preschoolers? How could this idea work for you? I don’t know karate, either, but for about 4 years, I taught Spanish and French to both adults and preschoolers as a side job/micro-business. Preschools were definitely my biggest and most reliable locations, but I also taught adults at wineries and after-school caregivers as a professional development option.

Is there something you love to teach that others would pay you for? Art? Soccer? Computer skills? Knitting? Vegan cooking? Couponing? (No joke, a lady in my hometown was advertising couponing classes and a lot of people seemed interested.) How about pet training?

The point is that if you have a skill that others want to learn and you can find a way to share it, you can earn great money per hour AND have fun at the same time. Cause let me tell you, teaching French at wineries to people who actually WANT to learn it?!? That is a French-teacher dream come true. For more ideas on locations, check out the blog post I wrote for The Comprehensible Classroom or for Fluency Matters. And if you want details on my Spanish classes, here are some posts on switching to preschoolers from older kids, pricing (part 1, part 2 and part 3), and tips for getting started.

Teaching French at a Winery

This is one I have done personally, and you want to talk crazy AWESOME! This is it. I’ve taught French for over 15 years in high school, but teaching French to adults who actually want to learn it at a winery and having them pay you? Trust me, it doesn’t get much better than that!

“But I don’t speak French,” you say. Well, the same winery where I taught French offered a ton of other fun stuff to get customers in during off-peak times. Tuesday? Henna tattoos. Wednesday? 10-minute chair massages. Another night it was tarot card readings. Each of us partnered with the winery to provide our service. The winery generously swiped payments through their system, and then cut a check. We had no overhead and the winery had an ever-changing line-up of attractions with no up-front cost. They just passed through the payments to us.

How you can make this side job work

Get creative. Do you have a trendy or unusual skill? Find a winery that offers fun activities, and see if they are interested in offering yours. You’re probably not going to be raking in the cash at first, but as you develop a clientele and they tell their friends, your numbers grow and it can be really lucrative.

Will Caricature for Cash $$$

When I heard of a woman who has created a side business around drawing caricatures, I knew I had to check it out. She was frustrated by her $8/hr job working for an amusement park as a caricature artist, so she decided to strike out on her own. Now she charges between $150 and $300/hr. drawing caricatures at weddings, corporate events, and other venues where people are looking for a unique and fun party favor.

After doing a little research, I found out there is actually a centralized web site where caricature artists can advertize. Who knew? You can check it out here. If you think you might be interested in being a caricature artist (or caricaturist, as they are actually called), face-painter, balloon animal creator, clown or other type of party entertainer, you can read the story of how Jeremy Drysdale started the Phoenix Caricature Company here.

How you can make this side job work

The point here is taking a common skill and niching it down. Maybe there are a ton of caterers in your town, but you just focus on selling your amazing frozen cookie dough. Maybe you do only vegan or gluten-free foods. Sometimes niching down and focusing on one tiny segment of the market actually sets you apart.

Cinderella Carriages and Horse-Drawn Wagons

A friend of mine since childhood (yep, we actually went to the junior prom together back the day!) supplements his yearly income to the tune of tens of thousands of dollars a year by building horse-drawn wagons and carriages. He makes both really practical people movers for country-themed resort areas and fancy “Cinderella” carriages. He also offers carriage rides at weddings and other special events. He has welding and woodworking skills and has always had horses, so what started as a novel idea has become a large portion of their family’s income. Because of this extra income, his wife (who is a big part of the business) has been able to stay at home with their kids for the past several years. You can check out boylebuiltwagons.com for some inspiration.  

How you can make this side job work

And this is the example of super niching down. As far as I know, Tony Boyle is one of the only people in the US who makes custom people movers. There were times he wasn’t getting a ton of orders, but he didn’t give up or offer to make other items. He just stuck with what he washing and trusted that he would built a following. last I heard, he had as much work as he wanted and even some names on his waiting list.

The last word

So there is a good chance that you don’t feel like welding and hammering together a wagon is part of your skill set. And you might not be someone that others would willingly pay for their art. (Lord knows I’m not!) It’s even conceivable that the idea of teaching karate to 3 year-olds makes you break out in hives. So why did I even mention these ideas if they will work for only a small fraction of people?

Well, there are two reasons. The first one goes back to the very first few paragraphs of the post. Hearing about the ways other people have created a side job – even with unusual skills – trains our brains to start thinking in that way. What could I do with my skill set, that I would really love doing, and would also make me some crazy awesome extra money?

The second reason is it shows us how to niche down. There are a ton of welders and woodworkers out there. But how many of them weld Cinderella carriages and horse-drawn wagons. Artists? A ton! But people who will come to your wedding reception, give your guests a truly one-of-a-kind favor, and have them asking, “Do you remember so-and-so’s wedding where we got those hilarious caricatures?’ for the next 20 years? Not too many of those! Tons of karate teachers, too. But ones who will come to your kids’ preschool so you don’t have to drive across town? Um, I think you get the picture, right.

Here are the two takeaways: get creative, and niche down. Oh, and one more thing: don’t dismiss ideas too quickly. Who would have known that horse-drawn wagons could be a viable home-based business? What’s your crazy awesome talent?

Do you want even more ideas for ways to make extra money? Check out my articles on indexing, pet-sitting, VIPKid, or other side hustle ideas.

The best, legitimate at-home side-job* for teachers             *(that you’ve never even heard of)

The best, legitimate at-home side-job* for teachers *(that you’ve never even heard of)

The times are hard in the teaching world right now. It seems like everybody is just piling on: parents, politicians, and worst of all, payroll deductions. A lot of teachers I talk to love their profession, but just don’t feel like they can handle 10 or 15 more years (sometimes more like even 10 or 15 more MINUTES – ahem – I’m looking at you, Friday before Spring break!!!!).

So they dream of finding a side hustle that could give them money for some extras, or maybe someday even replace their teaching income.  But every time they think they have found something, it turns out to be a scam or earns a whopping $1.50 per hour.

There is an option out there that no one seems to know about. And I wouldn’t know about it if it weren’t for my friend Meridith Murray, who turned it into her full-time(ish) job. It isn’t a get-rich scheme. It’s an actual side job that can replace a teacher’s salary with work and minimal investment, AND it doesn’t involve sales!

Here’s the best-kept work from home secret of 2020: Indexing.  An indexer does exactly what it sounds like – create the index at the back of non-fiction books. While most publishers have in-house editors and proofreaders, indexing is a function they often prefer to contract out to reliable freelancers.

Pros and Cons

Indexing has a ton of upsides, like good income potential, flexibility, and the ability to work from home. But it is a real job, and it requires hard work, a willingness to learn, and it doesn’t produce income on the first day. So let’s look at the pros and cons one by one to help you decide whether indexing might be your ticket to one again being the master of your own life.

Pro #1: Flexible location

Because the books indexers work on are sent via computer, you can work from anywhere there is reliable internet. Home: check. Starbucks: check. Tahiti: DOUBLE CHECK!

Pro #2: Flexible hours

Even though indexing usually has a firm deadline (and sometimes a short one, at that), the time you work on the project is up to you. Whether you’re a night owl or do your best work at 4AM before the family is stirring, there’s no problem for an indexer. As a teacher, you can also accept fewer jobs during the school year and more projects during the summer months.

Pro #3: #willreadforincome

Yes, you got that right. You get paid for reading books. OK, there is more to it than that, but reading books is definitely part of the job description. What’s more, you get to read and learn about topics from adoption to children’s book publishing to cookbooks to who knows what else, all while getting paid for it. If you are a book addict, it doesn’t get much better than that. Of course, since only non-fiction books have an index, you’re not going to be reading a page-turner novel, but once you have a steady stream of clients, you can actually choose which jobs to accept and which ones not to. A number of indexers are known for a specific type of work, often one that they really enjoy learning about.

The other side of the coin

“OK, sounds good,” you say, “but nothing is perfect.” True, that. This is a legitimate, long-term work at home option. And that means it’s going to take some commitment and investment before you see the money starts rolling in.

Of course, as with any legitimate work-at-home business, you will need to set up record keeping systems and have a quiet, distraction-free work environment. In other words, don’t plan on doing indexing while watching your kids out of the corner of your eye. That could be dangerous both for the kids and for the index.

Investment of money

Indexing is a side income that does require some up front investment and a little business acumen. First, you’ll need to learn to index by taking a class, which usually runs about $750 and can be done online in a self-paced course. Once you’re trained you’ll need to purchase indexing software, which varies in price from $225 to almost $600.

Investment of time

Besides the initial investment of money, you also have to allow time for your indexing business to take off. At first, you are not going to get many jobs because you are not well known and have no client base established. The jobs might trickle in pretty slowly, so don’t quit your teaching job after you’ve completed one project.

Unpredictability

Also, even though indexing is flexible, it is also somewhat unpredictable. The index of a book can’t be started until every other detail of the text itself is finalized, so if there is an unexpected delay, you might receive a project 1-2 weeks later than projected – quite a problem if you were counting on finishing it before a family vacation or if you have another big project that comes in at the same time.

And just like the timing, the income can’t always be relied on like a teacher paycheck can. There may be times when it seems like there aren’t any jobs coming your way, and others when you can’t accept all the jobs you’d really like to do. So if you are someone who spends money the minute she has it, indexing as a primary income could cause some pretty serious stress.

Paperwork

Unlike in teaching, you don’t have an employer who will be withholding your taxes, Medicare, or social security, you will need to educate yourself on how to set aside funds and avoid a big, nasty surprise come tax time – AND have the discipline to actually do it! If you have never had a side hustle before and that thought freaks you out, don’t get too worried. It is absolutely do-able. I just want to warn you beforehand.

The friend of mine who I mentioned earlier, Meredith Murray of MLM Indexing (her initials are MLM. Don’t worry. It has nothing to do with the MLMs that most people think of, I promise!), has been indexing either part-time or full-time for over 20 years.  When we worked together, she did it as a way to make extra income. When she retired from the school system, she had established a reputation for timeliness and accuracy that allowed her to make a solid living through her indexing business. After 20 years, she is still enthusiastic about indexing and says she often has more work than she can handle.

In summary, if you are looking for a work from home activity that allows you some control over your work schedule, but is a legitimate way to potentially match a teaching salary, indexing is a strong option. It works better for fast, avid readers who are also detail oriented. For outstanding resources, check out the American Society of Indexing website.

And if you found this article helpful, please feel free to share it on social media. You might have a teacher friend who has been looking for a work at home side job exactly like this one.

Congratulations!

You are taking the first step to overcome the obstacles standing in your way. Whether it is not knowing what jobs would be a good match for your skills and experiences, not knowing what job titles to search for, or being unsure about how to update your resume and conduct a job search, we’ll tackle it together.

One of the big challenges teachers face when they consider leaving is not knowing what they want to do or what jobs to apply for. It can be hard when you’ve been teaching for year, or when it is the only thing you ever really wanted to do. But you’ve got this.

The first step is knowing yourself, reconnecting with yourself outside of your identity as a teacher. So take a few minutes and think about who you are, what you’re good at, and the patterns that emerge. To help you, here are three guided reflections, with audio instruction and printable organizer.

In a few days, I’ll send some next steps to help you apply what you discover.

Audio explanation of Guided Reflection 1 “Identity List”
Audio Explanation of Guided Reflection 2 “Identity Pie”
Audio Explanation of Guided Refleciton 3 “Patterns”
I need to leave, but what if I miss teaching?

I need to leave, but what if I miss teaching?

One of the worries I see from teachers who are conflicted about leaving is “What if I miss it?”

And there is a remarkably, incredibly simple answer: Go back.

You CAN go back, and I’m proof

In the vast majority of cases, you can go back to teaching. Maybe not to the same role or the same school, but often to a position you like just as well, or even better. Let me tell you about how I “went back” to the same school on two separate occasions.

The first time, I was able to return to my exact same position after taking a break of two years. After my first year of teaching, I had a chance to study in France for a year. Yes, please!! It was an absolutely incredible year, and I am so happy I didn’t miss it. When I came back to the US, I worked at my college for a year, and then the person who had been hired for my teaching position resigned. A former colleague called me and encouraged me to re-apply. I taught there for another 3 years.

The second time, I resigned from what I truly thought was my dream job – teaching French at a very diverse high school under an administration I adored and that treated me great! But I had a micro-business and 3 kids (2 under age 5). I felt burned out, and didn’t want to miss the last years before my youngest went to kindergarten. So I regretfully, but resolutely, turned in my letter of resignation.

(True story: The day I turned it in, I noticed at the end of the day that the toes on one foot were hurting. Looking down at my feet , I realized I had worn two different shoes all day long! I took that as I sign that I was at a breaking point and resigning was indeed the right decision!)

Again, it was a good decision to resign, but I missed the students and my amazing co-workers.

Two years later, I bumped into my former AP, who mentioned that they might have a position opening up. She wanted to know if I’d be interested. As it turned out, they hired me for my honest-to-goodness dream position – teaching and supporting students who had recently arrived in the US and had almost no English language skills. I took it and brought a renewed sense of excitement with me. It was wonderful to be back!

Keeping your options open for a return

The bottom line is that very few decisions in life are final. So let’s talk about some best-practices if you want to keep those doors open for the future, just in case.

Leave on a positive note.

This has been a hugely rough year for all of us. You might be leaving with great feelings about your admin or really bitter feelings. My advice is that unless the admin has done something super sketchy, keep that resignation short and sweet, and leave out the drama. (Unless you are leaving because of something illegal or unethical, in which case you may have a duty to report issues.) This isn’t the time to air grievances, especially if there is a chance you might ever want to return. Also, with the passage of time, you may realize that your admin were doing their best during a really sh*tty time in education, just like the rest of us.

Keep in contact.

Once the stress and anxiety have faded and you are once again in a healthy place, go to the occasional concert or sporting event. (Did I mention that it was at a school fundraiser that I ran into that assistant principal, which led to getting re-hired?) Keep in touch with former colleagues, and keep it positive. Let them know you are still with them in spirit. If they miss you, they’ll be more likely to share potential job openings and let you in on the news before it’s public.

Maintain your network of contacts.

Let’s say you’ve had a bad experience at your current school and you never, NEVER want to go back there. That’s cool. But don’t shut yourself off from the teaching community. If you think you’d like to go back one day, stay in your teaching FB groups, especially local ones. Consider volunteering at your state professional conferences, or even presenting, if you have something worthwhile to share. Even though I live on a different continent and don’t ever plan to return to the States to teach, I’m still in touch with a number of former colleagues from each of the schools I taught at, as well as an active member in FB groups for US teachers. It’s not because I’m planning to return; it’s because I genuinely like them. However, it also won’t hurt me to have a ton of active contacts if I ever did need to go back.

Rethink your vision of a teaching career.

When I started teaching, the ideal teaching career was seen as hiring on at a particular school, remaining there for 35-40 years, then retiring. But things do change, you know. Given the current demands on educators, I think a much more manageable career track is to plan for a number of shorter teaching experiences, separated by jobs outside the field of education. Besides teaching, I have worked as a university admission counselor, been a stay-at-home mom, and run a micro-business. These breaks allowed me to re-evaluate my relationship with education. Each time I left teaching, I had to ask myself, “Do I really want to go back?” So far, the answer has always been “Yes.” (But only after a couple of years away!) 🙂 No, there isn’t any guarantee you will be re-hired, but given the teacher shortage, I’d say your chances are pretty good at the moment.

There you have it! My story of returning to teaching and my best tips to make it possible. Have you returned to teaching? What are your best tips to get back into education after leaving?

Make every big decision easier with these two rules

Make every big decision easier with these two rules

Any major life change can bring up self-doubt and fears, but leaving teaching can be especially challenging, especially if it’s the only career, you have ever known, perhaps the only one you ever dreamed of.

Uncertainty can be overwhelming at times. What if I miss teaching? What if I hate my new position? What if no one will hire me? What about insurance? Will my kids be sad that I can’t spend the whole summer with them anymore?

Our Big worry: What if I regret it?

That last question is, I think, at the heart of all the others. What if I take this huge, scary step, and then realize that I liked my life better the way it was before? In all honesty, I think it is sometimes the feeling of regret that we worry about more than anything else. What if I realize I made a mistake? What if I feel stupid?

It’s an understandable fear, isn’t it? We have a ton of proverbs and aphorisms that tell us to stay where we are. “Better the devil you know than the devil you don’t.” Out of the frying pan, into the fire.” “Fools rush in where angels fear to tread.”

But  never taking a chance is also a path to a ho-hum (or worse) life. And that’s not what you want, nor what I want for you.

If you are thinking about leaving teaching (or have already decided you need to), but are still plagued by these worries, I want to share a couple of guidelines with you that helped me stop worrying, and even better, kept me from regretting any well-informed decision I have made.

#1 I will make the best decision I can with the information I have now, and I will not expect myself to know the future.

Let me tell you a little story. As you know, we moved to Norway in 2019, and our kids were a huge reason why. We love the fact that our kids have more freedom, more safety, and less pressure in school (no standardized tests!) than we could have dreamed of in the US.  We love the fact that as long as they live here, they will never, ever go bankrupt trying to pay for a medical procedure or have to choose between paying the rent and buying necessary medication. We love the fact that even if they don’t go to college, they can earn a living wage and have a good life. So it’s fair to say that we are pretty happy with the choice we made.

For the record, we didn’t rush into the decision, either. We spent over 2 years planning, researching, talking, and preparing. At one point, I could probably tell you more about apartment availability and food prices in Oslo than anyone who hadn’t lived there!

But you can’t research the future. So when Putin invaded Ukraine, and I was running around looking for iodine tablets for the kids in case – well, you know – I could have had an absolutely huge meltdown/guilt trip/beat up on myself extravaganza.

I’m going to be honest, decisions don’t get a lot more serious than that. Did I move to Norway trying to give my kids a better life, only to put them in proximity to a nuclear disaster? I don’t know. No one does. No one knows what will happen in the next year or two or ten.

You don’t know the problems that would have come from the decision you don’t take

But I also don’t know what would have happened if we had stayed in the US. Would one of the kids been injured or killed in a car wreck? (Traffic fatalities are exceedingly rare in Norway.) Would my daughter have had to learn not to make eye contact with men because they might catcall her? Would my child with test anxiety have spent their school years in a state of “quiet desperation” trying to pass state tests and compete for a place at a top university?

I don’t know. I don’t know how any of this will turn out. But I do know one thing: my partner and I made the best decision I could with the information I had at that time. And it was a LOT of information.

Knowing that, I’m going to be gentle with my present and former self. I’m not going to let myself – or anyone else – make me regret making the best decision I could with the information I had.

Even if the day should come when we do, indeed, need to leave Norway for safety or other reasons, I will always honor myself and the decision I made.

What does that do?

What that does is actually massive. It frees you from guilt and regret. As long as you have done your research and acted on it reasonably (Please note: we would NOT have moved to Ukraine in the middle of a war. That would not have been prudent!), you don’t have to feel bad. You shouldn’t feel bad.

Honor yourself and the decision you made with the information you had, knowing you made the best decision you could at the time.

#2 I will pursue this course of action until it no longer makes sense to do so.

This part came from one of my absolute favorite business coaches, Bevin Ferrand. If you have never heard of her, I highly recommend her “Take the Damn Chance” FB group. So good!

But here is the genius in guideline #2. You don’t HAVE to continue just because you have started. Now, granted, there are points at which it is a LOT easier to put on the breaks than others, and I highly recommend listening to your gut here. (I know a woman who cried herself to sleep the night before she got married. She knew it wasn’t going to work out, but she couldn’t back out because everything was arranged and paid for. Please. Don’t. Do. That.)

Let’s say you turn in your letter of resignation. You search for jobs outside of education – no luck. You have already crunched the numbers and know exactly how much you need to make each month. You can make that working part-time at Starbucks, so you start there. But you don’t love it. You miss teaching. There is no law that says you can’t apply for teaching jobs again, possibly at your former school, and possibly at a different district.

This is coming from a teacher who not once, but twice returned to a former school. So I know that of which I speak! But that’s another story.

So let’s say you leave teaching and you miss it horribly. There is nothing that says you can’t go back. True, it can be more difficult as you earn more. Schools don’t like to hire expensive teachers. But there is also a “teacher shortage” of epic proportions, so use it to your advantage.

The bottom line is, almost no decision is truly final. In most cases, you can pivot more easily than you think, especially if you can be flexible. And goodness knows, if the past two years have taught us anything, it’s to be flexible.

There you have it folks, two ideas that will help you manage your transition trepidation.

You have so totally got this!

All the best,

Jill