Top 3 Ways I Make Money While Living With Chronic Pain 

By Crystal Lindell 

Living with chronic pain can make it difficult to navigate traditional employment, due to the physical challenges and the unpredictability of our symptoms   

Unfortunately, we still need money to exist in our society, so I cobble together a living every month with various side jobs that I try to make into a whole job. Below is a look at some of those jobs, and the pros and cons of doing them if you have chronic pain or any sort of chronic illness.  

One large disclaimer is that none of these jobs offer health insurance. For me, for now, that just means that I don’t have insurance and I pay for medical care with cash. But I know a lot of others in a similar situation who either qualify for government insurance or they are able to purchase insurance on the government marketplace. 

Another disclaimer is that having a bunch of side jobs will make doing your taxes much more difficult, so try to put money away for that throughout the year in preparation for it. 

DoorDash

Pros: Flexible schedule, options for same-day pay, low barrier to entry. 

Cons: Success varies greatly based on where you live; the work can be physically exhausting; customers can be unpredictable and difficult; and there’s wear and tear on your car.

I started doing DoorDash in March after my cat Princess D was diagnosed with feline diabetes, and I needed to come up with some extra money for her treatment fast. 

I had a friend who told me she made $400 in four days doing DoorDash, and that was enough incentive to get me to sign up for the Dasher app. 

I live in a rural area where there are few DoorDash customers, so I drive about 20 minutes to a mid-sized city, where there are more customers and I can easily make $100 in about 4-6 hours of work. I’ve noticed that about 10 percent of my earnings go to gas, so I usually do one extra order each night to cover that. 

While there is the possibility of very low-paying orders of just $2, as long as customers tip, each order is usually at least $5 or as much as $15 in my area. 

There’s also an option to do “shop and deliver” orders, where you basically do someone’s grocery shopping. You don’t get offered those jobs at first, but as you get more experience in the app, they will start to give them to you. I had one that paid $60 for a little over an hour of shopping, because I was shopping three grocery orders simultaneously. That’s a great way to increase your earnings. 

I really, really like how flexible DoorDash is and that they offer a couple different ways to get paid the day you work. So if you need some quick cash for something like a utility bill or even just a fun outing, it’s possible to make the money fast and get paid fast. 

In the beginning, I worked mostly dinner hours and focused on Thursday through Sunday, because that’s when the app is the busiest. But after you earn various status levels, they give you more options for working whatever hours you want. Now I’m able to go out during the day, if that works for me. 

Best of all, if I’m having a bad pain day, I don’t do Doordash or can I work a very short shift. That’s flexibility that most traditional jobs don’t offer. 

Plus, if you need to stay below certain income thresholds to qualify for government benefits, it allows you to work exactly as much as you want/need to. 

If you decide to try it, I highly recommend joining some online DoorDash support groups on places like Facebook and Reddit. They are full of tips for drivers and can help you navigate the app and the job as a whole. 

Obviously, doing gig work like DoorDash will put a lot of wear and tear on your car, so you’ll need to keep up with vehicle maintenance. 

But if you’re looking for quick cash that you can make working your own schedule, then DoorDash and other similar gig work like UberEats can be a great way to do that. 

Freelance Writing

Pros: Some flexibility, can pay well, and can often be done at home

Cons: High barrier to entry; basically have to have connections to get work; and the work can be very unsteady.

I have a lot of professional experience as a writer and editor, so after I got laid off from my full-time journalism job in 2022, I had a few people reach out to me with freelance opportunities. 

This has been one of the better paying ways I make money, with some jobs paying as much as $50/hour or more. 

Even if you don’t have experience, that doesn’t mean you can’t freelance. If you have a special skill of any sort, whether it’s painting, photography or house cleaning, you can usually just post on your social media that you’re looking for work and you may be surprised by how many people reach out. 

My main advice would be to charge by the project rather than by the hour, so that you don’t have to track your hours as you go, and you don’t have to worry about any awkwardness between you and the client regarding how fast you’re working. 

If you’re setting your own rates, you have to factor in taxes and healthcare, so you should aim to make about as much per hour as you’d want to make yearly if you multiplied it by 1,000. So if you want to make $60,000 a year, you’ll want to charge a rate that works out to about $60/hour.

The biggest con to freelancing is that the work can be unsteady, which means you can’t really count on the income from month to month. For me, it’s usually based on what the publication or company I’m writing for needs at any given time. If they don’t need me, there’s no work, and thus, no money. 

Also, in the last few years, Generative AI, like ChapGPT, has dried up some of the writing and marketing work that used to be more plentiful for me. I suspect that trend will continue for my industry and others. 

However, I love writing, and freelancing allows me to be choosy about which writing jobs I want to take, so that I can focus on the things l’m passionate about, like writing for Pain News Network. Plus, making any money at all from my writing always feels like a victory to me. 

Selling Used Lego Online 

Pros: Fully done at home, can lead to a decent daily income stream, immediate pay, and it’s fun.

Cons: Relatively high barrier to entry because you have to invest in Legos and set up your own virtual store. It takes many hours of work to get things off the ground.

My fiance and I also run a virtual store where we sell used Lego. We buy bulk Lego from private sellers, wash them, sort them, inventory what we have, and then sell them by the piece. 

I’m not entirely sure I would really recommend this unless it’s something you’re passionate about, as it has been a LOT of work to run the store. And we have to use multiple rooms in our house to store Lego. 

We’ve also had some generous help from relatives, who have helped front the cost of the bulk Lego purchases we get, which helps a lot. 

But we’ve been running the store for a few years now, and it brings in a very steady stream of daily proceeds. And the more we expand the store, the more we tend to make. 

It’s also great to be able to work on the store at home and on our own schedule. 

There are other ways to make money selling used items online, and I know a lot of people make a living selling things on sites like eBay. But again, I really don’t recommend it unless it’s a product you’re really passionate about. 

For example, if you already love thrifting clothes, you may be able to find some cheap but valuable items that you can resell online. But you’ll quickly grow bored and frustrated with how much work is involved if you don’t love the process of sourcing in the first place. 

I will confess that even with all of these jobs, we are often tight on money. But we are very rich in other ways. We choose our own schedules, we are happy, we are able to rest when our bodies need it, and we get to spend a lot of time with our beloved cats. 

Maybe some day I’ll be healthy enough, both mentally and physically, to work full-time again, but for now, I’m just enjoying this chapter in our lives and all the flexibility it gives us.