Freelancing and Self-Employment With Chronic Illness

Work from home. Set your own hours. Take a break when you need one. If you live with chronic illness, the usual selling points of self-employment can sound an awful lot like accommodations.

And sometimes, they are. But there’s a catch: you also get to be the sales team, bookkeeper, project manager, and person figuring out what happens when you can’t work.

Congratulations on all your new jobs! Being able to move a deadline is helpful; being able to pay rent after moving it is another question entirely.

I’ve been freelancing since 2013, with periods of employment and combinations of the two along the way. Chronic illness has been with me through all of it. I value having a say in how I work. But I also know that being allowed to take time off and being able to afford it are two very different things.

So, let’s look at what independent work actually asks of us and where we can make it more livable. Whether you’re considering freelancing or trying to keep an existing business going, start wherever you need help. The rest will still be here when you have the energy for it.

First, who gets to choose?

Freelancing can be an access strategy. It can also be a privilege. Savings, another household income, health coverage, equipment, professional contacts, and somewhere safe to work can all change how much risk a person can take.

Some people choose self-employment because they want it. Others come because jobs keep excluding them, accommodations fall short, or a schedule becomes impossible to sustain. Plenty of us have a bit of both.

Keep that in mind when someone tells you what worked for them. Waiting three months for a client to pay looks very different when you have another income covering the bills. If you need money this week, that same advice may be useless. No amount of entrepreneurial enthusiasm changes the payment date.

The useful question is: What arrangement gives you enough money, access, and room to live, with the resources you actually have?

Map the work before choosing a label

“Freelance,” “contract,” and “self-employed” can describe very different working lives. An assignment through an agency, an ongoing client relationship, a one-off project, and a small business selling digital products or services don’t ask the same things of you.

Before you decide which label fits, pull the arrangement apart a little. Who brings you the work? Who gets to decide how and when you do it? And, of course, when do you actually get paid?

Here are the layers I’d look at:

• Relationship: Direct client, agency, platform, customer, or employer.
• Classification: Employee or independent contractor. In the U.S., W-2 and 1099 forms show how a payer reports your work for tax purposes; by themselves, they don’t determine your legal work classification.
• Payment: Hourly or daily/per diem, per project, per deliverable, or retainer.
• Control: Required availability, meetings, location, methods, and deadlines.
• Risk: Unpaid preparation, cancellations, revisions, delayed payment, and gaps between assignments.

An hourly arrangement may offer predictable income and fit your needs. A project fee may give you flexibility but leave you absorbing extra revisions. A retainer may provide continuity, or it may purchase so much availability that you effectively lose control of your week. None is automatically the accessible option.

A note on classification: worker classification rules vary by location, and federal and state standards can change. Check current requirements where you work.

Can you do the work in the way it will be done?

You know you can do the job. Great. Now, can you do it under the conditions that come with it?

You might be an excellent designer and struggle with three video calls a day. You might be able to finish a writing project comfortably over two weeks but struggle when every assignment becomes a rush job. You might enjoy selling clothes and find that photography, storage, repairs, packing, and getting parcels to the carrier take more out of you than the selling itself.

Before accepting work, look at the whole route from inquiry to payment:

• How much preparation and administration does this require?
• Which parts must happen at a particular time or place?
• How many people need to review or approve it?
• What physical, cognitive, sensory, and social demands are involved?
• What does it cost afterward, including recovery?
• What can move when your capacity changes?

Try answering those questions for an ordinary week, rather than the unusually good one where you suddenly think you can do everything. It’s easy to make plans with that version of yourself. Leave some room for the version who needs to lie down.

You can test a smaller version when that’s possible: one paid project, a short engagement, or a limited number of orders. The test should tell you about the actual workload, including the parts nobody put in the job description.

Still figuring out your work preferences?

The question here is how to make those preferences part of an arrangement you can actually sustain.

Follow the money all the way home

Let’s talk about getting paid. The fee matters, obviously, but so does everything that happens before it reaches your bank account.

You do the work, send it in, wait for approval, invoice, and wait again. If the payment clock starts only after someone approves the final version, an apparently short payment term can stretch much longer than you expected.

Before you begin, establish the scope, fee, payment trigger, due date, revision allowance, and what happens if either side delays or cancels. A deposit or payment at agreed milestones may reduce the amount of work you finance yourself, where the client and arrangement allow it.

Some common payment terms to keep in mind and how you can use them:

• Due upon receipt: Perfect for project deposits and outstanding payments, it's the polite way of saying "Here's your hat, where's my money?"
• Net X days: You'll see and hear these when payment and timeline discussions come up. Net 30, 45, and 60 days (one to two months) are common. Net 7 to 14 days (one to two weeks) is my nirvana.
• Daily/Per diem rate: A rate for a day's worth of work, usually based on the hourly rate and used for temporary in-person work, projects, or meetings.
• Project rate: A flat fee for an agreed scope or deliverable, such as a set of articles with defined research and interview work.
• Retainer agreement: An ongoing client agreement with an agreed-upon cadence (e.g. monthly), usually with set deliverables or an hourly cap.

And don’t forget the work around the work. If a two-hour task takes another two hours of preparation, emails, and invoicing, you’ve used four hours. Your body doesn’t stop counting just because the client does. That lovely project fee may look a little less lovely after the fifth round of revisions.

Retainers need the same attention. What does the recurring payment include? What costs extra? When can the client expect to hear from you? “Ongoing support” is a very small phrase that can swallow a very large amount of your week.

You don’t have to love hourly billing, project pricing, or retainers. You do need to understand what each arrangement asks you to carry. If you need income quickly, the time between agreeing to work and receiving usable money belongs in the decision.

Need some capital to get your freelance business started?

PNC’s guide to loans for the self-employed offers a starting point for what lenders may ask you to document; check current requirements with the lender.

Find clients without making marketing another full-time job

Finding clients can become a job all by itself. Between networking, applications, portfolio updates, and the suggestion that you should post on every platform ever invented, you could easily run out of energy before you get to the paid work.

Start with a few routes you can realistically keep up with: former clients and colleagues, referrals, agencies, professional communities, relevant listings, or direct introductions. Which ones put you in touch with people who actually need what you do? You can add more later if you want to.

If working alongside other people helps you, Social Connection in Remote Work and It’s Time for Coworking 2.0 explore community workspaces. Consider whether one fits your access needs, sensory preferences, budget, and travel options.

Make the next step obvious. What do you do? Who is it for? Where can someone see your work? How do they contact you? A clear page or a few relevant samples can answer those questions before a call.

If direct outreach suits you, a letter of introduction can open the conversation without requiring you to invent a project for every prospective client. It introduces your services; it isn’t a journalism story pitch.

A five-sentence letter of introduction (LOI)

I like a short letter of introduction because it gives you something you can adapt instead of starting from scratch every time.

The five-sentence approach comes from one of the industry's best freelance writers, Jennifer Goforth Gregory, whose template I share in my LOI guide. Here’s a version for a freelance designer:

Hi [Name], do you work with freelance designers on your client projects?

I’m a designer who creates clear, accessible presentation materials for small organizations. I can help with slide layouts, reusable templates, and redesigning existing decks.

You can see three relevant examples here: [portfolio link].

If you use outside support, who would be the best person to contact about joining your freelance roster?

That’s enough to tell someone what you do, show them your work, and give them a way to respond. And if an introductory call takes more out of you than an email, you can make email the next step. An introduction doesn’t have to turn into an appointment.

LOIs are one way to reach potential clients, but they’re only one option.

Prefer looking for existing work opportunities?

Accommodating yourself is still work

Unfortunately, becoming your own boss doesn’t come with an accessibility department. You still need support; now you may also be the person finding it, paying for it, and explaining how it fits into the work.

You may need written updates, fewer meetings, a different workspace, longer lead times, assistive tools, or help with a task that drains you.

Some changes are inexpensive: putting communication preferences in your onboarding email, leaving space between appointments, or using a reusable checklist. Others cost money or require a client to cooperate.

Build those needs into the arrangement early, where you can. “I provide updates by email and schedule calls in advance” is a working process. You don’t have to turn every explanation of your process into a medical disclosure.

There is more to say here than one section can hold. I’ll cover self-employed accommodations in a separate TCW piece, including the limits of control when clients, platforms, money, and deadlines are involved.

I’ve shared some of the tools that have helped me in my accessibility tech guide. Your list may look completely different. Start with what you need help doing, then look for a tool or process that helps you do it. You don’t have to buy a subscription to make your work more accessible.

The smallest business still needs five functions

You can keep the setup small. These are functions to cover, not five departments to build or five apps to buy.

1. Bring work in. Keep a clear offer, relevant examples, a contact route, and a simple record of leads and follow-ups.
2. Agree on the work. Record the scope, price, timing, communication, revisions, and payment terms.
3. Deliver it. Keep the files, tasks, deadlines, approvals, and handover somewhere you can find them.
4. Handle the money. Invoice, follow up, record income and expenses, and keep the information needed for taxes and other reporting.
5. Keep the business workable. Build in rest, backup plans, and ways to adjust when your capacity changes.

The real test is whether you can use it when you’re tired. Where’s the deadline? Did that invoice get paid? What needs attention first? If answering requires opening six apps and remembering which one you updated, there’s probably a simpler way.

What happens when you can’t work?

Here’s where “just set your own hours” starts to fall apart. What if there aren’t any hours you can work right now?

You can love your work, take your commitments seriously, and plan carefully and still get too sick to do it. For those of us with chronic illness, that possibility belongs in the business plan. We need something to fall back on besides hoping we feel better by Monday.

Write down what can pause, who needs a message, what someone can take over with your permission, and what you need to close out. Keep a short client update ready so you don’t have to compose one from scratch when everything is hard:

My capacity has changed, and I need to adjust the schedule for [project]. I can offer [revised delivery date or reduced scope]. Please let me know whether that works for your timeline so we can agree on the next step.

Then look beyond the deadline. Which bills continue? Which payments are already due to you? What support is available? Who can help with the smallest necessary task? If there is no financial cushion, that belongs in the plan as a real constraint.

A plan for interrupted work should also make room for changing the arrangement: reducing the workload, combining income sources, taking employment, pausing the business, or leaving it. You cannot promise your body uninterrupted production.

And when you come back? Start small. Find the current project file. Send one message. Figure out what still needs doing and what no longer does. You don’t have to clear the entire backlog before you’re allowed to work again.

Build a self-employed benefits package

Then there are the benefits. Or, more accurately, the benefits you have to find for yourself: health coverage, time off, retirement savings, and support for longer stretches without income. Choosing your own hours doesn’t automatically provide any of them.

Before you start comparing options, take stock. What do you already have through your household, another job, or a benefit program? What’s missing? What can you afford? And which missing piece is making life hardest right now? Sometimes we get to pick and choose. Sometimes we’re trying to cover the essentials with money that simply isn’t there.

Time off needs space in the calendar and some way to cover the money that would otherwise come from working. Retirement needs a plan that can change with income and health. Neither becomes easy because you are allowed to choose your own hours.

When I wrote my self-employed benefits guide, I treated health coverage, retirement, and time off as parts of the same package. I also separated planned time off from slow-season savings. Those answer different questions: How do I pay for time I intend to take away from work? And what happens when the work itself dries up?

For the retirement side, I’ve already put together a guide to retiring when you’re self-employed. It’s a starting point for the options, though the financial figures are dated. Check current official guidance before using its contribution limits or eligibility rules.

You may keep the money together, but naming its jobs helps you see what it can actually cover. The same savings cannot pay for a holiday, a month without clients, and an extended illness all at once. If there is no money to set aside yet, start by recording the gap. A budget can show a shortfall; it cannot make the income appear.

For chronic workers, the next question is how these protections hold up when capacity changes for longer than expected. Which costs continue? Which support depends on a partner, employer, client, or benefit program? What becomes harder to access when your income changes? That is where this field guide needs to go beyond a list of accounts and policies.

You're allowed to change your mind

Self-employment is a way of arranging work. It is not a personality or a jail sentence.

You’re allowed to like freelancing and want a dependable paycheck. You’re allowed to build a business you’re proud of and later decide it asks too much of you. Maybe employment helps fund the independent work. Maybe independent work lets you reduce your employed hours. Maybe you need to stop for a while. None of those decisions erases the work you’ve done.

For those of us living with chronic illness, the goal is to find work we can do without spending everything else we have on doing it.

Living is, after all, the whole bloody point.