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Tips for working from home as a freelancer or independent contractor.

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Image © Julie R. Neidlinger. All rights reserved.

In August 2021, I was reading the posts of people in a forum who were concerned that they were about to lose their job because of mandates that they could not comply with. There was a lot of fear, understandably. While that has mostly passed, people are currently losing their jobs because of the economy.


The more I read that forum, the more I realized once again how accustomed I am to:


  • Working from home off and on

  • Always thinking in terms of my own business

  • Not relying on employer/paycheck income as the default option


For most people, I suspect that the typical existence involves being employed by someone else and while there might be a "side hustle" income ranging from MLM products, occasional hired work, or something similar, the general understanding is that your income comes from an employer who is not you.


I've had plenty of jobs, but I've also always had my own business since I graduated from college in the late 1990's and whether it's my sole income or a side income, my entire adult life has been one of thinking in terms of business expenses, quarterly tax payments, and being my own boss.


After reading the fear of losing a job (and knowing what it's like to lose my job), I decided to share what I knew about working from home during a recession or chaotic times.


Here is the information I posted back then, whether you choose to use it for a side job, extra income, or your sole path. I am not functioning as a career or financial advisor, but merely sharing what I've learned. I will try to update as needed based on changes to apps or recommendations. Use at your own discretion.


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Working From Home


Working from home means one of two options:


  1. Employee (W2)

  2. Independent Contractor / Freelancer (1099)


An employee is hired by the company and gets paid a regular wage or salary. Their employer controls their work in areas of how they work, what they do, when they do it, and what they use.


Independent contractors and freelancers are simply paid to do the job. They can’t be restricted or treated like an employee in terms of where, when, and how they work. They are simply hired to do the job, and then they bill the one who hired them for the job.


You can find out more about the differences here. It is not uncommon for independent contractors to slip into employee-type roles without that being the intention. The one hiring you has to be careful they don’t do this.


California’s AB5 law has made it difficult for folks in that state to be independent contractors as employers find it easier to use freelancers from other places with fewer restrictions.


[Note: State laws on labor, taxes, etc. are constantly changing so this is something you have to be aware of. It's a good idea to connect with your state's Small Business Administration, Secretary of State (register your business name), and so on to maintain updates on these things.]


The joy of being double taxed.


If you’ve always worked for an employer, being an independent contractor will surprise you. You will pay both employer tax, and individual tax. As an employee, you only were responsible for one.


You must estimate your taxes and pay them each quarter, otherwise there is a tax penalty. Significant underpayment also has a penalty. I generally estimate 18-20% of my income.


The two types of income.


There are two types of income:


  1. Passive. Income that continues to be earned on work completed in the past with no continued effort or work by you.

  2. Active. Income earned in exchange for performing a service or job.


Passive has the best ratio for time and income.


Examples of this include writing a book or ebook that people can order or download off of your website. You only write it once, yet you continue to make money each time it sells. It also includes selling items through companies like Zazzle or RedBubble, where people order shirts, cards, or mugs you’ve designed directly from Zazzle.


[Note: some companies create shirts and other products for you and ship them directly (called drop shipping). However, this might create the issue of paying sales tax to the state that company is located in because you are warehousing products and are creating what's called nexus. It's a good idea to research this more before going this route to avoid sales tax mistakes.]


Active income requires you to work each time money comes in. This might include writing articles for clients, painting one-off original art to sell, consulting, and so on.

Ideally, you find a way to make passive income. I do both, having active income from clients as well as selling items digital or drop-ship items from my website. Drop-ship means that when people order something, they order it directly from where it is made (e.g. the printer). I don’t have to deal with packaging up orders in boxes and getting them in the mail myself. I prefer to offer mostly digital items for sale on my website so I don’t have to deal with shipping and people can simply pay and download directly.


Potential work you can do at home.


If you aren’t an employee, there are several things you can do from home as an independent contractor, depending on your skills. Some of your skills overlap into a variety of areas; you just have to be creative in thinking about what you have to offer and not limit yourself to work or categories an employer might peg you into.


  • Website design or maintenance. You don’t have to be a coder to do this; if you know how to build and maintain a WordPress site, for example, you could be on retainer to manage someone’s site. Retainer is ideal for this, though if the client demands your time constantly you may have to revisit the retainer amount to make sure it covers the time you put in.

  • Writing. Blogs, articles, books, industry content, stringer reporter for local newspapers (paid per article, sit in on the public meetings and report back, etc.), editing...endless possibilities.

  • Graphic design or art. You can go it on your own, or use a website like Fivvr (which also has writing options, too) to find clients. Some folks use places like Creative Market or other similar platforms to generate passive income from the fonts, clipart, and designs they make. You might offer to be an illustrator for self-published authors who usually need help with cover and interior illustration.

  • Virtual assistant. Whether on your own or through a virtual agency who matches clients with assistants, this is an ideal option. Do internet searches for virtual executive assistant, subscription staffing, etc.

  • Virtual appointment booking. This is getting to be huge. And, in a labor shortage, you could contact places that take appointments (salons, dog grooming, service repair, etc.) and arrange to book appointments from home. If you’re not an employee, but are tracking time, they cannot demand when you are or aren’t online. But offer them a workable low-cost solution so they don’t have to hire someone to sit in their building? You could create your own job. I currently book appointments for a client. I have a browser open with tabs where I manage their booking system, browser-based incoming texts, and so forth. I periodically hop in to respond to clients while I do my writing for other clients, tracking my time via Toggl each time I’m working on booking.

  • Brand based exclusivity. You can generate income by creating a brand-based fan base through websites like Patreon or your own website if it offers membership capability (e.g. Wix, Squarespace). If you’re a podcaster, vlogger, blogger, artist, author, pastry chef, or whatever else, you can create exclusive content that only paid members get access to.

  • Consulting and coaching. If you have specific industry expertise (and even some network connections from your previous jobs) you may be well-suited for consulting with businesses. This might be coaching, writing technical manuals, meeting and discussing issues they want help with, or giving direction on decisions. Areas of expertise might include healthcare, business, aviation, education, design, management, productivity, manufacturing, etc. The key is to find out how to package your knowledge into something people can grasp as to why they should ask for your assistance, and why it’s worth paying for your opinion. You could offer packages that have you on retainer, or time-specific coaching. It can be virtual. It could be in reviewing their contracts and pointing out concerns that you’d know of because of your work experience. Think about all you know!

  • Phone tech help. If you’re good at helping people with tech, you could advertise doing it over the phone or internet.

  • Tutoring/teaching. As more people turn towards homeschooling or deal with hybrid, you could offer to help parents out. Last fall, two families paid me to watch their kids on their “at home” days due to the hybrid setup. The parents had to work and couldn’t do it themselves. You might also offer to teach homeschool pods or organizations something you’re an expert in (e.g. I’ve taught art classes).


I will say that as an art major and having sold art around the world online, it’s not a huge money-maker. I often see people frantic to make money think that they can do it with their hobby art or crafts. I tell you the truth: there’s no shortage of others doing the same thing.


The field of creative competition is really steep. One-off paintings here and there are hard to live off of.


You may be able to do it if you’re very good at painting pet portraits, steampunk, or some other very specific niche, have a known name in the art world, or a unique style or product with its own interesting backstory that stands out, but it’s hard to create art or craft items that people can’t get elsewhere.


Etsy and similar websites are full of amazing creativity and competition. You have to be creative not just in product execution, but in how you market and sell it, in order to find ways to create passive income. Production art is time-consuming with low return on the time investment of making and shipping.


I look at it this way, by asking a few questions:


  1. What’s the shortage? What’s the demand? What do I have or can do that fills it?

  2. How can I sell my idea to people who haven’t considered virtual service options?

  3. What unique benefits or experience am I selling along with the product or service that the client might not understand unless I show or explain it to them?

  4. What backstory, context, or marketing would make my product stand out from similar products or services? What is unique about me that will help sell the product?

  5. Is there anything I can throw in for "free" that adds value to the client at no or little additional time or financial cost to me?


Right now the demand shortage isn’t in arts and crafts of a certain sort.


Certain aspects of the creative industry are packed with people who want to make a dream living being creative. There’s more opportunity in the service or specific industries in content creation (the internet demands a lot of it every day), plugging holes in the labor shortage via booking/assistants, and virtual skilled services.


Sure, everyone wants to paint nice paintings and write creative, fulfilling things to make a living, but you might have to write the service manual for a plumbing company or design newspaper ads if you want to make a living as a writer.


Be ready to cold sell your work and services, doing it in a way where you believe you can help them meet a need enough so that you can sell them on the idea. Don’t worry about all the rejections. There will always be a lot of rejection as you gather up clients or sales venues. That’s normal and says nothing about you.


Determining how you’ll be paid for your work.


The first rule of successfully working from home as an independent contractor is to stay on top of your invoicing.


You may be getting paid:


  1. By the job. You agree to do the complete work for a flat fee, no matter how long it takes or what else arises.

  2. By a measurement of time. You agree to get paid by the hour. You will need to decide how you “round” that time. To avoid bloating my rate, I charge by the quarter hour. That means every time I move into a new 15 minutes, I round up to that quarter of the hour. Some people use half hours, and others charge a full hour even if you’ve only gone ten minutes in. Remember that time includes phone conversations, online meetings. preparation, and the actual work. That’s all part of the finished project. Track it all.

  3. By a measurement of work. Each kind of work has the possibility of being broken down into measurable components. Writers often get paid per word (e.g. 10 to 15 cents). Some artists charge by the size of canvas.

  4. On retainer. You are paid a regular payment (e.g. quarterly) with the understanding that whatever they ask you to do, you’ll do it without tracking time or anything else.


If you are doing different kinds of work, or come to different agreements with clients, you may use a mix of this. I use all of them, depending on the client. That means there must be a system and habit of tracking and managing this or I will fail to invoice correctly or in a timely manner, and will lose money.


It’s always tough to know how to set your pay rates. Internet searches will help you get a better idea of what to charge per word, per hour, or per quarter for the kind of work you’re doing.


Tools to use for getting paid.


There are many ways to get paid, but here are a few options (though they are constantly changing). If you are doing freelance work and are invoicing more than you are taking direct payments, the first two are your better option.


  • Wave Accounting. A kind of free version of Quickbooks, with paid options. I use this for my invoicing. Customers can pay by credit card directly from the emailed invoice. It’s very convenient.

  • PayPal. Invoice and payment processing, but has censored some in the past.

  • Stripe. This is a credit card processor that integrates with your website or other platform. It has also done some censoring of conservatives. 

  • AlignPay. A conservative version of Stripe Dan Bongino was involved in starting.

  • Square. Payment processor, but also offers some website options.

  • Toggl. This is a free timer that makes it easy to track your time for different clients and even different projects within clients. You can generate reports and use these to fill out your invoices.


I also backup all invoices, with information on client, total, date sent, date paid, etc. in a spreadsheet just in case one of the platforms succumbs to cancel culture, closes its doors, or puts some kind of restriction in place. I never like to have all of my data locked into one platform in case it fails, they shut down, or they censor.


Tips for getting paid.


I have a couple of rules I’ve come up with after 25 years of freelancing experience:


  1. I don’t work for free. Unless it’s a close family member or an organization or person I choose to do free work, I don’t work for free. Set up terms on your invoices for 15 or 30 days, with late fee penalty. If a client doesn’t pay and you’ve reminded them repeatedly, never take work from them again.

  2. Free promotion doesn’t pay bills. Many people have tried to coerce me to work for less or for free with the promise that the work I do will get lots of attention and bring me other clients. Don’t fall for this. It doesn’t happen. It’s just a way to get free work. And this isn’t a client you want to deal with again because they’ll keep doing it.

  3. You can fire clients. You don’t have to keep taking work from someone who is always late paying you, demands more time and attention than agreed upon or than you are being paid for (particularly for project-based payment), or makes your life difficult. Your time is money. Don’t waste it on high-energy drain low-financial return work. You can also let go of clients, or not take on new work, if you have a good income/time balance and you don’t want to throw that off.

  4. You can revisit payment terms. If a client begins giving you shorter deadlines than previously agreed, you can ask for a higher rate. If a repeat project is more work than you had originally estimated, you can ask for more. It doesn’t hurt. And it’ll let you know if it’s a client you want to keep, or one who simply wants the most return for the least amount of money.

  5. Watch your exhaustion ratio. If you find that you’re mentally or physically tired and constantly working but not really making much, something is off. You’re charging too little, or you have clients taking up more of your time than they originally promised.


Tools for managing your time.


Both Google and Windows offer built-in basic To-Do lists, note taking apps, calendars, etc. Use them, or find preferred alternatives.


  • Google tools. Calendar, Keep, Tasks. All have mobile apps, desktop versions, and are integrated into Drive and Gmail.

  • Proton tools. More private than Google, there are email, calendar, and drive options.

  • Windows tools. Very similar in offering to Google, these are found as mobile apps as well as in your Live account.

  • Plan. If you struggle getting everything done and like the idea of time blocking, this is a good app. There are other similar apps. If the Pomodoro technique is a better fit, there are plenty of apps for that.

  • Trello. Good for managing clients and projects. There are no shortage of free/paid project management apps (Asana, Podio, etc.) but this is a good one even in its free version. It can sync due dates to your Google calendar to keep you on track with client projects.


I’ll give you an idea of how I manage my time and clients. It might not be your best fit, but it’s an example.


SAMPLE SYSTEM

Some writing clients work with me through Trello, so I use that for their projects. Some use Slack, some use Google chat---the key is to have a systemized way of working with all the tools. Some apps feed directly to my own apps, such as with Trello where the due dates show up on my calendar. I also manually put a To Do in my task app (Google Tasks or Microsoft To Do will work) with a due date and necessary client or project details. I label/archive or delete emails as soon as they are dealt with and my inbox is always near zero. I see it as a work tool and it functions as a reminder of what's not done. Once I've read, completed, or am done with an email, I either archive or delete it.

Completed tasks are checked off the moment I finish. I then go into my spreadsheets and log the client job with all details for the invoicing or payment. I then go to my invoicing program and create the invoice or add to a current one. I don’t always send it right away (generally invoice once or twice a month), but if I don’t make the invoice right away, I may forget and that’s lost income. There’s usually about 10-15 minutes of work (spreadsheet tracking, invoice creation, etc.) for my own business requirements after each client project is done.

When income comes in, I put it on my income spreadsheet that I give to my accountant for tax time. When expenses occur, I put that on my expense spreadsheet. Don’t forget that the credit card fees taken out of your invoice totals when customers use a credit card are an expense you should track!


What works for you will be different, but the point is to make a habit/system that you do as faithfully as a pilot’s checklist so you don’t miss something.


Tips for managing your time.


When you get a lot of clients, especially if they are varied (e.g. writing, art, website maintenance, design, virtual assistant), it can be challenging managing your time. You need to find a way to get the right amount of clients for the time you have where you make the income you need while providing the best outcome to clients.


Don’t be a slave to the work.


Working as a freelancer from home carries the real danger of working 24/7 if you’re not careful. This is especially true if you have clients that are project based, retainer based, and so on. That's a tricky mix of different expectations of the demands on your time. Additionally, clients that insist on controlling how you spend your time are veering into the employee/W2 realm.


  1. Get organized. Client due dates MUST be met. If you’re disorganized, you miss deadlines. You don’t know how rare it is for clients to have freelancers meeting deadlines, but I've been told how nice it is that I meet deadlines. You don’t have to be the world’s greatest writer to keep a client; simply meet or be earlier on deadlines and show you’re reliable, and you’re already far above the rest of the pack. It’s that big of a deal.

  2. Make habits. I have procedural habits that I do when I get new client work, and I have procedural habits that I do when the project is done. This ensures that things get on the To Do lists, get put in the spreadsheet, and get invoiced. Make the habits! Never skip something. Do it the same all the time so you don’t miss an important step.

  3. Choose the tools. Don’t use a ton of different tools if you can help it. Use what you already use or are familiar with. Look for integration between tools, and then, where that isn’t possible, make habits. Keep it as simple and integrated as possible. Sometimes clients come with tools they use in-house and that’s what you’ll have to use with them. It happens. Make it part of your habit.


Time management will make or break you. Build the right habits quickly, or you’ll have a mess.


Building An Online Presence


As censorship, increased fees, subscription fees, and limited free plans continues to grow with a changing economy, this is getting trickier. Depending on what you are selling as a product or service may affect which platforms will allow you to use their tools. Some may include:


  • Weebly. The paid version makes it easy to build a store, and it integrates with Stripe. HOWEVER, they've vaguely announced they will be "supporting" their system through July 2025 so what that means, I don't know.

  • Squarespace. Popular, with modern templates.

  • Square. A payment processor, but also has an online store building option.

  • Shopify. Mostly a website builder for those with items to sell, but has some additional website options.

  • WordPress.com. Has limitations on selling, with paid and free versions.

  • WordPress.org. Requires you to pay for hosting somewhere and install various WordPress elements.


I would NOT recommend trusting a social platform to be your sole online presence. Too many people did that with Facebook and when they were censored or removed, they lost their client contacts and online everything.


Additionally, sending traffic to sites that aren't yours or have no monetization capabilities will impact your bottom line. I blog at Substack, but I also have that content on my website because I'm losing search traffic to Substack that I'd like to bring to my own website where my store and products are.


What your website should have.


Your website should say who you are, what you do, and how to contact you. Provide links or a sample of your work without revealing clients (if applicable). Put a digital version of your skills and CV on there without revealing past employers if it’s a problem.


Make it easy for people to contact you.


Build a website. Get your contact info there. Don’t use a street address. Use a P.O. Box if possible, though it isn't always an option.


Tips For Writers Who Work At Home


Writing is a great way to make income at home. You can write:


  • Blog posts

  • Articles

  • Your own books

  • Ebooks

  • White papers

  • Marketing or website copy

  • Research for content


Because content marketing is big, websites are looking to have a blog that has regular content so that search engines find them. While the search algorithms are always changing, which affects how content is created, this is still a viable option.


Let go of your ego and be a ghostwriter.


It is likely you will be ghostwriting. That is, you will write content, and someone else will put their name on it at the company after they’ve edited and set it up for their blog. That is very common and, if you want the work, you will have to accept it.


I understand there are some ethical qualms writers have. I had them. But now, personally, I prefer it. I don’t need my name associated with the wide variety of content I’ve written. Plus, in an era of cancel culture, my name doesn’t make a company a target and make it likely they’ll stop using me. People don’t know who I write for and can’t target my clients to get me fired.


The difference between vanity press and print-on-demand.


To have passive income with your writing on your own website, you will need your own books. This brings us to the difference between a publisher and a printer. A real publisher never makes you pay up front; they pay you. 


There are a lot of vanity presses out there who will ask you to pay them thousands to print your book. They may say they’ll list it on their website or give you some promotional help. What you get is usually negligible, and you will be forced to aggressively sell and promote your book yourself.


These are not publishers. They are printers. They are a vanity press.


Print-on-demand (POD) is popular because you don’t have to put in much, if any money, up front, nor do you have to buy hundreds or thousands of your books. You can list your book from the printer on your own site, and they will print it each time someone orders it. The only downside is that your book will be a bit more expensive than it would if you had a stockpile of thousands, and that your profit margin may be slightly less.


Nevertheless, the upfront and overall costs to you are next to nothing, and it’s the most affordable way to get a book available for passive income quickly.


Popular POD options:


  • Draft2Digital. It's an older looking website but what I currently use for my children's mystery series books. They make it extremely easy to create ebook and print books, and have simplified the distribution process so that I now recommend them.

  • Blurb. I used this one. Good service, including a free software to layout your book (though I use InDesign). They can list it in Ingram, meaning your book can be bought through them, or it can be bought wherever books are sold (Amazon, Barnes and Noble, etc.). If you want your local bookstore to get your book, you’ll need to be listed on Ingram.

  • Fine Art America. Intended for artists with imagery to sell.

  • Lulu. For those who want to print a book. Been around a long time.

  • Ingram Spark. You’ll get in the Ingram system, but this has a higher learning curve and isn’t as easy to use as others.

  • Amazon/Barnes and Noble. Both have their own book printing service. Amazon is probably the most popular one being used, since your book is immediately listed on their site. However, Amazon has indicated it censors content on its network, and some places don’t want to sell Amazon books in their store.


Building A Support (And Job) Community


There is a great need for platforms for alternative payment, job listings, services, and bartering to be created as the culture and economy shifts around us. Much of what I’ve listed above are “Big Tech” in some form, and are all susceptible to pulling the plug on content or access for users who don’t adhere to groupthink or don't align with their preferred customer.


But it's not just the fear of being de-platformed.


There is a real need to have a support community when you are working as a freelancer or independent contractor and are often alone or at home. Go to an industry-related social media group or forum, or even reddit, and find groups that fit your niche (making sure they are a group that is carefully moderated to be useful and honest without being cruel or full of trolls). Share your experiences and learn from others. Ask and answer questions.


I will continue to share tips and tricks on this blog, so stay tuned for more helpful advice on how to work from home.



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