Own It

Working from home requires discipline, whether that is ignoring distractions during the day or setting your work hours for when you're most productive.

You also have to determine how dependent you are on other people when you're at work. Working from home can be lonely, and increased isolation can even lead to sapped productivity and motivation. It also requires some unpredictable skills, such as the ability to troubleshoot your own IT problems.

Generally speaking, a successful remote worker is somebody who's going to be very comfortable in their own skin and able to have that focus and have the discipline.

And as I wrote earlier, some employers may say they support remote workers, but in reality maybe your manager isn't happy about giving you autonomy over where and when you work. They may equate remote work with less work. With the right discipline from you, it's really all about working hard and having a life.

Have a Specific Place Exclusively for Work for Productivity and for Tax Benefits

It's important to designate a space where you can set your own boundaries. This also means telling your friends and family not to infringe on that location. It's amazing how many people think you're not really working. They call you; they stop by. You have to approach it just like you do if you're going to work.

Not only can an at-home office potentially help your productivity, it can also save you money on your taxes, especially for those who may be self-employed and have to shell out expenses for both Social Security and Medicare taxes.

But you must file Form 8829, “Expenses for Business Use of Your Home.” You can read all the home-office rules in IRS Publication 587.

• My advice: In general, to write off home-office outlays, you must use the “area” for work only and on a regular or constant basis, either as your primary place of business or as a setting to meet with clients or to do paperwork such as writing invoices, ordering supplies, and making phone calls. I suggest you snap a pic of the space, too, so you have a record in case the IRS is ever curious.

If you're a full-time employee at a business, you will only qualify for the deductions if the company doesn't provide you with an office within their workplace. (See the list below of freelancer deductions that may apply to you.)

Make Time for Face-Time

Just because you work alone at home doesn't mean you can't network, as I said earlier. To avoid feeling like you're out of the loop, commute to your employer's local office from time to time to connect with your co-workers. That might mean inviting teammates to lunch or asking for a meeting with your managers.

Don't worry if your employer doesn't have a local office. Try to find other employees working remotely in your area, maybe even those who work at the same company, and invite them to happy hour or coffee. Attend conferences and events in your area if you don't have local co-workers.

Ask Your Manager to Evaluate Your Performance

What are the expectations of me? How will my performance be measured to ensure productivity? These are the two big questions you need to have answered for before you start your job. And you must always keep these issues on the front-burner. Not doing this could cost you.

If you're not working at the office, you can often be out of sight, out of mind for a promotion, or you could miss out on the opportunity to do a cool project. There are lots of ways that you're not top of mind for a manager to pull you in on something. To truly love and be engaged in your job, you want to be able to raise your hand and ask for new duties and new prospects.

When you work from home, you have to communicate more than ever. That includes asking for feedback from your manager as if you were an employee at the office. When you communicate with your manager and discuss your at-home work performance, you're ensuring that they feel they're getting what they need from you, and you're getting the feedback you need from them.

Make Sure You Have Enough Insurance

It's probably a good idea to get an insurance rider in case the FedEx man trips. If you file a homeowner's (or renter's) claim for losses that stemmed from an undisclosed home office, your insurer may not cover it. If you have valuable equipment, you might want to protect it from theft or damage as well.

• My advice: The least expensive way to add insurance is to tack on a rider to your existing homeowner's or renter's insurance policy. The cost might be around $100 a year for around $2,500 of additional coverage. For more, consult the Insurance Information Institute (www.iii.org) in New York City, an industry trade group and information clearinghouse.

Declutter Your Office

When people feel low on energy, often it's because they're not clearing out as they go. Their inbox is overflowing. Their desk is a disaster. Their file drawers are jammed.

Decluttering is liberating and empowering. You are saying, “This is valuable; this is not.” It's a physical, practical way to engage in making decisions about your life and what you want to do with it. Getting rid of stuff brings a new perspective.

Home-office clutter can take a toll on your productivity. You might make it a practice to scan receipts and documents, then shred or recycle them.

Set up an organized filing system. And spend the money to have a great chair that doesn't hurt your back. Arrange furniture so you're not at risk for falling over wires or cords. I make a point of straightening my desk up at the end of every day. Simple habits.

Find a Positive Image to Inspire You

I call mine “going to my happy place.” I close my eyes and visualize a green field in the Virginia countryside with a sweeping view of the Blue Ridge Mountains. I go there in my head and sit. It calms me down. I feel peaceful and my attitude shifts.

If you want a more concrete focal point, tape a picture of a special image on your office wall, away from your computer and phone. That way, you'll have to turn to look directly at it, which can be transporting. The very action of directing your attention away from your work opens up the door in your day for a respite, a restart, and a new view. It's reviving and centering at the same time.

Pay Attention to Your Eyes

Avoid eyestrain by placing your desktop or laptop monitor just above eye level and an arm's length away. And supplement any natural light in your home office without reducing the contrast on your computer screen.

Set up Your Computer and Desk to Prevent Repetitive-Motion Injuries

Things like good lighting and comfort are not to be ignored when you're spending hours in front of your computer.

Keep your keyboard and mouse level with where your elbows are when you're seated, as I mention above. Sometimes I sit on a couch and stretch out, but I always place a pillow beneath my laptop to bring it to the right level. I also place a rolled towel or pillow in the small of my back to keep me from hunching over.

A healthy and productive remote work setup is essential. Ergonomics matters. From picking the right monitor, laptop, and noise-cancelling headphones, to your chair and even a laptop stand can make a huge difference to your productivity, your physical health, and your mental well-being.

To save on some psychological frustration, make sure your Wi-Fi connection is as robust as you can: Shift your router or move your workstation near to get an enhanced connection.

Listen to your body. I've talked to many work-from-homers who complain of terrible neck pain or aching backs. Are you, like me, guilty of sitting on your sofa, hunched over your laptop, working for hours lost in the vacuum of time? That's a recipe for long-term physical ailments such as carpal tunnel syndrome, muscle strains, and lower back injuries.

There are simple solutions to help prevent this, among them ergonomic desk accessories and office furniture. I've found that, in many ways, it often comes down to good posture. (I taped a note to my mouse to remind me. It simply says: Shoulders!)

One easy fix is elevating your computer screen to prevent you from hunching over, as I do with my makeshift pillow, but there are better ways, so I would advise asking around or checking with your employer or even an office supply store manager to see what they recommend. A laptop stand, for example, with a remote keyboard and mouse, can help keep your arms in a 90-degree position while you type and can help combat the strain on your wrists.

Don't Neglect Your Retirement Savings

Freelancers without an employer retirement plan can set savings aside in a traditional IRA (Independent Retirement Arrangement), a Roth IRA, a simplified employee pension (SEP-IRA), or a solo 401(k). For more details, go to the IRS website (irs.gov/retirement-plans/individual-retirement-arrangements-iras).

With a traditional IRA, your contributions may be deductible if you aren't covered by another employer plan, and the growth is tax-deferred. But if you have a spouse covered by a plan, income limits may apply; for more details, check the IRS website.

With a Roth IRA, your contributions are not tax-deductible, but your money grows tax-free, and you'll pay no taxes on your distributions as long as you follow the withdrawal rules. (Normally, you must have held the account for five years and be 59½ or older.) There are income limits for Roth IRAs.

A simplified employee pension or SEP-IRA is a tax-deductible retirement plan that's appealing if you're a single employee. You can typically contribute up to 25 percent of your compensation.

A one-participant or solo 401(k) is a retirement plan for self-employed people without employees (a spouse is an exception). You can usually sock away pretax, up to 25 percent of your pay, with a cut-off contribution limit that fluctuates annually.

These retirement accounts are offered at most mutual fund companies and brokerage firms. They're easy to set up online: enter your bank information, how often you want to invest, and the amount you want to transfer.

When it comes to hassle-free tax and retirement planning for self-employed workers, repeat this mantra: automate, automate, automate.

Pay Attention to Taxes

If you work as a contractor, and not as a full-time employee, you are probably responsible for shepherding your taxes without someone parsing them out paycheck by paycheck.

I always balk when it's quarterly tax time again. I know that dreaded feeling. Still, send in that check to avoid a possible penalty from the IRS for underpayment of taxes. Independent contractors who are paid only for work performed, in general, must pay federal taxes and FICA on their income. You will probably need to pay estimated taxes throughout the year instead of once a year on April 15.

My advice: Go to the IRS Self-Employed Individual Tax Center (irs.gov) to help you understand how to pay federal taxes as an independent contractor. Depending on the location of your home office, you may be required to file state and local income and business taxes as well.

Diligent recording of business expenses is essential. The easiest way to differentiate personal from work expenses is to use a designated bank account and credit card for your work-related outlays.

Fluctuations in pay make it tricky to set aside the correct amount for yearly tax bills. And work-from-home job opportunities often fall under the contractor or self-employed category, so an employer may not withhold taxes for you, or allow you to qualify to participate in an employer-sponsored retirement plan.

The process can be a scramble. It's not uncommon for self-employed workers to have to write big checks in April to cover federal and state income taxes. Then they have to write another one to fund their retirement plans.

The chief reason for the sticker shock: Freelance pay can fluctuate from year to year, so it can be difficult to estimate your annual total income in advance. One year you might work a seasonal job, for instance, and the next year tackle a series of part-time or contract assignments. Those fluctuations make setting aside the correct amount for your yearly tax bills tricky. Meanwhile, how much income you collect also directly affects the sum you can set aside in many retirement accounts.

According to a recent T. Rowe Price study, 26 percent of Boomers and 32 percent of Gen X respondents work independently in some capacity.

Based on your previous year's federal tax return, you (or your accountant) must figure out the total amount you will owe Uncle Sam on April 15, and how much you should pay in quarterly estimated taxes throughout the year. If your state has an income tax, you are also typically required to make estimated tax payments. Certain cities, such as New York City, also collect income tax as part of your state filing, so check with your accountant if your employer doesn't automatically withhold this tax for you.

For federal returns, you can find the address for filing your payments and due dates as part of Form 1040-ES. You may face a penalty if you didn't pay enough estimated tax for the year, or if you didn't make the payments on time or in the required amount. You can avoid the penalty as long as you pay at least 90 percent of the tax for the current year, or 100 percent of the tax you owed for the previous year, whichever is smaller.

Even with the precarious nature of a freelancer's finances, when you're disciplined and automate the withdrawals from your paychecks on a regular basis, you can avoid the springtime surprise of a steep tax bill and save for retirement one paycheck at a time. Think cruise control.

If you pay your taxes via electronic filing, for instance, you can schedule all four estimated future quarterly payments at once and save yourself the headache of potentially forgetting to mail a check.

• One important caveat: When it comes to taxes, it's always an individual calculation. You should talk with a professional tax adviser to review your particular situation.

There are some potentially big savings for remote workers with business deductions. Here's a quick rundown of how the tax law could benefit those who work from home as freelancers or contractors.

• Qualified business income deduction. Between now and 2025, many independent contractors may be entitled to lop off a tax deduction of 20 percent on qualified business income, providing you earn under certain preset amounts. Check with the IRS for current limitations. The details are complicated. It's intended to apply to “pass-through” business income for freelancers who have set their businesses up as partnerships, limited liability corporations, S corporations, or sole proprietorships. The nonpartisan Tax Policy Center provides a detailed analysis of the complex sweetener.
• Standard deductions. The standard deduction is $12,200 for single filers and $24,400 for couples for 2020. The amount is set annually. If you're self-employed and fit the requirements, you can claim the standard deduction, plus the qualified business income deduction, and also deduct eligible business expenses such as rent, professional fees, training and education, licensing and certification fees, and supplies and travel costs.

Freelancers typically receive a form 1099-MISC, “Miscellaneous Income,” from each client and report 1099 income—as well as expenses for home offices, travel, and supplies—on Schedule C, which is attached to form 1040. Here's a rundown of the six big tax deductions for expenses that freelancers may qualify for this year.

• New equipment write-off. The tax law currently allows for the immediate expensing and a bonus depreciation percentage of 100 percent for qualified property acquired such as a new computer, software, office furniture, and even a car or truck, if the item was purchased and placed into service after September 27, 2017, and before January 1, 2023.
• Business expenses. Deductible expenses can range from business meals and travel to gasoline for your car to postage and shipping to rent for the artist studio where you create jewelry or other crafts.

  You can generally claim 50 percent of the cost of meals that you purchase for work purposes. Deductions claimed for client-entertainment costs (such as tickets to a sporting event or a concert) are not allowed. However, you typically can write off 50 percent of the cost for treating your client to a meal where you discuss business. Work-related travel expenses to meet with a client or attend a conference across town or across the country are 100 percent deductible.

• Medical expenses. For most freelancers, health insurance and medical bills are a weighty part of your budget. You may deduct only the amount of your total medical expenses that exceed 7.5% of your adjusted gross income. You figure the amount you're allowed to deduct on Schedule A (Form 1040 or 1040-SR). If you bought your own health insurance policy, your medical expenses will also include insurance premiums. If you're self-employed and pay supplemental Medicare premiums, such as for Part B coverage, you can deduct these premiums.
• Education and training. You can write off your costs for work-related education directly from your self-employment income as a business expense. These outlays include tuition, books, supplies, and transportation to and from classes, according to the IRS website. The expenses are deductible only if the education “maintains or improves skills needed in your present work.” If you're going back to school to switch careers, you're out of luck. The lifetime learning credit, though, offers a tax credit of up to $2,000 to cover up to 20 percent of annual tuition, and you don't have to be enrolled in a degree program. (The benefit phases out at specific income levels that adjust annually. For more, see IRS Publication 970.)
• Automobile expenses. You can deduct the number of miles you drive in your car for business, multiplied by the IRS’s preset standard mileage rate of 57.5 cents per mile in 2020. This figure is reset annually. Keep a mileage log; you'll need it if you're audited. (Take a picture of your odometer at the beginning and the end of the year for backup documentation.) Your other option is to subtract your actual car expenses. These include depreciation, gas, oil, tolls, parking fees, insurance, lease payments, registration fees, repairs, and tires. For more, IRS Publication 463 provides details.
• Your home office. If you work from your home or use part of it in your business, you should be able to deduct home-office expenses that are prorated, based on the size of your home and office. These are costs such as your mortgage or rent, insurance, and utility bills. If the square footage of your home office equals 10 percent of your home's total, you can claim 10 percent of its expenses. You might opt for the “simplified option” rule, which allows you to deduct $5 per square foot of your home office on your return, with a maximum write-off of $1,500 (based on a maximum of 300 square feet). You may want to take a picture of the space so that you have a record, in case the IRS does examine your return. To get the deduction, you must file form 8829, “Expenses for Business Use of Your Home,” along with your Schedule C. You can read all the home-office rules in IRS Publication 587.

In general, to write off home-office outlays, you must use the “area” for work only and on a regular or constant basis, either as your primary place of business or as a setting to meet with clients or to do paperwork such as writing invoices, ordering supplies, and making phone calls. I suggest you snap a pic of the space, too, so you have a record in case the IRS is ever curious.

(As noted above: If you're a full-time employee at a business, you will only qualify for the deductions if the company doesn't provide you with an office within their workplace.)

Consider a Financial Management App

There are several money management apps designed to help you plan for taxes and retirement savings that you might want to investigate. Here's a look at a few of them.

• Self-Saver (self-saver.org) offers a tax calculator, automated withholding on 1099 income, expense itemization, and quarterly filings to the IRS.
• Qapital (qapital.com) is an app that allows you to move a percentage of a deposit from your bank account to an FDIC-insured account at a partner bank, where it is held by Qapital. You can take the money from the account and transfer it back to your checking account whenever you opt to do so.

The app, designed in partnership with Duke University behavioral economist Dan Ariely, lets you name a savings goal and then apply “rules” to help you get there, using funds from your linked bank account. For example, say your goal is to fund an IRA; your rule might be to divert 30 percent of any deposit you get above $1,000 to your selected savings account. Then you shift the funds to your IRA at a brokerage or fund company when you're ready. There is no fee to use the app.

• Digit (digit.co) offers a smartphone app that connects to your checking account, analyzes spending habits, and every few days automatically sweeps a small amount of funds—typically between $5 and $50—into an FDIC-insured bank-level encrypted Digit savings account. Your funds can be shifted at any time to your personal checking account within one business day.
• Intuit's QuickBooks Self-Employed (quickbooks.intuit.com/self-employed) tracks business expenses by scanning bank accounts and credit card transactions. It also calculates mileage and can be used to send invoices.
• Expensify (use.expensify.com/self-employed) gathers expenses that need to be reimbursed, and you can create files to integrate with accounting software such as QuickBooks. The time-tracking can provide details of miles traveled and hours spent on a project.
• Shoeboxed (shoeboxed.com) lets you scan and organize uploaded receipts under categories of reimbursable or deductible. The app uses a GPS signal to track your mileage when you leave your home office for a business appointment.
• Do it yourself. You can also set up a comparable do-it-yourself automated process with your own bank. Each April, you can ask your accountant to tell you the amount you need for quarterly tax estimates based on the previous year's return. You divvy it up to sweep out a certain amount each month from your business checking account where your paychecks are deposited (usually electronically) and move it into a dedicated money market account. Not perfect, but at least it automates the process, and the funds are there when you need to tap them to pay quarterly estimates.

For retirement fund contributions, you likewise electronically sweep a preset amount of funds each month from your business checking account into a money market fund and make your annual contribution at tax time. You might also make regular contributions routinely to a retirement account you already hold and boost it at tax time, if you have the option.