Paying You: How to Pay Yourself When You’re the Business Owner

Freelance consultants and business owners dedicate a considerable chunk of mental bandwidth to thinking about how to generate business, because the top line matters. We think a lot about making money, but we may not devote much time to thinking through the mechanics of paying ourselves once the money arrives.

Sole Proprietors and single person LLC owners may consider the self-payment process a no-brainer—as invoices are paid, one simply deposits the money into the business bank account. But like so may actions that seem easy at first glance there is usually a right way, a smart way, to pay oneself as a self-employed person.

So—are you on your business’ payroll or do you take payments from your business in the form of owner draws? Do you and your business partners take guaranteed payments (salary)?  Are you paying yourself too much or not enough? How can you tell? Also, where in your business financials are the payments recorded?

Business type Payment Tax return Payroll Tax

Sole Proprietor Owner’s draw         1040/ Sched. C     Yes                                

Single LLC Member draw 1040/ Sched. C Yes

Multi LLC Member share 1040/ Sched. K-1 Yes

S Corporation Dividend/ wage 1040/ Sched. K-1 Yes

C Corporation Dividends 1040 dividends not on dividends

Sole Proprietor

Business owners and Freelancers who adopt this, the default business structure, pay themselves through an owner’s draw, i.e., the amount of money taken from business earnings, after expenses and taxes, by the owner for his/her personal use. The payment is called a draw because money is drawn out of the business.

Sole Proprietors usually take draws by writing a check to themselves from their business bank accounts. Smart Sole Proprietors will then deposit that check into a personal bank account and avoid co-mingling business and personal funds, a practice that inevitably leads to accounting and tax complications. The owner’s draw doesn’t affect business taxes because the net income has already been taxed. The draw is also not a business expense. From an accounting and tax perspective, the owner’s draw is income distribution. Owner draws are recorded on the Balance Sheet.

Limited Liability Company (LLC)

LLC owners, who are known as members, are not (always) considered employees of the entity and therefore they do not (always) take a salary as would an employee. LLC members, especially single member entities, usually pay themselves with a member’s draw, which is taken from the member’s capital account (business bank account). Multiple owner LLCs are considered to be partners in the business and pay themselves with a member’s share distribution, also taken from the member’s capital account. 

While members may periodically draw from their capital account, a draw is in reality an early withdrawal of anticipated year-end profits, a goal that is perhaps at top-of-mind at multi-member LLCs. Whenever a member receives a draw during the year, his/her capital account decreases, but if the business shows a profit at the end of the year, the member’s capital account will increase in accordance with the percentage of ownership. If a member owns 25 % of the LLC, then s/he can expect to receive 25 % of year-end profits. Single member LLCs own 100 % of the entity and are entitled to 100 % of the profits. Member draws are recorded on the Balance Sheet.

A working member in a multi-member LLC has the option of either receiving a guaranteed salary amount as an LLC employee, or paying oneself with a member’s share distribution, as will a single member LLC owner. Members who are strictly silent partner investors and do not work in the business are not entitled to period draws, but will receive their member’s distribution of profits in accordance with their ownership percentage at the end of the tax year. 

The member salary, known as a guaranteed payment, is not based on the percentage split agreed upon in the LLC operating agreement but based on the work the member performs in the business. Unlike member distributions, guaranteed payments are recorded on the Profit & Loss (Income) Statement and are taken from business profits.

The LLC must be diligent about filing the correct tax forms on behalf of members and maintain accurate accounting histories for everyone throughout the year, to reflect member payment choices. Members paid as LLC employees must file IRS Form W-4 to calculate the amount of payroll tax withholding taken from from each paycheck. The member is then treated as a W-2 employee of the LLC. If the member is paid as an Independent Contractor, then s/he must file IRS Form W-9 with the LLC and the LLC must file IRS Form 1099-MISC by the end of the year. All member draws or distributions are deducted from the amount of profits assigned to the capital accounts, based on ownership percentages.

Corporations

An S Corporation is in reality either an LLC or C Corporation that has elected for special tax treatment with the IRS. S Corp income, losses, deductions and credits pass through to its shareholders’ personal IRS Form 1040. Shareholders then report the business’s income and losses on form 1040 and are taxed at their individual income tax rates. C Corps are subject to double taxation—a separate corporation tax and when dividends are paid to shareholders, that amount is recorded on IRS 1040 (but there is no payroll tax).

S and C Corporation owners who work in the business pay themselves a regular “salary” and also distribution payments. S Corp owners are usually employees of the business. Owners who work as employees must be paid a “reasonable salary” before profits (dividend distributions) are paid and the salary is subject to payroll taxes. The IRS has guidelines that define a reasonable salary, based on job responsibilities. Salaries are generally taken from business profits.

Owners of C Corps can elect to pay its shareholders a cash dividend, which is a distribution of company profits. However, the C Corp board may choose to retain either the entirety or some portion of business net profits and decline to pay a dividend in a given quarter or year. If a dividend is paid, that amount is added to income reported on the shareholder’s personal IRS Form 1040. The company records dividend payments on the Balance Sheet.

S corporation owners have been known to request that their corporations pay them little or no salary, since salaries are taxed, and instead take payments as dividend distributions, which are not taxed. The IRS has stepped up enforcement on this issue and in 2000 audited thousands of S Corps whose owner the IRS concluded had received a suspiciously low salary and very generous dividend distribution, in an apparent attempt to evade payroll taxes by disguising their salary as corporate distributions.

Thanks for reading,

Kim

Photograph: Pay day on a U.S. Navy cruiser (1942)

2019 Tax Prep + Deductions

The Holidays are upon us and there is so much to do! Shopping (remember to buy gifts for special clients), holiday cards (everyone you’ve worked with over the past 5 years will receive one), parties and catching up with dear friends and colleagues. You may also find it advantageous to change your health insurance plan before open enrollment ends in your state, or make a retirement account contribution before January 1. It also makes sense to review the years’ invoices to calculate gross revenues and decide how to handle December billings.

Especially for invoices that are due on or after the 15th, should you keep those earnings in this year and invoice at the usual time, or invoice on January 2 and push earnings into next year? If you earned more than expected this year, consider pushing earnings forward, to limit taxable income. You could also make a retirement plan contribution, if you haven’t reached the year’s maximum amount (whether you bill clients in this year or the next). Here are a few more tax season preparation tactics to consider:

Find all invoices and confirm that they’ve been paid. Send a reminder to those clients who have not paid up. As noted above, calculate your revenues (i.e., income before deductions) and determine whether to invoice on time or later. Of course you can do other good things with your windfall, if you have one, such as registering for a class that will be held in the new year and paying for it now (and taking the deduction in this tax year).

Calculate your self-employment tax. In addition to our regular income tax, Freelancers are responsible for paying the 15.3 % self-employment tax levied on the first $132,900 of net income and 2.9% of net income beyond that amount. This tax represents the Social Security and Medicare taxes that traditional employees have taken out of their paychecks automatically. The amount includes as well the employer portion of those taxes, since Freelancers are considered both employer and employee.

Freelancers are able to write off business expenses for these categories:

Business-related travel, meals and lodging

Membership in business and professional associations

Office required equipment or materials

Home office. Most Freelancers work from home and are therefore eligible to take this deduction. The Internal Revenue Service allows independent workers to write off a corresponding percentage of rent/mortgage and utilities when our home is also our office. Get out your measuring tape and determine the dimensions of your workspace as a percentage of the square footage of your home to calculate the amount of your deduction. Be advised that office space must be used exclusively for self-employment work. One cannot, for example, “borrow” a child’s bedroom from 9:00 to 5:00 and consider that your home office.

Office equipment and supplies. One of the downsides of being a Freelancer is that we are unable to use an employer’s computer, scanner, printer, staples, or paper clips. We pay for that stuff out of our own budgets. But since we need certain resources to do client work, the IRS allows us to deduct their cost from gross sales revenues. To avoid IRS problems, keep your business and personal expenses separate. For example, check in with a smart accountant before you decide to deduct your cell phone or Internet service while using them only partly for work.

A real benefit for those who will buy office equipment is the Section 179 Deduction, which allows the business owner (or Freelancer) to write off the entire purchase price of qualifying equipment for the current tax year, up to $1,000,000. Qualifying items include office furniture, computers and software programs such as QuickBooks and InDesign.

Travel, meals, lodging. This category of deductions is the most confusing for Freelancers and business owners. We are allowed to deduct the costs of traveling to our work assignments, client meetings and conferences, including gasoline, tolls, parking, trains, planes, buses, or Uber/ Lyft. One cannot deduct costs associated with commuting to your separately leased or owned office space. Hotel/ airbnb/ B&B rooms are 100% deductible, except for personal expenses such as movie rentals or the mini-bar.

The cost of taking clients and prospects out for a meal are deductible at a 50% rate, while costs associated with company-wide parties, picnics and restaurant meals when at least half of your employees attend are 100% deductible. Keep all receipts —take a picture with your phone as back-up.

As with all Freelancing expenses, deductions must directly relate to one’s business. We cannot write off the tuition for a workshop on baking or flower arranging if one is a website developer, nor can we write off education that trains us for a new occupation. But if we take classes to earn certifications in our field or to enhance business knowledge, then we can typically write off all associated costs. The same is true for any licensing, registration, or certification costs that we incur.

Thanks for reading,

Kim

Illustration: Henry Holiday The Tax Collector at Work, created for the Lewis Carroll poem The Hunting of the Snark (1876)

2020 Health Insurance Open Enrollment: The Facts

Hello Freelancer Friend, the enrollment period for health insurance is here, now through mid-December (in most states). Because health insurance is a vital topic, I decided to defer to an expert and pass along info compiled by Les Masterson for Insure.com. For more detailed information, please visit the site. https://www.insure.com/health-insurance/open-enrollment-for-individual-health-insurance.html

We have 6 weeks to make a decision on individual/ family health insurance or the Affordable Care Act (ACA) exchanges plan (in most states). We can sign up for health insurance on our state’s health insurance exchange or individual marketplace only during the annual open enrollment period, unless one has a “qualifying life event.” Those events include getting married or having a baby.

If buying health insurance on your own, there are several options for purchasing a policy:

  • Your state’s health insurance marketplace — see healthcare.gov https://www.healthcare.gov
  • Directly from a health insurance company
  • Sites like Insure.com that offers insurance quotes from multiple carriers
  • A health insurance agent
Open enrollment for 2020 individual and family health insurance plans
Begins Ends
November 1, 2019 December 15, 2019

The open enrollment period differs in these states: 

  • CA – Oct. 15, 2019 to Jan. 15, 2020
  • CO – Nov. 1, 2019 to Jan. 15, 2020
  • DC – Nov. 1 , 2019 to Jan. 31, 2020
  • MA – Nov. 1, 2019 to Jan. 23, 2020
  • MN – Nov. 1, 2019 to Dec. 23, 2019
  • NY – Nov. 1, 2019 to Jan. 31, 2020
  • RI – Nov. 1, 2019 to Dec. 23, 2019

If you buy after December 15 in the states that are extending the enrollment period, confirm when the coverage will start. Most states require you to obtain your plan by December 15 for a January 1 start date. If you buy late, your plan might not start until February 1 or March 1.

Those who qualify for Medicaid or the Children’s Health Insurance Program (CHIP) can enroll at any time, because they are state/ federal programs created for people with limited incomes or disabilities.

Marketplace Open Enrollment is for health insurance only

The Open Enrollment period does not apply to life insurance, long-term care insurance, or Medicare. The fall open enrollment period for Medicare is October 15 to December 7, 2019. If you qualify for employer-sponsored health insurance, you will want to buy health insurance through your employer. Individual insurance usually costs more than employer-sponsored plans.

That said, if you qualify for subsidies based on your income, you may find an inexpensive plan on the Affordable Care Act (ACA) Exchange. Many states offer financial help for people with income below 400% of the federal poverty limit. You can find out more about these subsidies at insure.com. 

Remember to enroll!

It is not possible to sign up for coverage if you miss open enrollment, unless one qualifies for one of the special enrollment periods. The following events may grant entrance into a special enrollment period:

  • Divorce
  • Marriage
  • Birth or adoption of a child
  • Death of a spouse or partner that leaves you without coverage
  • Your spouse or partner, who has you covered, loses his/her job and health insurance
  • You lose your job and with it your health insurance
  • Your hours are cut making you ineligible for your employer’s health insurance plan
  • You are in an HMO and move outside its coverage area

Update your plan during Open Enrollment only

What you can do during open enrollment:

  • Renew your current individual or family health insurance plan
  • Choose a new health insurance plan through the marketplace in your state or through private insurance

If currently enrolled in a marketplace health insurance plan, it will automatically renew. However, the plan may make changes to its provider network, co-pays, co-insurance and drug coverage. Your plan must send you a notice of any changes it will make for 2020.

Read the health insurance update notice to learn what it means for youConfirm that your doctors and preferred hospital are still in your network. Be aware that you may be able to use out-of-network doctors and hospitals if you’re willing to pay more. That’s an option in Preferred Provider Organization (PPO) plans. In some cases, such as Health Maintenance Organization (HMO) plans, you’re covered if you go out of network. That means you’ll have to pick up the costs. 

Prescription drug coverage also could change. The plan may no longer cover the drugs you take to manage your chronic conditions. Confirm your plan’s drug benefits for 2020 before you allow it to renew. You may need to find a different plan for your needs and now’s the time to do it. Health plans must provide an online link to the list of drugs they will cover, known as formularies.

ACA Premiums set to decrease for some plans

The premium you pay depends on several factors, including income, your state and the plan type. The Centers for Medicare and Medicaid Services said the average ACA federal exchange plans premium costs dropped for the first time this year. However, because not all plans will be cheaper, it’s still important to shop around to find the right plan for you. 

Choose a level of health plan coverage

Plans in the health insurance marketplace are divided into 4 categories:

  • Bronze – highest out-of-pocket expenses for services (lower premiums)
  • Silver
  • Gold
  • Platinum – least out-of-pocket expenses for services (higher premiums)

Each level indicates how much cost-sharing each requires. Cost-sharing includes deductibles, co-pays and co-insurance that we must pay until the annual out-of-pocket maximum limit is reached.

Bronze plans have the highest deductibles and other cost-sharing expenses. That means more out-of-pocket costs when one uses healthcare services. Silver plans have lower cost-sharing than Bronze and Gold plans even lower than Silver. Platinum plans have the lowest deductibles and co-pays. Once one signs up for a level of coverage, changes are not allowed during that year. If you choose a Bronze plan and discover you need surgery, you cannot change to a plan with a lower deductible.

Generally, the more you pay in premiums the lower your cost-sharing.

In a 2019 report, eHealth estimated that 2-person families paid more than $1,000 in premiums monthly for the first time in the individual market in 2019. Premiums for individual coverage for a single person was $448 in 2019. 

The average premiums for individual coverage according to eHealth:

  • Bronze — $440
  • Silver — $481
  • Gold — $596
  • Platinum — $706

The average premiums for family coverage according to ehealth:

  • Bronze — $1,080
  • Silver — $1,179
  • Gold — $1.426
  • Platinum — $1,460

The health plans, no matter the level, must provide some coverage for at least 10 essential benefits. They are:

  • Outpatient care including chronic disease management
  • Emergency care
  • Hospitalization
  • Pregnancy and newborn care
  • Mental health and substance abuse services
  • Prescription drugs
  • Rehabilitation services and devices
  • Lab tests
  • Preventive and wellness services
  • Dental and vision care for children

The level of coverage for these services can vary. All the plans in the marketplace must provide consumers with a brief, understandable description of what they cover and how their plan works. The Summary of Benefits and Coverage (SBC) must be posted on the plan’s website. Check out the SBCs for the different plans you are considering. This is a good way to compare plans and benefits.

Not all states require health insurance

The ACA once required nearly all Americans to have health insurance. However, Congress decided in 2017 to eliminate the individual mandate penalty. Although the individual mandate is technically still on the books, the tax penalty is not. Still, a growing number of states have implemented their own individual mandate. Here are states that have an individual mandate in 2020:

  • California
  • District of Columbia
  • Massachusetts
  • New Jersey 
  • Rhode Island
  • Vermont

I hope you found this information helpful.

Thanks for reading,

Kim

Image: Thomas Eakins (Philadelphia 1844-1916) The Agnew Clinic, 1899 courtesy of The Philadelphia Museum of Art. The painting was commissioned to honor the anatomist and surgeon David Hayes Agnew, on his retirement from teaching at the University of Pennsylvania.

Harnessing the Cloud: You’ve Got an App for That

Freelancers and other business owners are nearly always pressed for time and we need to get things done, quickly, efficiently and accurately. Advances in technology have yielded many apps that can make our lives easier and make us look good as we take advantage of their features. Below is sampling of free to low cost apps that will help your business.

 SIMPLIFIED GRAPHIC DESIGN

Canva. If you’re in need of professionally-designed marketing materials for your business but don’t have the budget to hire a graphic designer, you can successfully DIY with Canva https://www.canva.com. This useful app features attractive design templates that allow you to create beautiful visual content for the images that are the core of social media marketing. You can also design logos, brochures, infographics, business cards and templates for Instagram, Twitter and Facebook posts. Canva will also allow users to crop images and enhance photos. The website provides good support, including tutorials on how to use Twitter for marketing. The free version of Canva offers most of the features a Freelancer or business owner will need and an upgrade to the Pro version costs $9.95/ user/ month.

MANAGE RECEIPTS AND EXPENSES

Expensify. All those who travel for business must collect and organize a stack of receipts very soon after returning, whether you’re a Freelancer who must save them for quarterly taxes or an employee who must submit receipts to your boss.  Expensify makes an onerous task much more bearable by automatically scanning the printed paper receipts and adding them to pre-designed templates that facilitate a seamless transition into your electronic records. Other features include reimbursement calculation based on the number of miles travelled, hourly billable amount or wage, a choice of four currencies for calculation and synchronizing directly with your bank account. Free  – $4.99/ month for most users.

ACCOUNTING AND INVOICING

FreshBooks. If you operate a B2B knowledge economy service business that doesn’t need a high-powered accounting solution, then FreshBooks  will give your organization a user-friendly option that offers a lot of functionality. You can track billable hours here as well and also log receipts and send invoices from your smartphone or tablet. The service integrates with several others, including Basecamp, PayPal, Google Apps and ZenPayroll.  The basic plan starts at $15 a month and allows management of up to 5 clients. More fully featured versions allow unlimited clients for up to $50 a month.

NEWSLETTERS AND EMAIL MARKETING

Mailchimp. This easy-to-use email marketing tool is a go-to for Freelancers and small businesses. It offers easy-to-use templates and intuitive drag-and-drop email building that anyone can use to create a professional-looking email that will enhance your company’s reputation. It also allows you to automate your email campaigns and track subscribers, so you can make the most of your communications campaign. Plus, Mailchimp https://mailchimp.com offers easy integration with many popular e-commerce tools. The basic service is free, but many will want to upgrade to either the $9.99/ month plan, which provides custom branding email design or the $14.99/ month option, which gives users custom newsletter and email templates and marketing automation.

SCAN BUSINESS CARDS

ScanBizCards.  Rather than taking a card from someone with whom you’d like to follow-up, it’s much more efficient—and cooler—to scan the business card or even a conference name tag and know you have that important person’s information will be saved automatically in your phonebook. ScanBizCards

VIDEO CONFERENCES

Skype for Business. The classic video conferencing app is owned by Microsoft and the functionality of its infrastructure is versatile, powerful and seamless. The service offers free online meetings for up to 10 participants, set-up from any device, PC or MAC, Android, iPad, or iPhone and PowerPoint upload capability, Instant Messaging and a white board feature. Unlimited free video conferencing, instant messaging, conferencing and audio calling are also offered and  Skype for Business runs ad free and without interruptions— excellent for a business interview or discussion.  Explore the premium features through Microsoft Office 365—$6.00 / user/ month – $15.00 / user/ month.

TEAM COMMUNICATION AND COLLABORATION

Slack. There are several real-time messaging and file-sharing apps available, but Slack prevails as a result of its simplicity. It has DropBox, Asana, Google+ Hangouts, Twitter and Zendesk compatibility built into the app and the platform is very responsive and user-friendly. Every message is archived, so searching is quick and easy.  Free – $15.00/ month / user for premium services.

BILLABLE HOURS MANAGEMENT AND INVOICING

Toggl.  This timer tracks how you spend your time, making it an ideal support system for those who must record billable hours in order to accurately and quickly prepare invoices so that they will get paid, Freelancer friend. You can track as many projects or clients as you want and assign your hourly rate to each project, so that you can quickly calculate what you’re earning, export timesheets and sync your numbers with several project management apps. Toggl is priced from $9.00 / month /user for the basic service to $18.00/ month/ user for team time tracking and other premium services.  

Thanks for reading,

Kim

Photograph: Kim Clark September 7, 2018. Fog x FLO, a “fog sculpture” installation by Fujiko Nakaya (Japan) that appeared in five Boston locations from August – October 2018. Every hour from dawn to dusk, a blast of steam would be emitted by a special mechanism and the fog would appear—and disappear in a minute or two, depending on how the wind blew. The fog sculpture pictured here was across the street from the Isabella Stewart Gardner Museum.

The Do’s and Don’ts of Email Sign-offs

As often noted by myself and countless other bloggers and journalists, the care and feeding of one’s brand is forever at top of mind.  Every touch point with a client, prospect, potential referral source, the public, or the media and every form of communication, whether verbal, visual, or print, must present a flattering portrayal of the brand. Even our ubiquitous, plebeian emails are now brand ambassadors.

Remember that admonition when you next compose an important email to a current or prospective client.  As you carefully evaluate the potential impact of every word, ensure that your valuable brand carries through to the sign-off. The brand is always on the line and it must be curated, even in emails, from the salutation to the sign-off.

For guidance in the matter of etiquette and branding I’ve consulted the writings of Suzanne Bates, executive coach, President and CEO of Bates Communication in Wellesley, MA (just west of Boston) and author of Speak Like a CEO: Secrets for Commanding Attention and Getting Results (2005).

Regarding written communications remember that as always, context is everything.  What is the purpose of your email and with whom are you corresponding? Are you and a client with whom you work regularly discussing a project or are you writing to a business colleague whom you’ve recently met? Then again, are replying with a proposal that a prospective client has invited you to submit? Each of these circumstances will impact the style of your email sign-off.  Let’s look at a few common closing words and phrases and examine their potential impact on the recipient.

Thanks

Use this term when you are actually thanking the person you’ve written, or asked for something to be done or said on your behalf. Thanks as a sign-off is business-like, but casual. Thank you is a better choice if you don’t have a familiar relationship with the other party.

Best

A borderline casual sign-off, but acceptable to use for a business associate whom you know.  BTW, I use this closing most of the time (I may need to re-think this choice).

Regards

Somewhat perfunctory and a little distant, but this closing generally works well.

Cordially

An old-fashioned sign-off that portrays the writer as well-mannered and formal, perhaps too formal. Nevertheless, this choice is safe and pleasant.

Sincerely

Here’s a tried and true business attire sign-off that will offend no one. However, this closing is more appropriate for a letter, rather than an email.

Cheers

You can use this to close an email with someone you know well, but if you’re trying to make a good impression in a business setting, it’s not a wise choice. Save this breezy term for after a bond has been established, for friends and colleagues you sometimes meet for coffee.

Talk soon

This term is usually used among friends and familiar business associates. The intention of quick follow-up is communicated clearly and that may be desirable. I like to use “To be continued.”

Yours truly

We’re a little too formal for an email here, as this term is closely associated with closing a letter. If your email is written for a very important person, you may use this sign-off with confidence.

Kind regards

Here is my favorite business sign-off and when I need to present my self and my brand in the best light, this is my go-to salutation. This term is warm, friendly and professional.

Thanks for reading,

Kim

Image: Artist unknown. Courtesy of the British Library, London.                                      Born in Venice and educated at the University of Bologna (Italy), Christine de Pizan (1364 – 1430) was among the best known writers in medieval Europe, in spite of her gender.  A prominent political thinker, novelist and poet, she authored the feminist treatise The Book of the City of Ladies, among other works. Pizan was the wife of Etienne du Castel and a mother of three.

Email Writing Perfected

Now that you’ve completed your business plan, you’re ready to put it in motion. Here’s the guide that will make sure you know how to get your entrepreneurial groove on! In Be Your Own Boss, Part 2: The Implementation and Beyond, you’ll learn to recognize the strengths or weaknesses in your proposed business model and develop an effective customer acquisition plan. You’ll get insight into what you should consider when choosing the right legal entity for your venture. Learn to implement savvy marketing, branding and social media strategies, get real about business financing options and build a solid financial strategy that will sustain your dream. Thursdays April 18 & 25 6:00 PM – 9:00 PM. Register here.

Every day, the typical professionally employed adult sends and receives an avalanche of emails. In response, dozens of articles that address the challenge of email management have appeared in business targeted media outlets. Those articles are all somewhat helpful but my feeling is, when emails are effectively written fewer of them are written, because writers express themselves clearly and recipients understand how to respond.

As luck would have it, an amazing and highly organized polymath named Kabir Seghal, who is a U.S. Navy veteran, former Vice President at J.P. Morgan, Grammy Award-winning producer (Afro-Latin Jazz) and author of seven books in both the children and adult genres including Coined: The Rich Life of Money and How its History Has Shaped Us (2015) has stepped up to guide mere mortals in the fine art of email writing. Seghal applies lessons he learned while in the military when advising us on how to write the ideal email communication.

Subject line

Subject lines are crucial. They can determine when or even if your email is opened. The wrong subject line can result in your email being ignored or deleted. A powerful subject line communicates the purpose of the email and the action the writer would like the recipient to take. A sampling of subject line verbs include:

Action                                 Meet

Decision                             Request

FYI                                      Sign

ACTION:  The recipient must do something, usually within a certain time frame.                                                                                                                                                                                                                                                                                                         frame.

DECISION: A decision must be made by the recipient, or a decision that impacts the recipient has been made.

FYI: For Your Information messages keep the recipient in the loop. Action is not required (choice of the recipient).

MEET: Consult your calendar and reserve time.

REQUEST: The writer seeks approval or permission from the recipient.

SIGN: The recipient must read and sign a document and return it with a certain time frame.

Bottom line up front (BLUF)

Begin the body of the email with a short statement that concisely answers Who, What, When, Where and Why to explain the purpose of your email and what you’d like the recipient to do. The BLUF distills the message and allows the recipient to easily digest the information you share and how s/he will be impacted. Seghal suggests that the writer lead with the heading Bottom Line to call attention to your email’s core messages.

Active voice

Seghal recommends that we use the active, rather than passive, voice when composing emails. It’s important to be clear about who has or is taking action, or who will be required to take action (and when) and the impact of that action.

Cut to the chase

Short emails are preferred by military personnel, but sometimes longer communications are unavoidable. Should your email exceed three paragraphs, follow-up your Bottom Line (BLUF) statement with bullet points, so the recipient can quickly focus on critical information.  Rather than adding files as attachments to the email, embed hyperlinks to the files and enable faster access.

Thanks for reading,

Kim

Photograph: Typist, circa 1930s.

 

Dates to Keep You Straight

Every year, Freelancers have an important list of dates to remember and act on, primarily those related to tax filings, retirement account management and health insurance plan enrollment. To help you stay organized, I’ve compiled this date planner that brings together all deadlines into one document that you can bookmark, copy into your calendar or even print out and post on your refrigerator.

TAXES

January 31, 2019: 1099-MISC due to contractors
Those who hired Freelancers (independent contractors) to whom they paid $600 or more in the previous year must send 1099-MISC forms by January 31, 2019.  If a client paid you less than $600, then you probably will not be mailed a 1099-MISC, although the IRS nevertheless requires you to report all income.

Do keep scrupulous records of who owes you a 1099-MISC so that you can accurately report your income on your tax return.  Your clients will also send 1099-MISC data re: you to the IRS and any differences between your numbers and the clients’ could trigger an audit.  If you haven’t received a 1099-MISC from a client by January 31, contact your client ASAP and request a re-send.

If you used any subcontractors to whom you paid at least $600 last year, you must likewise send them a 1099-MISC by January 31.

April 15, 2019: Individual income tax filing deadline
You have until April 15, 2019 to file your Form 1040 individual income tax return for 2018. Be aware that April 15 isn’t the deadline to pay your taxes — tax payments for Freelancers are due on a quarterly schedule (see 2019 quarterly estimated tax deadlines, below). If you wait until the tax filing deadline to pay your taxes, the IRS may charge you penalties and interest on top of the tax you owe.

If you’re still waiting for information, or you’re too busy to file a return by April 15, you may apply for a six-month extension that gives you until October 15, 2019 to file. The extension application needs to be filed by April 15, 2019. Remember again that the extension is for filing, not paying your taxes.  Payments are still due on the quarterly schedule no matter when you file and penalties and interest can accumulate if you wait to pay.

QUARTERLY TAX FILING DATES

The IRS requires business owners to pay income taxes on a quarterly schedule. This may seem like a hassle, but it’s easier to pay in four installments than to try and come up with a whole year’s worth of income taxes all at once.

Here are the 2019 deadlines for quarterly estimated tax payments. Note that the four quarters are not of equal lengths: the 2nd Quarter covers only April and May, while the 4th Quarter covers the last four months of the year.

DEADLINE                                                         PERIOD COVERED

April 15, 2019                                                     January 1 – March 31, 2019

June 17, 2019                                                      April 1 – May 31, 2019

September 16, 2019                                           June 1 – August 31, 2019

January 15, 2020                                                September 1 – December 31, 2019

 

RETIREMENT ACCOUNTS

April 15, 2019: Deadline to set up and contribute to an IRA for 2018
Even if you made no contributions to your retirement savings account in 2018, you can still make a 2018 contribution to an IRA up until April 15, 2019. This includes traditional, Roth and SEP IRAs. You can also make 2019 contributions to these plans from now up until next year’s tax filing deadline of April 15, 2020.

December 31, 2019: Deadline to set up an individual 401(K) 
An individual 401(K) is another type of plan that Freelancers can use to save for retirement. One important detail is that an individual 401(K) must be established by December 31st of the first plan year (as opposed to an IRA, which can be opened up until April 15 of the following year). That means it’s too late to set up an individual 401(K) for 2018, but you may set one up for 2019.

Contribution limits 2019 update:

Solo 401(K)                                                                                                                            Employer: 20% of net self-employment income                                                            Employee: 100 % of earned income up to $19,000 (for age 50 years +, up to $25,000)   Total combined contribution: $56,000

Traditional or Roth 401(K)                                                                                                     $6000 annually $7000 if age 50 years +

SEP IRA                                                                                                                                               The lesser of 20% of net self-employment income, or $56,000 annually

 

HEALTH INSURANCE

The open enrollment dates to purchase health insurance for 2020 on the Affordable Care Act exchange will be November 1 – December 15, 2019.  Open enrollment for 2020 through the national health insurance exchange will also be run from November 1 – December 15, 2019.

 

Thanks for reading,

Kim

 

 

Time-Tracking Options for Freelancers

We’re back with a review of more time-tracking services that are especially useful for Freelance consultants. Accurately documenting the time spent on project assignments is important in many ways, primarily to ensure that billable hours charged to clients are correct.  Plus, most time-tracking services will generate an invoice that you can click and send and some will also allow you to accept online payments with bank-level security.

In addition, time-tracking services generate useful reports that show the number of hours you spend on certain types of assignments, information that is useful when creating proposals for projects that you’d like to take on, since it will be necessary to predict the time you expect to spend on the proposed project, which will impact your pricing and determine whether it will be most advantageous for you and the client to choose an hourly rate or project fee payment arrangement.

Harvest

Track time spent on projects easily and efficiently with Harvest, even when you need to follow several projects that contain different tasks that are priced differently. Furthermore, when coordinating a team project, you’re able to assign and time-track various tasks within a project for specific team members.

Reporting is a strength: raw time sheet data will be presented in a visual summary that depicts how your time or the team’s time has been utilized, with key project metrics collated into intuitive reports. The service also generates professional-looking invoices based on your project fee or hourly rate, as determined by the time you’ve logged.  Click and send invoices to clients and receive online payment, confident that site security is bank-level.

Harvest is free for one person to track maximum two projects/month and $12 for one person to track an unlimited number of projects/month.  Harvest

RescueTime

Freelancers who’d like to document how they’re spending time when working on a project and who are not kept on a short leash by a manager will appreciate RescueTime.  It’s not possible to send reports to your client, but you can nevertheless track your time and obtain an accurate picture of your productivity.  You will also receive detailed reports that show you the apps and websites you visited.

As well, RescueTime will record time spent on email and the amount of time you linger on any website. If you’d like to limit the time spent on non-work related websites, then ask the system to block your browsing on any chosen site after a certain amount of time.  Further, you can set goals to inspire yourself to stay on schedule with your project. The premium service plan also allows tracking of off-line time for activities such as telephone calls and meetings. RescueTime Lite is free and RescueTime Premium costs $9.00/month, or $72.00/year.   RescueTime

Tick

Each time you submit a time entry, Tick updates your project and task budgets in real time and reports back to you.  If you regularly track time against an hourly rate determined budget, or a project fee that involves an important deadline or penalties for late completion, then Tick may be your ideal time-tracking solution. It’s also possible to track time on multiple projects simultaneously.  While the service can be used by a solo Freelancer, it is especially suited for a team.

Tick is free if a single user employs the service for one project per month, $19.00/month for an unlimited number of users who’ll track a maximum of 10 projects/month and up to $149.00 /month for an unlimited number of workers to time track an unlimited number of projects.   Tick

Toggl

If you neglect to click the session start button, the service will allow you to enter your working time after the fact, which is helpful for those who are very busy and prone to forget. The service is structured with a team in mind, but it works well for solo professionals.

The service works on all devices, desktop and mobile. Helpful analytic reports will be generated, so you’ll get the big picture of where your time is spent, depending on your assigned tasks.  There is a free version, plus Starter and Premium.  The $9.00 /month Starter package appears to give the best value to Freelancers.   Toggl

Klok

Most helpfully, the service lets users recall and analyze data from previous projects, information that enables you to develop proposals for future projects that will more accurately reflect the time needed to reach key milestones and achieve deadlines. The historical time-tracking data will also help you to price at a level that is fair to both you and the client.

The basic package includes a visual display of your time as you work, plus screenshots, exporting of time sheets, dashboard reporting and invoicing all for a one-time purchase price of $20.00 for up to three users.  Klok Cloud Sync, Klonk Pro and Klokwork Team Console are also available.   Klok

Happy Thanksgiving and thanks for reading,

Kim

Photograph: Orloj, the famous 15th century astrological clock in Prague, Czech Republic

Time-Tracking Freelance Work

How many of you use time-tracking so that you can accurately count your billable hours when on assignment? I still count hours the old-fashioned way and I know that I cheat myself out of no less than an hour or so every week. My bad! I’ve occasionally thought about time-tracking assistance, but I never knew where to begin. A new year will soon welcome us and that’s a traditional motivator to set goals and improve work habits.

As I suspected, time-tracking systems have their differences. Some are designed with remote teams in mind; others make a department manager’s life easier. Certain time-tracking systems have been created to address the needs of Freelancers and we’ll sort through a sampling here:

Due Time Tracking

Due Time is free and easy to use—just create a task, start the timer and launch your session. You can click and add notes to detail the project you’re working on. Due Time also includes an automatic idle time detection feature, so you’re able to make allowances for stepping away from your project now and again and still remain accurate in tracking your work hours.

You’ll be pleased to find that Due Time will generate hourly rate or project fee invoices when you enter the rate. Due Time makes it easy to organize client information by name, address, or even payment currency.  Due Time

TopTracker

Along with tracking the number of hours you spend on project tasks, Top Tracker offers screen shots and webcam shots that document your work. Screen shot pages can be deleted or configured to automatically blur before uploading, so that the image is recognizable to you but all text is obscured. The service works with nearly every freelancing platform and will produce a detailed project activity report to document your performance. The service is free.  TopTracker

Sighted Time Tracking and Invoicing

Sighted Time Tracking seamlessly integrates the functions of time-tracking and invoicing, packaged in either the free Basic Service plan or the Premium Plan at $4.00 /month. You can make detailed project notes for every session and also automatically send invoices for hours worked that are customized for billable hours or project fee.

Furthermore, users can send out quotes to prospects when invited to bid on a project and accept credit or debit card payments online and issue a receipt to the client. Plus, you can do it all on your desktop or mobile device.  Sighted

Tick

Each time you submit a time entry, Tick updates your project and task budgets in real time and reports it back to you.  If you regularly track your time against an hourly rate budget of project fee that involves an important deadline or penalties for late completion, then Tick may be your ideal time-tracking solution. It’s even possible to track time on multiple projects simultaneously.  While the service can be used by a solo Freelancer, it is especially suited for a team.

Tick is free if a single user employs the service for one project per month, $19.00/month for an unlimited number of users who’ll track a maximum of 10 projects/month and up to $149.00 /month for an unlimited number of workers to time track an unlimited number of projects.  Tick

Four more time-tracking options will be examined in the next post. Have a good week!

Thanks for reading,

Kim

Photograph: Sundial at the Gate of Honour at Gonville and Caius College in Cambridgeshire, England

Who Gets the 1099?

The year is drawing to a close and we’re crossing into the 11th month. Before you become enmeshed in the celebrations and obligations that the holidays demand of us, do yourself a favor and commence your tax planning. Create an accounts receivable and  invoicing strategy once you’ve decided when it would be most advantageous to receive payment for services rendered in this calendar/ tax year or the next. IRS Form 1099-MISC will be at the center of the action; understanding when you’ll need it and when you might avoid it is your goal.

The payment in question is $600, whether it was paid or received by your organization. Review the accounts receivable history of clients for whom you performed small jobs earlier in the year.  If a client paid you less than $600 in this calendar year, you will not receive or need to file a Form 1099-MISC for the money earned on that assignment.

Start with the easy stuff.  If you find yourself in mid-contract with a client as December approaches and the project isn’t urgent, might it be possible to work until just before Christmas and then resume work in the first week of January, if it appears that will allow you to cap your billable amount at less than $600 for the client in this calendar/ tax year?  That can be one less 1099-MISC to file and a little more money added to your P & L.

If the client has a deadline don’t even think of such a thing but if there is no urgency, why not ask the client if s/he might find it more convenient to take a “holiday break” starting in mid or late December? Many employees take vacation days at the end of the year in a “use it or lose it” strategy and offices can be short-handed just before Christmas and through the end of the year.  I suggest that you refrain from mentioning the tax implications.  Frame your suggestion as a way of being sensitive to what may be going on in the client’s office, i.e., customer service.

Similarly, might you be able to defer until the New Year certain invoices, as a way to keep a lid on this year’s income and taxes and wait until the first week of January to send accounts receivable for work that was performed in December? Let a couple of hours work spill over into January and make your New Year invoice legal.

Now let’s consider the 1099-MISC forms that you will generate and send.  Did you hire any sub-contractors to help you fulfill the terms of a project? Have you hired a part-time bookkeeper or social media expert or editor for your newsletter? If you paid $600 or more to anyone for business services or rents in this calendar/ tax year, then you must send that individual/ company a Form 1099-MISC no later than January 31 of the upcoming year.

So that you will have the information to complete the Form 1099-MISC, it will be necessary to request that all of your vendors and other business services providers complete a Form W-9, ideally before the work they perform commences.  Download Form W-9

Among the important pieces of information that the W-9 will surface is if your service provider’s business is incorporated as a chapter C or S entity, or an LLC or partnership that is taxed as a C or S corporation.  Along with commercial rent paid to or through a property management company (instead of the property owner), a 1099-MISC will not be required for those types of entities when payments for services rendered meet or surpass $600.

Payments for services rendered made by gift card, debit, or credit card are not to be included in the 1099-MISC tally.  Instead, the card issuers will send a Form 1099-K to your subcontractors, vendors, or you when the amount paid for business services rendered meets or surpasses $600.

Obtaining the 1099-MISC is an adventure. You must order forms from the IRS, or visit an IRS service center and pick up a few. The form is not available for downloading.  Click here to order Form 1099-MISC.

Thanks for reading,

Kim

Image: The Tax Collector, 1542   Marinus van Reymerswaele (1490 – 1546)                  Courtesy of Alte Pinakothek Museum in Munich, Germany