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Tax Year 2025 Updates for Freelance Workers

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There are two inevitables in human existence and one of them is taxes. The good news is that in many cases, one can prepare and develop a strategy to minimize the impact of the tax burden. The ability to devise a good strategy requires current information and that is the topic today.

You’re probably aware of Federal legislation known as the One, Big, Beautiful Bill. You may not know that parts of OBBB have been revised and proposed changes to federal tax Form 1099-K were tabled and guidelines from previous years have been restored.  

Officially titled the Payment Card and Third Party Network Transactions form,1099-K reports payments received from income generated by self-employed workers and paid to them by Third Party Settlement Organizations such as PayPal, Square, Stripe 2, or Venmo. Revenue received from transactions from online marketplaces, including Airbnb and eBay and also revenue derived from billable hours earned at Freelance B2B services platforms such as Fiverr and Upwork also trigger a 1099-K.

It’s important that Freelance professionals remain updated on federal and state tax legislation so that you can anticipate and prepare for your tax liability. If you’re able to choose your payment method—maybe you’re thinking of offering digital payment options for client invoices?—you would be wise to first assess the impact of that change to your finances. Giving clients additional payment options is now considered a competitive advantage and an aspect of customer service. But when you’d like to initiate payment flexibility, first discuss the matter with a tax accountant and let the tax filing implications, and also other financial advice, guide your invoice payment options.

Internal Revenue Service Form 1099-NEC

What will not change is IRS Form 1099-NEC (non-employee compensation). The form will be sent to self-employed workers, including Freelance professionals, other independent contractors and side-hustle specialists, who’ve been paid $600 or more in a given year. Your earnings most likely will not trigger a 1099-NEC if you billed the client less than under $600 in a calendar year, but you are still responsible for reporting all income whether or not you were sent a 1099-NEC. As a self-employed Freelance consultant, you are required to report self-employment income if your net earnings were $400 or more.

Internal Revenue Service Form 1099-K

As noted above, IRS Form 1099-K reports payments that Freelancers and other sellers of B2B or B2C goods and services received through Third Party Settlement Organizations such as PayPal, Square, Stripe 2, or Venmo for sales transactions between buyers and sellers have returned to the $20,000 billables and 200 transactions thresholds. Upwork and Fiverr will send 1099-K to Freelance workers whose billables equal or exceed $600 in a year, as noted above. Be advised that the proposed $2,500 (for 2025 earnings) and $600 (for 2026 earnings) thresholds are no longer in effect for 2025 and 2026.

As with 1099-NEC (and W-2), 1099-K statements must be sent to you, by email or hard copy, no later than January 31, 2026. If your clients pay you directly by credit, debit, or gift card, you’ll get a 1099-K from your payment card processor no matter how many payments you received or the total dollar amount of those payments.

Keep in mind that your state may have a lower reporting threshold for TPSOs, which could result in you receiving a Form 1099-K, even if your total gross payments and transactions did not exceed the federal $20,000 annual reporting threshold. Some states have their own rules for 1099-K reporting and your state threshold could be lower than the federal limit. While the IRS requires payment platforms to issue a 1099-K only if you have at least $20,000 in payments and 200 transactions for 2025, several states have set their reporting threshold at $600, regardless of the number of transactions.

Qualified Business Income (QBI) deduction

If your business entity is structured as a pass-through, you could be eligible for a 20% tax deduction by way of the IRS Section 199A Qualified Business Income (QBI) deduction. If you are an owner of a pass-through business entity, including S-corporations, Limited Liability Companies (LLC), Partnerships, including Limited Partnerships (LP) and Sole Proprietorships, can claim the QBI benefit whether or not they itemize deductions or take the standard deduction.

The QBI deduction allows eligible taxpayers to deduct up to 20 % of their QBI, plus 20 % of qualified real estate investment trust (REIT) dividends (not to be confused with income generated from rental property). Income earned through a C-corporation or W-2 wages are not eligible for the QBI Section 199A deduction. Eligible taxpayers can claim the deduction for tax years January 1, 2018 through December 31, 2025.

So who can do this? If taxable income (before the QBI deduction) is at or below the threshold amount—and thresholds are different for every year from 2018 – 2025, with the 2025 upper threshold at $197, 300 for single filing status and $394, 600 for married joint filing status—you’ll have access to the full deduction BUT the amount paid by an S-corp or a partnership that is treated as reasonable annual compensation for the taxpayer will not be eligible. To determine if your business may qualify for the QBI, click here to see this older, but useful, IRS form. Most of all, reach out to your tax accountant ASAP and verify your status.

Retirement Plan contribution deferral increase

Have you made a contribution to your retirement this year? If not, you have until December 31, 2025 to slide under the wire and save for your future. These retirement contributions come right off your income, lowering your tax bill and boosting your retirement financial readiness.

The Solo 401(k)—also known as the self-employed 401(k), individual 401(k), personal 401(k) or, to use the IRS’s preferred term, the one-participant 401—is known for its high contribution limits that enable Freelance consultants who have no employees for whom you provide benefits, to save for retirement. That includes Freelancers and gig workers who are Sole Proprietors, or structure their business entity as an LLC, S-corporations, C-corporations, or Partnership. If you have no employees, step right up to launch your preferred version of a single-person retirement fund.

  • In 2025, the maximum contribution is $23,500 (wearing your entity’s employee hat), plus an additional 25% of compensation (wearing your entity’s employer hat). You can also contribute an additional $7,500 in catch-up contributions if you are age 50-59 or age 64 or older. Those between age 60 and 63 may contribute an additional $11,250 in catch-up contributions if the plan allows.
  • In 2026, the maximum you can contribute is $24,500 as the entity employee plus an additional 25% of compensation as the entity employer, with additional catch-up contribution opportunities if you are 50 years or older.

If you file tax form Schedule C as a Sole Proprietor and have a SIMPLE IRA retirement plan, you are also treated as both employer and employee when calculating and reporting your plan contributions. Report both your salary reducing employee contributions and your employer contributions (non-elective or matching) for yourself on Part II – line 15 of Form 1040 Schedule 1, according to IRS info. You must deposit your salary reduction contributions within 30 days after the end of the tax year. For most people, this means salary reduction contributions for a given year must be made by January 30 of the following year. For most individuals, the annual contribution limit for a SIMPLE IRA is $16,500 in 2025 and $17,000 for 2026. Those who are age 50 years and older can also make an extra $3,500 catch-up contribution in 2025 and $4,000 for 2026 if their plan allows it. 

Self‑Employment Tax & Deductions

You already know that Freelance workers must file IRS Form SE no later than April 15, 2026 and pay 15.3% total (12.4% Social Security + 2.9% Medicare) on the net amount of your self‑employment income—because you must fund your own Social Security and Medicare benefits. The good news is that you can deduct half of the self‑employment tax (the “employer equivalent”) from your adjusted gross income.

  1. Social Security Cap: On the first $176,100 of combined wages + self‑employment income in 2025.
  2. Additional Medicare Tax:
  • 0.9% extra if income exceeds:
  • $200K (single/Head of Household),
  • $250K (married filing jointly),
  • $125K (married filing separately).
 Quarterly Estimated Taxes & Penalties

Because Freelancers file 1099-NEC and there is no withholding of earned income, you know that filing quarterly tax forms is a must-do if you expect to owe $1000 in federal tax, including self-employment tax; estimated tax payment must be paid with the quarterly filing. To avoid penalties, pay either 90% of 2025 tax or 100% of your 2024 earnings tax (or 110% of 2024 adjusted gross income if your earnings exceeded $150,000. Quarterly filing deadlines are April 15 (the annual filing), June 15, October 15 and January 15 (because 4Q earnings are reported in the new year).

In closing, I have a gift for those of you who will be 65 years old, or older, in 2025? if so, You’ll receive an extra $2,000 standard deduction (single filers) or $1,600 (joint filers).

Thanks for reading,

Kim

Image: The Tax Collector’s Office (1620-1640) Pieter Brueghel the Younger, courtesy of University of Southern California Fisher Museum of Art, Los Angeles

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Contract Management Promotes Business Growth

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Congratulations Freelancer colleague, as summer ends and the fourth quarter approaches, you’ve landed a client and have been asked to sign a contract. You are well aware that receiving a contract is the road to revenue but that’s only part of its power. When a contract and the arc of its lifecycle are recognized and utilized, you can initiate a mutually agreeable working relationship with your client and make the possibility of repeat business amenable to the client.

To the best of your ability you, Freelancer friend, should ensure that all contracts you sign advance and protect your interests, as well as the client’s. Keep at top-of-mind that expectations are foundational to contracts. A well-written contract defines and describes what the client expects of you—primarily, to produce the desired outcome or deliverable that also meets the client’s quality control standard and is completed and available by a specified date.

At its core, a contract is a commitment whose purpose is to guarantee that client expectations and your responsibilities are defined and achieved. When you think about it, a contract is potentially more than a method to certify a working agreement. In particular, contracts that pertain to B2B services or products can be considered strategic tools that provide risk management for both you and the client, in addition to revenue generation for you.

Contract management is the process of creating an official document that identifies client expectations and defines the responsibilities of the party that produces the outcome or deliverable and meets the deadlines. Contract management also includes the discussion and negotiation of factors such as payment for work performed and contingencies that, when agreement is reached, are written into the document. Contract management is considered completed after the outcome or deliverable are produced and the document is reviewed and analyzed to assess the execution of the work performed against the terms of the contract. This final step of contract management is of particular interest to B2B service providers, whether the deliverable is a one-off project or an ongoing subscription, as it may reveal where and how you could have utilized your company’s operational processes more efficiently to reduce monetary expenses or time associated with producing the deliverable.

A written agreement

Contracts typically begin with discussion and a verbal agreement, but that process should be viewed as only the first step of new client engagement. It is in the interest of both parties to commit all major business agreements to writing by creating a contract after first discussing client goals and expectations, timeline and budget to attain understanding and mutual agreement and then following-up with the development of a written document that will be signed by the parties involved.

The author of the contract will depend on the client. Corporate and not-for-profit organizations typically have a standard contract that is used for Freelance talent. Small businesses and organizations that engage with few Freelancers may be happy to allow you to author the document. Over time, many Freelancers develop a standard B2B professional services contract template; however, it will be worth your while to investigate contract templates that can streamline and speed up the contract management process, from creating the document, to negotiating terms and facilitating online docu-signing. You will find contract management software available on several platforms.

Regardless of its author, know that you owe it to yourself to carefully review all contracts that you intend to sign, to ensure that both signers will be able to meet the terms. Put questions and answers in writing (email), to provide documentation. When you are not the contract author, diplomatically suggest that you and the prospective client collaborate and negotiate when you find it necessary, to ensure that you can fulfill your responsibilities and please the client. All changes to the agreement should be in the form of written amendments, or at a minimum, an email that documents the changes.

Finally, caveat emptor—a contract is only as good as your ability to enforce it. A written agreement is nearly always useful, but if one of the parties fails to fulfill the agreed-upon terms, the other will be stuck. Even a contract written to anticipate nearly every contingency is only as good as the behavior of the signers. Integrity and trust matter and maintaining complete records is a must.

  • Document changes: If changes are made to the original contract, write them down. Make sure everyone signs off on all changes and attach amendments and signatory approval to the original agreement.
  • Keep original copies: Keep signed copies of all contracts safe and organized, whether they are in hard copy or digital format.
  • Track communications: Keep a record that includes notes and the dates of all contract discussions. This includes emails, letters, meeting notes and phone logs.

Payments

Let your contract specify when, how much and by what payment method you’ll be paid. While W-2 employees receive regular weekly or bi-weekly paychecks, that is not the scenario for Freelance consulting talent. At some organizations, we are the last to get paid and late, sometimes scandalously late, payments can be distressingly common.

Defend yourself by making it clear to the client that you expect to be paid according to the timeline that was discussed and agreed upon. In fact, once you and the client have committed to the amount of your project fee and scheduled the initial payment that you require before commencing work, as well as the milestone or other interim payments, if applicable, plus the timing of the final project payment, be certain to specify the amount and schedule of those payments in the contract. Furthermore, you might also note that all payment amounts and associated dates are non-negotiable. Trust is central to every contract and committing the agreement to writing encourages trustworthy behavior.

Along with a dispute resolution clause in your agreement, also specify how you will handle non-payment. You shouldn’t be expected to continue work if you aren’t getting paid but collecting unpaid debt can be a real challenge. Include a clause about debt collection, either through an agency or a lawyer— and that cost should be on the client, not on you.

Client expectations

Before you enter into a working agreement, you and your client must have similar expectations of one another’s roles. Assume nothing and in particular, ask questions to confirm the project deliverables and timeline—milestones and deadline. Ask also for your client’s description of a successfully achieved milestone and a successfully completed project.

In a Freelance B2B contract for professional services rendered, outline what you agree to do and how it will be done. There must be no ambiguity about the desired outcome or deliverable, or the quality of the work that the client expects. It’s also helpful to make clear what happens if you do not meet the agreed-upon deliverable deadline; usually, it means some portion of your payment is withheld until both parties are satisfied with the progress of the project.

Ensure that the client knows the full spectrum of services you’ll provide to satisfactorily produce the outcome or deliverable and the amount of time you expect will be needed. If there are complicated elements to the project, make sure the client comprehends what is needed to achieve the that vision.

Milestones

Milestones are essential for independent projects, as well as for organizations that hire Freelance talent. By detailing a project’s milestones, you can ensure that you and the client know when to expect key deliverables. If no milestones have been discussed and agreed upon before your hire, you might raise the issue yourself, in order to keep your client apprised of the project’s progress and document your intention and ability to satisfactorily complete all work by the deadline.

Intellectual property

If the assignment you’re hired to complete involves intellectual property of some sort, the contract should describe and define who owns what. Do you exclusively own the intellectual property, or does your client have some rights to it? Be sure that you understand precisely what you’re handing over and what rights you retain to make sure that you identify which party owns what rights and royalties for each product or service made available. It’s a good idea for both parties involved to have their IP attorney review a Freelance contract before signing on. The last thing either of you wants is a misunderstanding over ownership to break out after a project has been completed, especially if a significant amount of money is at stake.

Confidentiality

It is assumed that you will not share any information about your client’s business without written consent. You may be asked to sign a Non Disclosure Agreement and if so, maintain a copy in your records, along with the contract.

Confidentiality includes financial data, proprietary information and other protected details. There should be a clause that prohibits you from releasing any of your client’s personal information without permission. If you feel it necessary to disclose confidential or protected information for legal reasons, make sure that you obtain your client’s explicit permission before doing so.

Support and resources supplied by the client

Identify your client contact either in the contract or in an email and confirm that person’s availability to you and the type of support that will be provided. If on-site access to company resources, equipment, or materials is needed to execute the work you are hired to do, specify in writing what you’ll need to use and document your intention to return it and to whom it will be returned when your work is completed.

An out clause

It can be frustrating if you’ve been led to believe that signing a new client is imminent, only to have the agreement unexpectedly fall apart. In the Freelancing universe, it’s anticipated that some projects might end prematurely, whether the result of an unexpected hire of a W-2 employee or a sudden funding loss. Alternatively, you may face a health crisis or family emergency that will make it extremely difficult to fulfill the contract and forces you to terminate the agreement.

Regardless of the determining factors, a termination for convenience clause allows either party to unilaterally end a B2B contract without cause and without engaging in litigation. The client can simply provide notice that s/he must end the agreement and pay you for any work that’s been done, or you can inform the client in writing, in accordance to a predetermined specific termination notice period (14 to 30 days is common), and agree to certain post-termination obligations.

 Effective communication will be critical to soften negative perceptions and sustain future collaboration. A transparent explanation of the reason for termination is essential to preserving credibility and trust.

Next steps

Once the contract is signed, be certain to send your new client a welcome letter and schedule a face2face or videoconference meeting to begin onboarding and officially inaugurate your new client engagement!

Thanks for reading,

Kim

Image: Treaty of Paris, More Than Meets the Eye, 1783 (Benjamin West, 1738-1820) courtesy of The Winterthur Museum, Garden and Library, Winterthur, DE. The treaty officially ended the American Revolutionary War (1775-1783) and marked England’s acknowledgement of the U.S. as an independent sovereign entity with defined borders.

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States Pass New Laws to Help Freelancers

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According to the 10th annual Upwork survey Freelance Forward, 64 million Americans worked as Freelance professionals in 2023, labor that contributed $1.27 trillion to our national economy. It’s a ringing testament to our talented and ambitious community but unfortunately, 71% of the 3000 survey respondents also reported that they’ve struggled with the frustrating problem of late payment or even non-payment for their work.

The persistent occurrence of payment gaps that Freelancers and other gig workers endure exacts a terrible toll on the ability to live and work. Late payments and, worse still, nonpayment, wreaks havoc on cash-flow and may threaten the maintenance of normal business operations and the ability to plan for the future. When payment for services rendered doesn’t arrive within 30 days after the invoice is sent, the ability to pay bills can be undermined and the problem is exacerbated as the price of everything continues to increase. But for those of you working with clients based in California, Illinois, or the State of New York, things will soon get better.

New state laws protect Freelancers

It is said in legal circles that a contract is only as good as one’s ability to enforce it and that sometimes puts Freelance professionals at risk for exploitation. You seldom have the leverage to adequately defend yourself against unscrupulous clients who ignore their contractual responsibility, written or verbal, and decline to pay on time and in full for appropriately provided services rendered. But in NY State, IL and CA, a new day has dawned. Freelance professionals and gig workers, who are often in a comparatively vulnerable position when entering into work agreements with clients, are celebrating the passage of legislation that puts the force of law into contracts between the independently employed and their clients. The driving force behind the legislative victories was the Freelancers Union, a New York City-based advocacy group that has championed the rights of independent workers since its founding in 1995.

On August 4, 2023, Illinois became the first state in the country to adopt protections for an estimated 1.2 million Freelance workers when Governor J.B. Pritzker signed the Freelance Worker Protection Act, which took effect on July 1, 2024. The Act applies to work agreements between Freelance professionals and “contracting entities,” i.e., clients, in exchange for the Freelance worker’s services valued at $500 or more over a 120-day period. The Illinois Act excludes from the definition of “Freelance worker” any workers performing construction services, or those defined as an employee.

On November 22, 2023, New York Governor Kathy Hochul signed into law the Freelance Isn’t Free Act, groundbreaking legislation intended to shield Freelance consultants and other 1099-NEC workers from the financial damage done by non-paying or slow-paying clients. The Act was created to guarantee that Freelance workers retained as independent contractors who work with clients based in NY state receive timely compensation for all services rendered. The NY law went into effect on August 28, 2024 and some 2 million Freelance workers are expected to benefit from its much-needed legal protections.

In CA, the Freelance Worker Protection Act was signed by Governor Gavin Newsom on September 28th, 2024. As does the IL and NY legislation, the Freelance Worker Protection Act ratified in CA provides legal protection to Freelance professionals and the independently employed who work for clients located in CA. The CA law takes effect on January 1, 2025 and an estimated 2.2 million Freelancers (11.6% of the workforce as of 2022) are expected to benefit. The CA Freelance Worker Protection Act requires written contracts for Freelance services valued at $250 or more when working with clients based in CA. It is now mandated that contracts must outline the scope of work, payment method, deadlines and other important details that ensure transparency and fairness.

Written Contract
Per the Freelance Isn’t Free Act, all contracts pertaining to NY state clients and worth $800 or more must be in writing. This includes all agreements between the Freelancer and the hiring party (client) that total $800 in any 120-day period. The written contract must specify the work the Freelancer is expected to perform; the amount the Freelancer will be paid as compensation for the work; and the date the Freelancer will be paid for the work performed. Both Freelancer and client must keep a copy of the written contract. The NY Department of Consumer and Worker Protection (DCWP) created a model contract [English] that includes the terms required under the law and optional terms that may apply to different work types and arrangements. 

The Illinois Freelance Worker Protection Act requires that contracts for products or services must be in writing, and that the client provide a physical or electronic copy of the contract to the Freelance worker. Contracts must include certain information, such as the name and contact information of both parties (including the client’s mailing address), an itemized list of all products and services to be provided and their value, the rate and method of compensation and the payment date or mechanism by which such date will be determined. The client must retain a copy of the contract for a two-year period.

California’s Freelance Worker Protection Act likewise requires written contracts for Freelance services, when the value of services provided is $250 or more. Contracts must outline the scope of work, payment method, deadlines and other important details, to ensure transparency and fairness.

Timely Payment
In CA, IL and NY, your client is required to pay you for all completed work and you are entitled to receive payment on or before the date that is specified in the contract. If the contract does not specify a payment date, the client must pay you within 30 days after you complete the work.

No Retaliation
In all three states, it is illegal for a hiring party (the client) to penalize, threaten, blacklist, or otherwise deter Freelance workers from exercising their rights under the Freelance Isn’t Free Act or the Freelance Worker Protection Act. Denying an independently employed worker from obtaining future assignments and threatening to take unwarranted legal action against that worker is likewise now illegal. Freelancers who feel they have been targeted for retaliation as a result of pursuing a claim against a nonpaying or slow-paying client can file a complaint with DCWP (NY), or the IL Department of Labor, or in CA at the Labor Commissioner’s Office.

What is Freelance Isn’t Free (NY)?

  • 30-Day Payment Terms. Unless otherwise specified in a contract, clients must pay Freelancers within 30 days of work completion.
  • Mandatory Contracts. Clients must use a contract when hiring a Freelancer for over $800 of work and they can face fines if they refuse to provide one.
  • Payment Agreement Protections. Clients cannot require that Freelancers accept less than they’re owed in exchange for timely payment.
  • Anti-Retaliation. Clients cannot retaliate against a Freelancer for pursuing payment.
  • Legal Assistance. A city agency will investigate, may try to collect on the Freelancer’s behalf and will provide court navigation services if needed.
  • Double Damages. Freelancers can collect double damages and attorney fees in court and repeat offenders can face penalties of up to $25,000.

What is the Freelance Worker Protection Act (IL)?

  • Written Contract Required. A written contract outlining the products and services to be provided, the dates by which services are to be performed, and the rate and method of compensation (sample available online, and free Union contract templates available) 
  • 30-Day Payment. 30-day payment terms, unless otherwise specified in the contract.
  • Payment Agreement Protection. Protection against coercion for faster payment.
  • No Retaliation. Anti-retaliation measures against Freelancers pursuing payment.
  • Enforcement and Legal Remedies. Double damages for non-payment, covering costs and attorney’s fees.

What is the Freelance Worker Protection Act (CA)?

  • Written Contract Requirement. Freelancers must have a written agreement in place for work totaling $250 or more over a 120-day period. The contract must clearly outline the scope of services, deadlines, compensation rates and payment methods.
  • 30-Day Payment Terms. Freelancers are entitled to payment within 30 days of completing their work, unless the contract specifies otherwise. This provision eliminates the uncertainty many Freelancers face when waiting for payment.
  • Anti-Retaliation Protections. Freelancers are protected from any retaliation by hiring entities if they assert their right to fair payment under the law.
  • Enforcement and Legal Remedies. If a client fails to pay, Freelancers can seek legal recourse, including double damages and the recovery of attorney’s fees. Both Freelancers and public prosecutors can file claims to ensure compliance with the law.

Confirm milestones, invoicing, payment format

On your end, Freelancer friend, remember that the importance of providing a pleasantly efficient and smoothly delivered experience for your B2B clients cannot be overstated. Working together is a partnership and the dance is much more enjoyable when each partner understands his/her role. The contract between your company and the client describes and confirms your mutual agreement in a written document, specifying the responsibilities, terms and requirements and payments associated with the working relationship.

Once your hire has been confirmed, schedule a project kick-off meeting and review with your client the scope and timing of project deliverables, plus the associated payments or other payments. Also, include in the kick-off meeting agenda a discussion of the project or product performance goals, client expectations for the product or service you’ll provide and the ideal outcomes expected to be achieved when using your product or implementing your service. You and the client can then discuss how you’ll work together to make the client’s goals and expectations actionable and attainable. If an electronic invoice payment system will be used, ensure that your client sends the payment registration form to you, to promote a timely first payment.

  • Review and confirm project milestones
  • Review and confirm payments triggered when milestones are achieved
  • Review and confirm the invoicing schedule, if milestones are not used
  • Confirm the accepted payment methods—digital, credit/ debit card, check (electronic or physical)
  • Integrate info with your Client Relationship Management software (if applicable) to capture client data
  • Allow clients to view, comment on and sign e-documents

Thanks for reading,

Kim

Image: The Signing of the Treaty of Mortefontaine 30th September 1800 depicts the signing of the agreement that ratified the sale of Louisiana to the U.S. by France. The treaty was signed by Joseph Bonaparte, a diplomat and former ambassador, on behalf of France and Oliver Ellsworth, a framer of the Constitution and Senator from CT, on behalf of the US. Artist: Charles Etienne Pierre Motte

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Help Customers Trust Subscription Pricing

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The mere thought of guaranteed revenue arriving each month like clockwork will bring a smile to the face of every business owner. Recurring revenue is a dream come true; now you’ve got the cash-flow to pay expenses on time and in full. You can replace or upgrade business equipment when necessary. You can invest in professional development that makes you more knowledgeable, and therefore more useful to customers, and more respected in your professional community as well. Recurring revenue enables you to plan for the future of your business with confidence—and sleep well at night.

The leading way to generate recurring revenue is by introducing a subscription payment option to your business. Savvy Freelancers and SMBs are reviewing the buying habits of their best customers to determine if converting certain of their products or services to the subscription model can be successful. In the B2B sector, subscription pricing is a payment option where customers pay a recurring fee, typically monthly or annually, to receive access to a product or service, most often cloud-based software or storage, i.e., software as a service (SaaS). Freelancers and SMBs might offer subscription pricing for coaching, marketing, network and website management, or bookkeeping services.  

Thoughts of a subscription payment plan may make business owners salivate, but the process requires careful thought and planning. You’ve got to get things right from Day One and that is especially true for service-based businesses where value is not always immediately recognized. SaaS subscriptions, network and/or website management and bookkeeping services, on the other hand, have a readily apparent value that customers and prospects can picture themselves needing on a regular basis. For this reason, non-IT related service-based subscriptions may face challenges.

  • Value perception: To establish trust in a subscription payment plan, the business must demonstrate unambiguous value to prospective customers. If the customer begins to feel that s/he is not getting their money’s worth, there will be a risk of service cancellation. 
  • Service enhancements: There’s an ongoing customer expectation to continually sweeten the pot with (free) service upgrades. Global enterprise companies (like credit card companies and banks) can afford this strategy and the expectation has been set. SMBs and Freelancers may struggle to fulfill this wish, however.

Talk up value

Your subscription pricing model and everything related to it must align with the perceived value of what customers get in return. Customers must be able to see and/or believe the value of your product or service, consistently and at every touch point. Your job, Freelancer or SMB owner, is to continuously communicate that value, so customers will understand the benefits they’ll receive when opting-in to the subscription. Only when that is achieved will customer concerns fade and trust in your subscription grow.

Communicating value begins at the introduction of the subscription model sales process; the offer of a free trial will play a pivotal role in building the value you want to demonstrate. A short free trial invites prospective subscription customers to test the product or service, if it is new to them, or experience how subscription pricing can work to their benefit. Businesses acquired 50.0% of subscribers through trials, making it one of the most effective customer acquisition strategies. Additionally, as customization has become a growing preference, add-ons have become an essential part of personalized offers and 28.1% of customers offered add-on options to allow customers to tailor the subscription to their needs.

Prioritize quality control

The engine of a successful subscription-based payment model is customers who feel confident and happy to use and pay for your service or product. Your quality control procedures will play an integral part of making that possible. You must be forever vigilant and closely monitor the quality of your product or service performance and delivery, customer service/customer experience and the payment process.

Embed quality control into your workflow by making it part of someone’s job description (yours, Freelancer friend!) to confirm that customer expectations are met, respond to and document glitches and monitor the turnaround time for resolving issues. BTW, attentive quality control will make you quickly aware of brewing customer concerns, knowledge that can, for example, reveal service enhancements that customers may appreciate. You may discover another way to instill trust and value in your company. 

Expectations and the customer experience

Begin setting expectations when prospective customers first interact with your subscription sales funnel. Life is about managing expectations and it’s in your interest that every customer understands what is (and is not) included in the subscription you want them to buy—e.g., accessible services, products, tools, supporting technologies, change orders and how to reach customer service on the phone. In order to make an informed decision, subscription prospects must understand and accept what the service offers, channels for contact and the level of support offered by your organization.

Be advised that available payment methods are now an essential part of the customer experience. Economic uncertainty has made customers exceptionally price-sensitive and potentially influenced by their satisfaction, or disappointment, with the payment options you make available, along with the add-ons or upgrade options and other customization features. Debit cards remain the most popular payment method (68.6%), but the desire for access to alternative payment methods is now undeniable. Including subscription payment methods that were once seldom available can address the growing preference for a convenient, seamless payment experience that recognizes customer needs.  Alternative payment methods have been proven to generate more revenue (5.0% renewal invoice decline rate) and help prevent fraud (0.9% of failed fraud transactions). 

Customer retention

The smartest business owners will implement customer retention strategies designed to discourage customer churn and grow the subscriber base. The customer experience presents numerous opportunities to appeal to customers by offering potent sweeteners that may include loyalty rewards, product or service bundling, hybrid models, subscription pausing options, or other special offers designed to promote customer satisfaction and loyalty. In 2023, the average consumer churn rate was 4.1%, staying consistent year-over-year. As customers become more particular with spending, their purchases become more intentional, making them less likely to churn once a decision to buy has been made.

BTW, subscription pauses are a convenient alternative to sidestep cancellation when a customer needs relief from monthly payments or product deliveries. 39.7% of merchant sites enabled the pause functionality and prevented over 400,000 plan cancellations.

Thanks for reading,

Kim

Image: © Lucy Lambriex /Getty Images 2015

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Third Party Payments and 2022 Taxes

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The Internal Revenue Service announced in December that it will delay by one year implementation of a new policy that will tax funds you receive by way of third-party payment processors. All entities using third-party payers to transfer funds derived from business activity must, at the close of the calendar year, report said payments on the appropriate IRS Form 1099 and send the documents to recipients of the payments, who will then include the amount of funds reported as part of annual income. The annual taxation threshold has been lowered to $600 for all types of 1099 income.

This new IRS policy was originally scheduled to take effect in 2023 and impact 2022 income, however, many who regularly receive funds through Venmo, Apple Pay, Samsung Pay and other peer2peer digital wallets apparently only recently learned that payments received would not only be reported on Form 1099-K but, alarmingly, will be taxed in the same fashion as 1099-NEC income.

Furthermore, because a significant number of personal financial transactions are also conducted on peer2peer platforms, users are concerned about both an unexpected tax bill and its accuracy. Can your electronic payment processor be trusted to recognize the difference between side hustle income and monies you received from friends to reimburse you for laying down your credit card when you all went out for drinks one night? Will the promised line of demarcation between business and personal fund transactions be consistently respected? Inquiring minds want to know.

Before the rule change, peer2peer payment services reported recipient income on Form 1099-K only when payments reached $20,000 and the number of transactions reached 200. If those conditions were met, the1099-K was required to be submitted to the IRS along with the tax return. The new policy has lowered 1099-K taxable income to $600 per year, aligned with 1099-NEC and 1099-MISC reporting income requirements. The number of payment transactions made will be irrelevant.

You’ve figured out by now that the tax law change will significantly increase the number of folks who will face a higher tax bill. Another loophole closes for the little guy! Still, the IRS has decided that the peer2 peer payments tax rule scheduled to expire on December 31, 2022 will instead remain in place until December 31, 2023 and the new ruling will apply to 2023 income.

Regardless of when the new IRS reporting rule takes effect, Freelancers and small business owners are not liking it. There is resentment that the tax change is specifically intended to crack down on suspected tax evasion within this cohort and others who toil in the gig economy, saddling you with more paperwork and headaches. The population that will be most affected often cannot afford to hire a tax attorney to defend themselves against suspected IRS or payment processor inaccuracies.

Venmo, which was bought out by PayPal in 2012, has been trying to prepare its customers for tax changes that could affect them. The company has emphasized that payments not specifically designated as being for goods or services will not be included on the 1099-K and that the company will not list individual transactions.

FYI, Venmo customers will be wise to familiarize yourselves with the differences between its business and personal accounts. Business users may be better off quittng that service, to avoid the additional fees charged, and instead track business transactions manually from the “friends” setting.

Finally, there is an intriguing twist to the story and a possible loophole has been revealed. Payment processor Zelle insists that the new IRS rule doesn’t apply to its bank2bank payment service, since its network doesn’t hold funds. The company is run by Early Warning Services LLC, which is jointly owned by seven banks (Bank of America, Truist, PNC, US Bancorp, JPMorgan Chase, Wells Fargo and Capital One). In fact, Zelle is included on users’ bank dashboards.

While Zelle offers a service similar to Cash App, Google Pay, PayPal and other peer2peer digital payment platforms, it was built as clearXchange, a peer2peer payment service created by and for its member banks. Zelle is an electronic network that manages automated clearinghouse (ACH) transactions.

According to Wendy Walker, chair of the Information Reporting Subgroup of the IRS Advisory Council, “ACH networks are not subject to 1099-K reporting.” She went on to say, in an email, that payments sent through its network “are not subject to this law” and that small business banking customers choose Zelle “because it makes it easier to complete digital payments where they bank, enabling easier bookkeeping and accounting by having the banking data at one source.” Ms. Walker seemed to infer that bank customers see a benefit in having money in their bank accounts that is not held by third parties.

OK. Of course, Congress could extend the law to include Zelle and similar “by banks, for banks” platforms. Stay tuned for updates.

Thanks for reading,

Kim

Image: © The New Yorker June 13, 2022. The End of the Year, Liana Finck, illustrator

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

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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)