No. 16

How Can I Plan — and Save — to Take a Leave From My Business?

How Can I Plan — and Save — to Take a Leave From My Business?
Three things to keep track of when you’re a business owner: resources, finances, and the laws.
by Keila Hill-Trawick, Aja Evans May 24, 2024 — 6 min read
How Can I Plan — and Save — to Take a Leave From My Business?

About this series



Discover the more surprising sides of your business finances. From unique seller spotlights (did anybody say taxidermy?) on tackling cash flow to monthly advice from a Financial Therapist and CPA — check out these stories and more from our banking newsletter.

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This article is for educational purposes and does not constitute legal, financial, or tax advice. For specific advice applicable to your business, please contact a professional.
The Ides of May kicks off the busy season for many businesses. And for that reason, it’s a good time to plan for the unexpected. Whether you’re having a baby, need an extended vacation, or just want to ensure you’re covered during an illness, planning for a future leave of absence by taking action now can give you peace of mind. More than anyone else, business owners know that they have to keep their businesses running when life happens. Why not leverage this season’s extra earnings to save for paid time off? Given the overwhelming responsibilities that come with being an entrepreneur, knowing how to take time off isn’t something that comes naturally to many business owners. Here are a few expert tips to help.


1. Create a succession plan.  

Keila Hill-Trawick knows what it’s like to plan for a business: As a CPA and founder/CEO of Little Fish Accounting, a firm that supports small businesses, she’s done it herself. Her number one piece of advice? “Do succession planning, and make sure you’re cross-training employees as much as possible because you never know when you’ll need to be out for something,” she said.

That means training your employees to know their jobs, plus the tasks of one or two more employees. “If there’s an emergency, you already have established roles and contacts,” Hill-Trawick said. “But business owners should start from the day the employee starts working.” 

That advice works even if you’re a sole proprietor. CeCee Nedrow, a mom of three and owner of Payton’s Photography in Batavia, Illinois, says she works with two or three other photographers that she can recommend in an emergency.

“When I was pregnant, I built that into my wedding contracts, saying, ‘If I am not able to shoot your wedding, this person is who’s going to be shooting it. And we’ll set up an appointment so you can meet them ahead of time,” Nedrow said. That guaranteed safety net made her clients happy. “They weren’t worried that somebody wasn’t going to show up.”

Pro tip 1: Incorporate training goals in regular performance management meetings so “you’re transparent with everybody about what that training and your time off could look like,” Hill-Trawick said.

Pro tip 2: Plan around deadlines. If you’re planning a leave spanning weeks, “know when your tax returns are due, when your estimates are due, and what your books look like to ensure your business is in good standing,” Hill-Trawick added. 

2. Build a savings strategy.

“You can’t prepare for what you don’t know,” Nedrow said with a laugh. But you can keep track of the unknown, and having a financial buffer, whether savings or access to emergency funds to cover periods when you might not be earning, is crucial. 

Hill-Trawick recommends starting with saving for a three-month buffer — which includes payroll and operating expenses — as the goal. “Depending on how big your team is, how complex it is, and how long it takes to get a new client, you want to inch your way up to a six-month buffer.”

92,603 Square sellers use automated Square Savings so they have funds ready for taxes, rent, payroll, or a rainy day.¹

Creating business projections using online tools and resources also helps. Nedrow said various Square products help her save, track, and manage business performance, such as sales analytics and financial products from payment processors. In 2020, when her business shut down temporarily due to the COVID pandemic, Nedrow said Square helped ease her burden with its Paycheck Protection Program (PPP) loan.2

Pro tip 3: Get started with Square Savings.

Automatically set aside a percentage of your daily sales and organize it into folders for future leave, taxes, or a rainy day. Explore Square Savings ->

3. Understand local employment regulations and requirements.

Genessa Hager, owner of Exemplary HR, a consulting firm that specializes in supporting small businesses, agencies, and startups, said small business employees and business owners are eligible for a lot of state programs. As these laws vary state by state, she recommends using online resources, such as the free site Homebase and state websites, to familiarize yourself with the law.

Pro tip 4: If you own your business, pay yourself. “To be eligible for paid family leave, generally, you have to contribute every paycheck, and you have to have paid a certain amount into this program to be able to use it,” Hagar said. “If you aren’t paying yourself, you don’t have those deductions, and the state won’t pay you when you need to take a leave of absence.” 

Pro tip 5: Implement an employee handbook. Developing an employee handbook can help clarify company policies, which set clear expectations and procedures for leaves, disciplinary actions, and other workplace policies. “That can be as easy as working with an HR consultant or going on Upwork and hiring someone to make them a handbook,” Hagar said. Establishing a relationship with a consultant or a legal advisor to have ongoing support can be highly beneficial for a business owner to navigate complex scenarios as they arise.

Editor’s note: The following columns were first featured in the Square Banking newsletter. Aja Evans and Keila Hill-Trawick are not employees or consultants of Square and the views expressed in this article are solely those of the authors and are not endorsed by Square.

Finance in Focus: Managing the mental toll during your busy season

Aja Evans.jpeg

Aja Evans is a licensed mental health counselor who specializes in financial therapy. She owns and operates a private practice in New York City.

Dear Aja,

The unspoken burden of owning a business is constant anxiety over cash flow. Fluctuations in sales, unexpected costs — it can take a huge mental toll. Having real-time visibility into finances through Square has significantly reduced my cash flow stress. 

— Fumio, tea house owner, Brooklyn, NY

Being a business owner requires constant mental context switching throughout the day. At any given time, you may go from doing profit and loss updates to manning the register, checking inventory, and cleaning up — no job is unimportant. This switching from one task to another can create a heavy cognitive load, which may zap your productivity, cause you to miss small details, and feel overwhelmed and anxious.

  • Delegate. Some tasks can be left to someone else. Identify the to-dos that take up too much of your time but don’t drive the business strategy forward. These are perfect to give to someone on your team or outsource completely.
  • Automate. Free up mental space by using tools that eliminate repetitive financial tasks. Maybe having a cash-flow cushion for emergencies has been weighing on you. Try setting up automatic contributions to a savings account. Tip: Set aside as little as 1% with Square Savings folders.
  • Step away. If you can, take time off when things slow down. Until then, create a regular self-care practice you can do now. Twenty minutes of journaling, deep breathing, reading, working out, or just sitting in silence can lower your stress levels. Try building one of these into your day and see how you feel.

Good With Numbers: Build a best-selling menu — that’s on-budget 

Keila Hill.jpeg

Keila Hill-Trawick is founder and CEO of Little Fish Accounting, a boutique CPA firm dedicated to serving micro businesses through accounting and tax support.

Dear Keila, 

If an item doesn’t sell, I simply remove it from the menu. No guesswork, just confidence. When you know the correct answer and you know the numbers and figures, you can say yes or no without being iffy. 

Tee, restaurant owner, Oakland, California

Margins are already very thin in restaurants, so all business decisions need to be intentional and strategic. Here are three factors to consider to help you build a money-making menu:

  • Choose your vendors wisely. When you order ingredients, they need to be high quality, timely, and cost-effective. Who can get you what you need when you need it — and at a cost that fits your budget? Consider seasonality and holidays, when menu items might cost more.
  • Create an inventory strategy. Inventory has both purchasing and storage costs. When buying ingredients, take into account the shelf life and how much it costs to determine whether it’s better to buy in bulk or as needed.
  • Track recipe costs. As inputs increase, so might the price of the items on the menu. Getting a true sense of how much it costs to make a dish gives you insight into whether the selling price meets your customers’ desires or if it is ultimately too expensive to continue offering.

When you understand your numbers, making menu decisions is much easier and you can have confidence that you’re on the right track.

¹Based on internal data calculation from the 2023 year. Savings accounts are provided by Square Financial Services, Inc. Member FDIC.

2All loans are issued by Square Financial Services, Inc. Actual fee depends upon payment card processing history, loan amount, and other eligibility factors. A minimum payment of 1/18th of the initial loan balance is required every 60 days and full loan repayment is required within 18 months. Loan eligibility is not guaranteed. All loans are subject to credit approval.


Keila Hill-Trawick
Keila Hill-Trawick is the Founder and CEO of Little Fish Accounting, a boutique CPA firm dedicated to serving micro businesses through accounting and tax support. Based out of Washington, D.C. by way of Atlanta, GA, Little Fish serves clients nationwide.
Aja Evans
Aja Evans, a Licensed Mental Health Counselor who specializes in Financial Therapy. She owns and operates a private practice in New York City.

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