Simply Business homepage
Call Us(844) 654-7272
Get a QuoteSign In

28 Simple Secrets That Will Help Your Biz Crush the End of 2019

5-minute read

Our end-of-year secrets will help your small business successfully wrap up 2019, like this excited barista.
Mariah Bliss

Mariah Bliss

17 September 2019

Share on FacebookShare on TwitterShare on LinkedIn

Ever wondered how other small business owners handle the last four months of the year?

We did too. That’s why we investigated what small businesses are doing to prepare for the end of the year, whether their work is slowing down for winter (contractors, landscapers) or speeding up for the holidays (retailers, restaurants).

While a lot of small businesses had different seasonality challenges, we found dozens or tried-and-true strategies that every business can use to close out the remaining year on a high note.

So whether you’re a contractor or a photographer, these 28 simple secrets from other small business owners will have you ready for whatever the upcoming season may throw at you.

The Most Wonderful Time of the Year: Prepping for the Holidays

If you work in retail, hospitality, or the restaurant industry, you know that the holidays can be the busiest time of the year for your business. That’s why — even though it may be a little early — it’s worth thinking about how you want to approach the holiday season. The National Retail Federation reports that holiday spending in 2018 increased by almost 3% and will continue to grow in 2019, meaning there’s plenty of opportunity for small business owners to take advantage of that extra money.

Some ways small business owners are preparing for the upcoming holidays include:

  1. Ordering supplies and products
  2. Mapping out hiring needs and starting the hiring process
  3. Updating websites and social media accounts
  4. Planning and executing holiday marketing campaigns

Additionally, many small business owners are already planning how they’ll participate in niche holidays, like Small Business Saturday. If you don’t already participate in Small Business Saturday, you should!

64% said they shop on Small Business Saturday to support their communities

TIP: Small Business Saturday is held the day after Black Friday; this year, it falls on November 30.

Even if you don’t have a traditional retail business, you can still take advantage of Small Business Saturday. A few ideas include:

  1. Running a special sale for your services on that day only
  2. Posting on social media and driving visitors to your site
  3. Sending out a special newsletter
  4. Launching a big announcement over your social media accounts and website

Of course, the holiday season doesn’t always mean more work.

For many businesses — especially in the construction, landscaping, and manufacturing industries — work slows down, leading to fewer projects and a lot more free time.

Some businesses in these industries work to supplement their slow season by:

  1. Offering snow plowing services
  2. Specializing in decorating services (e.g., hanging outdoor seasonal lighting)
  3. Transitioning to handyman or more interior-based services
  4. Providing seasonal discounts to attract more business

Small business owners who may have planned their cash flow in anticipation of the winter season choose to take the time off. They view this time as their chance to rest or to prepare their business for the new year by finding more customers.

Don’t get too comfortable, though: Despite the overall drop-off, changing weather might keep some businesses busier than what they’re accustomed to. For example, record-low freezing temperatures in early 2019 forced a lot of plumbers to deal with higher call volumes than normal, thanks to an epidemic of frozen pipes. Even contractors found themselves busy during traditionally slower months, as heavy snow accumulations caused a lot of roof damage.

Hiring & Firing: How Your Team Is Affected by the Upcoming Season

Hiring is always a big concern for small business owners; in fact, a recent Indeed survey found that more than half of small businesses struggle with finding the right employees.

And if your business experiences a huge upswing during the holiday months (hello, retail), then the struggle to find good talent might feel even more difficult.

Here’s how business owners surmount the challenges associated with hiring great seasonal workers:

  1. Offer more hours to existing workers
  2. Ask for referrals
  3. Create a hiring plan in early fall (hey, great timing!)
  4. Place hiring ads on social media
  5. Get extra help if seasonal applications become overwhelming

Of course, a lot of businesses don’t experience a big increase in hiring for the end of the year.

Many contractors, landscapers, and painters experience a drop-off during the colder months, especially if they’re based in the North or Midwest regions.

Recent research shows that while construction hiring peaks in August, hiring grinds to a halt in February, with construction employment levels about 10 percent lower than the annual average.

Business owners who must slow down their work over the winter months may need to start letting employees go. If you’re an established business, your employees might already be accustomed to this process; however, if your business is new, the following tips may help you manage the process a bit better:

  1. Give your employees an idea of when they can expect to come back to work, especially your most talented ones
  2. Provide a heads-up as to when you’ll be cutting staff so your employees can find supplemental work
  3. Create a plan for how you’ll manage your remaining work with fewer staff
  4. Provide your employees with referrals if they need help finding temporary work

How Seasonal Changes Affect Your Expenses

The upcoming holiday season doesn’t just impact your cash flow; it can also affect your business expenses.

For example, if you’re on a hiring spree to get your business ready for the holidays, take a look at how adding seasonal workers may affect your tax obligations (specifically social security).

You should also assess your insurance policies to make sure your coverage protects your business and your new seasonal workers.

We recommend expanding your general liability, professional liability, and/or workers compensation coverage to give your business the protection it needs to stay safe during the holidays.

If your work is slowing down, it pays to see how you can manage expenses so you can stretch your budget. Insurance premiums, tax payments, and other variable expenses may be difficult to plan for during this time, so it pays to get close to your insurance company or accountant to see how you can adjust your bills so you’re not overpaying.

Are You Preparing for 2020?

For many small business owners, they’re not just prepping for the end of 2019 — they’re gearing up for 2020 as well.

Here’s why: When the beginning of the year rolls around, income tax season isn’t too far behind. And in 2019, a lot of people were frustrated to find out that they owed more in taxes than they anticipated, thanks to the new tax laws.

To avoid getting caught off-guard, small business owners should be putting aside at least 30% of earnings

Other ways small business owners are getting ready for 2020 include:

  1. Creating a hiring plan for seasonal work in the spring
  2. Updating/finalizing their accounting/financial documents
  3. Reflecting on the previous year’s victories and misses
  4. Creating and sharing new goals for the upcoming year
  5. Preparing or issuing IRS Forms 1099 or W-2
  6. Following up with outstanding invoices from 2019
  7. Mapping out what equipment, tools, or supplies need to be replaced or repaired in 2020

Speaking of getting ready for 2020, there have been recent rumblings about an upcoming recession, and some small business owners are taking notice. While small business confidence was at an all-time high earlier in 2019, stock market volatility and pre-recession signs may cause some business owners to be more cautious when planning their goals for 2020.

Even with the Seasonal Changes, You’re Feeling Good

The end of the year can be a hectic time for small business owners, whether you’re gearing up for a big holiday rush or winding down for the season.

But no matter which end of the spectrum you fall in, you’re probably feeling pretty good about things:

According to a 2019 Guidant Financial Report, 53% of small business owners ranked their happiness at 8 or above on a scale of 1 to 10

The majority of folks attributed their sense of high satisfaction with being independent.

More importantly, this sense of happiness doesn’t seem to change, even in the midst of seasonal work, economic news, and other daily stresses that are common to the small business experience.

And in a world where all the news is focused on how very unhappy Americans are, being a small business owner seems to be a key to feeling the kind of satisfaction and contentment that can weather any storm.

So no matter what the end of the year might bring you, the good news is that you’re in charge of what your business can do about it.

We reached out to a lot of business owners to get their feedback about how they’re preparing for the end of the year, but now we want to hear from you. How are you getting ready for the end of 2019? Does work slow down or does it get super busy?

Tell us and we may feature your story in a future post!

Get Insured in Under 10 Minutes

Get an affordable & customized policy in just minutes. So you can get back to what matters: Your business.

Start Here >
Mariah Bliss

Written by

Mariah Bliss

I love writing about the small business experience because I happen to be a small business owner - I've had a freelance copywriting business for over 10 years. In addition to that, I also head up the content strategy here at Simply Business. Reach out if you have a great idea for an article or just want to say hi!

Mariah writes on a number of topics such as small business planning, contractor insurance, and business licenses.

This content is for general, informational purposes only and is not intended to provide legal, tax, accounting, or financial advice. Please obtain expert advice from industry specific professionals who may better understand your business’s needs. Read our full disclaimer

Find this article useful? Spread the word.

Share on Facebook
Share on Twitter
Share on LinkedIn


Business InsuranceGeneral Liability InsuranceWorkers Compensation InsuranceProfessional Liability InsuranceErrors & Omissions InsuranceSole Proprietors Workers CompensationCyber InsuranceSelf-Employed Insurance


Contractors InsuranceCleaners InsuranceE-commerce InsuranceHandyman InsuranceHome Improvement Contractor InsuranceLandscaping InsuranceLawn Care InsurancePhotographers Insurance


About usContact UsCareersSite MapInsurance Providers


General BusinessProtect Your BusinessStart Your Business


Simply Business1 Beacon Street, 15th FloorBoston, MA02108


Terms & ConditionsPrivacy PolicyPrivacy Notice for CA ResidentsResponsible Disclosure Policy

*Harborway Insurance policies are underwritten by Spinnaker Insurance Company and reinsured by Munich Re, an A+ (Superior) rated insurance carrier by AM Best. Harborway Insurance is a brand name of Harborway Insurance Agency, LLC, a licensed insurance producer in all 50 states and the District of Columbia. California license #6004217.

© Copyright 2024 Simply Business. All Rights Reserved. Simply Business, LLC is a licensed insurance producer in all U.S. States and the District of Columbia. Simply Business has its registered office at Simply Business, 1 Beacon Street, 15th Floor, Boston, MA, 02108. In California, we operate under the name Simply Business Insurance Agency, LLC, License #0M20593. In Colorado, we operate under the name Simply Business, LLC DBA Simply Business Insurance Agency. In New York, we operate under the name Simply Business Insurance Agency. In Pennsylvania, we operate under the name Simply Business Insurance Agency, LLC. In Texas, we operate under the name, U.S. Simply Business, LLC. For more information, please refer to our Privacy Policy and Terms & Conditions.