If you don’t treat your business like a business, nobody else will.

– Heather, The Legal Website Warrior®

It’s now December, and many entrepreneurs and small businesses are wondering what they should be doing for their end of year planning as they prepare to wrap up the current calendar year and transition into a new year.

End of year planning may look a bit different business to business, but I wanted to provide a quick check list reminder that could support you in your end of year planning efforts.

The following items are generally categories that you should assess each year, particularly if you have not handled these things yet within the current calendar year. I do not provide tax or financial advice, but there may be tax and financial advantages to handling many of these before the year’s end.

1. Rolling Risk Assessment for Legal Needs

I teach clients about a concept I call performing a “rolling risk assessment” of their business, from a legal needs stand point. In a nutshell, this means asking yourself when you make certain changes in your business, whether you have a new legal need (gap) that needs to be met, whether with a contract to cover that scenario, a consultation to discuss strategy, or something else:

  • Did you expand your team? (Whether with an employee or independent contractor.) And if so, did you properly protect your IP and business?
  • Did you offer a new service or launch a new online course, program, or offer? (Requiring a new client services agreement, or online terms?)
  • Did you add a new collaboration opportunity? (Mastermind, Joint Venture, Affiliate Program, or “informal” collaboration).
  • Did you move, relocate your business, or add a new office?
  • Did you create a new tagline, program or course name, or other “signature” name that may require trademark protection? See this article for more trademark information.
  • Did you engage in some other business activity that would necessitate legal support to protect your growth this year?

And if you need help assessing a new growth strategy, offering, a potential tagline, or other strategic move, you can always schedule a consultation. I regularly help clients assess their (legal) options, and potential impacts related to various strategic moves. I recommend a check-in quarterly, but absolutely no less than once a year.

2. Entity / Tax Election Status

Does your business entity or tax election status need to change or be updated?

If you are sole proprietor, it is time to create your business entity to line up with a new tax & calendar year.

And if you already have a business entity (LLC, C-corp, etc), is it time to update the tax election status?

Perhaps you are making enough money through your LLC now that it’s time to make an s-corp election. Perhaps you’ve created enough income you want to keep some of it in your business and not be taxed on all of your income each calendar year and a c-corp election is actually a better fit for you. (This is decision best made with the support of legal counsel and your CPA or accountant.)

3. Business Insurance

Insurance of all kinds should be assessed on at least an annual basis. Do you have the right amount of coverage? Did you have any updates to your business or life this year that require a new or different kind of insurance policy?

Maybe you added a home office? (Don’t assume this is covered by your current homeowner’s policy).

Perhaps you added live events to your business? (This likely requires a different kind of coverage).

Is this the year to put cybersecurity or data protection insurance in place?

If you don’t have business insurance, it may be time to explore the resources available to you in this bucket and get something in place.

4. “Catch Up” Corporate Books

Each year it is important to maintain up-to-date corporate books. You can get a formal “corporate kit” (use the google), or you can create your own binder where you keep all of your important documents (legal, incorporation, meeting minutes, etc) related to your business.

The vast majority of small businesses do not maintain adequate corporate records.

This opens up your business to significant risk in the event you were to be audited for tax, or legal reasons, or as part of a formal, legal proceeding (litigation, for example).

What should be included in your corporate book?

  • Articles of Organization (if you are an LLC), or Articles of Incorporation (for a c-corp)
  • Certificate of Formation (returned from your Secretary of State)
  • Operating Agreement (if you are an LLC), or your Corporate Bylaws (for a c-corp)
  • Registered Agent Information / contact
  • FEIN confirmation (from the IRS)
  • Entity Election Status (form that you file with the IRS), plus any confirmation received documenting the status change
  • State Business License
  • Local Business Licenses (unless required to be posted in your place of business)
  • Insurance Policies (for the business)
  • Annual Reports
  • Meeting Minutes, especially those documenting important decisions: hiring, obtaining loans, acquiring assets, etc.
  • Trademark Registration Certificate
  • Business loan documents, including documentation of any personal loans made to the business, etc.

There may be other important documents that should be added to your corporate books, but this list should get you started! Just remember you want to be able to show that at all times you “treated your business like a business” including by keeping clean corporate (or LLC) record books.

5. Financial Planning for End of Year Wrap Up & Next Year Impact

By the first week of December you should also have already scheduled or accomplished meetings with your CPA or accountant, your financial planner or advisor, and your attorney if you have one, to assess any actions you should be taking before the end of the calendar year or sometimes at the start of the next year. (Contributions to IRAs, for example).

You will want to have a summary of:

  • your current year’s financials,
  • any questions you have about any outstanding items in your business,
  • any new financial issues that are relevant for the year
  • plans for making any final donations or charitable contributions or gifts (for tax purposes), and
  • revenue predictions for the remainder of the year.

This will help you to get a better understanding of your likely tax obligation, as well as any actions you can take before the end of the year that will either minimize your taxes or help you to meet any other financial or investment goals you have.

6. Putting Important Dates on Your Calendar for Next Year

I recommend that you also go through your calendar for next year and place any important dates on your calendar that you need to track:

  • Tax deadlines for your business & personal tax filings
  • Local reporting requirements & tax filings (quarterly, for example, for your state Department of Revenue; monthly, quarterly, or annually for your City taxes as required, etc).
  • If you have any major renewals in your business (for software, independent contractor support, vendor or supplier contracts), put these dates on your calendars as well – especially if they include any notice period for cancellation. You do not want to miss these important dates and have a simple error have a detrimental impact to your business.
  • Business insurance renewals or “revisit” dates
  • Personal insurance renewals or “revisit” dates (It’s good to shop around for insurance products / policies every once in a while to keep your rates competitive)
  • Vacations!! (to make sure you take them, incentivize your business progress, and make sure that you prioritize any support in your business in order to make sure they – i.e. vacations — happen!)

If you’d like access to my Small Business Important Dates Checklist – reach out. Drop me a quick email and I will happily share it with you.

7. Assess Your Professional Team

Every small business needs certain key professionals “on their team.” These include:

  • A CPA or accountant that supports you with financial and tax strategy in your business & personal life (Wondering how to choose a CPA? This article might help).
  • Financial Advisor so that you can be proactive with your money and invest it wisely
  • A bookkeeper to help you manage your day to day tracking in your business
  • Insurance Broker(s) who can help you at least on an annual basis assess your current policies and put any updates or new policies in place as you grow or your business evolves
  • An attorney to support your business with the proper legal structure that it needs to grow and thrive, while also minimizing your risk in key areas
  • Business Banker – yes! A real, live person at your bank that can support you with your business banking (and talk to you about lines of credits, loans, etc, as your business grows)

There may be others given your unique business – but regardless, how is your team performing? Are they helping your business grow? Are they providing the right support for your business?

On an annual basis, assess your team, and if you need to make changes, reach out to colleagues or others in your industry (who are a few steps ahead of you), and get referrals to new professionals.

8. Assess Your Support Team

On an annual basis (and hopefully more frequently), you should also be assessing your “internal” support team. This includes any employees or independent contractors who are supporting your business (as well as yourself!). You likely need to hire additional support, if you are like most small businesses and entrepreneurs who keep far too much on your plate for far too long.

Are you tracking performance? Have you created a meaningful way to document duties and measure performance? If you have not done so already, it is time to have an end-of-year review and document performance, goals, etc., before rounding of the new year.

Because it’s also a great time of year to celebrate the fabulous team you have!

(The topic of employment could send us deep into a topic with lots of potential pitfalls and risks – but this is critical to the growth of many small businesses!) If you need help with employment or HR related issues, get it sooner rather than later with an attorney who is in the same jurisdiction as your business, especially if there is the chance that you may be facing a potential difficult scenario, including litigation. You do not want to delay. Employees are the greatest asset, and can be one of the greatest risks for small businesses.

As part of assessing your team, current performance, and whether you need additional support, you should also be assessing team rhythms.

Do you have a consistent meeting rhythm and systems in place to support communication amongst your team in a way that is working? That supports everyone in doing their best work? Assess your teams and rhythms at the same time to determine whether anything needs to change, and how you might improve support and communication for everyone.

9. Update your Business Mission or Values Statement

Similarly, has the direction or clarity of your business changed a bit this year?

If so, perhaps it is time to update your Business Mission Statement or your Values Statement – and as a small business, you should have these things in place! It matters, especially if you building team.

The time to have these things in place is before you bring (potentially the wrong people) onto your team.

Small businesses don’t have the budgets to have consistent misalignments between their hiring choices and their visions. Being clear on your business mission and your values statement, knowing where you fit in the marketplace and what makes your business unique will help you to make better hiring decisions.

10. Goals to Meet this Year + Goals to Meet Next Year + Goals to Release

Of course it is also an excellent time of year to do a quick assessment of your goals.

Did you meet your goals for the current year? Are you close to meeting some of them with an additional push? What might that look like? A flash sale? A campaign to reach out to current clients? Offering an “end-of-year” assessment which helps them to better understand your services?

What goals do you have for next year, given your progress this year? I recommend spending some time on this before the new year so that you start strong in January with a plan. Maybe your goals for next year look similar to the goals for this year, or maybe they take then to a whole new level.

And what goals do you need to release? Maybe you had something on your plate that turned out not to be a priority this year? Maybe the direction of your business or one of your services changed and you can release a former goal that is still hanging out there?

The process of “releasing” goals is also important so that we feel complete in our current efforts, acknowledge what worked, see clearly what didn’t, and start the next year with a fresh and updated plan for success.

11. Technology Assessment

None of us can be in business for long if our business is outdated or lagging behind others in the marketplace.

I believe wholeheartedly in innovation, not for the sake of innovation, but for the sake of efficiency and becoming more effective at what we do – essentially creating win-win-win scenarios based upon improving efficiency and effectiveness. Wins for your clients, wins for your business, and wins for those who support your business.

This is a constant goal in my own business.

How can we do better and more work in less time so that we can achieve cost savings in our businesses while providing an improved product or service for our clients?

Technology is sometimes the answer. It is nearly always a part of the puzzle.

Which is why the end-of-the-year assessment and planning phase is an excellent time to also assess your current technology supports and any technology needs.

  • What would make your life easier?
  • What would make your business flow more smoothly?
  • What, if it existed, would solve a problem for you and your team?
  • What, if it existed, would solve a problem for your client?
  • How might you access these new technologies?

And then ask around. Get referrals. Talk with other business owners about what they use. And also, add a Technology Support person to your team!

12. Data Protection Practices

Of course we cannot talk about technology without talking about data protection practices. If you have listened to any of my trainings or Ask Me Anything LIVE sessions, you know the importance of protecting data in our businesses.

The first step is to understand and “map” the data you have.

  • What data are you collecting in your business?
  • How are you collecting it?
  • Where is it being stored?
  • How is it being backed up or protected?
  • Who has access to it and at what points?

Map your data flows.

Literally write this all down and make sure you are looking at the data that is coming into your business from others, especially your clients, customers, or list. (And of course, do you have a privacy policy in place that you follow? You must both disclose your policies and follow them!)

The other data to look at is internal data – systems, processes, intellectual property, employee or support staff information, internal communications, documentation, etc. These are the systems and information that help you run your business.

  • How are these items being stored?
  • Who has access to them?
  • How are they being protected before disclosures are made (intentionally or accidentally)?
  • What documentation do you need to protect these things?

And finally how are you backing up or expunging this data, as necessary?

  • Do you have automatic back-up processes on all of your internal data? (You should).
  • Do you have duplicate back-ups, especially for anything stored on a hard drive? (You should).
  • Do you have malware protection for any hard drives? (You should).
  • Do you have all of your passwords regularly updated and stored in a password keeper like KeyPass or Lastpass (You should).
  • Do you have any remote or international support staff accessing your internal company information via a VPN (virtual private network) or other encrypted connection? (You should).
  • Do you have someone on your team running regular updates to your website, keeping all software up to date, and taking other simple, but essential measures to protect your business and data?
  • Do you have your data back-up and expungement policies written down?
  • Do you have your data protection policies (for internal information) written down?

Some quick facts:

One in three hard drives fail in a given year which means you should have THREE copies of all important sets of data. Including at least one or more hard drives, and one copy in the cloud. (Backblaze, dropbox, etc. have automatic back-up functionality).

Biggest risks to small business include employees who are not following data protection policies, inadvertently expose passwords, spend time on social media or in email and click links they are not supposed to click, or who otherwise inadvertently expose data.

The biggest risk to your website and computer in regards to malware, viruses etc is in not keeping your website and system software up to date, and performing functions on a public network or connection that makes your log-ins and other actions visible to others who know how to get access to such information.

Simple measures go a long way to protecting your data, and of course more complex measures are becoming increasingly required.

Don’t let your data or policies become stale. As part of your annual review, begin assessing your data and putting systems in place that help your team help you take good care of your business and the data within your business that you need to protect.

13. Market Assessment

In line with #11 above regarding technology and innovation, the other question you should be asking yourself is how your business is doing in relationship to your marketplace.

Some questions to ask yourself:

  • What developments did you see in your industry this year?
  • What are other businesses doing?
  • What new business are making their way into the marketplace? (And why? What problem are they solving?)
  • What new trends are you seeing?
  • What is the biggest issue in your industry that keeps customers dissatisfied?
  • How might you, using creativity and innovation, improve your market positioning by solving that problem?

A lot of small businesses in certain industries (especially traditional, long-standing industries) are very wary of competitors in the marketplace because they feel that they have such a small share of the market that they have to fiercely protect their standing and their share. This is often rooted in “tradition” and the way things “have been” etc.

What if instead you could utilize what competitors are doing to your advantage, to explore “what’s working” with their approach?

What if you could observe major trends, but also what is happening in the fringe of the marketplace to make your business more agile and responsive to your clients needs and to actually gain market share?

What if you could tap into a whole new type or level of client who is underserved by the current version of your industry?

What if you could adopt the best of both worlds – and utilize what has been already working, with elements of trends or client experiences that are improving the industry?

What if you could improve your clients’ access to the industry, and contribute to positive forward momentum both for your business and for your client?

Look for the win-win-wins, including from opportunities created by your competitors, or opportunities created simply by listening to and observing the marketplace, and make strategic pivots and improvements as necessary, of course in line with your Business Mission and Values Statement.

14. Continuing Education

If you are a licensed professional, continuing education is likely already on your radar.

But sometimes it sneaks up on us, and has to be crammed in to the final months before the conclusion of our reporting period. Which is why it is also beneficial to schedule your continuing education in advance for the coming calendar year as well.

Especially with how frequently continuing education is now offered in pre-recorded formats online.

But even if you are not a licensed professional, I would encourage you to ask yourself how are you ensuring that you are getting essential continuing education given what you do in your business?

The irony of continuing education is that it is a bit of work, especially if you are working against a deadline, and it can also be so refreshing.

It reminds me constantly of the joy of learning and honing our skills in certain areas, as well as the importance of being exposed to entirely new topics that expand the way that we think about or approach our businesses.

On this point, what are you doing to expand your perspective outside of your business or industry? How might you include some “education” in your business building plan that allows you to benefit from the perspectives or trends in other businesses or industries?

Whether this comes through online programs, courses or trainings, education hubs (like CreativeLive or Masterclass), live workshops in the world – i.e. in a new physical space, or in collaborative, self-created environments like book clubs or masterminds — how can you incorporate continuing education into your business building plan?

This is an excellent time of year to assess this topic as well, and put plans in place for the new year that will support your goals and growth including in creative and potentially surprising ways.

15. Finally – Time Off!

The beginning of December is also the time to begin notifying current clients or customers regarding your time away from your business for the holidays. This is especially critical if you are a service provider, or have 1:1 client services where people may be relying on you for certain things.

Protecting your vacation time, and making sure time off is truly time off, requires taking steps up to your vacation that help you and others to respect your schedule.

  • Make sure your time off is clearly noted on your calendar and communicated with your team.
  • Make sure that if you need support while you are away that you have adequate team support in place.
  • Send any updates or notifications to your clients or customers well in advance of your scheduled time off.
  • Preschedule any udpates or notifications to your clients or customers that let them know in the new year when you are back and “open for business.”

And how do you also ensure that your team gets adequate time off to enjoy the holidays?

Put those systems in place as well so that your team feels like they can have true time off as well. And don’t be afraid to just not be available.

As we have learned, businesses can gain customers by taking an approach in alignment with their values that bucks the system (i.e. REI’s #OptOutside movement instead of participating in “Black Friday”) even if it means they are not always available to their customers or clients.

You’ve got this!


Obviously this list could be as overwhelming as you let it become. Don’t do that. Take a quick inventory and prioritize your biggest needs and start there. Some of these items are definitely more important than others.

And as your business grows, you can implement systems throughout the year that support these items.

But if you have not considered them, now is a great time to set some time aside to assess your current position and needs in regards to each of these items, and put a plan in place to tackle these topics or get the right support for tackling these topics.

You got this! The joy of building a business includes all these interesting problems we get to solve. 🙂 And when we spend the time addressing the right things at the right time, it pays dividends in our businesses and for our clients.

Happy Happy Holidays! Wishing you a wonderful end of the year and new year!

As always, to your success!

Heather, The Legal Website Warrior®

PS. Have a question that you would like to tackle in your business? Just schedule a consultation and let’s chat about it!


Here are my last three posts in case you missed them!

What is Spam and is it Illegal in the U.S.?

Trademarks: Frequently Asked Questions

3 Things You Can Do Today (Without a Lawyer) to Protect Your Online Content


If you are interested in other ways to plan your business then visit these posts…..

© 2021 Heather Pearce Campbell, The Legal Website Warrior® – www.legalwebsitewarrior.com