It’s mid-year. The year is half over.  But we still have half a year to go.

It’s time to re-evaluate and recharge. We still have time to achieve our goals by the end of the year.

So let’s get started with the mid-year checklist.

mid-year checklist for small businesses
Mid-Year Checklist

Financial/Money Stuff


Recordkeeping (paper) – organize your physical documents  

If you still have paper around for your income and expenses, organize them and file them in an orderly fashion.  You don’t need to be extra fancy.  You’re filing system can be as simple as monthly envelopes for your bank deposit receipts and expense receipts.


Recordkeeping (digital) – Organize Your Electronic Documents

Getting organized doesn’t stop with just the physical paper, update and organize your digital files too.  I don’t know about you but every year, I have the best intentions.  I intend to keep my inbox and electronic files neat and orderly…it’s when I’m looking for something that I realize that I haven’t been as successful as I would have liked to be.  This is as good of a time as any to clean up your digital file cabinet too.


Bookkeeping & Accounting

You want to make sure to make the most of not only tax deductions (expenses) but also make sure that you know who owes you so that you collect on your receivables in a timely manner… you can’t do that without a bookkeeping system.  There’s nothing wrong with using a spreadsheet for this if you’re in the beginning stages of your business but if you want to get really snazzy, starting using accounting software like Wave or Xero.


Budgeting & Reforecasting

Budget/Goals – update your money goals (aka your budget).  Look to see where you’re hitting or exceeding the mark…and update your goals.  Look to see where you’re not doing so well and update those goals/budget line items as well.


Legal & Tax Stuff


Re-evaluate your business entity

You want to make sure that the business structure you have is the right one for your legal needs as a business owner. Check to see if there are any legal things you need to be aware of.  Ignorance is NOT bliss (nor is it a defense).


Re-evaluate your business entity (part two)

Secondly, you want to make sure that you understand the tax implications of any legal entity changes.  Again, you can’t claim lack of knowledge when the tax man (or woman) comes knocking because you forgot to file something.


Estimates Taxes

Review your tax position. Review the prior year and prior two quarters.  If you owed or would owe, you probably should be paying quarterly estimated tax. So review, check it out. And get started now.  You don’t want to be penalized later.


Vendor Documentation & Updates

If you work with independent contractors, double check to make sure that you have IRS Form W9s on file for them if you’ve paid or will pay more than $600 USD for your tax year. Review your paperwork now and get your ducks in a row now so that you won’t be scrambling to get the documentation from them at year end.


Marketing Stuff



Do a little “site audit”.  Make sure all the information on your static pages, like the contact us and about us pages, are up to date and all the links still work.


Customer Check In

Send your best (and not so best) customers an email to say hello and check on them.  Or even better, give them a call.  You never know, this small gesture might bring you some new business and revenue.  😉


Social Media Review

Do a little “audit” of all your social media profiles.  Cleanup of your profiles.  Make sure all the information is up to date (especially contact information).




Legal Planning Meeting

Meet with/have a conversation with your business attorney – discuss the legal stuff…you don’t have to wait until there is a problem to contact him/her.


Money/Tax Planning Meeting

Meet with/have a conversation with your CPA – discuss the accounting and tax stuff… you don’t have to wait until tax time to talk.

These checklist items may seem like small things but when you look at the big picture, they all sum up to being  proactive instead of reactive.  Getting ahead of the “crisis” …and taking care of things before they are issues instead of  waiting until things get out of hand, messy and overwhelming.

It’s all about awareness… being purposeful and systematic so that you can grow & maintain a business that you love.

Did I miss anything?  What’s on your mid-year checklist?

Let me hear it in the comments below.

Until next time,



7 Steps to Better Books Checklist

Money Matters Checklist

Editor’s note: This post was originally published in July 2014 and has been completely revamped and updated

Pin It on Pinterest

Share This
Skip to content