Share Post

How to Manage Bookkeeping & Accounting as a Freelancer or Contract Worker

As a freelancer, your business can be seen as an extension of your personal financials by many banks, lenders, and even the IRS. Here's how to get your books under control...

Affiliate Disclaimer: We occasionally partner with companies and services that we love and recommend to our members and readers. By clicking on the links and/or signing up for the products recommended in this post, we may receive affiliate commissions.


There is always something to tend to when you’re running your own business.

As a freelancer, categorizing expenses and keeping accurate financial documents, like monthly or quarterly profit-and-loss statements often ends up on the list of “to-dos” rather than a list of completed items.


Tracking finances, filing taxes, all while you’re running and growing your own business can be complicated and stressful. Bookkeeping is one of those things that can be scary to do yourself, and it also may seem too expensive, or like overkill to have it done professionally.


We are all guilty of putting off mundane tasks like categorizing business expenses, at some point in time. 

The truth is that correctly managing the finances for your business, regardless of how big or small, is critically important to your success. This is because as a freelancer, your business financials can be seen as an extension of your personal financials by many banks, lenders, and even the IRS.


Say you want to buy a house... mortgage lenders will require tax returns, bank statements, pay stubs, and additional documentation from your business. As a freelancer, your lender may require profit-and-loss statements that show revenues, expenses, and net income. 


This process can be much, much easier (and less stressful) with proper bookkeeping.  


As a small business owner, 1099 contractor, or sole proprietor, you are also able to claim tax deductions based on your expenses. By categorizing your expenses, you can also save hundreds or even thousands of dollars a year come tax time.


Here is a quick list of expenses you may be able to write off each year:


  • Home office expenses
  • Rent
  • Home mortgage interest
  • Internet & cell phone bills
  • Computers, laptops, & other electronics
  • Advertising
  • Childcare expenses (including paying a babysitter)
  • Meals
  • Travel
  • Training & education
  • Medical expenses
  • Professional services 


You can find more comprehensive lists out there, as there are dozens, if not hundreds of various deductions for small business owners. 


This just illustrates the fact that taking time to set up proper bookkeeping and categorize your expenses can quickly pay for itself and is something you should be doing yesterday!

This is why we love Bench.


Bench is a bookkeeping service that scales up with the success of your business, which is what makes it such a great fit for most freelancers. Their service is built around the idea that flexibility is key for their users.

Meet the "magic" accounting service that every freelancer should have...

We first discovered Bench way back in 2015, when we were looking for a CPA for a little side project that would eventually become Contena.


The Bench Dashboard


What attracted us to Bench was that unlike other services, there were no major up-front commitments. It’s a simple month-to-month rate for bookkeeping. This allowed us to first test the service, and see if it was a good fit.


After a few months we were so impressed with Bench that we ended up paying for a year in advance to get the biggest discount.

The Bench Process

As part of the sign up process, we had an initial call that helped the team at Bench get to know our business and understand our various clients, and sources of revenue, and also how to best classify many of our routine expenses.


We were also able to connect info for our financial accounts directly with the Bench platform so there is no need to send over your various financial statements manually each month. This also means that expenses get classified in near real time, vs having to wait until the end of the month to see how things are being organized.


Connect accounts directly to Bench to automatically sync your transactions. 


With our accounts connected, and our intro call completed, the Bench bookkeeping team got to work.


Occasionally, the team would reach out when more clarification was needed with a certain expense or transaction. For example, shortly after making a large one-time purchase, Bench reached out to clarify what was purchased so they could correctly categorize the expense.


Bench is like having a dedicated assistant that completes most of those mundane bookkeeping tasks for you, and politely asks when more clarification is needed to complete a certain task.

Overall, we were super impressed by how “it just worked” and how much less time we were spending on these tasks each month. The time saved was better spent on doing things we actually enjoyed doing and more importantly, things that would grow our business.


Once accounts are integrated, the only thing left to do is to clarify a few expenses.


But, the best part of the experience was when tax time rolled around, and all of our expenses were categorized so that we were able to get the maximum dedication, which far exceeded the cost of the actual bookkeeping service.


This is why the notion that bookkeeping costs money…. Not only can it save you the time and stress of doing much of this stuff yourself - it also can pay for itself.

Bench can actually save you money during the filing process with their extensive knowledge of tax advantages and benefits.

Bookeeping Catch-up

It can sometimes feel completely overwhelming for freelancers if you don’t even know where to begin with your financial records and bookkeeping. Maybe you’ve been putting it off and the paperwork is piling up, but you’re not sure what to keep and what to file away. 


Bench offers a catch up service, to help you get your accounting under control, even if you have months or even years of messy or unkept books. 

Also, if you're more than 2 years behind on your bookkeeping, the dedicated Bench Retro team will work with you to sort through everything so you're ready for tax season -- and beyond. 


While we eventually graduated from Bench to a dedicated CPA - Bench helped us grow from a little side project, into a real company, generating millions of dollars a year.


So regardless of if freelance writing is a full-time gig or a side hustle, make the commitment to set yourself up for success with a strong foundation: beginning with your books.


Your future self will thank you!

Special Discount for Contena Readers:


The team at Bench has been kind enough to create a discount for our readers. Join Bench through this link to get 30% off your first three months
of bookkeeping.

Subscribe to Contena®

Want to have Contena®'s latest posts delivered to your inbox?