Self-Employment Basics

There is a ton of information out there for self-employed business owners. With enough time and dedication, you could learn absolutely everything you need to know about running a business. But you’re self-employed. You do not have time to sift through everything there is to know. After working with business owners as a bookkeeper, accountant, and tax preparer in California for twenty years, I think I can save you some time. Here are the basic things you need to do if you are self-employed. (None of these recommendations or links are currently sponsored. Please see our legal disclaimer.)

1. Track your tasks

First, you’ll need to establish a system to keep track of what you need to do. This can be through pen and paper or with an app, but decide early how you will keep track of what you need to do. Develop a habit of tracking everything that comes up so the tasks can be scheduled and prioritized. Here are a few recommendations:

The Bullet Journal method is fantastic for tracking long-term goals and big-picture vision. For day-to-day, I highly recommend using a digital task-tracking method, especially if you have recurring tasks. These should include your specific process for completing the tasks described next.

2. Separate your business and personal finances

As a sole-proprietor you as an individual and you as a business are indistinguishable, one and the same. However, keeping your business finances separate from your personal finances (money you take out of your business to pay for your rent/mortgage, groceries, gas, clothes, etc.) will go a long way in protecting your non-taxable business deductions. Also, if/when you ever apply for a business loan and the creditor requests your bank statements, you can maintain your personal privacy by having your personal transactions in a separate account.

Only run business transactions through your business account. These include depositing money received from customers, checks you write and debit transactions you authorize to pay vendors for expenses (supplies, advertising, software, etc.), and business loan payments. Do not pay for personal expenses out of your business account. Instead, transfer the funds you need for personal expenses from your business account to a separate, personal account on a bi-weekly or monthly basis. These transfers are considered to be an “Owner’s Draw” (an equity account) and should never exceed your net business income.

3. Maintain your bookkeeping

If your business completes fewer than 25 transactions a month (incoming and outgoing money), you might be able to get maintain your bookkeeping in Excel or even pen-and-paper with some office supply forms. If you have more transactions, I definitely recommend subscribing to an online bookkeeping software like QuickBooks Online or Xero. Desktop software can get you by for awhile, but unless you need it for something specific (like certified payroll in the contracting world), online software is the way to go. Some of those recurring tasks I mentioned above should include these bookkeeping tasks:

  1. Complete weekly bookkeeping (bank deposit, invoicing, bill pay, filing).
  2. Complete monthly bookkeeping (reconcile accounts, review financial reports).
  3. Pay quarterly income tax estimates. Don’t wait to see what your tax bill is at the end of the year. Meet with your tax preparer, estimate your taxes for the year, and make a habit of setting aside a percentage of every dollar you bring in. Divide your total estimated tax by your total estimated gross income to get the percentage. Then, every two weeks transfer that percentage (of the money received during that period) to a tax savings account. You can learn more about this method at Profit First.
  4. Collect W-9 forms for any independent contractors (sole-proprietors) you pay more than $600 during the year. I review this on a quarterly basis to save a lot of stress in January when I have to issue 1099-NEC forms (formerly 1099-MISC).
  5. Prepare your records for annual income tax return preparation. At the end of each year, you’ll want to review both your Profit & Loss Detail Report and Balance Sheet Detail Report for the entire year to ensure consistency. These reports will show you every transaction entered in your bookkeeping system for the year. If bookkeeping is not your forte and you want to be sure things are right, you can always setup an appointment with us to take care of this for you at the end of the year.
  6. Run payroll (if applicable). If you have employees, I cannot recommend paying for a full service payroll subscription highly enough. If you already have QuickBooks, their core payroll service is fine. I also highly recommend OnPay. After the setup, all you have to do with either service is enter the employee hours and click done. The payroll service will direct-deposit your employees pay, remit your payroll tax payments in full and file your payroll tax returns on time. It’s just not worth it to try to do all that yourself or even hire an employee to do it.
  7. File and pay quarterly sales tax returns (if applicable). Again, if your situation is simple, you can probably take care of this on your own. If you sell tangible goods that are subject to sales tax, you will want to be sure to keep track of your taxable and non-taxable sales.

By the way, congratulations! If you’ve added these tasks to your online task tracking system, you now have an online, Standard Operating Procedure for your business where the tasks can eventually be assigned to other people if/when needed! This puts you way ahead of the curve when it comes to small business organization.

My final word on bookkeeping is to caution you against not claiming all your taxable business income and against deducting non-business expenses. The benefits to claiming all the income you make and only writing off the expenses relating to business far outweigh any benefit you might gain from not paying the resulting tax bil. There is a lot of misinformation out there (even from professionals) about “tax write-offs.” Check out my post on maximizing your take-home pay for more on that topic.

4. Keep your paperwork organized

If you haven’t noticed yet, daily business turns out paperwork of all sorts at an alarming rate. Keeping all these papers organized and, most importantly, retrievable, can be a daunting task if you don’t establish a system. In my experience you have two options. Both are perfectly legitimate and you can decide which to use based on your own preference.

Paper or Digital

If you prefer physical paper, I highly recommend the FreedomFiler system for keeping your paperwork organized. In fact, the digital system I’ve developed over the years is largely based on the logic and layout used by this paper system. At the end of each year, you’ll want to box up all your yearly files (described below) in Bankers Boxes and store them for 7-10 years.

Digital filing typically prompts mixed feelings from those who consider going paperless. On the one hand, it grants a lot of freedom. On the other hand, it’s not as maintenance-free as you might think. Using an on-site hard drive to store files can free up a lot of room once used for storing files. However, most on-site file servers must be replaced within three years and require anti-virus maintenance among other professional maintenance.

Unless they’re in the tech industry, cloud-based digital file storage is normally the route I advise my client’s to take. Depending on the level of security needed for the documents, you could use SmartVault, Box.com, Dropbox, or even Google Drive. All these services provide web-based access to your files which will give you an immense amount of freedom, especially in considering where you prefer to work.

Accessibility, however, is limited to the standards maintained in the digital filing setup and maintenance. If you intend to store your files digitally, I cannot stress the next point strongly enough: Decide on a filing naming convention for your files and use it, without fail.

If you had paper files, you would probably setup file folders for each vendor and customer for each year. You would sort them in alphabetical order. You might even punch holes in the documents and secure them to the folders to keep your documents neat. Digital filing needs the same level of care.

I recommend writing and updating a text file in your root directory with the naming convention that should be used for each file. For example:

VENDOR/CUSTOMER NAME YYYY-MM-DD Document Title or Description

I’ve personally used this file naming convention for all my business files since 2012, and it has yet to let me down. This way, your files can line up nicely in any sub directory, and any orphaned or misplaced files can be found with a simple search (and moved if needed).

  • SEQUOIA BUSINESS SOLUTIONS 2020-10-05 Inv 1000
  • SEQUOIA BUSINESS SOLUTIONS 2020-11-05 Inv 1050
  • SEQUOIA BUSINESS SOLUTIONS 2020-12-05 Inv 1100

The text file with your filing naming convention should also include acceptable abbreviations (e.g. Inv for Invoice, Stmt for Statement, PO for Purchase Order).

In addition to a solid file naming convention, you will also need a workhorse of a scanner. On that front, I can highly recommend the Fujitsu ScanSnap products.

Once you’ve decided whether to use paper or digital files, you should keep and organize the following documents:

Permanent Files

  1. Legal name: Copy of your personal, social security card
  2. The IRS letter which assigned you an EIN (Employer Identification Number). Side note: If you’re operating as a sole-proprietor, even if you don’t have employees, I recommend you get an EIN to protect your social security number. It doesn’t cost anything, and it will allow you to freely share your business tax ID number with customers, vendors, banks, etc.
  3. Bank, credit card, loan account setup documents
  4. Online merchant account setup documents (e.g. Paypal, Square, QuickBooks Payments, other credit card processor)
  5. If applicable:
    1. IRS S-Election effective date
    2. California EDD (Employment Development Department) Employer Tax ID Number
    3. California Secretary of State ID
    4. CDTFA (California Department of Tax and Fee Administration) Sales Tax Resale License / Account No.
    5. DBA(s): Fictitious business name statement(s)
    6. Business vehicle records

Files Updated as Needed

  1. Insurance policies, such as:
    1. General liability
    2. Workers’ compensation
    3. Fidelity or surety bonds/policies
  2. Property and equipment lease/renewal documents
  3. Vendor contracts/renewals for ongoing services (e.g. phone, internet, janitorial, bookkeeping)

Yearly Files

  1. Income tax records (current year + 7-10 past years)
    1. Customer invoices
    2. Vendor bills
    3. Bank statements
    4. Financial reports
    5. Income tax returns
    6. Vehicle records (for any vehicles used for business)
    7. Bottom line: Keep the documents that will back you up in case of a tax audit.
  2. Payroll records (current year + minimum 4 past years)
    1. Time sheets
    2. Payroll reports
    3. Check stubs
  3. Work product documents (by customer or work order/job)
    1. Signed estimates, proposals, or contracts
    2. (Other documents are highly variable, depending on industry).
    3. Bottom line, keep the documents that will back you up in case of a claim against the business by a customer or vendor. If there’s any suspected fraud, these documents could back you up in a tax audit as well.

Employee Records

Current + anyone employed in the past 4 years

  1. Resume, employee application
  2. Employment contract
  3. Form W-4
  4. Two forms of ID (usually) and Form I-9
  5. Direct deposit authorization
  6. Status change records (change in pay, work duties, schedule, etc.)
  7. Time off requests
  8. Performance evaluations

5. Do the work you set out to do

Unless you’re a bookkeeper, this area is probably jam-packed with a hundred other tasks you need to do to serve your customers. Keeping up with this ever-expanding list can be overwhelming and result in only taking care of the squeakiest of squeaky wheels. If (when) that happens, take a deep breath and return to your task-tracking system. Listing what you have to do will ensure your priorities remain clear.

Also, in product-based industries, when your customers ask about lead times you can be 100% honest with them and establish clear expectations. For example, if you observe over time that you can process a maximum of 5 orders a day and your order list is nearing 100, your customer deserves to know you’re deliveries are four to six weeks out.

When you first started your business, you might have given the most thought to this one area: Doing the work your customers and clients pay you to deliver. If this area is maxing-out your ability to keep up with the first four areas discussed above, by all means let us know how we can help free up your time.

Maximize Your Take-Home Cash instead of Minimizing Your Taxes

It’s October 21st and many of you just completed your 2018 taxes. There might be a few who managed to get their documents to their tax preparer in plenty of time to file by the April 15th deadline, but for the most part, if you just filed, it was because you needed the time to sort out your records. Frustration and stress followed by likely disappointment because of how much you had to pay in taxes and how much you had to pay your tax preparer to tell you how much you owed. And here comes the end of 2019, just around the corner, raising a curious eyebrow at you to see if this year will be any different. It’s a vicious, debilitating cycle and it often steals the joy out of what business owners manage to accomplish from year to year.

If you’re just starting your business, please do yourself the biggest favor of your professional life right now. Call the bank that has your personal checking account, open a savings account, and transfer 15% of your checking balance to the savings account. From now on, do not spend a penny of the money you pull out of your business until you’ve transferred 15% of it in the savings account. Because here’s the deal: If you’re a sole proprietor, then 15% of every dollar you take home, every dollar you spend on personal expenses, will have to be paid back in federal self-employment taxes.

If this comes as a shock to you, please consider the fact that you no longer have an employer who is withholding taxes from your check. As a self-employed individual, you will have to withhold and pay your own taxes (social security and medicare). This simple fact, I am convinced, is the bane of the sole proprietor’s existence, and it can be defeated with some basic cash flow planning. That savings account you just opened is your new best friend. It’s going to ensure that you have enough money to pay your tax estimates throughout the year. It’s also a friend you’ll never see or talk to except four times a year when it’s time to pay taxes. Don’t check the balance. Don’t wonder how much is in there. Don’t tempt yourself to use it for an emergency and pay it back. If you need to nickname the account “The Government’s Money” or “Don’t Even Think About It,” to help yourself out, you should go ahead and do that.

I actually ended up separating my funds entirely. My tax savings account is at a different bank entirely from my personal checking account which is a different bank from my business checking. I linked the tax savings account to my business account so I can transfer funds, but there’s no fast way for me to move funds from my tax savings to my personal checking. In fact, I never do. Once it’s in my tax savings account earning interest, I don’t touch the funds until it’s time to pay my estimates. Then I transfer the balance directly from the savings account to the IRS. It never hits my personal checking account. It’s like the funds don’t even exist except for the bit of interest it accumulates, thanks to Alliant Credit Union‘s 1.884% interest rates on their savings accounts. Other than the few dollars a month it earns, the funds just sit around looking pretty for no one to see for most of the year. It’s the practice that’s kept me and my firm stress-free when it comes to tax planning.

Many owners I work with will kick the tax plan down the road as far as possible and hope to God that their tax preparer will be able to work some magic when it comes time to file. I have to tell you though – that magic usually comes in the form of your purchasing an expensive, depreciable asset. If you go out and buy a $75 thousand truck, your tax preparer will be able to write off a majority of that truck under section 179 and wallah! No taxable net income. But now you have five years of paying $1400 a month on a truck payment and an insane gas expense and insurance bill to go with it and guess what? You’ve already written off all five years of those truck payments to avoid paying taxes. Next year, your tax preparer will likely tell you to buy some new equipment so they can write it off and save you on taxes again. Genius, right!? But now you have another monthly payment and your cash flow takes another giant hit.

It absolutely kills me that tax preparers advise their clients to buy assets they can’t afford in order to avoid taxes. It makes the tax preparer a hero in the moment, but it often signs the death warrant of the client’s business. You cannot sustain a healthy cash flow with that kind of planning. It should be illegal, punishable by fines and prison time for a tax preparer to tell you to take out a loan for a vehicle or equipment or a building so you can avoid income taxes. It’s asinine and irresponsible and short-sighted. By minimizing your tax bill, they have insured that your take-home cash is virtually non-existent.

Instead, your tax preparer should estimate the total taxes you will owe each year, divide that by the amount of revenue you expect to earn and give you a percentage of your revenue to set aside. Mike Michalowicz’s Profit First is the absolute king for describing this method in detail. This calculation should be completed quarterly to ensure that you aren’t setting aside too much or too little. You want to maximize your take-home cash, not minimize your tax bill.

Taxes are inevitable. What I witness in the form of avoidance and frustration and aggravation every year far surpasses the alternate reality business owners could live in if they could just take a deep breath and talk to someone about how to maximize their take-home cash rather than worrying about how to minimize their tax bill.