Self-employment and sole proprietorships: quick and dirty tax and retirement calculations

This is the first year my income has been almost exclusively derived from my self-employment/sole proprietorship and I have never been so furious in my life at our tax code. The assumption built into the system appears to be that within two years of being self-employed you should be raking in sufficient gobs of cash that you can just afford to pay professionals to take care of all retirement and tax issues.

Well, I make a hell of a lot less money now than I did before I became self-employed, so CPA's and CFP's are not in my near future.

Which reminds me of the absolute most infuriating thing about the tax code, which is that everybody is so freaking terrified of actually giving anyone any advice. They have to recite the entire goddamn tax code chapter and verse to make sure they're not leaving anything out. Well, guess what, none of this applies to you if you're a clergyman or a displaced person or a refugee or a victim of human trafficking. It's just for self-employed people trying to pay their taxes and save for retirement.

There are so many things wrong with the tax treatment of self-employment, but the most infuriating one is that tax obligations and tax-advantaged retirement account contributions are based on calendar-year income, while for actually existing sole proprietors like me calendar-year income is completely unknowable.

So with that in mind, I want to lay out some simple formulas you can use to calculate your estimated tax payments and allowed retirement contributions at the end of each calendar month, both in order to avoid tax penalties for underpayment and to avoid scrambling to max out retirement savings contributions at the end of the year, which is too close to timing the market for my taste.

All the calculations below are for poor self-employed people and sole proprietors (if you make over $117,000 you can afford an accountant, which I am not, nor do I have any training in tax law). But since I cannot find any other resource that lays out all these calculations in simple language, I had to write my own.

Additionally, since obligations and limits work on a tax-year basis the following calculations will only work if you make at least a small profit each month. Otherwise, the months where you make a loss will offset your profitable months and throw the whole thing into chaos.

Below I am not using any gibberish IRS terms of art. Just plain English (IRS math in parentheses).

Self-employment taxes

Self-employment taxes are 14.13% of your profit from self-employment. Calculate each month’s self-employment tax by taking all your income from self-employment and deducting each month’s business expenses (which you plan to itemize on Schedule C), then multiply that number by 0.1413 (15.3% of 92.35%).

There are a number of reasons that this formula will lead to overpaying self-employment taxes, the most obvious one being deductions that you’ll calculate when filing your taxes annually, but that aren’t incurred monthly, for example home-office expenses. If you have already lived in the home your home-office is located in for an entire tax year, you may already know your monthly home office deduction and be able to add it to your monthly expenses when calculating your self-employment taxes. Otherwise you’ll overpay by 14.13% of your home office deduction.

Pay your estimated taxes by April 15 (for profit from self-employment between January 1 and March 31), June 15 (for profit from self-employment in April and May), September 15 (for profit from self-employment in June, July and August), and January 15 (for profit from self-employment in September, October, November, and December).

SEP IRA contributions

SEP IRA’s are very easy to set up and make contributions to.

You can deduct contributions of up to 18.59% of your profit from self-employment to a SEP IRA each month (20% of (100% minus half of 15.3% of 92.35%)).

If you aren’t deducting your home office and other annual business expenses monthly, you’ll contribute slightly more than you’re technically allowed to deduct each month (since lower profit from self-employment lowers the calculation above). You can make it up at the end of the year by skipping a contribution until you find out the exact amount you're eligible to deduct.

Enter the amount you contribute (up to the deductible maximum calculated above) on Form 1040, line 28.

One-participant 401(k) contributions

Instead of or in addition to a SEP IRA, you can set up a one-participant 401(k) plan, which shares the same deductible contribution limit as above (18.59% of profit from self-employment).

The key advantage of the one-participant 401(k) over the SEP IRA is that you’re able to make contributions “as the employee" as well as “as the employer.” Your “as the employer” contributions are deducted on Form 1040, line 28, as above, with the 18.59% of self-employment profit limit.

But you can also contribute up to 74.35% of your profit from self-employment “as the employee" (the remaining 80% of (100% minus (half of 15.3% of 92.35%))). If you choose to make that contribution as a traditional (pre-tax) contribution, it’s added to your Form 1040, line 28 “as the employer” contribution. If you make it as a Roth (after-tax) contribution, it’s not deducted (you pay taxes on the amount of your contribution in the year you make it, but not on any withdrawals in retirement).

One-participant 401(k)’s may have higher fees, so there’s no point in setting one up unless you want to make that “as the employee” contribution as well.

Retirement Savings Contribution Credit

The RSCC is one of my absolute favorites. Unfortunately, it has several moving parts which interact in a very frustrating way.

The RSCC is calculated based on your traditional and Roth IRA contributions, and the “as the employee” contributions described in the section above. It’s calculated on up to $2,000 combined of all three kind of contributions (you can mix and match).

The RSCC is calculated as a percentage of those contributions. The lower your Adjusted Gross Income (Form 1040, line 38), the higher a percentage of your combined contributions (up to $2,000) you’re eligible to claim as a credit, up to a maximum of 50% of $2,000.

But the RSCC is additionally capped at the total federal income tax owed (unrelated to self-employment tax described in the first section), for example on Form 1040, line 47.

That means if you’re already in the AGI band that gives you the highest percentage credit (AGI less than $18,000 for single filers), traditional IRA and pre-tax one-participant 401(k) contributions will lower the cap on the amount of RSCC you can claim by lowering the federal income tax owed (Form 1040, line 47).

On the other hand, if your AGI puts you in a lower percentage band, making traditional IRA and pre-tax “as the employee” one-participant 401(k) contributions can lower your AGI, making you eligible for a higher percentage credit.

There’s unfortunately no way to calculate this on a month-by-month basis, since it can only be calculated at year-end once you know your final profit from self-employment.

Finally, let me point out the most infuriating thing about the RSCC: a single filer making exactly $18,000 in AGI will, after the standard deduction and personal exemption only owe $788 on Form 1040, line 47, meaning even though they’re in the highest credit calculation band, if they contribute the full $2,000 they’ll still only be able to claim a credit for $788!

That’s how the rich get richer, my friends.

Earned Income Credit

Self-employed people are eligible to claim the Earned Income Credit (as long as their profit from self-employment and AGI fall within certain ranges).

To calculate your earned income credit, you have to check the EIC table for both 92.94% of your profit from self-employment (100% minus half of 15.3% of 92.35%) and your AGI from Form 1040, line 38. You’re entitled to the lesser of the two amounts, so there’s no way to goose your EIC with AGI deductions (although there is in combination with business deductions).

Conclusion

Well. I’m glad I got all this off my chest.

Are there other common tax situations self-employed people face which could stand for some simplified calculations?
 
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BlkHat

New Member
This is a good start. One item I would suggest modifying, estimated payment due dates: First payment based on income through March 31st due April 15th. Second payment based on income through May 31st due June 15th. Third payment based on income through August 31st due September 15th. And the Fourth payment is due January 15th based on income through December 15th. Your estimated payments must equal 90% of your ultimate liability or 100% of prior year liability...unless you have enough income to hire a CPA.
 
This is a good start. One item I would suggest modifying, estimated payment due dates: First payment based on income through March 31st due April 15th. Second payment based on income through May 31st due June 15th. Third payment based on income through August 31st due September 15th. And the Fourth payment is due January 15th based on income through December 15th. Your estimated payments must equal 90% of your ultimate liability or 100% of prior year liability...unless you have enough income to hire a CPA.
Unbelievable. What the hell is wrong with these people? I'll fix my post shortly.
 

thorax

Level 90 ( ͡° ͜ʖ ͡°) Warlock
I'm recently self-employed (well, started last year anyway) and tax shit has been the scariest part of all of it. Thanks for this. Any chance there is some easy way to calculate the income tax that I also owe? I'm guessing not, but I figured I'd ask.
 

Matt

Administrator
Staff member
I'm recently self-employed (well, started last year anyway) and tax shit has been the scariest part of all of it. Thanks for this. Any chance there is some easy way to calculate the income tax that I also owe? I'm guessing not, but I figured I'd ask.
I tried out Wave for this, its cheap but a little dirty in parts, IE you need to sign up for certain access/forms on Dept Social Security sites etc, more hassle than it's worth.

I'm currently looking at quickbooks self employed, for $9 per month it provides you with Estimated Taxes (along with managing your books) and for $30 includes payroll.

I personally hate paying monthly for payroll since I tend to pay myself sporadically, sometimes annually, so holding a monthly service is annoying.
 

thorax

Level 90 ( ͡° ͜ʖ ͡°) Warlock
I tried out Wave for this, its cheap but a little dirty in parts, IE you need to sign up for certain access/forms on Dept Social Security sites etc, more hassle than it's worth.

I'm currently looking at quickbooks self employed, for $9 per month it provides you with Estimated Taxes (along with managing your books) and for $30 includes payroll.

I personally hate paying monthly for payroll since I tend to pay myself sporadically, sometimes annually, so holding a monthly service is annoying.
Im using Wave now. I heard good things about Free Agent, so I tried that. I was paralyzed by all the options. To be honest, and this is terrible, my problem is that I run a business and have ZERO understanding of the accounting side of things. I'm slowly learning, but it seems like everything I look at expects me to be an accountant.

Maybe I'll check out Quickbooks. I'm just so lost.
 

Matt

Administrator
Staff member
Im using Wave now. I heard good things about Free Agent, so I tried that. I was paralyzed by all the options. To be honest, and this is terrible, my problem is that I run a business and have ZERO understanding of the accounting side of things. I'm slowly learning, but it seems like everything I look at expects me to be an accountant.

Maybe I'll check out Quickbooks. I'm just so lost.
Just outsource your payroll properly- will cost $30 per month (or included in QB for that price). Then you've only got business estimated taxes to worry about, which aren't awful. I sometimes just throw them a giftcard.

This stuff shouldn't cause distress or distraction from your core earning, if you are hurting then you need to pay more until you get rid of the problem. I think the pricepoint for QB is fair.
 

dcb

Level 2 Member
You might want to check out being an S-Corp. We started off as self-employed and switched about 10 years ago. We use Quick books, and do our own payroll. The key for us is, we have an awesome accountant that will let us do as little or as much as we want to take on ourselves. However, she always looks over our books to make sure everything is on the up and up.
 

Haley

I am not a robot
My 75 year old Mother uses Quick Books.
She likes it for ease of use, I think someone set it up for her but she does everything else herself.
 

RWC75

Level 2 Member
OK, question for the audience...

I have a regular job that will pay over the maximum for SS/FICA withholding. Do I only need to pay the 2.9% tax on my self employment income for my quarterly estimated taxes?
 

thorax

Level 90 ( ͡° ͜ʖ ͡°) Warlock
My 75 year old Mother uses Quick Books.
She likes it for ease of use, I think someone set it up for her but she does everything else herself.
Now I'm going to feel super terrible if I can't figure it out. Thanks!
 

Matt

Administrator
Staff member
OK, question for the audience...

I have a regular job that will pay over the maximum for SS/FICA withholding. Do I only need to pay the 2.9% tax on my self employment income for my quarterly estimated taxes?
You'd still have to consider Federal and State.
 

RWC75

Level 2 Member
You'd still have to consider Federal and State.
Ah, gotcha. Ok that makes sense - was wondering why my estimated taxes would be so low given that I've read so often about he 14%+ self employment tax on top of the income taxes.

Thanks!
 

Matt

Administrator
Staff member
Ah, gotcha. Ok that makes sense - was wondering why my estimated taxes would be so low given that I've read so often about he 14%+ self employment tax on top of the income taxes.

Thanks!
Well, you are right regarding the self employment tax aspect. You only pay that up to the cap regardless of how many jobs/sources you have. Here's a good example:

If you have wages, as well as self-employment earnings, the tax on your wages is paid first. But this rule only applies if your total earnings are more than $118,500. For example, if you will have $30,000 in wages and $40,000 in selfemployment income in 2015, you will pay the appropriate Social Security taxes on both your wages and business earnings. In 2015, however, if your wages are $78,000, and you have $40,700 in net earnings from a business, you don’t pay dual Social Security taxes on earnings more than $118,500. Your employer will withhold 7.65 percent in Social Security and Medicare taxes on your $78,000 in earnings. You must pay 15.3 percent in Social Security and Medicare taxes on your first $40,500 in self-employment earnings and 2.9 percent in Medicare tax on the remaining $200 in net earnings.

You can see here (bolded by me) would reflect your situation.

Source: http://www.ssa.gov/pubs/EN-05-10022.pdf

However, if you run a payroll then you need to remember to deduct state/federal taxes from that.
 

Matt

Administrator
Staff member
Now I'm going to feel super terrible if I can't figure it out. Thanks!
I just decided to not go with Quickbooks and instead try out Xero. I had someone help me fix the Saverocity QB account recently and what I learned from both experiences is that the key is to get started early, and balance things out the right way.

What I wasn't doing previously is creating 'bills' enough. EG, for my new firm I have a situation where I have to pay FINRA $200 for a license. My compliance guy instructed me to pay in $250 to a FINRA 'flex fund account' $200 of which would cover the license, and $50 for incidentals.

The way I set this up was as follows:

  • Built a Chase bank account with integration in Xero (QB is the same thing) linked it up to show my paid in capital amount of $X
  • Built a Finra 'Flex Fund' Account manually (doesn't exist in accounting SW integration)
  • Transfer $250 from Chase to Finra within Xero (doesn't actually move the money, just changes the balance.
  • Create $200 Bill/Expense within Finra for license.
The key is to create the proper accounts, so you can move money between them, this is the core idea behind the AR/AP system, but I found that when I set up Saverocity books mid year it was already such a mess with small transactions that doing that right went pear shaped...

Definately start out with accounting SW as early as possible.
 

Matt

Administrator
Staff member
@Matt, what made you move from QB to Xero?
Nothing really special. I had just heard they were easy to use, and I wasn't blown away with QB (mainly because I started late) I also got 40% off for 6 months with code:

40% off the first 6 months of service with Xero (good through 6/12)

Promo Code

https://login.xero.com/

"Upgrade Now"

Promo Code: 40xero6

At this time it seems to be working well enough, I set up the $30 account with payroll pretty easily. Note that not all states are available for Xero payroll...
 

RWC75

Level 2 Member
However, if you run a payroll then you need to remember to deduct state/federal taxes from that.
Thanks, that was a very clear rundown - I am fortunate to have a well-paying job in addition to my side hustles. So for paying estimated quarterly taxes on my resale/hustle profits, I'll be paying 2.9% Medicare plus Federal/State income tax at the normal rates.
 
I created a spreadsheet to calculate all these values for my own sole proprietorship, and thought others might find it useful as a model.

Also, it has all my actual income and expenses, in case it makes anyone feel bad for me and want to sign up for a blog subscription. Hint hint.
 

Attachments

Annie H.

Egalatarian
If you are deducting home office expenses as self employed, just know that this can be an audit trigger if your income is high enough. Make sure you document (take pictures) of your home office where you spend 100% of your time doing business. If it's not exclusive use you need to look at the very restricted exceptions:

You do not have to meet the exclusive use test if either of the following applies.

  • You use part of your home for the storage of inventory or product samples (discussed next).

  • You use part of your home as a daycare facility, discussed later under Daycare Facility
http://www.irs.gov/publications/p587/ar02.html#en_US_2014_publink1000226294
 

El Ingeniero

Level 2 Member
Thanks for this post.

DW got her ex-boss in China to pony up for 1 year of her present salary + self employment tax + 401K match to drum up sales for PP woven bags. DW is scared shitless of the amount of work she's going to feel compelled to do, I'm scared shitless of the tax/accounting situation.
 

Annie H.

Egalatarian
Thanks for this post.

DW got her ex-boss in China to pony up for 1 year of her present salary + self employment tax + 401K match to drum up sales for PP woven bags. DW is scared shitless of the amount of work she's going to feel compelled to do, I'm scared shitless of the tax/accounting situation.
Adding self-employment income to your tax return (Sch. C) isn't all that hard. The two spreadsheets provided are very helpful but make it look harder than it is. It does become more complicated if there is salary/payroll involved but I don't think that's the case for your wife? Figuring in retirement deductions can also make it a bit more complicated.

The most basic thing you need to do is keep track of "business" expenses. Some find it easier to devote a separate checking account and/or credit card just for business expenses to make them easier to track. It's quite helpful to use a online version of Turbo Tax or last year's version you may already own to project for 2015. Just "start new tax return" and save it with a different name-- 2015 projections, etc. (be careful not to overwrite your actuall 2014 return.

Also be aware of safe harbor rules: "
  1. Estimated tax safe harbor for higher income taxpayers. If your 2014 adjusted gross income was more than $150,000 ($75,000 if you are married filing a separate return), you must pay the smaller of 90% of your expected tax for 2015 or 110% of the tax shown on your 2014 return to avoid an estimated tax penalty."
http://www.irs.gov/publications/p17/ch04.html

http://www.irs.gov/Businesses/Small-Businesses-&-Self-Employed/Estimated-Taxes

Check out the instructions for 1040-ES which says:

General Rule
In most cases, you must pay estimated tax for 2015 if both
of the following apply.
1. You expect to owe at least $1,000 in tax for 2015,
after subtracting your withholding and refundable credits.
2. You expect your withholding and refundable credits
to be less than the smaller of:
a. 90% of the tax to be shown on your 2015 tax return,
or
b. 100% of the tax shown on your 2014 tax return.
Your 2014 tax return must cover all 12 months.

A tip: if for some reason you find yourself close to the end of the year and have underestimated your "estimated tax" you can have *extra* withheld from a salaried W-2 job-- i.e. increase your withholding during November and December to comply with the above rules.

Feel free to PM me with any questions.
 
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