My trips are serving an increasingly messy combination of purposes. I work one W2 job and have multiple 1099 jobs that I do as an independent contractor. A common trip looks like this; 46 miles from home to a health care provider for a regular visit, 2 miles from there to a work location for my job, 101 miles from there to a work location for my business, 144 miles from there to a work location for both my job and my business, 6 miles from there to another work location for both my job and my business, 11 miles from there to a work location for only my job and 17 miles from there back home.
My employer reimburses me for the round-trip distance from my home to the first work location only (since it's located in another city). They are aware that I don't go straight there and back.
I do not have a qualified home office.
Which segments are deductible and which aren't?
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Your mileage between your home and a regular job location (such as your employer's place of business) is always nondeductible commuting mileage.
You should track all of the trips that qualify for your employer's accountable plan separately.
Unlike business miles, what the IRS considers "commuting miles" aren't tax-deductible. If a business mile takes you from one workplace to another, a commuting mile takes you between your home and a workplace.
For your Schedule C / self-employment, trips between business locations and trips outside your commuting area (such as travel away overnight) are deductible.
See IRS Publication 463 for more guidance.
See also this TurboTax tips article for more information on Federal tax laws and employer-accountable plans.
So is driving from my 'day job' (if you will) to a location for my business considered commuting or business? And what about vice versa (when I'm done working for clients for the day and drive directly to my place of employment)?
Your business mileage deduction depends on what these “work locations” are. Driving to a regular place of work is a non-deductible commuting expense, whether you are an employee or an independent contractor. So is driving from one regular place of work to another.
If these are client visits, you may deducible business miles. However, you said you don't have a qualified home office, so I'm unsure how you are defining the primary work location for your business.
What you can and can not deduct is all clarified in IRS Publication 463 at https://www.irs.gov/pub/irs-pdf/p463.pdf in chapters 1, 4 and 5 of that document. Chapter 1 basically deals with travel expenses away from home and outside of your "tax home" area. Chapter 4 will probably be more applicable here.
These are shopping malls where I maintain and repair vending machines contracted by the owner of the machines. There are two that I visit once a week and another that I visit once every three weeks plus additional visits for service orders as needed (which would be special trips from my home). I have looked and can't seem to find an IRS definition for 'regular place of work' in publication 463. Mostly, it seems to refer to it in terms of a city for purposes of defining business travel rather than a particular building within a city. I'm pretty sure I would count as not having a regular place of work. Does that make trips to or from my home deductible along with trips between the various malls?
You said you have a regular job and you have a side job where you maintain vending machines at various locations.
Commuting is not deductible to your regular job. Mileage to and from work is not deductible. It is important that you create a system for determining your business miles and be consistent. I would simply deduct whatever the commuting miles would be from the total miles for the day while doing my side job. Keep records to show how you computed the business miles.
My temp agency has me drive to the jobite from my house, instead of having to meet at the office, i go directly to the jobsite everyday. Can i atill write these miles off?
No, this would be considered commuting.
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