u/dave36756
dave36756
dave36756
I was in a similar spot doing 1099 work with a ton of driving and it only “hit” at tax time. The biggest thing I wish someone told me earlier: the deduction is only as good as your mileage log. If you don’t have a day-by-day record (date, start/stop, purpose, miles), guessing 50k later is where people get burned.
If you didn’t track it in 2024/2025, start tracking today so at least you stop the bleeding going forward. I ended up using MyCarTracks because it just ran in the background and I stopped forgetting to write trips down. For the past years, you can try rebuilding from your calendar, email/texts with addresses, listing appointments, Google Maps timeline, oil change records, etc, but it’s time-consuming.
Also, that “write everything off” advice is sloppy. Mileage is usually the cleanest method for a car, but you still need business vs personal. And yeah, single-member LLC usually doesn’t magically fix anything tax-wise. VITA can be a good start if they’ll take the situation, otherwise a CPA who’s dealt with late-filed 1099s might be worth it just to get you filed and on a payment plan.
dave36756
Texas is one of those states where they treat DD like self-employment for UI purposes, so they’re basically asking for net profit (gross minus actual business expenses). The catch is you usually can’t just take the IRS mileage rate in that weekly UI box unless the form explicitly says that’s allowed, because the mileage rate is a tax deduction method, not a literal reimbursement you got paid.
What I did when I had to report gig income was: report the gross DD payout for the week, then subtract real out of pocket stuff I could actually support (gas receipts, tolls, parking, maybe a portion of phone if you’re tracking it). Then I reconciled the bigger mileage deduction on my taxes later.
Also, answer “yes I worked” even if you net to zero, because they’ll cross-check 1099/earnings and you don’t want the headache. I started tracking miles/trips in an app (I use MyCarTracks) mainly so if they ever ask how I got to my numbers I’m not guessing months later.
dave36756
Big thing is not which brand, it’s whether you’ll actually keep it running every shift. I started with Stride and it was fine, but I kept forgetting to hit start and stop and I’d miss a bunch of miles, especially driving back to a busy zone. After that I switched to MyCarTracks because it just runs in the background and I don’t have to think about it as much.
If you’re only doing 4 days a week, you can also do the cheap-and-boring method: write down odometer at start and end of dash and log it in a notes app or spreadsheet. Whatever you pick, just be consistent and export or save the report monthly so you’re not scrambling at tax time.
dave36756
Yep, I've had the same thing happen with MileIQ (and honestly a couple other auto trackers). It's not just "bad cell service" but more the phone killing background location, low power mode, app not getting to run, etc. The result looks exactly like what you're seeing: it records chunks of the shift and just drops the rest.
What saved my butt was treating the app as a convenience and the odometer as the source of truth. I snap a pic of the dash at start and end of the shift (takes 5 seconds) and then I'll reconcile the app later. If the app is short, I log the difference as a manual trip so I'm not donating deductions.
Also worth checking: iPhone/Android battery optimization for the tracker (set to always allow location + no battery restriction), and make sure it isn't getting forced closed. Since switching to MyCarTracks I've had way fewer "half a route disappeared" days because it keeps logging in the background, but I still do the odometer pics because audits don't care what app you used, they care that you can back it up.
dave36756
That mileage reimbursement being reported as regular income is exactly the kind of admin screwup that wrecks people later.
Not sure if this helps now, but when I had an employer mix up mileage reimbursement vs wages, the only thing that saved me was building a paper trail: old pay stubs showing the mileage line separate, any expense policy docs, bank deposits matching the reimbursements, and my own mileage logs (even if it's just calendar notes + gas receipts). CRA/Service Canada don't really care that the company is gone, they care whether you can prove what that "income" actually was.
If you haven't already, I'd pull your CRA account to see what slip they used (T4 vs something else) and whether it's coded as taxable. If the slip is wrong, sometimes you can still request a T4 amendment or submit a taxpayer adjustment with supporting docs. I know it's brutal once garnishment starts, but this sounds more like misreported reimbursement than "you made too much."
dave36756
That mileage reimbursement being reported as regular income is exactly the kind of admin screwup that wrecks people later.
Not sure if this helps now, but when I had an employer mix up mileage reimbursement vs wages, the only thing that saved me was building a paper trail: old pay stubs showing the mileage line separate, any expense policy docs, bank deposits matching the reimbursements, and my own mileage logs (even if it's just calendar notes + gas receipts). CRA/Service Canada don't really care that the company is gone, they care whether you can prove what that "income" actually was.
If you haven't already, I'd pull your CRA account to see what slip they used (T4 vs something else) and whether it's coded as taxable. If the slip is wrong, sometimes you can still request a T4 amendment or submit a taxpayer adjustment with supporting docs. I know it's brutal once garnishment starts, but this sounds more like misreported reimbursement than "you made too much."
dave36756
Yeah DD is 1099, so nobody's withholding taxes for you. I was freaked out my first year too.
What it looked like for me in real life:
- You get a 1099-NEC (and sometimes a 1099-K depending on the year/payment processor stuff). That's basically "here's what we paid you."
- You report that on Schedule C as self-employment income.
- The biggest thing to track is MILES. Most dashers I know just take the standard mileage deduction and don't mess with saving every gas receipt.
Important part: you generally do *either* standard mileage *or* actual expenses (gas, repairs, etc). If you take standard mileage, you don't also deduct gas on top of that.
Mileage tracking: I learned the hard way that DoorDash's in-app mileage estimates aren't enough. You want something that auto-tracks so you're not trying to recreate trips in April. I've used MyCarTracks because it runs in the background and I stopped forgetting to start/stop it.
Also, don't play the "some drivers don't file" game. It's fine until it isn't, and the 1099 is already reported to the IRS.
If you only dash a little at first, you can keep it simple: track miles + keep a note of any tolls/parking + stash like 20-25% of profit in a separate bucket so tax time doesn't smack you.
In the “boring” world (fleet + field service), people absolutely use data, they just don’t call it that. The stuff owners will actually pay for is the boring weekly decisions:
Where I’ve seen these projects die is when it turns into a pretty spreadsheet that doesn’t change Monday morning. The win is usually one tight loop like: ‘here are the 5 stops that blew up time last week + why + what to change.’
Also, if you’re thinking logistics, don’t underestimate how messy the raw data is. A lot of people swear they have “routes in Excel” but the actual truth is in texts, timestamps, and mileage. We ended up tracking trips automatically (I use MyCarTracks) because relying on manual logs was a constant fight and the numbers never matched reality.
On pricing, if you charge like admin help, you’ll get treated like admin help. Packaging it as a specific outcome (catch route overruns, reduce dead miles, flag jobs that are always underquoted) makes it way easier to justify real money vs $20/mo.