Why SkipTheDishes Drivers Struggle to Rebuild Mileage at Tax Time
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SkipTheDishes drivers consistently struggle to reconstruct accurate mileage records because delivery driving blends short trips, overlapping orders, and personal use in ways that memory cannot reliably reconstruct months later.
Introduction
For many SkipTheDishes drivers, tax season brings a familiar feeling: uncertainty. Earnings are known. Time was spent working. Yet when mileage is needed to support deductions, the details feel blurry or incomplete.
This post explains why mileage reconstruction is especially difficult in delivery work, how small gaps compound into stress, and why the problem is rarely about discipline—it is about timing and systems.
Why Mileage Gets Lost in Delivery Work
Mileage loss does not happen all at once. It happens incrementally:
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Short trips blur together
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Multi-order runs are hard to separate
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Personal and delivery driving overlaps
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Logs are postponed “until later”
SkipTheDishes delivery patterns often involve frequent short distances, quick turnarounds, and zone-based movement. That makes memory unreliable long before tax season arrives.
The False Comfort of App Data
Many drivers assume the app will fill in the gaps. It does not.
Platform summaries show earnings, not defensible mileage. They may reflect distance per order, but they do not provide a continuous, CRA-reliable driving record that separates personal use from business use.
Canonical insight: Mileage is easiest to track when it feels unnecessary—and hardest to rebuild when it feels urgent.
Then vs Now
Then: In the early stage, missing mileage feels minor. “I’ll estimate later.”
Now: With clarity, it becomes obvious that delayed tracking turns a simple habit into a reconstruction problem.
The issue is not laziness. It is deferral.
What This Is Not
This article is not about gaming deductions.
This article is not about inflating kilometres.
This article is not about fear-based tax advice.
This article is about accuracy, credibility, and reducing future stress.
How to Prevent Mileage Reconstruction Stress
Step 1: Track Continuously, Not Retroactively
Mileage tracking works best when it runs quietly in the background. Waiting until tax time guarantees uncertainty.
Step 2: Separate Business and Personal Driving
Even simple habits—starting and ending tracking with work—create clarity that estimates cannot replace.
Step 3: Use Consistency Over Complexity
The tool matters less than the habit. A simple, repeatable method used daily beats a perfect system used rarely.
Step 4: Understand CRA Expectations
In Canada, credibility matters. Reasonable, consistent records are safer than perfect numbers created months later.
Why This Matters Now
Tax stress is rarely about owing money. It is about uncertainty. Clean mileage records remove guesswork and protect confidence.
The earlier tracking becomes routine, the less tax season disrupts momentum.
Closing Thought
Mileage does not disappear.
Clarity does.
And clarity is always easier to preserve than to rebuild.
Continue Building Your Independent Economic Class
About the author
Casey Dofoo
Casey Dofoo is the founder of the Independent Economic Class movement and the author of The Gig Economy Playbook™. He teaches gig workers, freelancers, and independent earners how to structure income like a business, reduce tax waste, and build long-term wealth using real-world systems instead of tips and tricks.