From Commissioned Employee to Self-Employed: Navigating Tax Treatment After Bankruptcy

Barbara Britto

When a commissioned salesperson receives a T2200 form from their employer, it opens the door to deducting employment expenses that are typically off-limits to salaried employees. But what happens when that employer goes bankrupt and the salesperson pivots to self-employment? This article explores the tax treatment of such a transition, using a realistic scenario to illustrate the rules and opportunities available under Canadian tax law.

Scenario: Meet Steve, the Commissioned Salesperson
Steve worked for a mid-sized home renovation company in Toronto, earning income primarily through commissions. His role required frequent travel to client sites, use of his personal vehicle, and occasional home office work. Fortunately, his employer issued him a signed T2200—Declaration of Conditions of Employment—confirming that he was required to cover these expenses himself.

During the year, the company unexpectedly declared bankruptcy. With no severance and limited job prospects, Steve decided to launch his own home renovation consulting business as a sole proprietor. He began earning income directly from clients and managing all aspects of his business independently.

Phase 1: Tax Treatment as a Commissioned Employee
While employed, Steve was eligible to deduct certain expenses on his personal tax return under Line 22900 (Other Employment Expenses), provided he met the CRA’s conditions:

·       He was paid in whole or in part by commissions.

·       He was required to pay his own expenses under his employment contract.

·       He did not receive a non-taxable allowance for travel.

·       He worked away from his employer’s place of business.

With the T2200 form in hand, Steve could claim expenses such as:

·       Vehicle expenses (fuel, maintenance, insurance, lease payments)

·       Travel costs (meals, lodging, airfare)

·       Advertising and promotion

·       Office supplies and cell phone usage

·       Workspace in the home (if used regularly and exclusively for work)

These deductions were reported using Form T777, which breaks down employment expenses. Steve kept detailed records and receipts to support his claims.

Phase 2: Transition to Self-Employment
After the bankruptcy, Steve registered his business and began working for himself. This shift changed his tax obligations significantly. As a sole proprietor, Steve was now responsible for:

·       Reporting business income on Form T2125 (Statement of Business or Professional Activities)

·       Deducting eligible business expenses directly

·       Paying both the employee and employer portions of CPP

·       Making quarterly tax instalments if required

Unlike his employment situation, Steve no longer needed a T2200. Instead, he could deduct a broader range of expenses, including:

·       Start-up costs (website, branding, legal fees)

·       Professional development and training

·       Business use of home expenses (based on square footage and usage)

·       Capital cost allowance (depreciation on equipment and vehicle)

·       Bank fees and interest on business loans

The CRA allows self-employed individuals to deduct any reasonable expense incurred to earn income, provided it’s not personal in nature and is supported by documentation.

Overlap and Transition-Year Considerations
In the year of transition, Steve had both employment and self-employment income. This required careful tax planning:

·       Filing both Form T777 and Form T2125

·       Allocating expenses based on the period they applied to—employment before bankruptcy, business afterward

·       Prorating vehicle and home office expenses based on usage and time

·       Ensuring expenses were not duplicated

For example, if Steve used his vehicle for both employment and business, he had to divide the usage and claim each portion separately.

Key Tax Implications

·       CPP Contributions: Steve now pays both portions of CPP, increasing contributions but also boosting future benefits.

·       GST/HST Registration: Once his revenue exceeded $30,000, he was required to register and begin collecting/remitting tax.

·       Quarterly Instalments: If his net tax exceeded $3,000 in the previous year, quarterly instalments were required to avoid interest and penalties.

·       Recordkeeping: CRA expects meticulous documentation, so Steve used accounting software to track income, expenses, and receipts.

The Bottom Line
Steve’s journey from commissioned employee to self-employed entrepreneur illustrates the importance of understanding tax treatment during career transitions. While the bankruptcy was a setback, the move to self-employment offered greater flexibility and broader tax deductions. With proper planning, accurate records, and awareness of CRA rules, Steve was able to navigate the shift successfully and build a sustainable business.