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Keep More: Tax Strategies for the Self-Employed Trade

The practical tax playbook for contractors, tradespeople, and service operators who want to stop overpaying and start keeping what they earn.

Enroll now — $99

105 min · 30 video lectures · quizzes · assignments · workbook

About this course

Most self-employed tradespeople and service operators overpay their taxes by hundreds or thousands of dollars every year — not because they are doing anything wrong, but because nobody ever showed them the full picture of what they are legally entitled to deduct and how to structure their business to keep more of what they earn. This course covers the tax fundamentals that apply across every trade and service business: plumbers, electricians, landscapers, cleaners, mobile operators, contractors, and independent service providers of every kind.

Why it pays for itself:

  • You will learn how your business structure affects your tax bill, which deductions tradespeople and service operators routinely miss, how to handle vehicle and home office deductions correctly, how to calculate and pay quarterly estimates without penalty, and how to use retirement accounts to reduce taxable income while building long-term wealth.
  • Each section connects directly to real decisions you make in your business: how you pay yourself, how you classify your vehicle expenses, which receipts you need to keep and why, and how to work productively with an accountant so you are not paying for time spent reconstructing records you should have maintained year-round.
  • This is educational content covering general tax principles applicable to self-employed individuals in the United States and Canada.
  • It is not tax advice or legal advice, and nothing here replaces a qualified tax professional who knows your specific situation.
  • The welcome lecture repeats this clearly.
  • The goal of this course is to make you a better-informed client when you do sit down with a professional, and to help you stop leaving legally available deductions on the table.
  • No accounting background required.
  • No complex software.
  • Just clear, specific, actionable content built for people who work with their hands and run their own operations.

What you'll learn

  • You will be able to evaluate whether a sole proprietorship, LLC, or S-corp structure is appropriate for your income level and risk profile
  • You will be able to identify the vehicle deduction method — standard mileage versus actual costs — that produces the larger deduction for your situation
  • You will be able to build a home office deduction calculation if you use a dedicated workspace for your business
  • You will be able to calculate your quarterly estimated tax payments and set up a payment schedule that avoids underpayment penalties
  • You will be able to identify at least five deduction categories that tradespeople commonly miss or underreport on their returns
  • You will be able to open and fund a SEP-IRA or Solo 401(k) to reduce taxable income while building retirement assets
  • You will be able to organize your receipts, mileage logs, and expense records into a year-round system your accountant can use efficiently
  • You will be able to evaluate whether your current accountant is a genuine tax strategist or simply a return preparer, and ask the right questions to find out

Course curriculum

Section 1: Section 1: Business Structure — LLC, S-Corp, and What the Choice Costs You

  • Welcome: What This Course Will and Will Not Do for You
  • Sole Proprietorship: The Default and Its Real Cost
  • The LLC: Protection vs. Tax Treatment
  • The S-Corp Election: When It Saves Real Money
  • Choosing Your Structure: A Decision Framework

Section 2: Section 2: The Deductions Tradespeople Miss

  • How Deductions Actually Work: The Mechanics
  • Tools, Materials, and Small Equipment You Are Probably Not Deducting
  • Phone, Software, Insurance, and the Costs You Forget Each Month
  • Meals, Travel, and Client Entertainment: What Survives Post-2018
  • Subcontractors, 1099s, and Keeping Your Books Clean

Section 3: Section 3: Vehicle, Tools, and Home Office Deductions

  • Standard Mileage vs. Actual Costs: Choosing the Right Method
  • The Mileage Log: What It Must Contain and How to Maintain It
  • Deducting Vehicle Purchase Cost: Section 179 and Bonus Depreciation
  • Home Office Deduction: Who Qualifies and How to Calculate It
  • Depreciation Basics: Spreading the Cost of Long-Lived Assets

Section 4: Section 4: Quarterly Estimates and Avoiding Penalties

  • Why the IRS Requires Quarterly Payments and What Happens if You Skip Them
  • Calculating Your Quarterly Payment: A Simple Worksheet
  • The Tax Reserve Account: Never Be Surprised at Filing Time
  • Canadian Quarterly Installments: How the CRA System Works
  • Year-End Tax Planning: Four Moves to Make Before December 31

Section 5: Section 5: Retirement Accounts and Income Smoothing

  • Retirement Accounts as a Tax Tool, Not Just a Savings Plan
  • The SEP-IRA: The Easiest Account for Self-Employed Operators
  • The Solo 401(k): Higher Limits for Serious Savers
  • Income Smoothing: Managing Tax Exposure Across Variable Years
  • Health Insurance and HSA: Deductions Built for the Self-Employed

Section 6: Section 6: Working with an Accountant Effectively

  • Tax Preparer vs. Tax Strategist: Know the Difference
  • The Records Package: What to Deliver and How to Organize It
  • Audit Risk: What Triggers IRS Attention and How to Be Prepared
  • Amended Returns: Recovering Missed Deductions From Prior Years
  • Building a Year-Round Relationship With Your Accountant

Ready to start?

$99 Enroll now — instant access

Instant lifetime access · HD video · workbook & templates included

Who this course is for

Built for self-employed tradespeople and contractors who suspect they are overpaying taxes but are not sure where to start.

Everything you get, working together: