August, 2025 - Boldly Financial

August 31, 2025
Taxes

Meal and Entertainment Deductions After the Tax Cuts and Jobs Act: What’s Left

The 2017 TCJA dramatically curtailed meal and entertainment deductions. What remains deductible for self-employed professionals in 2025, and what the documentation requirements are.

August 28, 2025
Taxes

How to Handle a 1099 You Weren’t Expecting: Correcting Income Mismatches

Receiving a 1099 for income you believe was incorrectly reported creates a specific set of reporting obligations. How to handle it correctly.

August 25, 2025
Taxes

Audit Red Flags: What the IRS Actually Looks for in Self-Employed Returns

Certain patterns in self-employment tax returns significantly increase audit probability. Understanding which deductions are scrutinised most — and how to document them correctly.

August 22, 2025
Taxes

The Self-Employed Deductions Most Freelancers Miss — and How to Find Them

Research suggests that self-employed individuals miss an average of $8,000 in legitimate deductions annually. A systematic audit of the most commonly overlooked categories.

August 19, 2025
Wealth Building

HSA Accounts for the Self-Employed: The Triple Tax Advantage Most Freelancers Miss

A Health Savings Account offers a deduction on contributions, tax-free growth, and tax-free withdrawals for medical expenses. Why every self-employed professional with a qualifying plan should maximise it.

August 16, 2025
Wealth Building

Retirement Savings When You Have No Employer: The Self-Employed Contribution Guide

SEP-IRA, Solo 401(k), SIMPLE IRA, and traditional IRA — the four retirement accounts available to the self-employed, with 2025 contribution limits and when each makes sense.

August 13, 2025
Wealth Building

Building Net Worth on an Irregular Income: A 10-Year Framework

Long-term wealth accumulation is possible on irregular income — but it requires different structures than salaried wealth-building. A decade-long roadmap for independent workers.

August 10, 2025
Wealth Building

Tax-Loss Harvesting for Independents: How to Reduce Your Tax Bill Through Smart Investing

Tax-loss harvesting is a strategy for offsetting capital gains with investment losses. How freelancers with variable income can use this to reduce their annual tax burden.

August 7, 2025
Wealth Building

Real Estate as a Freelancer Investment: What the Income Requirements Look Like

Mortgage qualification is harder for self-employed borrowers. The documentation requirements, debt-to-income calculations, and lender expectations every freelancer should know.

August 4, 2025
Wealth Building

Investing While Self-Employed: How to Build Long-Term Wealth Without an Employer Match

Without an employer 401(k) match, the entire burden of retirement funding falls on the individual. The account structures and contribution strategies that maximise long-term accumulation.