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As layoffs rise and job security declines, more individuals are shifting from W-2 employment to self-employment—often without proper planning. From an accountant’s perspective, this transition brings major tax, structural, and cash flow challenges.
One of the most common questions I get — and honestly, one of the biggest misconceptions — is this: “ If I’m self-employed… am I even paying into Social Security?” And I get it. Because when you leave a W-2 job, you no longer see:
For decades, the traditional career path looked something like this: Graduate from school. Get a stable job. Work your way up the corporate ladder. Retire after 30 or 40 years.
A Guide for Self-Employed Individuals Facing Large Tax Bills
Learn how to file taxes when you're self-employed—whether you're a 1099 contractor, freelancer, side hustler, or small business owner. This down-to-earth guide..
If the administration successfully implements a full income tax exemption for those earning up to $150,000, we have to look at the two different "bill" types you pay every year.
