Core Insights - A 26-year-old independent contractor from Texas, Jim, has increased his income from $25,000 in 2022 to $195,000 in 2023, yet he and his wife are burdened with $500,000 in debt, including a $330,000 mortgage and significant vehicle and credit card loans [1][2] - Despite a combined annual income of $250,000, the couple is financially struggling due to poor financial planning and tax management [2] - Jim has not filed his 2024 taxes and owes an estimated $25,000 for 2023, highlighting the importance of making quarterly tax payments for self-employed individuals [2][3] Tax Management Issues - The primary issue identified is Jim's failure to make quarterly tax payments, which is a requirement for self-employed individuals who expect to owe $1,000 or more [3] - Financial advisors recommend using IRS worksheets to estimate quarterly payments or dividing last year's tax liability by four as a starting point [4] - Establishing a solid record-keeping process for income and expenses is crucial, and utilizing expense tracking apps can streamline this process [5]