The Money with Katie Show

Episode: Financially Plan for 2026 with Katie: Self-Employment Tea & Contingency Planning

Host: Katie Gatti Tassin
Date: November 19, 2025

Overview

In this episode, Katie Gatti Tassin delivers a solo discussion focused on her personal financial planning process for 2026 as she transitions back to full self-employment. With the Money with Katie brand moving independent from Morning Brew, Katie dives into the real, nitty-gritty steps and mindset shifts needed for financial stability when leaving a W2 salary behind. The conversation ranges from health insurance and tax planning to budgeting, building a contingency fund, and adjusting investment strategies—all framed by her own lived experience and designed as a roadmap for anyone facing a major financial change or considering self-employment.

Key Discussion Points & Insights

1. Why a Solo Episode & Context of Big Changes

• Katie’s Return to Solo: After a streak of guest cancellations, Katie embraces a solo format, her first since January.

  “I am taking that as a sign that I should just lean into my instincts and do what is my first solo chat, I think since January, if you can believe it.” (02:00)

• End of an Era: The show’s final episode is on December 31, 2025, as Katie takes Money with Katie independent, buying back the brand from Morning Brew.

2. Life as a Newly Fully Self-Employed Person

• W2 vs. Full Self-Employment: Previously, Katie always had a regular paycheck and employer-provided health care atop her business projects. In 2026, all income is on her to generate.

  “I’ve never actually raw-dogged self-employment before...” (04:20)

• The Roadmap’s Purpose: Katie details her financial planning process for the benefit (and entertainment) of listeners, hoping portions are applicable for others in transition.

3. Practical Steps: Health Insurance & Tax Help

• Insurance Considerations: Spousal coverage is expensive (~$1,000/month for a high-deductible plan). Katie highlights the real need to project and budget for health insurance costs. (13:50)
• Hiring a CPA: Self-employment taxes require quarterly filings, a challenge Katie wisely chooses to outsource.
• CPA Tasks Outlined: Bookkeeping, tax record maintenance, 1099/contractor management, quarterly and annual filings, and creating a “payroll-like system” to smooth income volatility.

  “That was sort of the effort threshold for me where I was like, yeah, I’m not interested in that. I think it is actually time that I pay somebody else to do this for me.” (15:50)

4. Income Planning Amidst Uncertainty

• Source Diversification:
  • Main: Newsletter sponsorships (Money with Katie)
  • Secondary: Book royalties, speaking engagements, digital product sales, and podcast revenue (Diabolical Lies).
• Conservative Estimating: Katie assigns cautious yearly projections to each source and adds her husband’s income.
• Self-Employment Tax Nuances:

  “When you’re self-employed, you have to play both roles... so you pay both shares, which gives you the 15.3% self-employment tax.” (25:20)

• Solo 401(k) & SEP IRA Options: Outlines pros, cons, and administrative realities of popular self-employed retirement vehicles.
• Monthly Take-Home Calculations: Planning requires transforming annual projections into monthly estimates—essential due to income volatility.

5. Budgeting, Spending, & Cost of Living Choices

• Downsizing Intentionally: To reduce pressure, Katie downsized her home and cost of living. Major budget line items: rent, cat food, health care premiums.
• Calculating Monthly Outflows: Uses 2025 spending as the basis, cautions listeners to pull accurate monthly averages from their own data.

  “First I’m panicking. Then I’m swiftly moving through the stages of grief and I’m reaching the bargaining phase.” (41:20)

• Honest Numbers: Reveals household spending is “over $10,000” per month—a vulnerability she approaches with humor, transparency, and boundaries.

6. Contingency (Emergency) Planning

• Contingency (Not Just ‘Emergency’) Fund: Calculates how much net monthly income she’s responsible for, after her husband’s pay, and multiplies that by 12 to set aside a full year’s runway.

  “I want the ability to have a year-long crash out—shave my head, 2017, there is no explanation, only reputation-style crash out.” (47:30)

• Differences from Past: Historically relied on investments as backup. Now, designates a specific cash reserve in a high-yield account due to singular self-employment risk.

7. Budget Flexibility & Final Plan Checks

• Necessities vs. Luxuries: Intends to flag truly non-negotiable spending (like rent and pet care) and separate discretionary categories.
• Inflation of Other Costs: Colorado move cut rent but doubled car insurance and sustained healthcare/medical costs.
• Final Financial Independence Calculation:
  • Transfers current balances into a new Wealth Planner.
  • Uses the ‘financial independence’ tab to see how current assets map to sustainable withdrawals and the path to “FI” (financial independence).

  “Our safe withdrawal amount this year… would be enough to cover my half of those household expenses.” (59:00)

8. Wealth Planner Tool & Class

• Invitation to Learn: Katie plugs an upcoming December 3rd session unveiling enhancements to the Wealth Planner spreadsheet/tool, with special features like irregular expense planning and manual transaction tracking.

Notable Quotes & Memorable Moments

• “I’ve never actually raw-dogged self-employment before.” (04:20)
• “It is a little nerve-wracking because the average could mean making $0 for five months and then $100,000 in two weeks. Like, you just really don’t know.” (36:30)
• “First I’m panicking. Then I’m swiftly moving through the stages of grief and I’m reaching the bargaining phase.” (41:20)
• “I want the ability to have a year-long crash out—shave my head, 2017, there is no explanation, only reputation-style crash out.” (47:30)
• “If you are working in a household with multiple W2 incomes... I think you’re probably safer with three to six months [emergency fund], but with the transition to full-time self-employment... this just gives me a little bit of comfort that I can take my time.” (50:40)
• “It's a little bit like we talked about with the Jillian John's root episode, whether you find yourself in an intentional or unintentional mini retirement. It's nice to see what is my safe withdrawal amount right now?” (01:01:00)
• “Or maybe you're just a little homeschool jungle freak who likes listening to someone else make financial transitions. I don't know, you do you.” (01:05:20)

Important Timestamps

• Introduction & Show Update: 00:01–07:15
• Moving to Self-Employment—Insurance & CPA: 13:50–19:15
• Income Projections & Solo 401(k) Details: 25:00–33:00
• Budgeting and Expense Estimation: 36:00–44:00
• Contingency Planning (Emergency Fund): 47:00–53:00
• Budget Flexing & Spending Prioritization: 54:00–58:00
• Financial Independence Check: 59:00–61:30
• Invitation to Wealth Planner Workshop: 62:00–end

Final Thoughts and Tone

Katie’s frank, practical, and humorous style demystifies the intimidating realities of self-employment financial planning. By sharing her own numbers, apprehensions, and processes, she offers relatable guidance and genuine encouragement for anyone facing uncertain financial waters in the coming year.

Useful Resources:

• Wealth Planner tool (detailed in episode; class on Dec 3rd)
• Article on solo 401(k) vs SEP-IRA (promised in show notes)

For listeners in a similar transition, this episode offers both practical templates and emotional solidarity.