Podcast Summary: HerMoney with Jean Chatzky

Episode 503: Money Tips Every Freelancer Needs—Taxes, Retirement & Getting Paid on Time
Guest: Emily Guy Birkin (Personal Finance Author & Freelancing Expert)
Date: November 26, 2025

Episode Overview

This episode of HerMoney focuses on the financial realities of freelancing, with personal finance expert and long-time freelancer Emily Guy Birkin joining host Jean Chatzky. Prompted by a listener question about how to help young freelancers get their finances on track, the conversation dives deep into managing irregular income, taxes, retirement savings, business structure, avoiding common pitfalls, and fending off the solitude inherent in freelance work. The discussion is practical, reassuring, and candid, with Emily sharing her firsthand experiences and actionable tips.

Key Discussion Points & Insights

1. The Challenges & Realities of Freelance Finances

• Unique Challenges: Freelancers juggle irregular income, chase invoices, handle taxes, and must build their own financial stability (04:10).
• Reassurance: Most young freelancers are not focused on retirement early on—this is common and not a cause for panic. Using savings when needed is what savings are for (05:57).

“There are many 27 year olds who have saving money for retirement at top of mind, freelancer or not.”
—Emily Guy Birkin [05:57]

2. Strategies for Managing Irregular Income

• Base Budget First: Determine your bare-minimum monthly expenses—the amount needed to “keep the lights on” (11:13).
• Three-Budget System: Emily advocates having a “base budget” for essentials, a regular budget (when things are normal), and a “pie in the sky” budget for bigger aspirations (13:49).
• Consistency Through a Salary: The key is building up a buffer during high-earning months and paying yourself a regular salary from a separate account.

“You want to recreate the sense of having a regular paycheck … so that you can consistently pay yourself a salary … otherwise it lurches from feast to famine.”
—Emily Guy Birkin [13:21]

Emily’s Own System:

• 50% of freelance income into “the kitty” (salary account)
• 20% set aside for quarterly estimated taxes
• 20% for a solo 401(k)
• 10% for business expenses (conferences, reinvesting, etc.)
  (02:02, reiterated at 13:49)

3. Managing Accounts & Tracking Money

• Separation is Key: Open separate business and personal accounts as soon as possible—it makes taxes, organization, and expense tracking much easier (16:43).
• Tracking Tools: Use whatever system works: for Emily, it’s Excel spreadsheets; Jean likes her bank’s app; QuickBooks and Monarch are viable options (19:01).

“Most people aren’t like me. For most people, having a separate account … will make your life much easier. Do that way earlier than I did.”
—Emily Guy Birkin [16:51]

4. Tackling Taxes & Saving for Retirement

• Quarterly Taxes: Always set aside money for taxes from each payment—Emily’s “overcorrection” of 30% in her early years ended up building her a safety net (05:57).
• Retirement Accounts:
  • Solo 401(k): Allows for higher contribution limits.
  • Roth IRA: Funded with after-tax dollars, grows and can be withdrawn tax-free, serving as a buffer against tax issues in retirement (19:58).

“I prioritize my solo 401k mostly because it has a higher limit … [The Roth is] insurance against generally health problems in retirement, but any kind of major financial emergency…”
—Emily Guy Birkin [19:58]

Jean adds:

“Pulling from tax-deferred accounts can trigger tax domino effects and Medicare penalties (IRMAA)…” [21:39]

5. Business Structure & Legal Protection

• When to Form an LLC or Company:
  • Type of freelance work and liability matters—knowledge workers are more exposed and may benefit from insurance and LLC protection (26:02).
  • LLCs are generally low-cost and offer a layer of personal liability separation.
  • If you add employees or partners, consult an accountant or lawyer for the best structure.

“If you’re thinking about it, I would say go ahead and do it, because … it’s a way to … create a separation between yourself and your business.”
—Emily Guy Birkin [26:02]

6. Ensuring You Get Paid & Dealing with Nonpayment

• Contracts are Essential: Never work without a contract, and specify limits (e.g., rounds of revisions included) to protect yourself (28:50).
• Chasing Payment:
  • Don’t be afraid to be the “squeaky wheel.”
  • Professional associations/unions can give legal support or “muscle.”
  • Sometimes you must weigh whether to keep pursuing payment or let it go.
  • Share info about nonpaying clients with your freelance community (28:50).

“Never work without a contract. That is the first thing.”
—Emily Guy Birkin [28:50]

• Structuring Payment Schedules: Most reputable clients use clear net 30 or net 60 terms. Open transparency is key; reluctance to discuss payment timelines is a red flag (31:00).

7. The Emotional Side of Freelancing

• Combatting Loneliness:
  • Join mastermind groups or professional associations for solidarity, networking, and emotional support.
  • Work in public spaces (cafés, libraries) to change routines and meet people (32:19).
  • For Jean, even just going to the gym gave her social contact (33:43).

“Being a part of a writing mastermind group has been very, very helpful for me in a lot of ways … solidarity, dealing with complicated industry changes, and sharing work opportunities.”
—Emily Guy Birkin [32:19]

• Handling Slow Periods:
  • Use down time for personal growth (creative projects, pitching bigger ideas).
  • Try to reframe slow periods as opportunities rather than threats.
  • Remind yourself that freelance cycles—“the slow times aren’t forever, just as the boom times aren’t forever” (35:52).

Notable Quotes & Memorable Moments

• “Congratulations Mama. You did it right, you know.”
  —Jean Chatzky, affirming Janet’s support of her son’s freelance journey [05:57]
• “If post-it notes work for you, go for it.”
  —Emily Guy Birkin, on using any system that keeps you organized [19:12]
• “We all have those moments … especially early on. Once you get past that and recognize, no, this is sustainable … just as the boom times aren’t forever.”
  —Emily Guy Birkin, on staying resilient through cycles [35:52]

Timestamps for Key Segments

• [04:10] – Listener question introduction and the personal finance “house of cards” for freelancers
• [05:57] – Reassurance about using savings and early retirement worries
• [11:13] – How to handle irregular income, “base budget” philosophy
• [13:49] – Three budgets: survival, regular, “pie in the sky”; percentage breakdown
• [16:43] – Separate business vs. personal accounts advice
• [19:58] – Solo 401(k) vs. Roth IRA as a freelancer
• [26:02] – When and why to set up an LLC
• [28:50] – Payment protection, contracts, and action against nonpayers
• [32:19] – Mastermind groups, avoiding freelancer isolation
• [35:52] – Mindset: using slow periods for growth and resilience

Final Thoughts

Jean and Emily offer a deeply practical and reassuring guide for freelancers, seasoned or new, especially those struggling to build a sense of financial security amid unpredictability. The main takeaways stress organization, planning, protection—both legal and mental—and the power of community. This episode is a toolkit for anyone making their own way in the gig economy.

For more resources and ongoing financial guidance, check out HerMoney’s programs and join the conversation at HerMoney.com.