Overview of 272. What to Do If You’re 35+ and Feel Financially Behind with Jean Chatzky
This episode of Her First $100K features longtime financial journalist and founder of Her Money, Jean Chatzky. She shares her personal restart at 40 (divorce, job loss, parental death), practical financial steps for women in their late 30s–50s, and concrete tactics to recover or accelerate retirement progress. The conversation focuses on mindset (you’re not too late), priorities (what to fix first), tax-advantaged tools (HSAs, 401k, 529s), and behavioral advice (ask questions, get help).
Key takeaways
- It’s rarely “too late.” Starting at 40 is absolutely possible — Jean rebuilt savings, bought and paid off a house, and grew investments after starting over at 40.
- Owning your money = knowing what comes in, what goes out, and where it goes. That basic visibility is the foundation of control.
- Biggest financial mistake for midlife women: keeping too much in cash instead of invested assets. Cash won’t outpace inflation and taxes long-term.
- Practical priority order: capture employer 401(k) match → pay high-interest debt → max retirement accounts → use HSAs and 529s when appropriate → taxable brokerage account for extra savings.
- Ask questions until you understand. If professionals don’t explain clearly, find new ones. For divorce: get a lawyer, a therapist, and an accountant who work as a team.
Jean Chatzky’s story & lessons learned
- At 40 Jean experienced divorce, job loss, and a parent's death in a single year. She was prepared on technical questions (mortgage, assets), but wished she had prioritized accumulation earlier.
- Personal behavioral insight: she became over-conservative (saved a lot of cash) to feel secure. That made her miss some market growth; she later rebalanced to regain equity exposure.
- Lesson: knowledge is helpful, but confidence to act (and not hoard cash) matters.
Practical steps & action items
Immediate (within weeks)
- Audit your expenses to find “money leaks.” Decide what recurring costs to cut or reallocate.
- Capture any free money first: make sure you get your employer’s 401(k) match.
- If you have a fiduciary advisor and don’t understand explanations, demand clarity or find another advisor.
Short term (months)
- Aim to save toward a 15% annual retirement savings rate if possible — a helpful long-term target.
- Turn on HSA investment features if you have an HSA and don’t need it for near-term medical costs. Save receipts for future tax-free reimbursements.
- Use a retirement calculator to model small increases (e.g., $20–$50/month) and see how they change retirement timing.
Longer term (year+)
- Rebalance cash vs investments: move excess cash into diversified investments so your money can outpace inflation.
- If caregiving for aging parents is likely, have conversations with them early to plan expected costs and responsibilities.
- Consider delaying Social Security claiming if you need to maximize lifetime and survivor benefits.
Common concerns — summary of Q&A highlights
- Feeling behind / too late: Not true for most. Small consistent increases in savings and working a few extra months/years can materially improve outcomes.
- Divorce and retirement accounts: Not fatal. Reassess your retirement trajectory and adjust savings rates; course correct rather than panic-sell.
- HSAs: Triple tax-advantaged — contributions are pre-tax, investments grow tax-free, and withdrawals for qualified medical expenses are tax-free. Best for people comfortable with higher-deductible plans and who can invest HSA balances while paying current medical expenses out-of-pocket (save receipts).
- Caregiving for parents vs. kids: Toughest is parent care. Plan with siblings where possible; understand typical out-of-pocket caregiving costs and incorporate them into your financial plan.
- Career change / returning to school: Explore non-degree routes (on-the-job learning, targeted certificates) before incurring debt. If you must study, try to work while studying or ensure the ROI (post-degree salary uplift) covers the debt.
- How to teach kids money: Open linked checking/savings with debit cards, set up 529s for college, and consider UGMA/UTMA brokerage accounts for investments.
Mistakes to avoid
- Holding too much cash long-term (even good high-yield savings rates don’t match market growth needed for retirement).
- Being embarrassed to ask “basic” questions — financial systems often use jargon to confuse; insist on explanations.
- Quitting a steady income before you have a clear plan for the next step. Move slowly when reinventing midlife.
Notable, actionable lines
- “You have to make choices about how you allocate limited money to get what you want most.”
- “Get a good lawyer, get a good therapist, and get a good accountant” (especially during divorce).
- “If you don’t understand, say ‘I’m sorry, I don’t get it — can you explain it again?’” (persist until you understand).
Quick checklist (what to do this month)
- Run an expense audit and cancel or reallocate at least one recurring subscription.
- Confirm you’re getting any 401(k) match; increase contributions if possible.
- If you have an HSA, check whether you can invest the balance and enable that feature.
- Use a retirement calculator to model 1–2 incremental changes (extra $50/month, work 6 more months).
- If caregiving is possible in future, schedule one conversation with parents to assess finances/expectations.
Resources & where to find Jean
- Her Money: hermoney.com
- Her Money podcast and resources (Jean’s investing classes and other tools)
- Episode resources: herfirst100k.com/sspod (as referenced on the show)
If you want to prioritize one action from this episode: get clarity on your cash flow (what’s coming in and going out), lock in any free retirement match, then start moving excess cash into appropriate investments.