Posts tagged Jill Schlesinger
Navigating the Open Enrollment Process

11/6/26: The benefit selection process is upon us, and today we're discussing some tips for making the most of your open enrollment period.

Can I Retire From a Demanding Career at 55?

11/5/26: I'm in my late 40s and wondering if I'll be able to accomplish my goal of retiring at 55.

Will an Upcoming Move Set Us Back Financially?

11/4/26: Will a move from California to the Pacific Northwest set us back financially?

Can I Retire From My Toxic Job?

11/3/26: I am 53, caught up in a toxic work environment, and would like to know if I can retire early?

The Economics of Election Day

11/2/26: As Americans are facing tough financial choices right now, I joined The Middle with Jeremy Hobson to discuss how people are handling them, and how those pressures could shape the way they vote in the midterms. 

Why Medicare Is Quite a Shock for Many

10/30/26: Here's a snippet from our recent Medicare webinar with Marcia Mantell. This is just a few minutes, but there's a full hour of Marcia behind the paywall. You can purchase the individual webinar here.

To Roth or Not to Roth?

10/29/26: I am 58, looking to retire in two years, and trying to decide if doing Roth conversions is worth it or not.

Can I Retire When I Get Booted From Tech?

10/28/26: If, or perhaps when, I get booted from my tech industry job, will I need to find another job or can I retire?

Should I Take a 10% Pay Cut for a New Job?

10/27/26: I was recently offered a county job which comes with a pension and other good benefits but the offer is 10% less than my current salary. Would I be making a mistake by taking this offer?

Scared of Losing My Money

10/26/26: With about $300k in various accounts, I'm worried about the market and possibly losing this money. What should I do?

Should We Stick With Our Advisor?

10/23/26: We have a financial advisor who is okay, but now we're wondering if we should stick with him or make a change?

The Alphabet Soup of Medicare

10/22/26: Some people believe the murkiness of health care costs and lack of transparency is designed on purpose. Do you agree?

Making Sense of Life Insurance

10/21/26: Nearly 47% of American households say they feel financial hardship after a primary wage earner dies, according to a recent survey, which is where life insurance comes in.

Financing Our Dream Home

10/20/26: Given that we're already retired, what's the best way to finance the purchase and construction of our dream home?

Giving Myself Permission to Spend at 60

10/19/26: With plenty saved, and fairly low expenses, I'm having a hard time giving myself permission to spend some of my money.

Debt vs Investing in Pre-retirement Years

10/16/26: With a plan to retire in about six years, should I keep contributing to my workplace retirement plan or instead focus on some outstanding debt?

Is the Retirement Readiness Meter Accurate?

10/15/26: I have always managed my own retirement planning, but I would appreciate a second opinion to ensure my retirement readiness assessment is accurate.

I’m Fried, Can I Retire in a Few Months?

10/14/26: I'm fried, can I quit my job in six months at the age of 65?

Financial Decisions Ahead of Divorce

10/13/26: With my divorce set to be finalized in 2027, how should I be preparing for my new financial reality?

Needing Direction in Retirement

10/12/26: I’m retired and was the caregiver for my mom who recently passed, and now I’m not exactly sure how to move forward with my financial life.