Jill Schlesinger, host of Jill on Money and award-winning business analyst for CBS News, joins the show to talk about her latest book: The Great Money Reset.
Listen now and learn:
- What it means to do a great money reset
- The differences between money reset experiences by age
- Timely financial steps to build the life you really want
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Show Notes
Jill Schlesinger is an Emmy and two-time Gracie Award-winning business analyst for CBS News. She is the host of the podcast and nationally syndicated radio show Jill on Money and the author of The Dumb Things Smart People Do with Their Money.
In this episode, we discuss her latest book: The Great Money Reset, which gives readers ten timely financial steps to build the life they really want.
Below are my notes from our conversation.
What is a Great Money Reset? (1:56)
The great money reset is a transition people make to better align their financial lives with their deepest values and desires.
Jill has gone through two resets herself. The first was in her 20s when she was a trader and thought she would follow in her dad’s footsteps. After several years on the commodities exchange in New York, she realized she didn’t like it and pivoted to financial advice, which allowed her to continue solving problems and using her “little nerdy math head.”
Jill was a financial advisor for 14 years, using a radio show to help grow her business. Being on the radio in a small New England city made her a bit of a mini-celebrity, so eventually, she started doing local television. At that point, she wondered if she could do media work full-time.
At that moment, she wasn’t sure where to start, but a close friend said “You need a pink notebook” to figure things out. This pink notebook was really a three-ring binder with a section on money-related parts of the decision, another section with people you’ve met in TV and radio, and another section just for the conversations you have—the finished product will be a guide for you in making an informed life decision.
Much of how she talks about her “pink notebook” resembles the advice she gives throughout her book.
The idea for the book, though, really took shape during the pandemic. In the summer of 2020, listener questions shifted dramatically away from “We’re in this panic-stricken mode” to “I don’t know if I want to go back to the way things were.
In the 30 years Jill has been doing a radio show or podcast of some sort, she always had people asking questions at inflection points in their lives—a birth, a death, a divorce, a job loss, etc. But the pandemic was an event that gave people more time and space to really think about how they want to live their life. Listeners wanted to know how they could make different choices. If they do something different, what does that really mean? And how can they make smart decisions without blowing up their financial life in the process?
Jill’s book is the product of these questions and conversations.
How the Experience of a Great Money Reset Differs by Age (10:55)
At each point in your career, you might have the opportunity to ask different questions of yourself.
A few examples Jill shares from people of differing ages and life stages:
“I know that I chose to go into a field where I was going to make a lot of money. But as it turns out, now that I really see what this is like, and now that maybe I see what it is like to not have to be in an office every single day, and maybe to have a different lifestyle. Maybe I don’t want that, maybe that’s not so important to me”.
“I made some choices when I was single and trying to forge my life, but my priorities have shifted. I don’t want to be married to a job. I really liked my spouse and kids, so I’d really like to try to figure out a way to live a life with them”.
“I’m not going to make it to 65 there’s no way I’m going to do what I do until I’m 65. What choices can I make today to pivot to make maybe less money but be able to work longer?”
“How can I take my love of something that was a side hustle and turn it into a real hustle?”
“I have a business that I’ve been growing. It’s been great, but this is so hard.”
“Because my business was really impacted (either positively or negatively) by the pandemic, does it gives me different choices to make in the future?”
People want to have agency over their lives, they want to be able to make different choices, and they don’t want to feel trapped. They make better choices when they don’t feel trapped. Making good choices is all about laying out different opportunities and options. The world isn’t black or white.
The Importance of Scenario Analysis in Decision-Making (15:00)
Jill’s training as a trader makes thinking about the best-case, worst-case, and middle-case scenarios very natural. The best-case and worst-case are easy to define, but the middle is often the challenging one.
Jill uses her own decision of transitioning from being a financial advisor to doing full-time media work. She had a tab in her pink binder for each of the three possible scenarios that are filled with conversations and input from others.
I was particularly drawn to this idea because it is a technique I often use when speaking with individuals that are worried about something in their financial lives. Acting as an objective third party, I like to talk through what the best, worst, and middle possible outcomes might be—then, perhaps most importantly, assign probabilities to those potential outcomes.
The next time you get worried about markets, it’s an exercise you might consider.
Can You Pull Off a Great Money Reset? (22:05)
Jill’s book is laid out in a manner to help you work through important questions, such as:
- What’s the money you have?
- What are your resources?
- What are your debts?
- What do you think about your house?
- What do you think about your family?
I think that is something that’s quite profound about the pandemic. Specifically, it shifted some of those priorities around. I think there are plenty of people who were really psyched about like, “I moved 3000 miles away from my parents. See yah!”. Then the pandemic hits and your parents are getting older, and you’re saying to yourself, “Well, I don’t know if I want that”.
Jill notes that sometimes when you’re considering a reset, you arrive at a conclusion that is very different than what you thought you’d be doing. She shares a few stories where people are focused on something that is relatively insignificant before eventually realizing what’s really the important thing.
For example, it might start with a desire to quit your job for any number of small reasons. But it isn’t that you really want to quit, but instead want to have some longevity so that you aren’t limping to the finish line. Or maybe there is no finish line and you really want to be living a life without some sort of lifestyle or financial burden.
To Jill, this is the quintessential, beautiful surprise of a reset—you can really look at the numbers and start to conceive, “Hey, wait a minute, the way I thought I was going to live my next 10 years, my next 20, my next 30, it could be different. All I need to do is open my eyes, crunch the numbers, and be willing to just do it”.
Personal Finance in Shades of Grey (27:00)
Personal finance has evolved from being all about collecting the most wealth possible. It’s less of a “save at all costs” mentality and more of a “there isn’t one right answer for everyone” mentality.
There’s a quote from Jill’s book that perfectly captured her own experience in giving personal finance advice over the years:
“If the pandemic taught me anything, it’s to value the present more than I once did, and the future a bit less….We should invest in us, in ways that go beyond money and that embrace both the present and the future.”
As Jill explains in our conversation, all life decisions have some financial ramifications—the goal is to strike a good balance between living for now versus living for the future. In a perfect world, you’d have a financial plan that is flexible enough to change as we change.
Financial plans should be living, breathing documents. They act as a baseline for when things shift in your life. Jill thinks a good financial planner is someone who can work with you to develop a financial plan that is always adaptable and not just some 100-page plan that you stick in the back of your desk.
Resources:
- Jill’s podcast Jill on Money
- The Dumb Things Smart People Do with Their Money by Jill Schlesinger
- The Great Money Reset by Jill Schlesinger
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