Invest Retirement

The Four Money Moves To Make When Facing A Big Life Change

Chelsey Zhu  |  March 23, 2023

Whether you want to change careers, start a business, or retire, learn how to make your money work for your goals. 

Have you ever seen someone go through a midlife crisis? That’s usually how we describe a person who’s made a drastic life decision, like quitting a job they’ve had for years, or suddenly moving to the other side of the world. Only these days, more and more people seem to be going through it, and it’s not at all exclusive to a certain age range. The pandemic forced all of us to pause and reflect on our biggest goals. The result? Millions of people changed jobs or retired during the Great Resignation, applications for new businesses skyrocketed, and many of us are carrying forward a new resolve to live the life we truly want. 

If you’ve thought about taking a leap of faith in your career or personal life these past few years, but didn’t know where to start, it’s not too late. And the very first step is an easy one — take a close look at your budget. Digging deep into your money is “a way to take control of what is going on in your life,” says Jill Schlesinger, CBS News business analyst and host of the podcast Jill on Money. “When you get the numbers part right — or at least address it — then it’s a lot easier to go into the emotional part.” 

Schlesinger wrote the book “The Great Money Reset” to help people navigate these major life transitions with as little financial stress as possible. She joined us on the HerMoney Podcast to share her best insights, and we’ve got her top four pieces of advice below. 

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If you’re thinking of making a change that might affect your income, it’s a good idea to know exactly how much you’re earning, spending, and saving before you make any moves. First, calculate the value of all of your assets, including your bank accounts, retirement accounts, other investments, your house, and any other major pieces of property. And if you have a full-time job, “don’t forget to put in your benefits,” says Schlesinger. “Those benefits cost your employer quite a bit of money, and you usually don’t think of it that way.” This includes health insurance, life and disability insurance, the employer match on your 401(k), and any flexible spending or health savings accounts. 

Then move on to your everyday expenses and your debts, including credit card debt, car loans, student loans, and your mortgage. This also includes any financial obligations you may have to other people now or in the future, like paying for your children’s college expenses or your parents’ medical bills. 

At the end of the process, you’ll have a clearer picture of whether you can afford to take a big leap with your current lifestyle and what you could change to get there. “Once you have all these questions answered, you can start to build out some different scenarios,” Schlesinger says. “What’s the best case, what’s the worst case, and what’s the middle case? It helps you start to give yourself a framework for how to make a move.” 


You might find your financial review opens up doors that you hadn’t thought about before. Maybe you always assumed that you had to work full-time in your demanding job all the way until retirement — but after looking at the numbers, you realize you’d rather move to part-time now, have more freedom, and delay full retirement for a little bit longer. Or maybe you assumed that homeownership was necessary for building wealth, even if it meant taking on more debt. One couple that Schlesinger interviewed, Pam and Tom, found that selling their home to live in a rental was the best financial move for their lives. 

“They had a pretty big mortgage because they had to refinance to help their kid pay his loans down,” Schlesinger says. “There was a lot of debt, and to make those payments and still put money into retirement, Pam had to work a ton of overtime.” But once the couple got their home appraised during the 2020 housing market craze, they realized that there was much more equity locked in their home than they’d previously thought. “By selling, they could pay off all the outstanding debt, [Pam] wouldn’t have to work as much in terms of overtime, and they probably had more longevity in their careers because those hours were reduced.” 

“It’s a scary thing, especially if you’ve been owning some sort of real estate for [most of] your life,” Schlesinger says. “But imagine the freedom of feeling unburdened by all that debt, and the freedom in being a renter and not having to maintain a property.” 


Another assumption you might have about your financial situation is that you don’t have any breathing room with your expenses. It’s easy to feel that way, especially with inflation and the nationwide rise in credit card debt. But taking some time to reflect on what you buy and why could help you determine how much of your spending is absolutely necessary — and how much is going towards unfulfilling purchases. 

Schlesinger recommends working through a list of questions: What do you really need? What do you think you need? Do you ever feel guilty, insecure, or anxious about certain purchases? Do you make impulsive purchases, and if so, when and why do they happen? The answers might point you to changes you can make in your life that go beyond your finances. For example, if you’re feeling pressured to eat out so you can spend time with your friends, the solution could be to organize low-key dinners at home instead. If you’re buying a lot of professional clothes because you’re worried about being taken seriously at the office, there are other (cheaper!) ways to boost your confidence in the workplace. 

“I think it’s worth our while to just spend a minute not judging our spending or judging our spouse’s spending, but getting real and saying, ‘What is this doing? How is this serving me?’” Schlesinger says.


While taking control of your spending is important, no amount of penny-pinching will make you a millionaire. Another crucial step to securing the money you need for your big life change is knowing how to negotiate for better benefits at work. Doing that successfully means being able to articulate exactly what you’re asking for. Are you only looking for a raise, or would you rather have more PTO or more days working remotely? (Remember, time is also money.) Your manager might be more open to those latter options, especially if your company or industry is going through a rough patch. 

“I’ve been a boss before, and what I understand as the boss is that when someone comes marching into my office and the business isn’t doing well, the industry isn’t doing well, the economy isn’t doing well — even if that person is extraordinary, asking for a raise in that moment is not great,” says Schlesinger. 

She recommends thinking ahead of time about what you want, whether it’s reasonable given the circumstances, how your manager might react given their own situation at the company, and how you might continue to negotiate if their initial answer is “no.” If you’re nervous, ask a friend to help you practice the conversation. 


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