How Risky Can I Be With a Career Reset?

Summary

Podcast Summary: Jill on Money with Jill Schlesinger
Episode: How Risky Can I Be With a Career Reset?
Release Date: April 11, 2025

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Introduction

In the April 11th episode of Jill on Money with Jill Schlesinger, host Jill Schlesinger, CFP®, explores the financial intricacies of undertaking a career reset. The episode features a detailed discussion with Greg, a 52-year-old listener from Northern California, who is contemplating a significant career change. Joined by co-host Mark Teo, the conversation delves into Greg's financial landscape, the risks associated with changing careers, and actionable strategies to manage such a transition effectively.

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Caller Background: Greg's Situation

Greg reaches out to the show seeking advice on assessing the financial risks tied to his potential career reset. At 52, Greg and his 47-year-old wife find themselves in a stable financial position, despite Greg currently not working. Their household income primarily stems from Greg's wife's full-time job, supplemented by funds from an inherited IRA that Greg began drawing from five years ago.

Mark Teo [03:24]: "Excellent. I love these questions so much. I am one of the queens of resetting my career."

Greg provides a comprehensive overview of their finances, highlighting their income sources, assets, liabilities, and future financial projections.

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Financial Situation: Income, Assets, and Liabilities

Income Sources:

• Wife's Salary: $150,000 annually.
• Inherited IRA: Approximately $1.2 million, currently being drawn down to support their cash flow.

Monthly Household Expenses:

• Total Expenses: $18,000 per month, which includes mortgage payments on two rental properties.
• Essential Expenses (excluding rentals): $12,000 per month.

Assets:

• Primary Residence: Valued at approximately $1.4 million with an outstanding mortgage of $1 million.
• Rental Properties:
  • Property 1: Valued at $900,000 with a $310,000 mortgage.
  • Property 2: Valued at $1.8 million with a $500,000 mortgage.
• Savings and Investments:
  • 529 Plan for child’s education: $67,000 with ongoing contributions of $500 monthly.
  • Brokerage Accounts: $75,000 (split between two accounts).
  • Retirement Accounts: About $1 million.

Liabilities:

• Mortgages: Total outstanding mortgages amount to $1.81 million across all properties.

Greg emphasizes that the rental properties are cash-flow positive, providing additional financial stability.

Greg [04:01]: "Well, I'm currently not working right now, so we're probably getting about 150 a year."

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Career Reset Considerations: Exploring Options and Financial Impact

Greg is exploring several career paths, including:

1. Continuing in His Current Career: Potential earnings of $250,000 to $300,000 annually.
2. Starting a New Business Opportunity: May require an initial investment of $75,000 to $150,000.
3. Pursuing Writing: A lucrative yet income-variable option.
4. Returning to School for Certification: Involves costs ranging from $25,000 to $50,000.

Mark Teo assists Greg in assessing these options by analyzing his current financial stability and future projections.

Mark Teo [16:43]: "I think it can be done. If you said I want to do writing or I want to spend 25 grand getting certification and additional schooling, like that kind of thing, I think the new business opportunity I would be much more careful about..."

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Advice and Insights: Managing the Financial Risk of Career Change

Mark Teo provides a strategic breakdown of Greg’s financial situation, emphasizing that Greg and his wife are well-positioned to undertake a career transition without jeopardizing their financial security. Key points include:

1. Sufficient Financial Cushion: The combined income from Greg’s wife and the inherited IRA covers their necessary expenses for the next five years, with the inherited IRA set to be fully drawn within ten years.

   Mark Teo [14:40]: "The inherited IRA gets you through the next five years. That means it goes. That gets you to 57."

2. Asset Leverage: Selling the $1.8 million rental property could provide an additional $1 million post-tax, offering further financial flexibility for Greg’s new endeavors.

3. Future Retirement Security: With approximately $1 million in retirement accounts and an anticipated pension for his wife of $18,000 monthly upon her retirement at 65, their long-term financial outlook remains strong.

4. Investment in New Ventures: For business opportunities requiring capital investment, Mark advises cautious allocation, suggesting that smaller initial investments ($75,000 to $150,000) are manageable within their financial framework.

   Mark Teo [16:50]: "...make sure you got all your estate documents, your insurance is in place, all that stuff. But I think you're ready to make a leap."

5. Emotional Readiness: Beyond the numbers, Mark highlights the importance of emotional preparedness for a career change, encouraging Greg to seek affirmation and support from trusted advisors.

   Mark Teo [17:47]: "I think the friction here is probably more about you and your wife feeling comfortable doing it. And again, you can run the numbers in a... someone who is a fee only planner."

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Conclusion and Key Takeaways

The episode concludes with Mark Teo reinforcing the feasibility of Greg’s career reset, given his solid financial foundation. The discussion underscores the importance of detailed financial planning, leveraging existing assets, and considering both immediate and long-term financial impacts when contemplating a significant career change.

Key Takeaways:

• Comprehensive Financial Assessment: Understanding all income sources, assets, and liabilities is crucial before making a career transition.

• Strategic Asset Management: Utilizing assets like rental properties and inherited funds can provide the necessary financial buffer during career changes.

• Future Planning: Ensuring that retirement savings and pensions are on track can offer peace of mind and stability.

• Emotional Readiness: Financial feasibility is just one part of the equation; emotional preparedness and support are equally important.

• Professional Guidance: Engaging with a fee-only financial planner can help model different scenarios and provide tailored advice.

Mark Teo [17:54]: "It's possible to do. So the only other thing is, you know, kids, still young, make sure you got all your estate documents, your insurance is in place, all that stuff. But I think you're ready to make a leap."

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Notable Quotes

• Mark Teo [03:24]: "I am one of the queens of resetting my career... deal with the financial parts of it so then we can deal with the emotional parts after."

• Greg [16:43]: "I'm looking at a bunch of different things. And then of course, there's the old standby, which is, you know, going back to what I was doing."

• Mark Teo [17:54]: "It can totally be done. Do you manage your own money right now or do you have a broker or a financial advisor or financial kind."

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Final Thoughts

This episode serves as a valuable resource for anyone considering a career shift, particularly those in similar financial situations as Greg. By breaking down the complexities of personal finance and providing actionable advice, Jill Schlesinger and Mark Teo empower listeners to make informed decisions about their financial futures.

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For More Information:

Listeners are encouraged to visit jillonmoney.com for additional resources, to submit their own questions, and to explore the subscription service Jill on Money Live for exclusive content and webinars.

Transcript

[Jill Schlesinger]

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[Mark Teo]

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[Greg]

Welcome to the Jill on Money show. It's Friday, April 11th and we are here held in your hand, answering your questions, trying to make sure that you are not unnerved by all the volatility, all the news flow. Get in touch with us if you're feeling anxious, if you've got a financial question, go to jillonmoney.com click the contact us button. Of course, Let us know if you would like to come on the air live with us by checking the box. Don't forget to sign up for the free weekly newsletter comes out today every single Friday. Mark does a great job putting together stories you may have missed. So check that out. And don't forget also to check out our subscription service, Jill on Money Live. Access to quarterly live webinars, four of them, bonus audio and video content, the back catalog, all for 45 bucks for the next 12 months. Jill on Money Live. Okay. Right now let's talk to Greg, who joins us from Northern California.

[Mark Teo]

What's going on, man? How can we help you out?

[Caller]

Well, thanks for taking me my call here. And so like a lot of your listeners, I've been contemplating a job reset and I'm exploring a few options and it'd be really helpful if I can get your opinion kind of our on our financial outlook so that I can assess how big of a risk I can go in terms of a, a new career.

[Mark Teo]

Excellent. I love these questions so much. I am one of the queens of resetting my career. So I get that it's kind of daunting, but it's great to kind of run through the financial parts of it so then we can deal with the emotional parts after. So, Greg, how old are you?

[Caller]

I'm actually 52.

[Mark Teo]

Okay, and you said a we. Is there a partner, a wife, a husband, a somebody?

[Caller]

Yes, there is a wife.

[Mark Teo]

How old is she?

[Caller]

And she is 47.

[Mark Teo]

Okay. Is she working full time?

[Caller]

Yes, she is.

[Mark Teo]

Okay. And so together, how much do you guys earn right now?

[Caller]

Well, I'm currently not working right now, so we're probably getting about 150 a year.

[Mark Teo]

Okay, and how is that working for your cash flow? Is that enough?

[Caller]

Yeah, it's actually enough. And the reason being is because about five years ago, one of our parents had passed and we inherited some money along with property. And as part of that inheritance, there was inherited ira. And so we started drawing from that.

[Mark Teo]

So that's been helping the cash flow.

[Caller]

Correct.

[Mark Teo]

How much is left in the inherited IRA?

[Caller]

There's approximately 1.2.

[Mark Teo]

Do you have, what is the time horizon for pulling that money? Do you have the 10 year clock ticking?

[Caller]

Yeah, we do. So there's another five years.

[Mark Teo]

Okay, so we got to get that money out anyway.

[Caller]

Yeah, correct.

[Greg]

Okay.

[Mark Teo]

I'm sorry that someone had to die to get that. But it's good at this point that you have the money. What do you suppose you need to live on, really? I mean, if your wife makes 150 grand a year, what is the actual monthly nut do you think?

[Caller]

So I ran the numbers. We're probably going through about 18,000amonth. And the reason being is there's some rental properties that we have. There's still a mortgage on those.

[Mark Teo]

Okay, how much is the rental property worth?

[Caller]

So there's two of them. One of them is about 900,000.

[Mark Teo]

And that has a mortgage or no.

[Caller]

Mortgage is probably about 1.8.

[Mark Teo]

Is there a more which has a mortgage on it? The $900,000 or the 1.8?

[Caller]

They both do.

[Mark Teo]

Okay, what's the mortgage outstanding for these guys?

[Caller]

The one of them is 310,000 and the other is about 500,000.

[Mark Teo]

Okay, but they're cash flowing, positive, like your people renting them?

[Caller]

Correct.

[Mark Teo]

Okay, that's good. You have kids?

[Caller]

Yes, one kid.

[Mark Teo]

How old?

[Caller]

11.

[Mark Teo]

Any money saved for college for that one?

[Caller]

Yes. So we have a 529. It has about 67,000 in it.

[Mark Teo]

Okay.

[Caller]

We're contributing about $500 a month. And along with that, we were also gifted stocks for when she was little. And so those are in brokerage accounts. And there's one that's about 30,000. There's another that's about 45.

[Mark Teo]

So 75 total?

[Caller]

Correct.

[Mark Teo]

Why do we have to keep that in a brokerage account? I mean, should we. I mean, are they like UGMA or UTMA accounts or just plain old brokerage accounts that.

[Caller]

Just plain old brokerage accounts.

[Mark Teo]

So you could put the money into the 529 plan, correct?

[Caller]

Yes.

[Mark Teo]

But you'd have to pay the. Whatever the capital gains is, right?

[Caller]

Correct.

[Mark Teo]

Okay, but you'd have to do that anyway, I guess.

[Caller]

Yes.

[Mark Teo]

Okay. Any other brokerage account assets besides that? 75.

[Caller]

For education brokerage, we have about $160,000.

[Mark Teo]

And what about in retirement accounts? What have you guys squirreled away?

[Caller]

Roughly about a million.

[Mark Teo]

Right now all of your benefits are coming through your wife's job, right?

[Caller]

Yes.

[Mark Teo]

Okay, so for today, this is actually a pretty darn good story. Right. You own your own home as well, but in addition to these two rental properties.

[Caller]

Correct.

[Mark Teo]

How much is your house worth?

[Caller]

Probably about $1,400,000.

[Mark Teo]

Is there a mortgage outstanding on it?

[Caller]

Yes, there is.

[Mark Teo]

How much is left?

[Caller]

About $1,000,000. We just bought it.

[Mark Teo]

What's the interest rate?

[Caller]

$2,075,000.

[Mark Teo]

That's not so recently. That's a nice interest rate, right?

[Caller]

Right at the tail end. Yeah, we got in right Before, So we got lucky.

[Mark Teo]

Is there any reason that we should look at these rental properties in terms of selling them? In other words, do you want to maintain these properties? Obviously there's quite a bit of equity that's locked in them. Almost 2 million bucks. Are they performing assets? Are they doing well?

[Caller]

They're doing okay. So initially we weren't necessarily looking at these properties as rentals. So what happened was one of them I mentioned earlier, which is we inherited. The reason why we kept that was because if I decide to continue in my career path, a lot of the opportunities are actually closer in location to that property. It would make my commute so much easier. And so if I decide that I want to play out my career in continuing doing that, I think for just a work life balance, we would. We were considering potentially moving there.

[Mark Teo]

Is that the 1.8 million or the 900?

[Caller]

The 1.8 million.

[Mark Teo]

Okay, so that was the. But you're no longer on that path, right? I.

[Caller]

Well, I think you can, you can maybe help me with that.

[Mark Teo]

Okay. Okay. But the 900, how does that perform in terms of rental? Does it give you what you need? Like, what do you think?

[Caller]

Yeah, the 900. So the 900 was actually the house that we lived in prior. And you know, again, the reason why we kind of kept that one on is because we have some aging parents and on the off chance that we would need to have them move closer, you might want to move that available.

[Mark Teo]

Okay.

[Caller]

So far there's been resistance to, you know, to that.

[Mark Teo]

So that, does that mean by your wife or by the parents?

[Caller]

Probably both.

[Mark Teo]

Uh huh. Okay.

[Jill Schlesinger]

All right.

[Mark Teo]

But so far, But I get, I get. So you have, basically you're preserving the opportunity to use these properties differently. So I get that. Okay, so let's, let's keep going then. So tell me about the job reset. So before you stepped away from what you were doing, how much were you earning? Like, if you go back into that, you know, obviously this, this career. What would the career position pay you?

[Caller]

Yeah, it'd probably be somewhere around 2:50 to 300.

[Mark Teo]

Okay, and what about the, the new idea? Tell me about that. What would that mean for you?

[Caller]

Yeah, so I'm actually looking at a few different things. And you know, some of it may involve having to put money forward, like a potential business opportunity. I'm also looking at maybe doing some writing, which, you know, very lucrative career.

[Mark Teo]

Very lucrative.

[Caller]

Definitely.

[Jill Schlesinger]

Yeah.

[Mark Teo]

All right, so that would be a zero next to the income. What else?

[Caller]

You know, and there's, there's other Things I'm also interested in doing, which may require, you know, getting certification or possibly going back to school. So I'm looking at a bunch of different things. And then of course, there's the old standby, which is, you know, going back to what I was doing. Yeah.

[Mark Teo]

That doesn't sound like you want to do that, though. You don't want to go back and do your 250. I'll grind it out. Right. Is that kind of. It doesn't sound like you want to do that.

[Caller]

Right. If I can help it, I probably wouldn't be my first choice.

[Mark Teo]

Okay. Will your wife continue to work to fund your folly? I mean, your next career. I'm just kidding.

[Caller]

You know, she loves her job.

[Mark Teo]

Okay, that's great.

[Caller]

And, yeah, so she's. And, you know, we've kind of established roots around her work, so, you know, so, you know, when I. When I chose other roles prior, I kind of prioritized the earnings just so that, you know, we can live comfortably, you know, and I would bear to commute, you know, kind of throw off the work life balance.

[Mark Teo]

Okay, I got it. So the 18 grand a month is the amount of money, you know, kind of. If you had to scrub some of like, your. What your real expenses are. Because I'm less concerned about the 18 grand a month with the rental property. Because you're. They're paying for themselves, essentially, right?

[Caller]

Yes.

[Mark Teo]

Okay. So I want you to pull out the monthly nut, which is really just like what it costs for you and your wife and your kid in your primary residence. What do you think that number is? Is that more like 14, 15? Like, what is the actual cash flow? Because, you know, we're going to look at the rental properties as businesses unto themselves. We. They have their own cash flow, they have their own income. So I'm not even concerned about that, But I really am concerned with how much you actually spend.

[Caller]

12.

[Mark Teo]

Okay, that makes me feel better. Okay. 12 grand a month without the rental property. Okay. Is your wife going to be entitled to a pension?

[Caller]

She is.

[Mark Teo]

Tell me about that.

[Caller]

So if she works till she's 65, based on kind of their calculator, it looks like she can get 18,000amonth.

[Mark Teo]

18,000Amonth? You mean 1,800amonth?

[Caller]

18,000.

[Mark Teo]

She only makes 150 grand a year. Oh, you're saying in the future.

[Caller]

In the future, yeah. If she works till she's 65.

[Mark Teo]

Wow. So she's got like, that's about 20 years. 18 years. Okay.

[Caller]

Yeah, yeah.

[Mark Teo]

And she likes it. So she Might just do that.

[Caller]

She actually has no plans. I mean, you know, she'd probably want to work until she can't work anymore.

[Mark Teo]

Okay, so let me just go. Let's make sure we go through this. So right now, how much are you pulling out every year in the inherited ira? Have you spread it out across, you know, somewhat evenly, or have you front loaded it or how have you done that?

[Caller]

Yeah, we do a monthly. We would just.

[Mark Teo]

How much is coming out monthly?

[Caller]

Right now it's about 18amonth, which nets about, you know, so we'll put some aside for taxes and then so. And that's about 10.

[Mark Teo]

Okay. That is a pretty nice chunk of money to have an extra 10 grand a month coming in addition to your wife's $150,000 salary. So between the IRA distribution, forget about those rental properties, again from the IRA, plus your wife's salary, that floats your need, I imagine, right?

[Caller]

Yeah.

[Mark Teo]

Beautiful. I think you should do what you want to do. If you're like, should I go make a 250 grand a year? Even though I hated it. No, something great. I mean, it's terrible that someone died, but you have an opportunity. Something fell in your lap. Money, okay? Which means you have permission to do what you want to do. I mean, unless your wife is like, I cannot bear this idea that you are not working in, like, a career, and I don't want to have that kind of burden if that's the case. That's a different conversation from the money point of view. Here's how I look at it. You're fine for five years. That means it goes. That gets you to 57. Now, another 10 years. Honestly, if you're not going to take the job, that's going to put you back on the career path. Sell the $1.8 million house and you got another 1.3 million. And maybe it's after taxes, it's a million dollars. You have another million dollars that is essentially available to you, which you can use and fund whatever you do next. At the same time, your wife is still putting money into retirement, is she not?

[Caller]

Yeah.

[Mark Teo]

So she's putting money. So we've got the million dollars in retirement. Here's. I mean, again, this is blunt, so it meaning very rough around the edges. But the way I look at it is the inherited IRA gets you through the next five years. Then for another 10 years, you can use the rental property, the big one, the 1.8 million. You can sell that. You can sell that now. Frankly, I don't really care. Whatever. Like, if you want to try to spread out some of your tax burden. I get it. Sell that thing, get done with it. Add that to the brokerage account. Don't worry about it. Now you've got that money in brokerage, you've got the money in retirement. We have her future pension. You've got two Social Security checks. This looks good to me. The one thing I'm a little nervous about. How much money do you think when you say, oh, I'm looking at a business opportunity, how much money you have to put into a business opportunity? It's one thing to not make any income, it's another thing to use the money. You have to sink it into something. So what would that require?

[Caller]

Yeah, so looking into that, It's I would say 75 to 150.

[Mark Teo]

You got to figure out what you want to do. I think you can do any of these. If you're telling me it's like 250 or 500 grand, then no, I don't think so. You have opportunities and I think, I think it's a shame for people who have opportunity to not consider taking advantage of them. So what I would say to you, Greg, is I think it's completely doable. If you said I want to do writing or I want to spend 25 grand getting certification and additional schooling, like that kind of thing, I think the new business opportunity I would be much more careful about because I always think that the first 75 or 150 turns into a lot more. When you talk about businesses, that's just my two cents. But I think you can do what you want to do. If you want to know, can you do a job reset? Absolutely. But you have to be able to give yourself permission. The numbers will work for you. They really will. It's just a question of whether you can emotionally do it. So what's going to hold you back if it's not the money?

[Caller]

Honestly, I'm not sure. I think I just need to hear other voices saying that it can be done.

[Mark Teo]

Oh, it can totally be done. Do you manage your own money right now or do you have a broker or a financial advisor or financial kind.

[Caller]

Of a dabble between both. What happened was with the inherited money, it was under a financial advisor, so we kind of took him on as well. But I've been a little bit reluctant to just turn everything over just because I've managed it for so long myself.

[Mark Teo]

Okay. I mean, you can hire a fee only financial planner to really run through numbers with you when you have, you know, a Better idea, you know, not just me doing back of the envelope. I think that you can do this. I really do. I just think that the friction here is probably more about you and your wife feeling comfortable doing it. And again, you can run the numbers in a. You can have someone really model this out for you. It doesn't have to be this financial planner. It can be somebody who is a fee only planner. And you're like, you know what? I need to pay you five grand to model out these three scenarios. One is I never make money again. I'm a writer. The second is that I go and get some education and spend some modest amount of money, 25, 30, 40, $50,000 to get the certification I need. And the third is I make an investment of $150,000 in this new venture. And you can hire someone to model that for you. You really can. But I don't think it's going to be a problem just from the raw numbers that you've given us. I think the hurdle is you being able to do this yourself and just emotionally get used to the idea I can do this. And you know, I have a very dear friend of mine, by the way, who was in a lucrative profession left it became a writer and his wife is the big money maker. And it's worked out beautifully, it really has. So, and in fact, he's made a few bucks, so shockingly, but it is true.

[Caller]

Awesome.

[Mark Teo]

So it's, it's possible to do. It's possible. So the only other thing is, you know, kids, still young, make sure you got all your estate documents, your insurance is in place, all that stuff. But I think you're, you're ready to make a leap.

[Greg]

If you have a financial question, if you are worried about markets, if you just can't stand the volatility, if you're thinking about a new career, anything going on in your financial life, get in touch with us. Go to Jill on money dot com, click the contact us button, write us that note. And of course, if you would like to join us on the air, check the box. Mark will do everything else. It's Friday, so we're going to do some business. Our music is composed by Joel Goodman. Mark Teo is our executive producer and king of all things web. We are distributed by our Odyssey. Try to lift someone up. Change your work, change your wealth, change your life. Thanks for listening. We'll talk to you on Monday. Need contract help for those workload peaks and backlog projects? You're not alone. Robert half found that 67% of companies surveyed said they will increase their use of contract talent. That's why their recruiters leverage their experience and use award winning AI to quickly find the skilled candidates you want. Learn about their specialized talent in finance, accounting, technology, marketing, legal and administrative Support@robert Half they know talent. Visit roberthal.com talent today.

[Courtney Harrell]

Imagine if you could ask someone anything you wanted about their finances. How much do you make? Who paid for that fancy dinner? What did your house actually cost? On every episode of what We Spend, a different guest opens up their wallets, opens up their lives, really, and tells us all about their finances. For one week, they tell us everything they spend their money on.

[Caller]

My son slammed like $6 with the.

[Mark Teo]

Blueberries in five minutes.

[Courtney Harrell]

This is a podcast about all the ways money comes into our lives and then leaves again. Which of course we all have a lot of feelings about.

[Mark Teo]

I really want these things. I want to own a house. I want to have a child.

[Courtney Harrell]

But this morning I really wanted a coffee. Because whatever you are buying or not buying or saving or spending, at the end of the day, money is always about more than your balance. I'm Courtney Harrell and this is what we spend, listen to and follow what We Spend An Odyssey Original podcast available now. Wherever you get your podcasts.