Retirement With Intention

Summary

Podcast Title: Jill on Money with Jill Schlesinger
Episode: Retirement With Intention
Host: Jill Schlesinger, CFP®
Release Date: July 11, 2025

---

Overview

In the "Retirement With Intention" episode of Jill on Money, host Jill Schlesinger engages in a profound conversation with Christine, a 56-year-old tech professional from the Bay Area who recently retired. The episode delves into the emotional and financial intricacies of transitioning into retirement, emphasizing the importance of intentional planning and the psychological adjustments that come with leaving a long-term career.

---

Guest Introduction

Christine introduces herself as a seasoned project manager with over 27 years in the tech industry. Having decided to retire earlier than initially planned, she shares her motivations for seeking a more balanced and less chaotic lifestyle.

Christine [03:04]: "I just finally decided, you know, what, I'm doing well and I don't need the chaos of tech. And so I made the decision to retire."

---

The Emotional Transition to Retirement

Jill explores Christine's initial feelings post-retirement, highlighting the common experience of relief followed by a sense of purposelessness. Christine candidly discusses her struggle with feeling unproductive outside of a structured work environment.

Christine [05:05]: "By the second week, because I wasn't busy 40, 50 hours a week, I felt like I wasn't contributing to myself, to the world in some way. I felt like I was being lazy."

Jill underscores the importance of self-compassion during this phase, reminding listeners that adjusting to retirement is a significant life change that requires time and grace.

---

Financial Stability and Planning

Christine reveals her impressive financial standing with total savings amounting to $4.2 million, enabling her to comfortably allocate $100,000 annually for her retirement needs. Jill commends Christine's financial foresight and stability.

Jill [07:54]: "Wow, that's amazing. Congratulations."

The conversation shifts to managing finances in retirement, especially concerning market volatility. Christine expresses anxiety over potential stock market downturns, fearing a 50% loss of her portfolio. Jill offers reassurance by explaining the benefits of a diversified and balanced investment strategy tailored for long-term growth.

Jill [16:46]: "You are going to be investing for three more decades. You can stay invested and you will be able to essentially ride it out."

---

Intentional Retirement: Creating Your Own Pension Plan

Jill introduces the concept of "Retirement with Intention," encouraging listeners to view their retirement savings as a personal pension plan. She advises Christine to set up structured withdrawals to provide steady income, akin to traditional pension distributions.

Jill [12:30]: "It's your own pension plan. You've worked really hard to accumulate this. So if you can be intentional about this, I think it's freeing."

Christine appreciates this framework, recognizing it as a means to validate her years of hard work and to provide financial security without the constant pressure to remain employed.

---

Balancing Financial Security and Personal Fulfillment

The discussion emphasizes the balance between financial management and personal fulfillment. Jill suggests that intentional financial planning can alleviate the stress associated with market fluctuations, allowing retirees like Christine to focus on meaningful activities such as volunteering, continuing education, and travel.

Jill [13:49]: "You deserve to take some time and just figure it out."

Christine reflects on her desire to possibly engage in part-time work or selective projects, highlighting the flexibility and control that intentional retirement planning affords her.

---

Final Thoughts and Takeaways

As the episode concludes, Jill encapsulates the essence of "Retirement with Intention," encouraging listeners to approach retirement proactively rather than reactively. She stresses the importance of working with financial advisors to create personalized strategies that align with individual goals and risk tolerances.

Jill [18:34]: "If you need a little retirement with intention session, be like Christine. Get in touch with us."

Christine expresses gratitude for the insightful discussion, feeling empowered to embrace her retirement with a clear plan and renewed sense of purpose.

Christine [18:34]: "This has been wonderful. Thank you so much, Jill."

---

Notable Quotes

• Christine [03:38]: "Originally, I was going to do it in about three years, but if I can do it now, what am I waiting for?"
• Christine [05:05]: "By the second week... I felt like I wasn't contributing... like I was being lazy."
• Jill [12:30]: "It's your own pension plan. You've worked really hard to accumulate this."
• Jill [16:46]: "You can stay invested and you will be able to essentially ride it out."
• Jill [18:34]: "If you need a little retirement with intention session, be like Christine."

---

Conclusion

"Retirement With Intention" offers a heartfelt exploration of the multifaceted journey into retirement. Through Christine's experiences and Jill's expert guidance, listeners gain valuable insights into balancing financial security with personal fulfillment. The episode serves as a compassionate reminder that retirement is not merely an end but a new beginning that, with intentional planning, can lead to a fulfilling and secure chapter of life.

---

Transcript

[Jill Schlesinger]

Hey gang. You know, I've often talked about how important it is to build your financial foundation and part of that is making sure that you have the right type and amount of life insurance. There's a really easy way to make this happen. Policygenius makes finding and buying life insurance simple, ensuring that your loved ones have a financial safety net that they can use in case something bad happens to you. With Policygenius you can find life insurance policies starting at just $276 a year for 1 million dol in coverage. It's an easy way to protect the people you love and feel good about the future. When you go to policygenius.com, you'll talk to a team of licensed agents who will walk you through the process step by step. They'll answer questions, handle the paperwork, and advocate for you throughout the process. So secure your family's future with Policygenius. Head to Policygenius.com to compare free life insurance quotes from top companies and and see how much you could save. That's policygenius.com 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 at Robert Half. They know talent. Visit roberthalf.com talent today. Welcome to the Jill on Money show. It's Friday, July 11th and we are here answering financial questions that you pose to us. And for many of you, a lot of the things that you're asking about are things that you probably feel in your heart of hearts you know the answer to. But you want another set of ears and eyes on the situation. That's great. Both Mark and I are certified financial planners. We don't do it for a living. We just use it here on the program and on this show and our other podcast, Money Watch and our radio show. But we just love to hear what's going on and to see how we might be able to guide you or reinforce what you already knew. So if you've got a question, just go to jillonmoney.com click the contact us button. Write us a note if you'd like to join us on the air. Check the box. Mark will do everything else, of course. While you're on the website, sign up for the free weekly newsletter and check out our subscription service. It's called Jill on Money Live. That's where you have access to quarterly live webinars, the back catalog of those webinars, and bonus audio and video content. It costs you 45 bucks for the next 12 months. That's it. Pretty good deal. Okay. Today we are talking to Christine, who joins us from the Bay Area. And it's very early there, so I apologize. Christine, I'm on that east coast hepped up time. You're kind of getting into your day, so welcome to the program. Warm us up. What do we need to know about you?

[Christine]

Thank you. Thank you. Well, so I just retired in February of this year. Some information about me. I'm 56. I worked in tech since I am in the Bay Area, so I did work in tech for over 27 years. I just finally decided, you know, what, I'm doing well and I don't need the chaos of tech. And so I made the decision to retire. Originally, I was going to do it in about three years, but if I can do it now, what am I waiting for? Because time is one thing that I can never get back.

[Jill Schlesinger]

That is such an excellent point. And, you know, I think that there have been many people who say to me, oh, Jill, you don't like it when anyone retires. It's not that I don't like that people retire. I want you to take your time and think about these big decisions, but also to contemplate, you know, at age 56, and you have put your time in what happens next. How do you, how do you think you're going to be managing this next, you know, hopefully three, four decades? So what's the game plan, Christine?

[Christine]

That is a good question. So I was a project manager. So, you know, I'm always thinking about what's going to happen next. So I am right now volunteering at at least two nonprofits. I say at least because I'm waiting for a third one. I just signed up for a community college course that would start in August. And obviously in between, I'm doing some traveling. So that's, that's, that's my plan right now. And I. But what I do recognize is that I do have the next three to four decades. And so I can't be too rigid. I want to be flexible, but I have to change that mindset. And I know I need to give myself a bit of grace since I just retired five months ago. So.

[Jill Schlesinger]

So let me ask you something. Let me ask you a few, like, pointed questions about this period of time. You clearly, as a project manager, probably could have lined up five different things to do.

[Christine]

Yeah.

[Jill Schlesinger]

How did it feel having nothing lined up?

[Christine]

You know, I have to say, the first week, it was really wonderful because as a project manager, the first thing I do when I wake up, even though it's early here, this is my normal schedule. I would wake up, pick up my phone, check my slack, check my email, and just start going at it for eight, nine hours. So it was refreshing. But then by the second week, because I wasn't busy 40, 50 hours a week, I felt like I wasn't contributing to myself, to the world in some way. I felt like I was being lazy. I had to let that go.

[Jill Schlesinger]

How'd you do that? How did you let it go? You just said to yourself, calm down. Like you just talked to yourself a little bit. Or did you have friends who also retired?

[Christine]

It was me just coming down. But also I keep in touch with my colleagues at work and they tell me about the chaos. So now I am their venting person. But I tell them, you know, I'm sorry for what you're going through, but I'm so glad I am not going through it. So it's the reinforcement that I made the right decision.

[Jill Schlesinger]

Great.

[Christine]

Also, though, now I have a calendar with intentions. I got to say, when I was working, I would sometimes by the end of the day go, what did I accomplish? Just a lot of meetings. I would be frank. A lot of BS meetings where people just talk and talking without whole lot of outcome. So now I'm volunteering and I feel like, okay, even though it's not the most mentally stimulating work sometimes, but I feel like I've accomplished something. I'm helping somebody from doing that right.

[Jill Schlesinger]

I mean, if I had to think about this, the name of this episode maybe would be Retirement with Intention. And I love that idea because intention doesn't have to be just to make money, but it does have to do with, you know, how am I spending my days? And you totally deserve to take some time and just figure it out. I'm not one of these folks who is mad about like, oh, you must have the next thing lined up before you leave your. That's not necessarily the case. So we're gonna find out whether you have lots and lots of money to take your time with this retirement with int. So tell us, how are you supporting yourself?

[Christine]

I saved a lot in the past few 35 years of working as a single person. I don't have a lot of overhead except my dog. I have a mortgage, but it's only about $80,000 at this point, at a 3.4% mortgage.

[Jill Schlesinger]

And how much is the place worth?

[Christine]

Let's say 600.

[Jill Schlesinger]

Okay, so that's good. And so any. Did you have any pension benefit or not?

[Christine]

No. No. Working in tech? Nope. I figured so. Yeah.

[Jill Schlesinger]

So what about in retirement? Assets? Tell me about what you saved overall total.

[Christine]

As of Friday it was 4.2 mil.

[Jill Schlesinger]

Wow, that's amazing. Congratulations.

[Christine]

Thank you.

[Jill Schlesinger]

How much are you. I mean, I know you're not. We don't really know what your real next phase looks like, but how much do you. Are you spending right now in general?

[Christine]

I have a budget sheet, of course.

[Jill Schlesinger]

Of course you do. Project manager.

[Christine]

I'm giving myself 100k a year.

[Jill Schlesinger]

That's it? That's all you need?

[Christine]

That's all I need.

[Jill Schlesinger]

Okay.

[Christine]

But. And so that's why I reached out to you because I've obviously gone through all the financial and retirement calculators. I even have a financial advisor and he said I could retire twice over mentally. I don't know how to let it go. And again, it's 35 years of, or 40 years of saving. And so how do I switch that? Is it a dimmer or is it a switch?

[Jill Schlesinger]

Well, I mean, in the same way that you approached the, the idea of, you know, first week was refreshing. Then you felt like you were being lazy. You have to, you really do have to grant yourself some grace. Even if the 4.2 million, I presume some of it hasn't been taxed. Some of it has been taxed, but it's very difficult for me to find a way. I agree with the advisor of, like, you're not going to be able to do what you want to do because you don't spend that much money relative to the assets you have created. So how can we do this? Well, is it possible that we replicate that feeling of being paid? So of the 4.2, how much money is in retirement assets that have not yet been taxed?

[Christine]

Well, my overall 401k is one point. I would say 1.8. Approximately 400 of that is Roth 401. So.

[Jill Schlesinger]

So 1.4.

[Christine]

Yeah.

[Jill Schlesinger]

Okay. Any IRA assets that are out there?

[Christine]

Roth IRA, which is. No.

[Jill Schlesinger]

Okay, that's a. Done. That's. Okay. So here's an idea of something you may be able to do. Okay. You say, and again, you're working with a financial advisor who's managing this for you. Okay. You can say to this person, you know that 1.4 million that I have. Let's try to set something up where I can turn the faucet on and you send me, let's just call it 100 grand a year from that account, okay? For the next 10 years, whatever it is, let's say it's 140 for 10 years, okay? And that way I can manage my tax liability. I know that money has to be taxed. Eventually I'm going to have to start taking it out. I'll start taking it out. Now. You send me the. I mean, I don't know how you feel about this. Some people would like to get this chunk of money just on the second day of January next year, maybe, or maybe you just say send it quarterly. However it feels goes into your account, you leave a little money aside for taxes, but you have the money to spend for that quarter you're paying yourself. This is a little workaround. This is instead of feeling lazy, this is a reminder that, like, actually, I've worked 27 years and I deserve it. It's the same thing. We're coming up with a workaround that will allow you to essentially pay yourself back in all of that money you saved. You now have to turn the faucet on to you. Now, the one thing that you're going to have to have the creative adjustment around is you're going to have to let yourself understand on like some major league visceral level, you are trying to deplete this $1.4 million over the next 10 or 12 years. That's your goal. You want it out of there. You want to pay the tax that's due, you're going to live on it. That's it.

[Christine]

Okay.

[Jill Schlesinger]

Now I'm thinking that the advisor is going to be like, terrific, because I can manage that. We'll set this up. We'll invest it in a way so that we know that every year we need to send you 140,000 divided up in four installments. Perfect. And if you needed more money, you still have other money that's available. So you have brokerage account, et cetera, you can use it. And then in 10 or 12 years or whenever you. Maybe it's age 70, when you decide you're going to collect Social Security, you get your Social Security. Now you're going to be able to do the same thing with these other accounts. I think that in the hierarchy, I would think get money out of the accounts that have not been taxed first, then start tapping into the brokerage accounts, and then you leave the Roth for last.

[Christine]

Okay.

[Jill Schlesinger]

I think if you do that, this retirement with intention theme, I think this is an incredibly powerful way to remind yourself that this is your own pension plan. In other words, let's say that you didn't work in tech. Let's say that you were a teacher and every year you paid into a system and that went into some pot of money called a pension. And then when you retired, someone turned the faucet on you and the municipality and they start sending you money. You're just doing the same thing. It's your own pension plan. You've worked really hard to accumulate this. So if you can be intentional about this, I think it's freeing. I think it is a way for you to really say to yourself, I deserve this. I've worked my ass off for almost three decades. I don't need, like, my project management skills are such that it might actually be a little bit of a liability in this phase. I don't have to do that so much and I can enjoy the fruits of all that labor. And you, you should, you should do it. It should be amazing. And at some point someone's going to reach out to you and they're like, oh, Christine, you're so great. Come and do a project for us. We want to pay you. And you're going to have to think long and hard about whether you want to do that or not.

[Christine]

Yep, yep. Yeah, that is true.

[Jill Schlesinger]

Right?

[Christine]

Yeah. Yeah. Well, frankly, I'm glad you said that because I'm giving myself a year to just enjoy life, like, well, but I feel like I can still give at least 10 more good years working years. So, like, maybe I'll do a part time job, but I only want to do part time. I don't want to. I can't imagine going back to full time ever again in my life.

[Jill Schlesinger]

I have a very good friend of mine, I just was out with him last week and he retired from a pretty intense career on Wall Street. And he said that he took a year off and that sometimes it was painful that he goes, you know, listen, I was floundering a little bit, like, I have nothing to do. I need to figure out how to, you know, what the next thing is. And then after a year, he dusted off his LinkedIn profile, which he said was like, hadn't been updated in 20 years or something since LinkedIn occurred started. And he said, I decided that, you know, I would be open to doing some board work, like I'd be on a board of a nonprofit or for profit. But he was very choosy and I think you have that ability to be choosy you should only do the things that make you feel good. Like, hey, I mean, maybe volunteering, you know, packing lunches for, you know, homeless people is not using my brain. So maybe I would like to use my brain. And then you, someone comes out of the pops out of the world and says, you know, we're doing this project. It's, it's for a nonprofit, but it's a tech project. Might you be interested and maybe that's something you would be interested in.

[Christine]

Yeah, yeah, yeah, yeah, I've thought about that. So. But back to the money side. And this is, I mean, this, this feels like a, a therapy session.

[Jill Schlesinger]

That's right.

[Christine]

What I can't let go of is like, oh my God, what are the stock market drops 50%, which it was starting at that point in April. Like, what's my threshold where I can still be okay with my.

[Jill Schlesinger]

No matter what? I want to tell you something. Here's why you will experience a bear market. You are going to be investing for three more decades. I have good news and bad news. The bad news is there will be a bear market. You will lose 20, you will lose 30. Maybe there will be one of these times where you will lose half of your portfolio, will go through a once in a 50 year period of a financial crisis and maybe that will happen, okay, but you don't have to sell everything. You can stay invested and you will be able to essentially ride it out. The key for you is really going to be, can you manage this, this, can you manage the stress of it without panicking and going back into work? But you're going to be. You're not 100% in stocks, are you? You're.

[Christine]

No, no, I'm 50. 50.

[Jill Schlesinger]

You're not going to have even the worst, like the worst year 2008, it wasn't a 50% loss if we're a balanced investor. And it came back pretty fast, right? So you're going to breathe deep. You're going to remind yourself that you're going to have one of these terrible periods. And this is why you work with somebody also, right? I mean, it is part of the reason that people like to work with advisors so that you can feel like, oh, you know, I do not have to panic when there's something bad going on in the universe. I can talk to somebody who will keep me on track. And that's what you're going to do. You're going to stay on track. It's going to be, I think that this is one of those situations where, you know, all of this, you need someone to reinforce it.

[Christine]

Exactly. Exactly.

[Jill Schlesinger]

And I think you got it. I think it's going to be good. So I'm going to send you off and say to you, I think this is all doable. I know that you are single. Do you have your estate documents done?

[Christine]

Yes. Okay, good.

[Jill Schlesinger]

So there's some very lucky nieces and nephews and take care of your dog.

[Christine]

Well, I told them I'm dying with zero, but since I don't understand the concept, I said, don't worry, you'll get money while ma still alive.

[Jill Schlesinger]

Yeah, I mean, I think. I think that it's funny that you should say that, because I think that it's good to try, if you can, to give the money away during your life to the people who you think could use it while you're living. And it's pretty nice to be able to do that. So I think it's awesome. All right, I'm releasing you. Any other questions for us?

[Christine]

No, this has been wonderful. Thank you so much, Jill.

[Jill Schlesinger]

And a little therapy. I'm sorry, our time is up. You can submit this to Met to your insurance on your own. Okay, gang. If you need a little retirement with intention session, be like Christine. Get in touch with us. Go to jillonmoney.com, click the contact us button. Write us a note. If you'd like to join us on the air live, check the box. Mark does everything else. Don't forget while you're on the website to sign up for the free weekly newsletter which comes out today every Friday. Hey, you can subscribe to us on the Odyssey app or wherever you find your favorite podcast. You should also check out our sister broadcast called Money Watch. That's on Saturdays and Sundays. Okay, it's Friday. Let's do some business. Our music is composed by Joel Goodman. Mark Tularsio is our executive executive producer, king of all things web. And we are distributed by the fine folks at Odyssey. Try to lift someone up. Change your work, Change your wealth, Change your life. Thank you for listening. We'll talk to you on Monday. As a business owner, you're not chasing the norm. You're building momentum. But your bank wasn't made for modern money management. You need Relay, an online money management platform that moves as fast as you do. With Relay, you can open up to 20 accounts so you can separate your cash for things like income, payroll, or operating expenses. All you need is a few minutes to sign [e-mail] Spotify. That's R E L A-Y-F I.com S-P O-T-I-F Y Relay is a financial technology company and is not a bank. Bank services provided by Threadbank member FDIC hey, I'm Ben Stiller. And I'm Adam Scott and we host a podcast called the Severance Podcast, where we used to break down every episode of the TV show Severance. Severance isn't back just yet, but the podcast is. Each week, we'll discuss the movies, TV shows, and ideas that influence the making of Severance. We're going to talk to the incredible artists who inspire us to do what we do. The Severance podcast returns Thursday, June 26th. Follow and listen everywhere you get your podcasts.