In this episode, we explore the emotional and structural challenges that come with transitioning from a lifetime of saving to actually spending in retirement. We focus especially on healthcare professionals—nurses, physicians, and leaders—who have spent their careers making cautious, life-impacting decisions and who now face a very different kind of responsibility: using the money they’ve carefully built.
We start by recognizing how identity plays a major role. Many in healthcare see themselves as protectors and planners. Saving becomes a symbol of safety, and shifting to spending can feel like breaking an internal rule. With the end of scheduled shifts and steady paychecks, many experience a sense of floating—losing the rhythm they’ve followed for decades. We clarify that this unease is normal, not a sign of poor planning, but a psychological adjustment.
We emphasize that the solution lies in structure. By creating an income plan that mimics the regularity of a paycheck, we restore the stability many retirees need. We walk through how to assemble an “income playbook”—a way to integrate pensions, IRAs, 403(b)s, HSAs, and savings into a cohesive plan. Each account gets a role, whether it’s for essentials or discretionary goals, and cash buffers protect against market swings. Automation is key here—turning on scheduled withdrawals and tax withholding brings back the rhythm retirees are used to.
We also break down the concept of retirement into phases: go-go, slow-go, and no-go years. Spending shifts naturally, so we help clients build flexibility into their plans. Travel and hobbies may define the early years, while later stages often involve more home time or increased healthcare costs. By projecting different scenarios and using guardrails, we help people make confident adjustments as life evolves.
Throughout, we stress that it’s okay to spend what you’ve saved. Retirement isn’t about hoarding your wealth—it’s about enjoying the life you worked hard to build. We suggest starting with a snapshot of your financial picture, visualizing what your days might look like, and even running a test month on future income to see how it feels. Ultimately, retirement is about shifting into a new, well-supported identity—one that still reflects who you are but in a new chapter of life.
ThimbleberryU 151 - The Shift From Saver to Spender - Transitioning to Retirement
Speakers: Jon Gay & Amy Walls
Jon Jag (00:08):
Welcome back to ThimbleberryU, I'm Jon Jag Gay, joined as always by Amy Walls from Thimbleberry Financial. Hello, Amy.
Amy Walls (00:13):
Hi, Jag.
Jon Jag (00:15):
Today, we're talking about something that surprises a lot of people in healthcare as they get closer to retirement. It's not the timing, it's not the math. It's that mental shift from being a lifelong saver to actually becoming a spender. And what it takes to feel confident using the money you've worked so hard to build.
If you've spent years following order sets and caring for others, that transition can feel pretty unfamiliar. Amy's here to help us unpack what's behind that feeling and how an income plan can bring structure back into the picture.
Amy Walls (00:44):
Yeah, Jag, I am so excited about today's topic. Many people in healthcare are used to being the steady one. You can serve resources, anticipate needs, and protect people, and that mindset we found with clients really becomes part of your identity. So, shifting to spending feels like breaking a rule, a really important rule you've lived by your whole adult life.
Jon Jag (01:13):
I can see that, yeah.
Amy Walls (01:15):
Yeah. Retirement also removes familiar rhythm. And if we think about the day-to-day of someone in healthcare, it's obviously got different patients and such, but there's rhythm to that. All of a sudden, that's broken too.
And so, when the shifts stop and the paycheck stop, it can create a sense of, if you will, floating without a framework. And for those healthcare professionals who thrive on structure, that's especially unsettling.
Jon Jag (01:45):
Yeah.
Amy Walls (01:46):
So, adding a clear income plan brings that structure back, it’s recreating a paycheck and understanding where that's coming from, how it will be replenished. And when you do that, spending starts to feel responsible rather than risky.
Jon Jag (02:06):
Comes down to having a plan.
Amy Walls (02:08):
It does, and it's finding a way to transition into retirement without changing who you are, because who you are is great. You don't need to change that; you just need a new system that works for you in this phase of life. So, it's giving this next chapter the same thoughtful planning that you used and brought you through your career.
Jon Jag (02:32):
I mean, this is something that all retirees have to deal with, that shift from earning money to spending the money that you've earned. But I know this really resonates with the healthcare professionals you work with.
You work with a lot of nurses, physicians, and even hospital leaders who struggle with this transition, even though they're financially ready for it. What makes this shift so emotionally difficult in the healthcare realm?
Amy Walls (02:53):
Well, emotionally is the right word. Healthcare work reinforces responsibility. You make decisions that matter, and you learn early that caution protects people.
Jon Jag (03:05):
Sure.
Amy Walls (03:06):
And it is natural, absolutely natural, for that to spill into money habits. So, saving becomes a symbol of safety. Watching accounts grow feels reassuring, and watching them go down, even in a planned way, can trigger a bit of anxiety (chuckles).
Jon Jag (03:25):
Sure.
Amy Walls (03:26):
So many clients tell me they expected retirement to feel like relief, but instead, when they get there and actually have made the jump, they've felt uneasy because the structure disappeared overnight. Now, we're plugging in a new structure and understanding that helps that. But there is still often a sense of unease. And so, this is normal.
That's what I want our listeners right now to hear, is experiencing these emotional ups and downs is normal, especially for people who've spent their careers serving others. So, really, the point here is the shift becomes easier when we name what's happening.
You're not just changing how money moves, you're adjusting to a new identity, one where you're still you, but that new phase of life creates this change. And once we understand that, once you understand that, we can really build a spending plan that feels aligned with the same discipline and care that was brought throughout your working years.
Jon Jag (04:34):
That makes a lot of sense. I know a lot of our listeners are in the healthcare field and they understand order sets better than retirement planning. How do you translate that clinical structure into your area of expertise, the financial one?
Amy Walls (04:46):
Yeah. Well, most people enter retirement with a collection of accounts, a 403(b), a 457 plan, pensions, IRAs, HSAs, personal savings. On their own, these are all individual pieces. An income playbook, if you will, brings those pieces together. It defines what each account is responsible for, how everything works together to create stable income.
Jag, in the past, I think I've shared with you that how I envision planning is like a puzzle, and our client's vision of what they want the rest of their life to look like is that picture that belongs on that puzzle. But all these pieces we've just talked about plus more, tax situation today, tax situation tomorrow, your home or homes, all these other pieces – those are the puzzle pieces. And so, we have to fit them together to make that picture as beautiful as it can be.
Jon Jag (05:41):
Makes sense.
Amy Walls (05:42):
In this, with those puzzle pieces, we have to lay out which accounts fund predictable paychecks and which ones support goals like travel, home projects, or hobbies. And then really, we're creating a step-by-step flow for where withdrawals are going to come from, when they happen, and how that cash buffer, your cash reserves really is getting replenished to recreate that paycheck.
And so, for many of our healthcare clients, once we've mapped that out, that feels familiar, it mirrors clinical protocols. You have clarity, you have order, a plan that you can trust.
Jon Jag (06:16):
Everything you're saying makes sense, Amy. You've got this goal of retirement at the end of the road, go go. And you get there and it's like, now what? And you kind of need that plan. So, that paycheck has been the backbone of life for decades.
How do you help somebody rebuild that feeling of stability once that weekly or monthly or biweekly paycheck is gone?
Amy Walls (06:34):
One of the first steps is identifying true essentials: housing, groceries, medical expenses, transportation, the parts of life that you consider non-negotiable, and for different people that's different.
Then we map out stable income sources. That could be a pension, it could be social security or a portion of a portfolio earmarked for steady monthly withdrawals.
First, we're going to focus on protecting the essentials because when we know the basics are covered, when you know the basics in your life are covered, no matter what the market is doing, it really becomes easier to enjoy the rest of your life.
Jon Jag (07:11):
Yeah.
Amy Walls (07:12):
Would you agree?
Jon Jag (07:12):
Absolutely.
Amy Walls (07:14):
So, from there, we add layers for travel and hobbies and spontaneous joy, if you will.
Jon Jag (07:21):
I like that, spontaneous joy.
Amy Walls (07:23):
(Chuckles) These layers can flex over time, which keeps the plan more realistic. So, for example, if the market goes down, we don't want our clients saying, “Oh gosh, let's tighten our belts on everything because I don't want to pull a lot of my accounts right now.”
And we can remind that we have the steady income to cover all of these things. But maybe if you're feeling uncertain about the market being down and not wanting to pull out extra, this is a year for lighter travel, or if you're planning your travel a year and ahead, maybe the next year is the lighter travel year, depending on how you look at it.
So, research shows that people spend more confidently when their income feels like a paycheck. And so, that's why we focus so much on recreating a paycheck in retirement because our goal is to make retirement income feel familiar, predictable, and really dependable.
Jon Jag (08:18):
You want it to be concrete, not this abstract out of the universe, right?
Amy Walls (08:22):
Yes, absolutely.
Jon Jag (08:24):
So, when it comes to retirement, we've talked about this in previous episodes, they refer to it sometimes in three phases: the go-go, the slow go, and the no-go years. How do you help healthcare professionals, Amy, plan for the reality that your spending is going to change over the course of the retirement?
Amy Walls (08:40):
Retirement has seasons, and I think if we think about it that way, rather than a single long chapter, it becomes easier. Early on, you may want to travel more, you may want more movement and more experience just because you've got the energy and zest for life that you may not have later on.
And then as life settles, spending naturally shifts. People often spend more time at home or with family and less on big trips. There's a point at which (and it's different for each person) – but I have heard from our clients who have gone through this phase, almost to a T: at a certain point, travel's no longer fun. Sitting in a plane is uncomfortable. Doesn't matter what kind of ticket I get.
Jon Jag (09:29):
(Chuckles) I think that's true for everybody these days. But your point is well-taken.
Amy Walls (09:33):
Yeah. And it's really interesting, there's this phase where I like these things, and then no, I don't like to deal with airports. I don't want to deal with this.
Jon Jag (09:48):
With people.
Amy Walls (09:49):
Yeah, exactly. So, then sometime around that time or after, healthcare costs may rise while these other expenses decrease.
Jon Jag (10:00):
Sure.
Amy Walls (10:00):
So, that new season allows us to kind of shift what we expect in terms of costs. Obviously, projections are not reality, but we can use people's preferences, your preferences, as well as data that exists around how these things change to make informed decisions of what that might look like for you.
So, basically, the plan flexes with you. It's not one rigid number. And then we can use some guardrails to say, “Oh, this combination along with market performance means maybe your chance of success has dropped just a little bit lower than what you're comfortable with. Maybe we need to tighten just a little bit as we move along to make those decisions.”
But I do love the go-go, slow go, and no-go- because it is something we can all visualize without needing to get really specific and pinpoint something that for a lot of people is hard to pinpoint until you're actually there.
Jon Jag (11:10):
This is why you and I are in good balance, Amy (chuckles), and actually why my wife and I are in good balance too. I do things on gut and feel; you're here talking about data and having those numbers to create and backup a plan is so important. Especially when we're talking about going from something as rigid as a paycheck to something as nebulous as retirement.
Amy Walls (11:29):
Absolutely. And you're right. Couples often think about things differently. So, we have to make sure we're creating a plan that works for both people.
Jon Jag (11:40):
So, from data to systems, we've talked about kind of having some not rigidity (I mean, that's too strong of a word), but some structure to this. A lot of people feel nervous when they have to manually pull money from those accounts. How does automating that process change the experience?
Amy Walls (11:56):
Automation brings back the rhythm that you're used to with paychecks. Your income shows up on a schedule, your withholding is happening behind the scenes. Now, that can't happen with all account types, but with IRA withdrawals, 403(b) withdrawals, all of that, you can make that happen.
You can also have a cash buffer that protects you from market swings. I alluded to that earlier. So, when markets are volatile, you're not forced to sell investments just to cover expenses. So, let me paint that in a different way.
If we have two years’ worth of cash sitting in cash reserves, maybe we consider that more like a money market, so somebody doesn't think this is sitting in a checking account, not earning anything,
Jon Jag (12:43):
Right.
Amy Walls (12:43):
Two years of expenses sitting there, and we have monthly withdrawals coming out of an IRA with tax withholding to cover cashflow needs and the market drops, and let's say the market drops over 20%. Probably wouldn't want to do this if it only drops 5%, but it drops over 20%.
We might say, “Hey, remember how we have this backup plan that the money you're taking from IRAs aren't part of required minimum distributions, or you've already met that. Let's turn those off until we get some market recovery and let you use some of the cash you have on hand because it's there for this exact purpose.”
So, if you were taking $5,000 net per month out of your IRA, well, just pull that out of your cash accounts at this point.
Jon Jag (13:43):
Got it. Okay.
Amy Walls (13:45):
And even that, you can turn on, so it's coming out of your money market account into your checking account on a monthly basis. So, again, automation.
What I've found Jag is that when clients see money land in their checking account the same way it always has, that tension goes down, shoulders relax because it feels like what they know. It’s a paycheck is landing rather than I'm taking a withdrawal.
Jon Jag (14:15):
Okay, that makes sense. If someone's listening today on their commute, on their break, like me walking the dog, what should they start doing today to make this transition smoother as they approach retirement, Amy?
Amy Walls (14:26):
Jag, are you saying you listen to our podcast while you're walking your dog?
Jon Jag (14:30):
Yes, I do listen to many podcasts while I'm walking the dog. I listen to our podcast when I edit it.
[Laughter]
Amy Walls (14:38):
Fair enough. So, what should they start doing today to make this transition smoother? First step, begin with a simple snapshot. Pull together pension details, retirement account savings, and a rough idea of spending. This doesn't need to be perfect. It's a simple snapshot.
Start picturing, visualizing your future routines. What's intriguing to you during this phase of life? What's not intriguing? I plan to ski a lot in the winter, I'm looking forward to that. The boogie boarding with grandkids and trips. These are all things in my visual picture, but you have your own.
So, think about what will give you purpose and rhythm when your shifts are no longer structuring your days.
Jon Jag (15:29):
Got it.
Amy Walls (15:29):
And then this is where you may need a professional. Run projections with someone who can stress test your plan.
Jon Jag (15:36):
Yes.
Amy Walls (15:38):
You want to see a range of outcomes because that helps you make decisions with confidence. Try a trial paycheck. For some people, this is helpful. Live for a month or two on your future retirement income based on that and direct the rest into savings. How does that feel? You can learn a lot about what feels realistic and what doesn't.
Jon Jag (15:58):
That's a really good point because you talk about planning and all this, but the best laid plans may not work in reality when you stress test them.
Amy Walls (16:07):
Absolutely. So, if it needs some tweaks, test it. And lastly, I'm going to say, remember that you built this nest egg for a reason, and I can almost guarantee, which is very rare in this industry, that the goal is not to hold onto the money for forever. The goal is to enjoy the life you worked so hard to create. And so, by keeping that front and center, it can really help.
Jon Jag (16:36):
Our regular listeners will know this is not a case we are going to say, “It depends.” Most people don't want to take it all with them to the grave.
Amy Walls (16:42):
Absolutely.
Jon Jag (16:44):
Alright. As we wrap up, Amy, what are some key takeaways from today?
Amy Walls (16:47):
First, that transition, this transition we're talking about from saver to spender is emotional, not just financial. And so, embrace it, it is what it is. And the sooner I find that people embrace that fact, the easier it is to overcome.
Structure brings confidence, and having an income playbook, recreating a paycheck, whatever we want to call it, recreates the rhythm that you're used to and protects the essentials. And that can create a lot of confidence.
Third, I'm going to say flexibility matters. Spending will shift as life shifts, and your plan needs to be able to adjust with you into whatever phase of life you find yourself in expected or unexpected.
And fourth, and I think perhaps most importantly, you deserve to use what you built. Retirement is a time to let your money support you in the same way that you've given to others throughout your career.
Jon Jag (17:53):
And for our medical professionals especially who have given so much over so many years, you've worked hard to enjoy your retirement, so enjoy it.
Amy Walls (18:01):
Absolutely.
Jon Jag (18:02):
Amy, if anybody listening or watching this podcast (because we’re now on video as well) wants to contact you and your team at Thimbleberry Financial, what are the best ways to reach you?
Amy Walls (18:10):
They can give us a call at (503)-610-6510, or find us online at thimbleberryfinancial.com
Jon Jag (18:20):
Great stuff, Amy, we'll talk again in a couple of weeks.
Amy Walls (18:22):
Sounds great, Jag.
Voiceover (18:24):
Securities offered through registry representatives of Cambridge Investment Research, Inc, a broker, dealer, member of FINRA/SIPC, advisory services through Cambridge Investment Research Advisors, Inc, a registered investment advisor. Cambridge and Thimbleberry Financial are not affiliated.
Discussions in this show should not be construed as specific recommendations or investment advice. Always consult with your investment professional before making important investment decisions.
Securities offered through registered representatives of Cambridge Investment Research, Inc, a broker dealer, member FINRA/SIPC, advisory services through Cambridge Investment Research Advisors, Inc, a registered investment advisor. Cambridge and Thimbleberry Financial are not affiliated.