The Influential Advisor Podcast

120: Edward Gaskey on Finding Financial Clarity Before You Retire

• Paul G. McManus and Gabe McManus

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Edward Gaskey has spent almost 30 years helping people move from financial uncertainty to financial clarity, and in this episode he explains why that shift matters more than any single investment decision. He walks through the "million-dollar question" retirees rarely ask correctly, why most people plan for a worst case that almost never happens, and how a Social Security mistake nearly cost one client thousands. Ed also talks about his office's "dream boards," the surprising reason clients struggle to spend the money they worked so hard to save, and what he calls giving a client a "verbal hug." Listeners will walk away with a clearer sense of what actually needs to happen, financially and emotionally, before retirement feels real.

About Edward Gaskey

Edward Gaskey is a Private Wealth Advisor, CRPC®, APMA®, with Gaskey & Associates, a private wealth advisory practice of Ameriprise Financial Services based in Greensburg, Pennsylvania. He has nearly 30 years of experience in financial services and has helped guide clients through some of the biggest financial decisions of their lives, including retirement, Social Security timing, and multi-generational wealth planning. Gaskey & Associates was named to the Forbes Best-in-State Wealth Management Teams list in both 2025 and 2026. Ed is the author of Creating Your Next Chapter: How to Gain Financial Clarity, Purpose, Passion, and Vision Before You Retire.

What We Cover

  • Why Ed's math background shapes how he breaks down complex retirement decisions into "one page" of clarity
  • The "million-dollar question" of retirement, and why it isn't about investment returns or Social Security strategy
  • How a client named Robert almost cost himself years of higher Social Security benefits by taking advice from a coworker
  • Why the worst-case scenario clients imagine at 2 a.m. almost never happens, and how Ed helps clients see the realistic middle ground
  • The office "dream boards" Ed uses to help clients turn retirement goals like a Porsche 911 or a family trip to Italy into reality
  • Why inflation and taxes are the two most commonly underestimated factors in retirement projections

Connect with Edward Gaskey

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Clarity Before Retirement

SPEAKER_00

A man approaching retirement had done almost everything right. He was analytical. He believed he had his finances in order. But as retirement got closer, uncertainty started to creep in. Was he really prepared to make one of the biggest decisions of his life? When he sat down with financial advisor Edward Gasky, Ed didn't overwhelm him with more complexity. He did the opposite. He broke the situation into manageable pieces and gave him something the client had been missing. Clarity. That idea sits at the heart of Edward Gasky's new book, Creating Your Next Chapter: How to Gain Financial Clarity, Purpose, Passion, and Vision Before You Retire. Today, on the Influential Advisor Podcast, Edward draws on nearly 30 years in financial services to explore what it really takes to prepare for retirement. He'll explain what he calls the million-dollar question of retirement. But underneath all of it is a larger question. Once the financial uncertainty is replaced with clarity, what do you want your next chapter to look like?

Ed’s Math Mindset

SPEAKER_01

Hi, Ed. Welcome to the program. So glad to get to talk to you today. Good morning, Gabe. Thank you for having me. Ed, the first thing I wanted to ask you is could you walk us through, tell us about your background and how you arrived to where you're at now?

SPEAKER_02

Yeah, I appreciate that. It probably all started with math by education. I have a math degree. And I always enjoyed that process of picking large problems and kind of breaking it down into something that was a little bit more manageable, more bite-sized, even complex issues, kind of came gifted to me as something that I could do very easily and relate to people. You know, I had a client one time that had mentioned to me that she was, she was getting ready to retire. It was a complicated situation for her, something she'd never been through. And she felt that I was able to guide her and navigate her through something that was, you know, new to her, very complicated, and break it down into smaller and manageable pieces that she could digest. I think that math background has allowed me to really be in a position where I could talk with clients and guide them in a better way.

SPEAKER_01

Yeah.

From Phone Calls To Trust

SPEAKER_01

So when you started off in the business, what was it like and how has it shifted over the years to now? What's changed, Ed?

SPEAKER_02

Yeah, it was a lot different back in the day, almost 30 years ago, Gabe. You know, it was something where it was not uncommon to be on the phone for hours at a time. I was building a business. I didn't have a client. And it was very common, you know, 500,000 calls a week, hearing no, you know, a lot of clients. It wasn't cold calling, but we were calling on leads. And so it was just a lot different. There was a lot of reps, a lot of repetitions of talking to people. And I wouldn't change that for the world, to be honest with you. I mean, that really instilled the skills that I needed to be successful later in this career. Just the people skills, being able to talk to people and navigate them was very, very beneficial for me early on in my career. A thousand calls a week.

SPEAKER_01

That sounds insane to have to get through that many.

SPEAKER_02

Yeah, phone clinics each night. I worked half a day on Saturday. They were leads, if you will. So we were allowed to call them. But it was was not uncommon to be on the phone, you know, 100, 150 calls a day, easy because we had no clients, right? We were trying to build a business. That repetition was very, very helpful.

SPEAKER_01

Yeah. But things have shifted to now, haven't they? And so what's it like now, the way that you help people in your practice?

SPEAKER_02

Yeah, a lot has changed over the years and been blessed to be very successful with build a practice that have been able to help a lot of clients, you know, really live in their God-given purpose and help them to figure out. Cold calling is a thing of the past. You know, we want to build trust with our clients, build relationships with our clients. And over the years, as you build a client base, it goes a little bit more towards those trust relationships that really develop over years and years of working with a client and helping them through the good and the bad complicated times that they have in life.

Purpose Beyond The Numbers

SPEAKER_01

Yeah. Ed, what does it mean to you to help people to find and be able to live that God-given purpose?

SPEAKER_02

Yeah, but I think that's why I exist. I mean, that's what I'm here to do. You know, obviously my skill set is around financial advice, but I really think that taking that a level deeper is that I'm here to help people find clarity and purpose. You do that by helping them to navigate their financial, oftentimes taking stress from them and being able to think clear about what that next step might be for them, what that next chapter is. And so I really find a lot of satisfaction at this point in my career.

SPEAKER_01

Yeah,

Writing Creating Your Next Chapter

SPEAKER_01

that's great. And so recently, now Ed, you've written a book to be able to help people understand these ideas and the direction that they should head. Can you tell me about the book and who you wrote it for, who it's meant to help?

SPEAKER_02

Yeah, it's for people who are, you know, navigating different stages in life, but primarily getting ready to retire, helping them to find some clarity and purpose, um, and maybe even a little bit of passion prior to them making that decision of retirement. I think it's it's there to help people really understand what is required for them to get to a position where they can make a life decision like retirement and really to put clarity around the financial aspects of it so that they can then pursue whatever their God-given purpose is in life. And I don't think that it's possible to really thoroughly do that until you have that clarity around your financial situation.

SPEAKER_01

Well, because you talk about in the book that sometimes people they're lying awake at night and convinced that they're maybe never going to be able to retire. And then they sit down with you and something shifts. And so can you tell me a story maybe from your practice that is an example of that, Ed?

Turning Anxiety Into One-Page Clarity

SPEAKER_02

I mean, there's many stories. Uh, you know, uh, one that comes to mind is a gentleman that was getting ready to retire. He's let's just call it an engineer type, so very analytical, came to me and he thought he had all of his ducks in a row, but there was something missing, right? And and and we're humans, we tend to think extremes, right? We think the worst case scenario, he's coming to me thinking the absolute worst case scenario that he's missed something, he's not ready to retire. And so those extremes that in our mind that we play coming into that, we all do it. And we lay awake at night thinking, oh, can I do this? Can I make that decision? Can I buy that house? Can I afford to do this? So we played the worst case scenario. So what I found is that the worst case scenario rarely happens, the best case scenario rarely happens. The reality generally lies somewhere in between. And that's what I help clients to define and put some parameters around kind of where they stand.

SPEAKER_01

So, what happened in his case? Did he reach the point where he felt clear and he felt that he could move forward confidently? Yeah, in his case, he was overthinking it, to be honest with you.

SPEAKER_02

His analytical tendencies got in the way. He was overthinking it. And when we sat down and walked through the process that we follow, I was able to break it down into something that was manageable. And in fact, I think he said I simplified his life on one page, and that's a good thing. But he was able then to real see the clarity that I was speaking of and realize that he did have all his ducks in a row. He just needed somebody to kind of, you know, lead him and say, everything's gonna be okay. I've been here before. We've done this with other clients, and you're no different. Just follow me and we'll walk you through the steps. I educated him on what his options were and just gave him a peace of mind and the clarity that he needed to kind of move forward.

SPEAKER_01

I think we'd all appreciate having our life simplified down onto one page. It seems like it made things a lot easier. Yeah, absolutely.

The Million-Dollar Monthly Spending Plan

SPEAKER_01

Ed, you talk about something that you call the million-dollar question, and you say it's not about investment returns or social security strategy. Can you tell me what it is and why does getting it wrong change everything else?

SPEAKER_02

Yeah. The million-dollar question is that I referred to it, is what are you going to spend on a monthly basis when you get to that retirement? In our world, we break it down into a couple of two types of expenses. It's either your core expenses or your lifestyle expenses. And so I think people can discern between the two. Core expenses are the costs that you incur every day, every month, I should say, to be able to live your life, run your ship, if you will, whatever that looks like. It could be, you know, mortgage payment, it could be so housing, utilities, those types of things, car expenses. And then there's the fun stuff. There's the lifestyle things, right? It's the trips and the travel and the bucket list types of things that the people really want to spend money on and enjoy it. And so what I've found is that when clients come to me and they get to that point where maybe they're 60 years old, they generally don't change too much who they are, right? They're kind of set in their ways. Their expenses are the same. Yeah, you're gonna have some different things that pop up from time to time, but generally they're kind of set in their way. They don't change who they are too much. They now have time so they can enjoy some of the lifestyle things. But that's just been my finding. And, you know, I'm a big believer, and it's probably contradictory. A lot of advisors may think, but why did we save it, right? If you're not gonna enjoy it, why did you work all your life to save to build up this nest egg and then and then not enjoy it? So we're a big proponent of helping clients wisely be a good steward of those resources and spend their money. You know, in our office, we have what we refer to as our dream boards. And now on those dream boards, on the very top of it, is a goal without a plan is just a dream. And so that's a phrase that I have said for years. And so I truly believe that there is something about writing down your goals, putting it to print. The connection between your brain and your hand, when you write that down, you commit to that goal and your brain immediately starts to solve for it. So we have these dream boards. They're fun, they're meant to be visual, but they're also fun. We've got trips to different places, Italy, you know, beaches, you know, things that clients want to accomplish. One client had a goal of a Porsche 9-11, happy to say he accomplished that. We've had these in our office for about five, six years now. And what's really been fun is to see those goals being checked off, right? Clients who come in and say, Oh, yeah, I did that two, three years ago already. They're still adding to the boards, but they're checking things off. So it's been kind of a cool visual in our office that those goals can definitely be accomplished if you write them down and if you focus on them. Yeah, I think that's amazing.

SPEAKER_01

And also interesting what you said, Ed, that people don't change much from when they hit 60. So if they've been in that accumulation phase and they're just saving, saving, saving, it must be difficult to turn that around and go out and do fun things and spend on experiences. But with your help and guidance, if they feel that there's permission to do it, do you think that leads to them living a better life in retirement where they actually get to have some fun and use that hard-earned money in interesting and incredible ways? Absolutely, 100%.

SPEAKER_02

You know, I think it's difficult for some to really make that shift. Yeah. Right. Because in their mind, they're afraid they're gonna run out of money. Again, going back to what I said a few minutes ago, is we play the extreme. We we simply imagine the worst case scenario that, oh, I'm gonna retire and I'm gonna just run out of money, even though they may have a seven-figure portfolio. So we imagine the worst case scenario, and really the process of what I do is to show them, and under different assumptions and scenarios, that look, you're gonna be okay. In fact, you're gonna be better than okay. And if you want to take these trips and create these experiences with your kids, your grandkids, or whomever that might be, yeah, you have my permission to do so because we've looked at the numbers together and been able to prove to you that, hey, you can do these things. It sometimes is a tough journey to get clients to think that way. But uh, through our process, I think we can make it happen for them.

SPEAKER_01

Yeah,

Social Security Traps And Timing

SPEAKER_01

that's good. Yeah, tell me about a client named Robert who was about to make a social security decision that was going to cost him significantly and he didn't even know it. So can you tell me what happened to that story?

SPEAKER_02

Yeah, I think we can all relate to a story like this. You know, unfortunately, we get a lot of advice from not great sources, right? It's the uncle at a reunion that says, hey, you should retire and take your social security now or at the office, maybe at lunch. You know, everybody's an expert, right? But but rarely are those situations unique to yours. And so Robert was that, you know, that exact example that I just laid out. I someone, a colleague of his had told him to take Social Security. And when we sat down, I said, Let me educate you a little bit on Social Security. And, you know, what he was not aware of was the fact that he was 62 and based off his birth year, his full retirement age was 67. So he was five years under his normal retirement age, and he wasn't aware that there was a reduction, a permanent reduction in benefits that would occur if he chose to take it. He also was not planning to stop working. So he also didn't understand that there was an earnings limit. So he would get a reduction in benefit because his wages were higher than a certain amount. And so all I simply did, Gabe, was just educate him on what the rules were about social security. And ultimately, he delayed taking his social security till, I believe it was around 65 or 66, which was a much better situation for him. But had he not been aware of the rules, he would have taken that advice from that co-worker, which would have been an and, you know, not a great scenario for him.

SPEAKER_01

Yeah. I think that's so relatable because as you said it, I'm thinking about the different people that have told me when to take Social Security, and they're not experts. And so I think talking to somebody who really helps you think uniquely through your situation and when it makes the most sense for you is probably the better, the better way to go on that. Yeah, I would

Inflation And Taxes In Retirement

SPEAKER_01

agree. I wanted to ask you, Ed, about inflation because that's been something that's been on most of our minds the past few years. And you describe it as a silent thief and also taxes as something that can ambush people when they are least expecting it. And so can you give me an example of what that actually looks like for somebody who maybe thought they were doing fine, but then it comes up?

SPEAKER_02

Yeah, I I think that the two biggest mistakes that people make as they they prepare for their retirement is that they fail to factor in inflation and taxes into their projections. You know, it's pretty simple to do a budget and look at what you're spending now, you know, versus what you might be spending. But in the future, people have a hard time understanding what that is. Even a simple 3% inflation over the period of five, 10, 15, 20 years can have big, big implications. And I think inflation is something that we incorporate in all of our situations. We've seen recent years, you know, a high inflation higher than we've seen in quite some time. And it just erodes the purchasing power of that dollar. I'm not gonna sit here and you know predict what inflation is gonna be in the future, but we do run scenarios where we factor in inflation into all of our retirement projections so that people realize that, hey, things are gonna cost more in the future than they do now. And they have to factor that if they're gonna live the same lifestyle. The other thing is taxes. Look, it's out of our control, but we need to look at taking averages, effective tax rates, and just put that into our retirement projections so that people are not surprised by that. They can budget, they can understand their budget, but you also have to factor in taxes and inflation into those projections to make sure that you remain on track for that retirement goal.

SPEAKER_01

So, what are they missing in on taxes? Because you're looking at your 401k and thinking, all right, I think I'm good. I've got enough money for retirement, but they're not factoring in how much of that is not actually theirs to use.

SPEAKER_02

Yeah, unfortunately, a lot of people over the years have been conditioned to put all of their monies into their 401k plans, right? All of their retirement savings. And then they forget that in most cases, those monies are taxable when you take that out. And so, you know, they're looking at net numbers in their pocket, right? You need $5,000 a month to live or whatever it is. We look at gross numbers because we factor in taxes off of that. You know, everybody's a little different depending on how they live their lifestyle. And this is what gets it complicated because it, you know, boils down to what are you going to spend on a monthly basis, whatever that lifestyle is. How much do we need to pull out, factor in taxes, factor in inflation so that you're in a position that you can live comfortably throughout your retirement years?

Market Volatility And The Verbal Hug

SPEAKER_02

Right.

SPEAKER_01

In the book, Ed, you write about a client who called you and they were nervous about retiring. The market was down and fear was starting to sit in, which I think is understandable when we're looking at volatility. And by the end of the call, his wife said that you gave him a verbal hug. What did you actually do in that conversation to make him feel better?

SPEAKER_02

Yeah, I never thought of it that way when she said that, but that's what I do, right? I do a lot of that. I mean, I give a lot of verbal hugs.

SPEAKER_01

Probably sometimes when we do choppiness in the market.

SPEAKER_02

Yeah, yeah. I mean, we do that in his particular situation. We had been planning for years with this retirement and definitely on track. Called me one morning, a little bit of a panic, and said that, you know, hey, I'm gonna postpone retirement. And as we talked through, there were concerns about the market, there were concerns about some health things that he had going on that he wanted to get taken care of. And and so I knew without a doubt that he was okay whenever he retired. In fact, years earlier, he was able to retire. He just needed to hear my voice to say, you're gonna be okay. And so she steps into the conversation and simply said it, he just needed to have that verbal hug from you. And I find that, you know, over the 30 years I've been doing this, almost 30 years, clients built trust with us and they just want to have someone else that they can kind of reconfirm that their decisions are the right decisions. You know, in that particular case, that's all he needed to hear. He just needed to hear my voice to say you're gonna be okay. So we phrased that as a verbal hug. So we give a lot of those.

SPEAKER_01

That's great. And Ed, when there's volatility, when things are going down or there's trouble in the news, what keeps you steady? What keeps you focused on the bigger picture in those instances?

SPEAKER_02

Yeah, so because we have a plan, right? We have a game plan for these clients. I often remind clients that I can't predict the future, but we do factor in a lot of those considerations. We do factor in market downturns. So we've planned for all of this. In some cases, the clients just need to understand that through long-term investing, that there's going to be ups and downs, market volatilities. But if you plan for that in advance, we're not changing your retirement date just because the market is down. We've already planned for it. Just being a constant, steady rock, if you will, for clients to say, you know, when I get nervous, when I get excited or uncertain, because all of this media is in our ears. We're seeing it on the news. Nowadays, it's it's instantaneous. There's a question mark that pops into their mind. And, you know, oh, is that going to force me to work longer? And I take them back to our planning and just show them that, hey, you you still are on track to be able to retire. Yeah, that's great.

Legacy Across Generations

SPEAKER_01

Ed, you have clients whose families you've been serving across generations. This is the kids, the grandkids. Sometimes it's three generations deep. Can you tell me about a time where the length of that relationship made it possible to do something for a family that wouldn't have been possible in any other way?

SPEAKER_02

Yeah, Dave. Um, when the the older generations have done the work and they're financially secure, things change a little bit, right? It can have some really big impact on the other generations. Oftentimes I see that with trips and travel, where I have grandparents who have been traveling all their lives and want to share those experiences, not just with the kids, but also with the grandkids. I've had several situations where I've had clients been financially secure enough to be able to take the entire family on a cruise somewhere and you know, be able to share that experience with multiple generations. Um, a lot of those vacations trips are what we see. The one thing that I think is really important is that the older generation have the ability to share their experiences with the younger generations. And oftentimes I challenge my clients that, you know, pass on some words of wisdom to them because, you know, they've got to this point by doing something right, if they're able to financially take the entire family on a cruise. I think it's invaluable for that information to be shared with the younger generation. And I often tell my my older clients, look, it's the legacy is not what you leave them, it's what you leave in them, right? So those pieces of advice, the words of wisdom to share with them, maybe not the numbers, but at least what they did or did not do to get them to that point and being able to take this entire family. Those kids, grandkids, they're gonna remember that trip, right? They're not gonna remember the exact dollar amount at some point they may inherit. They're gonna remember those experiences in life. And I think it's a great lesson along the way.

How To Get The Book

SPEAKER_02

Right.

SPEAKER_01

Ed, for listeners that would like to get in touch with you or your team or get a copy of your book, how should they do that?

SPEAKER_02

Yeah, you can go to edgasky.com. That's E D G A S K E Y dot com, edgasky.com, and get a free copy of the book. Fantastic. Ed, I've enjoyed speaking with you.

SPEAKER_01

Thank you so much. It's been great, Dave. Thank you.