The Retirement Guide Podcast

You’ve worked hard, you’ve planned, and now the moment is almost here, or maybe it’s already arrived. Welcome to The Retirement Guide, the podcast that helps you navigate the transition to and through retirement with confidence, clarity, and a whole lot of heart. Whether you’re five years out or five days in, this is your space to get the guidance, stories, and straight talk you need to make the most of this next incredible chapter.Let’s get into it.Hey, I’m Anders Skagerberg. I’m a Certified Financial Planner and an Enrolled Agent, which is a tax planning designation. I spend most of my time helping people plan for and navigate retirement.I also happen to be one of those weird humans who has become incredibly fascinated with the whole concept of a work-optional lifestyle. I don’t know why. Maybe it’s because I got my first job when I was nine or ten, delivering newspapers on a paper route. I’m in my mid-thirties now, so I’ve had a solid two-and-a-half-decade career at this point doing a variety of different things. But it’s had me realize: hey, work is good. I like adding value and I like getting paid money. But I don’t love working all the time. And that got me interested in what a work-optional lifestyle looks like, what it takes to get there, what it looks like when you arrive, and all the stuff that nobody really talks about in between.So with that, I spend a ton of time reading, thinking, advising on, and researching retirement strategies. And I got to a point where I figured, okay, why not just start writing about this? That turned into my newsletter, The Retirement Guide. And now, apparently, it’s also turning into this.I’m recording this as my first video. I’m also going to do this as a podcast, and I figured if I’m putting this content out there anyway, I might as well capture it in as many ways as possible.So welcome. Whether you’re five years out from retirement, five months into it, or just starting to think about what work-optional could look like for you, this is the place to be.I’m going to talk about the financial side. The tax side. I have been affectionately referred to many times as a tax nerd, and I think people mean it in a nice way. But it’s very true. I am one of those unique humans that loves to understand the tax code and different tax planning strategies. Anytime I can save a client any amount of money in taxes, I am all for it.I also want to explore the deeply human side of this transition, because at the end of the day, this move into retirement is one of the biggest transitions people face in their lives. I think through my own life up until this point: you go through school as a kid, you graduate, and that’s like, oh my God, I’m an adult now, I’m in the real world. Then you start a career, maybe you go to college, whatever it is. All those are big transitions. Personally for me, having kids, becoming a dad, some of these things are just huge life moments. And I put the transition to retirement right up there with them.As a financial advisor who works with clients that are retiring all the time, this is a huge, pivotal moment in their lives, and it can be a little nerve-wracking. I really look at myself as somebody who has the skillset to help guide folks through that transition. And my personal mentality is that the financial planning is actually the easy part. It’s the purpose, the values, the human side of the conversation that are a lot more tricky. And the emotions of it all.You Can Absolutely Crush RetirementAlright, let’s get into it. The first topic I want to cover today is just this idea that you can absolutely crush retirement.This transition from your working years to retirement is different for everybody, and it’s harder for some folks than it is for others. But that’s kind of everything in life. If I go and try to pick up a new sport, I may or may not pick it up quickly. And I’ve got friends who are those people that you look at and think, man, you’re the worst, because they’re just really good at everything right off the bat. Some people just pick this up a little easier, and for some people, whether knowingly or not, they had set up the prerequisites for a smoother transition into retirement. I’ll explore some of those prereqs in future conversations.But if you’re listening to this and you’re somewhere in your mid-fifties or early sixties, there’s a good chance you’re starting to feel a little bit of angst about this transition into retirement.For many folks, especially the people I have the pleasure of working with, they’ve done really well. They’ve saved, they’ve been very responsible. They’ve probably spent years, honestly decades, making very smart financial decisions. Delaying gratification. Building a solid foundation. Maybe on paper everything looks good. Maybe really good. I typically work with clients that have two to ten million dollars in investable assets. They’ve done phenomenally well.But as retirement gets a little closer, the confidence hasn’t quite shown up the way they might have thought it would.The Questions That Keep Coming UpInstead, a lot of questions pop up:Am I on track? Am I going to be okay? Is my money going to last?I hear this from clients every single day as they’re approaching retirement. “Anders, does this make sense? Am I in a good position? How am I doing relative to others?”Are they missing something? What don’t I know? What should I look out for? Should I have done more?And regardless of how much money somebody has, there’s always this feeling that they missed out. Like they missed an opportunity. And they should be in a better position.I think a lot of that comes from just our human nature and the fact that we will always compare ourselves to others. You can always find somebody who’s doing maybe just slightly better than you in whatever area of life we’re choosing to compare. I personally believe comparison is the thief of joy. I think there’s a lot of truth in that quote. But regardless, we all do it.This Feeling Crosses All Wealth LevelsWhat’s interesting, and kind of the big takeaway for me as I’ve worked with more and more clients, is that clients across all ends of the wealth spectrum feel this. I have clients with $800,000 approaching retirement saying, “I should have done more.” And I have clients with five to six million dollars saying, “I know I could have done more. I wish I had done more.”It’s important. I think the work I do is giving clients almost like a safe space to be able to say that out loud. For them to literally say, “Wow, I wish I had done more.” So that I can say, knowing every element of their financial situation: of course, anybody could have done more, but you are in a phenomenal financial position. And let me tell you why.That’s typically where I dive into every element of their retirement plan. I like to highlight for them not only that they’re doing well based on general benchmarks, but here are some unique things about your situation that I really like. Here’s what’s different about what you’ve got going on compared to the average person.Because I feel like if nothing else, that gives people some peace of mind to say, okay, yeah, I could have done more, but at the end of the day, I’m working with somebody who knows my situation inside and out. They’re an expert in this area of financial planning. And they think I’m going to be okay.The Leap Into the UnknownMy big takeaway, and what I hope to leave people with, is that everybody feels this sense of anxiety as they’re headed into retirement. You’re not alone in that. That is a very normal feeling as you’re approaching a big and unknown transition.It’s like this leap into the unknown. You’re looking over the edge of a cliff and you can’t see the bottom. You’re hoping everything’s okay down there, but you just don’t know for certain, because you’ve never been down this road before. And obviously, that’s a heavy thing to carry alone.What I typically experience with clients is that once they voice this and we have this conversation and I assure them, and typically this takes a number of meetings, because as you can imagine, it’s good to hear it once, maybe it’s good to hear it twice. But by the third, fourth, and fifth time that I have this conversation with clients, it finally starts to really feel reassuring and starts to click that, hey, I am okay.Stress-Testing the PlanFor clients as we go through this work, they’ll typically, and I like to think of it as them testing me, they’ll come into a meeting and say, “Hey, but what if I do this? Or what if we look at this a different way? What if inflation stays higher? Returns are lower? What if I do need long-term care for both me and my spouse?”And I look at all these numbers with them. Sometimes adjustments need to be made, but oftentimes what we find is, hey, this plan still makes sense and we can solve for tail-risk, black-swan events.I show people what that looks like, but then I also ground it in reality. For example, we’ve got long-term care built in for you and your spouse lasting five years at roughly $120,000 per year. And I also show them that this is a very tail-risk scenario. Odds are, because we plan for long-term care to happen in the last five years of life, ages 90 to 95, you’re not going to make it that far. So if we bump up that long-term care even sooner, that’s fewer years that your portfolio had to sustain you before you got to that long-term care event.And then on average, out of a couple, it’s roughly 50/50 in terms of whether both spouses will end up needing paid long-term care. Typically only one of the two will, and even then, most people don’t need paid long-term care for a period of five years or more. Typically it’s two to three years, which intuitively makes sense. By the time you get to the point where you need paid long-term care, there’s not a lot of life left. Not to be morbid, but that’s what the data shows.Freeing Up Mental BandwidthAll of this to say, and I know that’s diving into the weeds, but these are the pieces that I help people realize. Yeah, there are a lot of unknowns. Nobody knows what the future holds. At the end of the day, retirement planning is making a whole ton of assumptions about what potential outcomes the future might hold. But we just don’t know, and nobody does.But if nothing else, this process of laying out your entire financial life and creating a plan that says, here’s what I know about your situation right now, here are some assumptions we’ve made about the future, and here’s why this does or does not work, that starts to put people’s minds at ease.And then, and this is the most important part, you can redirect that energy towards the most important pieces. Maybe the bigger risks that people face in retirement: developing new relationships, because oftentimes when you leave your career, you’re leaving behind your strongest day-to-day relationships. Maybe you’ve been working so hard leading up to this that your health has suffered, or your involvement in the community. Pick your poison. There are a lot of pieces of your life that may need to be reinvented in this next phase.But the beauty is, once you’ve freed up the mental bandwidth on the financial elements of that retirement transition, you’ve got so much more brain space for the things that truly matter and drive satisfaction and drive purpose in this next phase of life.You’re Not BrokenTo wrap this up: if you are feeling a sense of anxiety as you approach retirement, even if the numbers say you’re fine, you are not broken. This is a very normal part of the retirement experience across all bands of the wealth spectrum. You’re not missing something obvious that everybody else has figured out. You’re just having a human experience.At the end of the day, the fear is typically in the unknown and in the waiting. Anytime you’re approaching a transition, you don’t know exactly how it’s going to play out, and it’s normal to have anxiety about that.The good news? You don’t have to have all the answers before you start. You just need enough clarity to know that next step in the process.And that is my hope with my newsletter, The Retirement Guide, and this podcast, and these videos: just to be there. I work with about 60 clients right now, but with this content, my hope is that I can broaden that out. Not that I’ll take on additional relationships, but I can be that guide for people I’ve never even met by talking through typical pitfalls, typical risks, typical situations I see with my clients. Here’s how we solve it. Here’s how we move past it. Here’s how we take that next step.That’s my whole goal with this. Step by step, help more people who are retiring figure out: I can crush this. I am going to be okay. I can figure out the financial piece and free up that mental bandwidth for the things that are actually important.Not that money isn’t important. But money is a means to an end. It’s not all about the money. And if it is, you probably need to recenter on some more important and more impactful pieces in your life.So that’s my goal with all this. I appreciate you either listening or watching or reading along as we go. And like I said, I’ll put out this information, and if it helps one person navigate that transition to retirement, I’ll consider it a success.Thanks for checking out the info. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theretirementguide.substack.com