We are going to start the  year off with a podcast series called “The Retirement Challenge”.  The idea is that each podcast I am going to bring you one thing to work on so that by the end of the series you will know if you are ready to retire and if the numbers will work.

Most retirement planning starts with a number.

“How much do I need?”
“When can I retire?”
“Am I going to run out of money?”

Those are important questions — and we’ll get to all of them in this retirement challenge.

But today, I want to start somewhere else.

Because here’s what I’ve seen after years of working with retirees:

Retirement isn’t just a financial transition, it’s a life transition.

That’s why the first step in the 2026 Retirement Challenge isn’t about Social Security, taxes, or investments.

It’s about your why.

Why are you retiring?
What are you retiring to?
And what kind of life do you actually want to design?

I

Articles, Links & Resources:

Designing A Great Year – Ebook by Jason Parker
Skylight Family Calendar and Photos

Transcript:

466 The 2026 Retirement Challenge: Start With Why

Announder: Welcome back America to Sound Retirement Radio, where we bring you concepts, ideas, and strategies designed to help you achieve clarity, confidence, and freedom as you prepare for and transition through retirement. And now here is your host, Jason Parker,

Jason Parker: America. Welcome back to another round of Sound Retirement Radio.

So glad to have you tuning in. To episode number 466. The title is the 2026 Retirement Challenge. Start with why. I have to tell you, I love the first part of the year. I like getting together with friends and setting goals and setting direction and. And thinking about the destination, you know, where do I wanna end up, not just at the end of this year, but the end of my life.

And, um, it’s just, it’s an exciting time. And so I’m, I’m really excited to share this podcast with you. But before we get started, let’s start by renewing our mind. And this first comes to us from Proverbs 29 18, where there is no vision, the people perish. And then something fun for the grandkids. Why did the man stand on one leg at midnight on New Year’s?

He wanted to start the year on the right foot. I heard there’s a great restaurant on the moon. It has great food, but no atmosphere.

We’re gonna start the year with a podcast series called The Retirement Challenge. The idea is that each podcast, I’m gonna bring you one thing to work on so that by the end of the series, you’ll know if you’re ready to retire and if the numbers will work. Most retirement planning starts with a number.

How much money do I need? When can I retire? Am I gonna run out of money in retirement? Those are important questions, and we’ll get to all of them in the retirement challenge, but today I wanna start somewhere else because here’s what I’ve seen after years of working with retirees. Retirement isn’t just a financial transition.

It’s a life transition, and that’s why the first step in the 2026 retirement challenge, isn’t it, about social security or taxes or investments. It’s about your why. Why are you retiring? What are you retiring to? What kind of life do you actually want to design? Most people think of retirement as a finish line.

You’ve worked hard, you saved, you endured the commutes and the stress and the deadlines, the responsibility. You put the kids through college and you help them to become independent. And retirement feels like a reward, a time to rest, a time to explore. But retirement isn’t a finish line. It’s a redesign.

And redesigning your life without clarity is a dangerous thing. Just stopping work with no plan can leave you feeling disoriented. One woman described it this way, she said, I feel adrift, because if you don’t design retirement intentionally, it gets designed by default. I was talking to a woman recently and I asked her how she’s planning for the year ahead.

She said, I’m just gonna take it as it comes. Which is fine, but if you really want to make progress, you need to be intentional about the life that you’re creating. I found that it’s better to be proactive than reactive. If you retire at age 65 and you live to average life expectancy, you might have 20 years of retirement, and those years are not equal.

What you’re gonna be able to do at age 65 will be a lot different than what you can do at age 80 and a default Retirement with no planning often looks like too much tv. Too little purpose, fewer relationships, and a vague sense of boredom or restlessness. So before we ever talk about money, we need to talk about meaning about your why.

Let’s start with a simple question. Why are you going to retire? Not why are you tired? Why are you burned out? Why do you wanna stop working? What do you dislike about the culture? Those are push reasons. Those are the things that are pushing you out the door. I want you to think about the poll reasons.

What are you moving toward? If work wasn’t bad, if the stress was not overwhelming, would you still retire? What do you want more of in your life that work currently? Crowds out. Oftentimes I’ll ask people who have recently retired what they like the most about being retired. The number one answer that I hear is sleep.

They like being able to sleep and not having an alarm clock, and I just wonder if they were to go to their employer and request a schedule that allowed them to start later, perhaps working part-time, it would allow them to have the sleep they desire and still get to maintain the work that they do. See, I don’t think work is a bad thing.

I think work is contribution. That’s what we’re designed to do. It’s a good thing. Now, retirement’s a good thing also, but I just don’t want you to retire from something which can feel good initially, but can start to wane as the months tick on. I want you to retire so that you’re excited about what comes next.

To help people get clarity, I wanna borrow a framework from a ebook called Designing a Great Year. Although this framework was originally created for annual goal setting, I still use it today. I just used it last week for my annual goal setting. It applies to retirement planning because retirement isn’t a single event, it’s a series of years.

You intentionally are designing, and I don’t want you to get hung up on the word goals. You may not like setting goals, and that’s okay. Instead of thinking in terms of goals, think in terms of direction. Ask yourself, what direction do I want my life to move? Think destination. Where do you want to end up?

So let’s walk through a few of the key ideas. I’ll include a link in the show notes if you want to download the free ebook called Designing a Great Year. Number one, wisdom before you plan the future. Pause and look back. What has life already taught you? What mistakes shaped you? What seasons stretched you?

What lesson did you learn the hard way? Is there anything in life that you would do differently? Knowing what you know now? What are your favorite things? Retirement is about clarity to know what’s most important in your life. Confidence comes from knowing the numbers are gonna work, and then when you have clarity and confidence, you get to experience freedom.

Number two. The second exercise is I want you to fast forward into the future. Imagine you’re now 85 years old and you’re looking back on your life. What do you hope is true? Not about your net worth or your investment returns, but your life who’s around you? What relationships are thriving? How active are you?

How does your body look and feel? Where did you go? How did you serve others and contribute? What do you stand for? What made it a good life? How will people remember you? How will you measure your retirement? If you don’t know where you’re going, any road will take you there. We want you to know where you’re going so that you get on the right road as soon as possible.

The third exercise is gratitude. One of the fastest ways to understand what matters most is gratitude. You ask yourself, who am I grateful for? What parts of life am I deeply thankful for? What would I miss the most if it disappeared? One of the best exercises I’ve found for gratitude is to pull out your phone and look back at the pictures you’ve taken over the last 12 months.

As you scroll through the moments that made up the last year, what do you want more of? Who do you wanna spend time with? Which experiences were worth capturing? My wife bought us a skylight calendar, and it’s a great way for our family to stay in sync using the calendar feature, but it also doubles as a family photo album.

And when I’m up early in the morning, I enjoy watching the slideshow of those pictures, and it really invokes a sense of gratitude in me. It helps remind me of what’s most important in my life. And I’ll include a link to that in the show notes if you want to check it out. Number four is purpose. And this is where retirement often breaks down.

When I ask people how they envision retirement, people say, I’m gonna travel on golf and relax, and those are all fine, but are they enough? Leisure alone doesn’t create meaning sit too long in the La-Z-Boy recliner, and you might just become lazy. So ask yourself, who do I want to spend time with and do they have the time to spend with me?

What kind of impact do I still want to have? What problems do I care enough about to help with? And there’s a quote that I love. It said, you make a living by what you get. You make a life by what you give. Retirement doesn’t end our usefulness, it expands it. Think of this next phase of life as the giving phase.

Money might be part of the equation, but what does it mean to give of your time? Number five is designing a perfect day. One of the most practical exercises you can do is just design a perfect retirement day. Sit down with a piece of paper. I don’t want you to write out a vacation day, not a once a year day, just a regular old Tuesday.

When do you wake up in retirement? What’s the first thing you do? When do you move your body? How do you connect with people? How would you enjoy nourishing your body and your mind and your soul? When do you create? When do you rest? What time do you go to bed? A great retirement isn’t built in big moments.

It’s built one ordinary day at a time. Sometimes I personally feel like I’m wasting my days. Do you ever feel like that? Like you have this gift of life and health and mobility and wealth? You can go where you want, eat what you want, give how you want, and you find yourself eating fast food, sitting on the couch, watching tv, scrolling through social media, playing pickleball, and asking, is there anything more?

Well, some friends of mine just got home from a medical mission trip to Malawi, Africa. They sent me some amazing pictures. And the one that really impacted me was seeing this group of kids sitting in the dirt, eyes closed, hands pressed together so tightly, and they were deep in prayer. And when I see that photo, I think we can be the people to help answer those prayers.

Even if we can’t be in Africa, we can help support the people who can be, and that feels deep, meaningful, and rewarding to me. Number six is service. Many of us underestimate how important service is. Work provides structure, identity, belonging, comradery, contribution, progress, checklists. I mean, who doesn’t love a good checklist when work ends?

Those don’t magically replace themselves. So ask, where will I serve? Who will benefit because I exist. Where can my skills still make a difference? That might be simple and just look like, you know, trail maintenance with your hiking club or reading to kids at the library or mentoring, coaching. Community involvement, missions, trips, serving meals to those in need.

I’ve found that serving others creates connection and belonging and just a wonderful sense of fulfillment. And I’ve also found that when I’ve struggled with depression and anxiety, it’s usually because I’m thinking too much about me. And I’ve discovered that a simple and powerful way out of anxiety and depression is to pray and to serve others.

Serving is purpose. Jesus said It’s better to give than to receive. You can give money, you can give time, you can give encouragement. A rich life will be measured in what we give, how we serve, not what we get. And number seven is to invert. I was listening to a recorded speech by Charlie Munger, who is Warren Buffet’s right hand man.

His advice was to invert, always invert. In other words, think for a moment about the life and the retirement that you wanna avoid. What life, what retirement would you hate? What makes you angry? What makes you sad? What are you afraid of? Boredom, irrelevance, addiction, suffering, loneliness. Declining health.

Broken relationships. If you know what you wanna avoid, you gain clarity about the decisions to avoid for your own future. But when you realize what breaks your heart, you’ll have a better understanding of where you’re needed, what your gifts are. Where you can serve. Here’s the big takeaway. Every future part of this retirement challenge is social security spending, taxes, investments, withdrawal strategies, housing decisions, health insurance.

That all exists to support an amazing life. Money’s the tool. Purpose is the goal. Serving is the reward. My friend and mentor Dean used to remind me, he would say, Jason, life’s not a dress rehearsal. This is the real deal, baby. You get one shot, go give it everything you’ve got with everything you’ve got, and that’s what I want for you and for me to go for it.

Let’s give it everything we’ve got with everything we’ve got. When you start with why financial decisions get clear. When you realize your time and your health is limited and you feel confident that you’re gonna be okay financially, you’re not gonna hesitate to take the family vacation, to attend the graduation, to book the cruise, to go on a missions trip to give, because you know what you’re optimizing for.

You know what a great retirement looks like. You’ve seen the destination you want, and you also know what a really bad retirement could look like. Let me leave you with one more question. If your retirement were wildly successful. Not financially, but personally, what would be true about your life five years into retirement?

And at your funeral, how will people remember you? What will you be proud to say that you had contributed by answering these questions? It’s a starting point for designing a great retirement. In the next episode of the 2026 Retirement Challenge, we’ll begin by connect. This clarity to real practical decisions.

I’m gonna focus that episode on spending because at the end of the day, retirement planning is really about cash flow. It’s about making sure you have enough income to cover both your essential expenses and your discretionary spending, because it’s your spending that ultimately allows you to live your best life.

In fact, knowing how much you spend is the single most important number in retirement planning. Every other decision, social security, timing, investment strategy, tax planning, it all revolves around that one number. So in the next episode, we’ll take time to think through where your money actually goes.

We’ll break down essential versus discretionary spending. We’re gonna look at expenses that tend to show up early in retirement and plan for the spending. That often comes later. And this is where retirement plans really start to come together. I’m excited to be on this journey with you. Thank you for giving me the opportunity to.

Be your guide for this retirement challenge in 2026.

Announder: Thank you for tuning in to Sound Retirement Radio. For articles, links, and resources from today’s show, visit sound retirement planning.com. If you enjoy the podcast, share it with a friend and give us a five star review. Ready to kickstart your retirement planning head over to retirement budget calculator.com.

Need assistance with an. Investment management explore our services@parkerfinancial.net. Information and opinions expressed here are believed to be accurate and complete for general information only. It should not be construed as specific tax, legal, or financial advice for any individual and does not constitute a solicitation for any securities or insurance products.

Please consult with your financial professional before taking action on anything discussed in this program. Parker Financial, its representatives or its affiliates have no liability for investment decisions or other actions taken or made by you based on the information provided in this program. All insurance related discussions are subject to the claims paying ability of the company.

Investing involves risk. Jason Parker is the president of Parker Financial LLC, an independent fee-based wealth management firm. Located at 9 2 3 0 Bayshore Drive Northwest Suite 2 0 1, Silverdale, Washington. For additional information, call 3 6 0 3 3 7 2 7 0 1 or visit us online@soundretirementplanning.com.