STOP Doing These 8 Things After 55 If You Want a Better Retirement

Answer Box: TL;DR

The happiest retirees don’t add more—they deliberately cut things out. In this video, Dan shares eight habits people over 55 need to stop if they want a better retirement: taking time for granted, oversaving out of fear, sacrificing health, worrying excessively, staying around negative people, spending out of alignment with their values, over-supporting adult children, and living for others’ expectations. The goal isn’t a busier retirement—it’s a simpler, more intentional life built around health, relationships, purpose, and authenticity.

Key Takeaways

Stop taking time for granted.
- As we age, time and health become more valuable than raw net worth.
- Your wealth may grow, but health and energy create the window to enjoy it.
- Think of your life as weeks on a calendar—each week is a unit you never get back.
- If work still brings joy and purpose, keep going; if it drains you, start planning a different path.
Stop saving unnecessarily out of fear.
- Many people keep working and saving long after they already “have enough.”
- That extra year (or years) is often driven by anxiety, not math.
- Create an income plan so you can see how much difference another year of work truly makes.
- If working one more year only improves retirement success by 1%, it may be time to start enjoying life now.
Stop compromising your health for more income.
- Chronic stress, poor sleep, and no time to move or recharge compound over time.
- Dan shares a couple’s story where the husband’s job was clearly costing him his health.
- They chose to prioritize sleep, nutrition, exercise, and mental health over marginal extra income.
- Your portfolio can recover; your health is much harder to rebuild.
Stop worrying excessively about everything you can’t control.
- News and media constantly amplify fear and extreme scenarios.
- As Mark Twain put it: “I’ve had a lot of worries in my life, most of which never actually happened.”
- Shift focus to what you can control: spending, portfolio structure, your media diet, your habits.
- Simply consuming less news can directly increase your happiness and reduce anxiety.
Stop spending time with negative people.
- Persistent negativity—even from family—can drain joy and energy.
- One couple tried to be “a light in the darkness” with a toxic family member, but it wore them down.
- Sometimes you need an honest conversation; if nothing changes, distance may be necessary.
- Your emotional well-being is worth protecting, even when it’s hard.
Stop spending money on things that don’t match your values.
- Many people buy out of habit, status, or impulse—without asking if it truly creates joy.
- Dan recommends a simple values exercise to clarify what really matters to you.
- Then, shift spending from “stuff” toward experiences, relationships, and aligned priorities.
- You’ll often find meaningful life upgrades without needing to spend more.
Stop oversupporting adult children.
- It’s natural to want to help, but too much help can create dependence—for them and stress for you.
- Your kids have time and earning years to recover from financial setbacks—you may not.
- It’s okay to set boundaries and protect your own retirement security first.
- Healthy support empowers; unhealthy support subsidizes poor habits and delays your freedom.
Stop pretending and living with regret.
- A common end-of-life regret: not living true to yourself.
- We spend years trying to meet expectations of employers, family, or “society.”
- As we age, we realize most people weren’t thinking about us as much as we thought.
- Let go of regret, embrace who you’ve become, and design your next chapter intentionally—studies show life satisfaction often peaks in our 70s.

Key Moments

(00:00) – The surprising pattern of happy retirees. Dan explains that the happiest retirees weren’t chasing more—they were intentionally cutting things out of their lives.
(00:25) – Stop taking time for granted. He talks about the tradeoff between increasing wealth and declining health and urges viewers to treat each week as precious.
(00:48–01:14) – Stop oversaving when you already have enough. Dan describes how fear—not need—keeps many people working and saving long past sufficiency, and encourages using an income plan to quantify the impact of “one more year.”
(01:35) – Stop compromising health for work. He shares a couple’s story where the husband’s job was harming his health, and their choice to prioritize well-being over additional income.
(01:59–02:22) – Stop worrying about everything. Dan quotes Mark Twain and highlights the benefit of focusing on controllables and reducing news consumption.
(02:22–02:46) – Stop spending time with negative people. He tells the story of a couple dealing with a toxic family member and how sometimes distance, not more effort, is the healthiest choice.
(03:08) – Stop spending out of alignment with your values. Dan encourages a values exercise to reorient spending toward what truly matters.
(03:29) – Stop oversupporting adult children. He explains why putting kids’ finances ahead of your own retirement security can be dangerous.
(03:53–04:21) – Stop pretending and carrying regret. Dan talks about authenticity, the realization that people think about us less than we imagine, and research showing life satisfaction often peaks in our 70s.
(04:21–end) – Letting go to find peace. He closes by challenging viewers to identify what they’re still holding on to—and how letting go can lead to the peace they’ve been searching for.

Episode Summary

In this reflective video, Dan shares eight things people over 55 need to stop doing if they want a better, more fulfilling retirement. Drawing on decades of working with retirees, he observes that the happiest ones weren’t the people who simply accumulated the most assets—they were the ones who deliberately cut out what no longer served them. The theme is clear: retirement isn’t about filling your life with more; it’s about pursuing less, with intention.

Dan begins with time and health. As we age, our net worth may rise, but our health and energy become more limited. He urges viewers to stop taking time for granted, to treat each week as a finite unit, and to question whether work still brings purpose or simply drains them. He then tackles the habit of oversaving—continuing to work and save out of fear rather than math. A solid income plan, he argues, often reveals that an extra year of work changes the numbers far less than people think.

The conversation moves into health, worry, and relationships. Dan shares a story of a couple where the husband’s demanding job was clearly eroding his health, and how they chose to prioritize sleep, nutrition, and exercise over incremental income. He challenges viewers to stop worrying excessively, pointing out that most fears never materialize and that managing what you consume—especially news—can significantly improve happiness. When it comes to people, he acknowledges the difficulty of dealing with negative or toxic relationships, including family. Sometimes, he says, even after honest conversations, creating distance is the most loving choice you can make for your own well-being.

Dan then turns to values and money. Many people spend on autopilot, buying things that don’t reflect their deepest priorities. A simple values exercise can reveal misalignments and open the door to spending more on experiences, relationships, and causes that truly matter. He also cautions against oversupporting adult children, reminding viewers that their kids have time to rebuild, while they may not. Setting healthy boundaries and protecting your own retirement is not selfish—it’s wise.

Finally, he addresses authenticity and regret. One of the most common end-of-life regrets is not living true to oneself. Dan encourages viewers to stop pretending, stop living for others’ expectations, and recognize that most people think about us far less than we imagine. Research shows life satisfaction often peaks in our 70s; the invitation is to embrace who you are now and let go of what no longer serves you. Retiring well, in his view, isn’t about doing more—it’s about doing less with intention.

Full Transcript

Dan: After decades of helping retirees, I noticed something strange. The happiest ones weren’t chasing more. They were cutting things out. And these are the eight habits that they stopped and why it changed everything.

Dan: First, stop taking time for granted. Time becomes more valuable as we age as our health naturally declines. While our wealth typically increases, enjoying it can be harder as our health limits what we can do.

Dan: Imagine your life as weeks on the calendar. Each week counts. Treat each one as precious. If work brings you joy and purpose, well, keep going. But if it drains you, it may be time to plan for something different.

Dan: Stop saving unnecessarily. Many people keep working even when they have enough saved. This extra work is often driven by fear, not need. Adding more savings may feel like it provides additional security, but it rarely moves the needle significantly.

Dan: Create an income plan to see how much of a difference an additional year of work would actually make. If a one percent increase in retirement success isn’t worth an extra year of work, well, maybe it’s time to enjoy what you have now.

Dan: Stop compromising health. One couple I recently started working with shared their story. The husband was really stressed from work. He couldn’t sleep. He didn’t have time to exercise. And the worry was taking a major toll on him.

Dan: His wife expressed concern. And he finally realized that his job was costing him his health. So, this couple chose to focus on well-being, sleep, nutrition, and physical health instead of extra income.

Dan: Stop worrying excessively. The media consistently feeds our fears of constant risk and disaster. But most of these worries are either overblown or will never come to pass.

Dan: Mark Twain said it well. I’ve had a lot of worries in my life, most of which never actually happen. Focus on what you can control like your spending, your portfolio, and how much media you consume. Cutting down on news can actually directly increase your happiness.

Dan: Stop spending time with negative people. Negative energy can drain your joy. One couple I know faced this with a toxic family member. They saw themselves as a light pushing back against darkness.

Dan: But sometimes even the strongest light can get dimmed by too much negativity. Sometimes you need to have an honest conversation and if it doesn’t work, distance might be necessary. It’s not easy, especially when the person is family. But your happiness is worth protecting.

Dan: Stop spending on things that are misaligned with your values. Take a look at how you’re spending your money. Are you buying things that don’t actually make you happy? Instead of more stuff, consider investing in experiences and relationships.

Dan: Doing a quick values exercise can help you to see what truly matters to you. And you might be surprised to see how much you’re spending on items that don’t truly align with your values.

Dan: Stop oversupporting adult children. Listen, it’s natural to want to help your kids, but sometimes giving too much creates financial dependence. Your kids have time to rebuild financially. You may not. It’s okay to set boundaries and put your retirement security first.

Dan: Stop pretending and living with regret. One of the top regrets that people have at the end of life is not staying true to themselves. Don’t waste time trying to meet everyone else’s expectations. Be authentic.

Dan: The older we get, the more we realize most people weren’t thinking about us as much as we thought. Let go of regrets and focus on your future. Studies show that life satisfaction actually peaks in our 70s. So, embrace the person you’ve become.

Dan: So, if retirement isn’t about doing more, but doing less with intention, well, maybe it’s time to ask, what are you still holding on to? Let go of what no longer serves you. And you might just find the peace you’ve been searching for all along.

Dan: If this resonated with you, give it a like and drop a comment with which habit hit home the most. I’d love to hear your thoughts.

Resources & Concepts Mentioned

Retirement income planning: Building a plan to see if additional work years materially improve retirement success.
Values exercise: A simple reflection or written exercise to clarify what matters most, then align spending and time with those priorities.
Media diet: Intentionally limiting news and negative inputs to reduce anxiety and increase happiness.
Boundary-setting with adult children: Structuring support so it doesn’t jeopardize your own retirement security.
End-of-life regrets research: Studies showing common regrets, including not staying true to oneself and overvaluing others’ expectations.

FAQs

How do I know if I’m working and saving more than I actually need to?

The only way to move from fear to clarity is to build a retirement income plan. Model your current savings, spending, and retirement age across different market environments. If adding another year of work barely changes your probability of success, you may already have more financial flexibility than you think.

Is it irresponsible to give less financial support to my adult children?

Not necessarily. If supporting them jeopardizes your retirement, it can create long-term problems for everyone. Healthy support has boundaries: you can help with guidance, one-time boosts, or temporary aid—while still putting your own retirement security first. Your children still have time to rebuild; you may not.

What’s a simple way to start aligning my spending with my values?

Start by listing your top 3–5 core values—things like family, health, travel, service, creativity. Then review the last few months of spending and ask: “Does this reflect what I say I care about?” Begin shifting dollars away from low-joy, low-alignment categories toward experiences, relationships, and priorities that truly matter to you.

How can I reduce worry without ignoring real risks?

Focus on what you can control—your spending, portfolio mix, safety net, and media consumption—and let go of the rest. Have a plan for major risks (healthcare, market volatility, long-term care), then intentionally limit the amount of fear-based news and commentary you consume. Planning plus boundaries usually reduces anxiety more than more information.

What if the negative person in my life is a close family member?

That’s especially hard, and Dan acknowledges that. Start with an honest, compassionate conversation about how their behavior affects you. If nothing changes, you may need to create more distance, clearer boundaries, or different expectations. Protecting your emotional health isn’t selfish—it’s a key part of living well in retirement.

Is it too late to change these habits if I’m already in my 60s or 70s?

No. Many people make their most meaningful changes later in life. Research suggests life satisfaction often peaks in our 70s, especially when people lean into authenticity, relationships, and purpose. It’s never too late to stop what’s draining you and build a simpler, more intentional next chapter.

Disclaimer

This video and written summary are for educational and informational purposes only and do not constitute financial, tax, medical, or legal advice. They do not create a client relationship with Tailored Wealth or any related entity.

Decisions about work, retirement timing, health, supporting family members, spending, and investing involve personal trade-offs that depend on your specific circumstances. Before making any major decisions, you should consult with:

A licensed financial advisor or planner
A qualified tax professional (CPA or EA)
Healthcare professionals for medical or mental health concerns
Legal counsel, where appropriate

Any examples or stories mentioned are illustrative and not guarantees of results for any individual.

Next Steps

If you’re 55+ and thinking about your next chapter, consider:

Audit your time: Look at how you actually spend your weeks and ask if it reflects what matters most.
Run a retirement income plan: See if continued work is adding significant security—or just delaying your life.
Check your health “balance sheet”: Sleep, movement, nutrition, stress. Where do you need to invest more?
List your top values: Compare them to your current spending and relationships. Start shifting in small, concrete ways.
Set one boundary: With media, money, or relationships—pick one area where you can say “no” to protect your peace.

Retirement doesn’t have to be about doing more. It can be about doing less, on purpose, so the years ahead feel lighter, more aligned, and deeply satisfying.