If You Answer “YES” to These 6 Questions… RETIRE NOW

Answer Box: TL;DR

Being “financially ready” is only half the retirement equation. In this video, Dan walks through six key questions that go beyond the numbers to help you decide if you’re truly ready to retire—emotionally, physically, mentally, and socially. He explores whether you’ve been deferring your life, how your health is holding up under work demands, whether you could work less instead of fully quitting, if you’re truly prioritizing time with loved ones, whether you have a clear sense of purpose for retirement, and if you’ve actually run the numbers on income, taxes, and longevity. If you can genuinely answer “yes” to all six, you may be ready to step into retirement with clarity and intention—not just a resignation letter.

Key Takeaways

Retirement readiness is more than a portfolio value.
- Most people obsess over “Do I have enough money?” but ignore health, purpose, relationships, and emotional readiness.
- Retiring too early can stress your finances; retiring too late can cost you health, time, and experiences you can’t get back.
Question 1: Have you been deferring your life?
- Many high achievers postpone joy: “I’ll travel later” or “I’ll slow down after I retire.”
- “Someday” isn’t a real date—if you’ve been putting life on hold, that’s a signal something needs to change now, not in 10 years.
- Retirement (or semi-retirement) should support an “and” life—purposeful work and meaningful living.
Question 2: Is your health suffering because of work?
- Chronic stress, poor sleep, constant travel, and anxiety quietly erode long-term health.
- Time and energy are nonrenewable—if work is costing you health, more money may not be worth “one more year.”
- Investing in your own wellbeing may be the highest-return decision you can make in your 50s and 60s.
Question 3: Is it possible to work less instead of not at all?
- Not everyone wants (or needs) a hard stop. Options include phased retirement, part-time roles, or consulting.
- In some environments that’s not offered—then you may need to design your own off-ramp instead of waiting for permission.
- Healthy boundaries (e.g., not answering email at 9 p.m.) are part of testing whether you can dial back before you fully exit.
Question 4: Do you wish you had more time for loved ones?
- Every hour you spend working is an hour you’re not spending with family and close friends.
- Retirement isn’t just financial freedom; it’s relational freedom—the ability to be present for what matters.
- If you’re consistently missing important moments, that’s a signal your time allocation and priorities may be misaligned.
Question 5: Do you know what you’re retiring to?
- Many people know exactly what they’re retiring from (meetings, travel, pressure) but not what they’re retiring to.
- Without a plan for how you’ll spend your days, retirement can feel empty or disorienting despite having “enough” money.
- You don’t need every detail, but you do need meaningful activities, projects, relationships, or service that light you up.
Question 6: Have you actually run the numbers?
- You need a clear plan for:
  - Income sources and timing
  - Spending patterns in different phases of retirement
  - Taxes, healthcare, and potential long-term care
  - Market volatility and “what if” scenarios
- Guessing based on rules of thumb can lead to “paycheck to panic” if markets or expenses don’t cooperate.
- You can DIY with tools or partner with a professional who understands tax planning, income sequencing, and withdrawal strategies.
Honest “no” answers are a gift, not a failure.
- If even one of the six questions gives you pause, that’s a sign to slow down and shore up that area, not just push through.
- Retirement is the beginning of a new chapter, not the end of the book—you want to enter it with both clarity and confidence.

Key Moments

(00:00) – The real retirement question. Dan opens by contrasting saving and planning for retirement with actually asking, “Am I truly ready to retire?” on multiple levels.
(00:26) – The danger of too early vs. too late. He lays out the tradeoff: retire too early and you may harm your finances; wait too long and you may sacrifice health, relationships, and irreplaceable time.
(00:50) – The six-question framework. Dan introduces the six questions that every professional should answer before handing in their notice.
(01:17) – Question 1: Are you deferring your life? He describes high achievers who keep pushing joy to “someday” and challenges the “either work now or enjoy later” mindset.
(02:04) – Question 2: Is your health suffering? Dan highlights the cumulative toll of long hours, travel, and stress—and asks what an extra year of work is really costing you.
(02:54) – Question 3: Can you work less instead of quitting? He explores phased retirement, part-time roles, consulting, and boundaries as alternatives to an all-or-nothing exit.
(03:40) – Question 4: Do you want more time for loved ones? He emphasizes that you can have anything but not everything—and that time with family doesn’t come back.
(04:27) – Question 5: What are you retiring to? Dan notes that many people know what they’re leaving behind, but not what they’re moving toward, which can make retirement feel aimless.
(05:14) – Question 6: Have you run the numbers? He stresses the need for a concrete plan around income, spending, taxes, healthcare, and market risk before retiring.
(05:44) – DIY vs. professional help. Dan explains you can use tools to model scenarios yourself or work with a professional—Tailored Wealth does this for clients.
(06:34) – What your answers mean. If you answered “yes” to all six questions, you might be ready; if even one answer is “no,” that’s a signal to pause and adjust.
(06:56) – Closing & next steps. He reframes retirement as the beginning of the life you’ve been building, not the end—then invites viewers to subscribe for more no-fluff guidance.

Episode Summary

In this video, Dan challenges the idea that retirement readiness is purely a financial milestone. He argues that while savings, investments, and projections matter, they don’t tell the whole story. Retiring too early can compromise financial security, but delaying indefinitely can quietly erode health, strain relationships, and steal time that can’t be replaced. To bridge that gap, he offers a practical six-question framework to assess whether you’re truly ready to retire in a holistic way.

He begins by asking whether you’ve been deferring your life—pushing joy, travel, and meaningful experiences into a vague “someday” after retirement. Many successful professionals have built an either/or life: either work hard now or enjoy life later. But as he points out, “someday” isn’t on the calendar, and there’s no guarantee that later will be available in the way you imagine. That leads into the second question: Is your health suffering? Years of intense work, constant travel, sleep deprivation, and chronic stress can have a compounding effect, making it crucial to ask whether one more year at full speed is worth the physical and emotional cost.

Next, Dan explores whether you can work less instead of stopping completely. Not everyone wants to quit cold turkey. For many, an ideal path might be phased retirement, part-time work, consulting, or simply putting firmer boundaries around time and energy. If your current role doesn’t allow that, you may need to architect your own off-ramp rather than waiting for a perfect option to appear. This naturally connects to relationships: Do you want more time with loved ones? He reminds viewers that every hour spent working is an hour that can’t be spent with spouses, children, parents, or close friends—and that retirement is as much about relational freedom as financial freedom.

The fifth question focuses on purpose: Do you know what you’re retiring to? Many people are clear about what they want to leave behind (early flights, constant meetings, performance reviews) but less clear about what they want to move toward. Without some vision for meaningful activity—whether that’s projects, hobbies, volunteering, mentoring, or travel—retirement can feel disorienting or empty, even if the finances are solid. Freedom without direction can feel less like a gift and more like a void.

Finally, Dan asks whether you’ve actually run the numbers. That means more than a back-of-the-envelope estimate. It involves mapping income sources and timing, understanding spending across different retirement phases, planning for taxes and healthcare, and stress-testing the plan against market volatility. You can do this yourself with planning tools, he says, or work with a professional who understands tax planning, income sequencing, and withdrawal strategies—Tailored Wealth does this work for clients. He closes by encouraging viewers to treat their answers seriously: if you can say “yes” to all six questions, you may be ready to retire with confidence. If even one answer is “no,” that’s an invitation to refine your plan before making the leap.

Full Transcript

Dan: Most people spend decades preparing for retirement. They save diligently, invest smartly, and maybe even fantasize about what they’ll do with all that free time. But here’s the problem. Very few people actually stop to ask, “Am I actually ready to retire?” Not just financially, but emotionally, physically, mentally, socially.

Dan: Because retiring too early, that can wreck your finances. But waiting too long, that could cost you your health, your relationships, and time that you can’t get back.

Dan: I’ve worked with hundreds of business leaders and executives navigating this exact decision. And in this video, I want to walk you through six questions that I believe that every professional should answer before they even think about handing in their notice.

Dan: If you say yes to all six, well, then you just might be ready to live the life that you’ve worked so hard for. Let’s dive in.

Dan: Question one. Have you been deferring your life? Here’s what I see all the time. Someone who’s crushed it in their career, made great money, climbed the ladder, but keeps putting joy on hold. They say, “One day I’ll travel, or after I retire, that’s when I’ll finally slow down.”

Dan: But there’s a brutal truth here. Someday isn’t a day on the calendar. And as someone once told me, a bucket list is where dreams go to die. Now, I know that’s harsh, but it often times can be very true.

Dan: If you’ve built a life of either or either I work hard now or I enjoy life later, well, I want you to rethink that. Because here’s the catch. What if later doesn’t actually come?

Dan: If you’ve been deferring the life you actually want to live, this is your wakeup call. You’ve earned the right to live an and life. Work with purpose and live with intention. And if that’s not happening right now, this may be your sign.

Dan: Question two, is your health suffering? Decades of early mornings, late nights, and cross-country flights with a carry-on, it adds up. And it’s not just physical pain. It’s sleep, stress, anxiety, inflammation, the slow erosion of vitality.

Dan: And the truth is, when you’re in your prime earning years, it’s easy to say, “I’ll deal with it later.” But if your health is in decline, even subtly, ask yourself this. What’s the real cost of one more year at full tilt?

Dan: Time and energy are nonrenewable. And if you’re sacrificing both in the name of work, it may be time to invest in the portfolio that matters most, you.

Dan: Question number three, is it possible to work less? Here’s something I often talk about with my clients. Not everybody wants to fully retire. Some just want freedom to do work they enjoy at a pace that they control.

Dan: But the corporate world doesn’t always make that easy. So what are your options? A phase retirement, which is somewhat rare, but could be ideal. Part-time work or consulting, which is becoming more and more prominent and could be worth exploring, or staying put, but establishing boundaries, which might mean not logging in at 9:00 p.m. just to prove your value.

Dan: Look, I’m not saying mail it in, but if you’ve spent decades overcommitting, overextending, and overcompensating, you might already be in the red. And if there’s no off-ramp where you are, it may be time to build your own.

Dan: Question four, do you wish that you had more time for loved ones? You can have anything, but you can’t have everything. Every hour at work is an hour not spent with your kids, your spouse, your parents, or your friends.

Dan: If you’ve found yourself missing important events, feeling guilty about being always on, or losing connections with people who matter to you, then I want you to sit with this. Time with loved ones doesn’t come back around. And retirement isn’t just about financial freedom. It’s about relational freedom.

Dan: And if you’re not making time for those relationships now, you may be sacrificing something that money can’t buy back.

Dan: Question five, do you know what you’re going to do in retirement? I’ve had dozens of conversations where a client says, “I can’t wait to be done. No more meetings, no more early flights, no more performance reviews.”

Dan: And I get it. That grind wears you down. But then I ask, “What are you retiring to?” And then the room goes quiet. Because here’s the truth. Many people spend their careers sprinting toward the finish line. And when they finally cross it, they look around and say, “Now what? No more calendar, no title, no urgency.”

Dan: For some people, that can be liberating. And for others, it’s unsettling. If you don’t have a plan for how you’ll spend your days, not just ideas, but something meaningful that lights you up, retirement can start to feel aimless.

Dan: Freedom is great, but without purpose, it can feel like you’ve stepped off a cliff. So, if you’re not clear on what this important next chapter looks like, don’t rush it. Take the time to design it.

Dan: And lastly, question six. Have you run the numbers? This one’s simple, but so many people skip it. Have you actually mapped out your income plan, your spending pattern, and how that will change in the different phases of retirement, taxes, health care, and potential long-term care?

Dan: How long will your assets last? And have you modeled for market volatility? If not, don’t even think about retiring.

Dan: Now, you have two options here. First, you can do it yourself. There are some great tools out there, and this channel has resources that can help, or you can work with a professional, someone who understands stuff like tax planning, income sequencing, and withdrawal strategies.

Dan: And yes, if that’s something you want help with, we do all of that at Tailored Wealth. And you can check out our site in the description. But whatever you do, don’t go from paycheck to panic because you didn’t pencil it out.

Dan: So, how did you answer those six questions? If you went six for six, you might be ready to retire, not just with confidence, but with clarity, health, and purpose. But if even one gave you a pause, don’t ignore that. This isn’t about fear.

Dan: It’s about freedom. Because retirement isn’t the end of something. It’s the beginning of the life that you’ve spent decades building. The only question is, are you stepping into the next chapter with a plan or just a hope?

Dan: And if you found this helpful, hit subscribe. We’ve got more no fluff guides to help you make smart, confident moves for the future. Take the next step.

Resources & Concepts Mentioned

Deferring life: Pushing joy, travel, and meaningful experiences into an undefined “later.”
Health as a retirement input: Recognizing that health, energy, and stress levels are as important as account balances.
Hybrid / phased retirement: Working less, consulting, or changing roles instead of a full stop.
Relational freedom: Using retirement (or semi-retirement) to reclaim time for loved ones and key relationships.
Purpose in retirement: Designing what you’re retiring to—projects, service, hobbies, and connection.
Comprehensive retirement planning: Income, spending, taxes, healthcare, long-term care, and market risk modeling.

FAQs

What if I answered “no” to one or more of the six questions?

That’s actually useful information. A “no” doesn’t mean you’ve failed—it highlights an area to work on before you retire. You might need to refine the financial plan, address health, create a clearer vision for your days, or adjust work/relationship balance.

Is it okay to retire even if I’m not 100% sure what I’m retiring to?

You don’t need a perfectly scripted schedule, but having some meaningful activities, projects, or roles in mind makes the transition smoother. If your answer is, “I just want to stop,” consider taking time to sketch out what an ideal week in retirement might look like.

What if I want to work less but my employer doesn’t offer phased retirement?

That’s common. In that case, you may need to design your own off-ramp—through consulting, part-time work elsewhere, or creating a different role for yourself. A good plan can show you how much income you actually need, which increases your flexibility.

How often should I “run the numbers” on my retirement plan?

At least annually, and any time there’s a major change (job shift, big market move, health event, relocation, etc.). That’s true whether you’re 10 years out from retirement or already retired and making adjustments.

Do I need a financial advisor to make this decision?

No, but many people find it helpful. A qualified advisor who understands tax planning, withdrawal strategies, and retirement income sequencing can help you avoid costly missteps and stress-test your answers to these six questions against real-world scenarios.

Disclaimer

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

Retirement timing, income strategies, tax planning, and health-related decisions all involve risks and trade-offs that depend on your personal situation. Before making any decisions, you should consult with:

A licensed financial advisor or planner
A qualified tax professional (CPA or EA)
Legal and medical professionals, where appropriate

Any examples mentioned are illustrative only and not guarantees of outcome.

Next Steps

If you’re considering retirement in the next few years, try this:

Answer the six questions honestly: Write down your responses and where you feel the most tension.
Talk with your partner/family: Align on health, lifestyle, and relationship priorities—not just money.
Map out your “retire to” plan: Sketch an ideal week or month in retirement to clarify purpose and rhythm.
Run the numbers: Model income, spending, taxes, and volatility (DIY tools or with a professional).
Explore hybrid options: Consider whether working less, not quitting entirely, might be the best next step.
Schedule a planning conversation: If you want guidance, connect with a planner who can integrate all six dimensions into one coherent plan.

Retirement isn’t a finish line—it’s the start of a new chapter. Make sure you’re stepping into it with both a plan and a purpose.