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How to Retire Happy: Avoid these 4 Mistakes

George Grombacher August 24, 2022

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How to Retire Happy: Avoid these 4 Mistakes

What does it mean to you to retire happy? 


I want everyone to have a happy and fulfilling retirement. If you want to travel the world, open a winery, or spend every day with grandkids, that’s what I want for you. And all those things are possible. But financial security is the starting point for all of it. 

Without financial security, you’re at risk. Worrying about money causes stress, anxiety, and will affect your ability to retire happy. My goal is to help you avoid two costly financial mistakes, and two costly general mistakes people make in retirement. 


I’ve been helping people retire happy for 20+ years as a financial advisor. I’m honored to be named to Investopedia’s list of the top 100 financial advisors many years running. 


Here’s what we’ll cover:


  • Don’t run out of money

  • Don’t forget about liquidity

  • Don’t let yourself get bored

  • Don’t go unfulfilled


Let’s get started.


Don’t run out of money


This sounds obvious, but it’s a serious risk that needs to be addressed. Too often, failure to plan your retirement income results in one of two scenarios; you spend too much and run out of money, or you’re terrified of running out, so don’t spend and live hand to mouth. I don’t want you to fall into either trap. 


If you retire at 65, how long do you expect to live for (learn more about life expectancy)? Is it possible you could live to 100? I think it is. While it’s a blessing to have a long life, living longer than expected could cause you running out of money. What can be done? 


A solution is to have enough guaranteed lifetime income to cover your fixed expenses. There are three common ways to generate guaranteed lifetime income: Social Security, pensions, and annuities. 


Social Security


You can determine how much your Social Security benefit will be by creating an account. This will also help you understand when you should elect to receive your benefit. Your payment increases over time in order to keep up with inflation, and it will last for as long as you’re alive. 




It used to be that we worked at the same company for 30 years, then retired with a gold watch and a pension. Fewer companies are offering this benefit, but if you’re fortunate to have access to one, it will provide you with lifetime income. Like Social Security, you’ll have options on how you’d like to receive your pension payments. 




If you Googled the word annuity, you’d get positive and negative results. But annuities are neither good nor bad. They are a financial product like many others. When considering an annuity, it’s important to weigh the features and benefits you’ll receive against any fees. 


An annuity can be a great way to fill out any shortfall you have in creating enough guaranteed lifetime income to cover your fixed expenses. 


In order to determine how much your fixed expenses will be, you need to complete a pre and post-retirement budget. While there may be similarities, there will be a lot of differences as well. Don’t skip this part of the planning process.  


Longevity is a risk that needs to be addressed. Guaranteed lifetime income is the most efficient way to do it. 


Don’t forget about liquidity


Emergencies happen in retirement just the same as they happen pre-retirement. How much money do you have in your emergency fund today?


While it is a matter of preference, I recommend people have six month’s worth of expenses in cash. If you currently have less than that, I highly encourage you to get to that number before you retire. This will help you find financial peace of mind. 


I’m guessing you’ll also want to be able to help loved ones should they have an emergency. This will put you in a position to do that.  


Health care costs can also be high in our retirement years. It’s estimated a married couple may pay upwards of $300,000 for healthcare costs during retirement. This could influence how much money you keep in accounts with liquidity. 


Don’t let yourself get bored


Ben Franklin famously said, “If you fail to plan, you are planning to fail.” Don’t do this. 


What are you planning to do in retirement? How will you fill your days? 


Unless you’re currently playing golf five times a week, or sitting on the beach all day, I don’t think you’ll be happy doing it every day in retirement. I want to help you develop a sustainable strategy for how you’re going to spend your most valuable resources of time, attention, and money. 


Just like budgeting, it’s wise to create a post-retirement calendar. While this will change and evolve, the more intentional you can be with your time, the happier you’ll be. There are six key areas I encourage you to focus on:


  • Family
  • Community
  • Work and money
  • Wellbeing
  • Personal development
  • Peace of mind 


With family, think about how you’d like your relationships with loved ones to be. How often will you see them, and what will you do?


Regarding community, who and what will your community be? How will you be active with it, and how will you nurture it? 


Do you intend to work? What will you spend money on? What will you not spend on? 


As we get older, focusing on wellbeing becomes more important. How will you protect your physical, mental, and emotional health? 


Lifelong learning is also a hallmark of a happy and healthy retirement. It’s important to continue consistently learning and pushing yourself. How will you do that? 


What will you do to have peace of mind? Will you have religious practice? Will you do yoga or spend time outside every day? 


The more time you can spend thinking about these areas, the better positioned you’ll be for success. In service of helping you do that, you can access our Goals course for free. 


Don’t go unfulfilled 


When you enter “fulfillment” into Google, most of the results are about how great Amazon is at delivering packages. That’s not what I’m talking about.  


Work gives us a lot more than a paycheck. It gives us a place to go, friends and community, position and prestige, and it also gives us meaning and responsibility. Without meaning and responsibility, people are unfulfilled. Have you considered this?


I’m not advocating you find a job for the sake of finding a job, nor do I think you should immediately join a nonprofit. I am suggesting you think about where you currently find meaning, and where you’ll find it during retirement. 


This is one key to having a happy retirement. 




I want you to have an amazing retirement filled with family and peace of mind. Working to avoid these four mistakes will position you to make it happen. 


Want more? Check out our Retire Happily course


You can also have a no-cost conversation with one of our Certified Partners


We’ve got three free courses as well: Our Goals Course, Values Course, and our Get Out of Debt course. 


Stay up to date by getting our monthly updates.


Check out the LifeBlood podcast.


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