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Emotional Signs You’re Ready to Retire and 4 Actions to Take

George Grombacher August 26, 2022

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Emotional Signs You're Ready to Retire and 4 Actions to Take

What are some of the emotional signs you’re ready to retire? What do you do when you experience them?


My hope is you’re not planning on retiring tomorrow. Even if that’s the case, it’s better to consider what I’m going to share than to not. 


A successful transition from full-time work to retirement is different for everyone. Ideally, you’ll start recognizing the signs you may be ready and begin creating a transition plan. The happiest retirees I know took a thoughtful planning approach. 


Over the course of my 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) I’ve helped countless people through this transition. My goal is to give you some practical steps you can take immediately which can help you in your transition.  


Here’s what we’ll cover:


  • 4 emotional signs you’re ready to retire

  • 4 steps for getting your affairs in order


Let’s get started.


4 emotional signs you’re ready to retire


When did you think you may be ready to retire? How long have you been thinking about it? 


We derive a lot of meaning and identity from our work, so it’s understandably a big decision to step away from it. We can think about it logically, but our heart and emotions may be the ultimate deciding factors. Here are four common signs people are ready to retire.


The obvious signs


You’re over it. All of it. 


The thought of waking up, going through your morning routine and driving into your office sounds terrible. You’re sick of the grind, and you can’t imagine doing it for another week, let alone another year. These are clear signs you’re ready to retire. 


Fear of missing out


In my interview with Steve Lopez on the LifeBlood podcast, he talked about his experience of watching a close friend pass away after only a couple of years of retirement. He said it scared him. The thought of only having five years of retirement, and not doing all the things he wanted to do was a giant motivator for his decision to transition to retirement. 


He talked about wanting to be healthy enough to remain physically active. To be able to climb mountains and enjoy time with family.


Does this resonate with you? 


Feeling at ease


Do any of these statements sound familiar? “I could step away/scale back.” “I can definitely see myself doing other things.” 


Feeling at peace with the professional work you’ve done is a strong emotional sign you’re ready to retire. If you feel you’ve got a lot more work to do, that’s a sign you’re not ready. 


As you’re reading that, does your head nod? Does this resonate with you? 


Excitement for what’s next


What are you being pulled towards? Do you have big plans? Are you excited to have no plans at all? 


What will you do with more flexibility, time, and freedom? Is there a new endeavor you’re going to jump into? Do you have a hobby picked out that you’ve been wanting to do for a long time? What adventures will you go on? 


Does any of this resonate with you? 


4 steps for getting your affairs in order


It’s one thing to want to retire, and another to be able to retire. To have financial peace of mind, you need to ensure your affairs are in order. 


You’ve saved, invested and accumulated enough assets to step away from full-time work. Now how do you take that money and turn it into income that will last for as long as you need it to? How do you ensure your post-retirement lifestyle will be sustainable? These are the questions I want to help you answer.  


Cash flow planning


Your pre-retirement cash flow will differ from your retirement cash flow. Your income will be different, as will your expenses. Failure to plan for this is a mistake, and you may scramble for answers and solutions. 


I encourage you to go through your previous 12 months’ expenses. Look for opportunities to make cuts, and for things you no longer value. Unless money is no object, the more you optimize your cash flow, the better.   




Just as your pre-retirement cash flow will be different, so will your budget. In retirement, every day is Saturday. You’ve been a good steward of your money leading up to this point. Putting together your retirement budget will help you continue that positive stewardship. 


Designing retirement income


You’ve got a lot to think about. You need to ensure you don’t run out of money, and you don’t want to squeeze every penny to death. I want to touch on three key areas to focus on:




Emergencies happen in retirement the same way they happen during your working years. It’s prudent to maintain your emergency fund. I recommend having six months’ worth of expenses in cash. 




You may live to 100, and inflation will most certainly play a role in your retirement. Because of that, you may need to keep a portion of your net worth invested to keep pace with whatever the inflation rate will be. 


Guaranteed lifetime income


Guaranteed lifetime income is like your paycheck. We get it from Social Security, pensions, and annuities. I recommend you have enough guaranteed lifetime income to cover your fixed expenses. This is another interesting reason to get your retirement budget together as soon as possible. If you don’t have enough coming from Social Security and a pension, consider an annuity to cover the shortfall. These streams of income will be there for as long as you’re alive. That’s peace of mind. 


Goals and desires


How will you spend your most valuable resources of time, attention, and money? The more clarity we can get around our goals and desires before retirement, the better. 


Specifically, I want you to think about how you’ll spend your time. I’m not saying you should fill up every hour with something, but I also don’t want your calendar to be full of white space. Think about some activities you think you’d like to do and start doing them now. Look at it as a trial retirement activity. If you find you love it, great! But you may find it’s not for you, and that’s great too. 


Work gives us a lot of things. It provides us with somewhere to go, something to do, prestige and position, community, and meaning. That’s a lot. Where will you find those things in retirement? The most important part of that is meaning. Without that, you will not be happy. Figure out what’s going to make you matter and make sure you’re doing it. 


To help you dig deeper into this process, you can access our Goals course for free. 


To help you get organized, you can download our Personal Financial Statement for free. 


Finally, check out our Retire Happily course




The happiest retirees create and follow a transition plan. They’re thoughtful and intentional about how and who they’ll spend their time with. They create a financial plan, and pay close attention to their money. 


You can be a happy retiree too… whenever you’re ready to make it happen. 


You can connect with one of our Certified Partners to get any question answered. 


Stay up to date by getting our monthly updates.


Check out the LifeBlood podcast.


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