Wealth Blog Post

Three Signs You’re Ready to Retire and Three Steps to Take Immediately

George Grombacher August 26, 2022

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Three Signs You're Ready to Retire and Three Steps to Take Immediately

Is it time? Have you had enough?


Are you excited for the future? I want to talk about three signs you’re ready to retire. If you are, there are three steps to take immediately. 


When you’re in your 20s, retirement is an abstraction. In your 40s, it becomes more real. When you hit 60, it’s as real as it gets. 


I’m assuming you’ve been thinking about transitioning away from full-time work, and that’s what I’m interested in helping you with. The happiest retirees I know did exactly that; they transitioned. 


Once you know you’re ready to retire, there are three key actions which will position you for a long and happy retirement. 


I’ve been helping people retire happily for over 20 years. I’m honored to be named to Investopedia’s list of the top 100 financial advisors many years running. Wherever you are in your process, I’m confident you’ll gain insight from this post.  


Here’s what we’ll cover:


  • Three signs you’re ready to retire

  • Three steps to take immediately 


Let’s get started.


Three signs you’re ready to retire


We want to make good decisions. Determining the “best” time to retire qualifies as a big decision that deserves thoughtfulness. How long have you been thinking about it? What has your thought process been? Have you taken any action(s)? Who have you discussed it with?


While everyone’s circumstances are unique to them, I’ve found there are three common reasons people give for deciding to retire. 


You’re afraid of missing out


FOMO (fear of missing out) is a real thing. I recently had the opportunity to interview award-winning author Steve Lopez on the Lifeblood podcast. He pointed to this as one of main reasons he transitioned into retirement. In his book, Independence Day, he talks about how a friend passed away after only five years of retirement. 


When that happened, it triggered concerns about being able to do all the things he hopes to do. He wants to be physically healthy enough to be active, and mentally strong enough to maintain great relationships. It’s his desire to be able to continue working and being productive, just on his terms. 


Does any of that resonate with you? Do you share similar concerns and desires? 


You’ve accomplished enough


It’s wonderful to reflect on professional experiences and accomplishments. When you look back, have you accomplished everything you set out to do? Have you accomplished enough to be satisfied with your work? 


When you retire, I don’t imagine you’ll stop being productive. In fact, I think it’s imperative you remain active and I’ll cover how best to do that later on. But have you done enough up to this point? 


If you can answer “yes,” it may be time to plan your transition. 


You’re over it


This is an easy one. If you’re totally over work, it’s time to retire. If you can’t imagine another day of waking up, going through your morning routine, and commuting into work, it’s time to plan your transition. 


And I’m not talking about the casual dismissals of work we all engage in. I mean, you’re 100% fed up and you’re not going to take it anymore. 

If that’s you, it’s time to plan your escape- I mean, transition. 


Three steps to take immediately


It’s decided. You’re pulling the ripcord and moving on. I’m excited for you. 


Where do we go from here? Hopefully, you have the luxury of planning a transition away from full-time employment into retirement. The three steps I’m going to cover will ideally be part of a greater plan. Either way, you’ll benefit from following them. 


Set your financial foundation


We all crave certainty. Peace of mind means, “A feeling of being safe and protected.” Without financial peace of mind, it’s hard to confidently retire. Sadly, most Americans are nowhere near financial security and peace of mind. Almost two-thirds of us are living paycheck-to-paycheck, and the average credit card debt is over $6,000. I want to make sure you don’t fall into either of those categories. 


To find financial security and peace of mind at every stage of life, you need a strong foundation. That foundation is built on cash flow, budgeting, and liquidity. 


With cash flow, you need to gain an understanding of how yours will be different pre and post-retirement. There will be similarities, and there will also be important differences. Because you’ll be on more of a fixed income, paying close attention to your spending will be important. I encourage you to review the previous 12 months of spending. Look for any expenses you can cut out or reduce. If you’re not sure if you’ll miss something, get rid of it; you can always add it back in later. 


In retirement, every day is Saturday. Because of that, budgeting becomes even more important. Work to figure out what your income will be, as well as your monthly expenses. Once you have that baseline information, you’ll be able to fine-tune and make any necessary changes.


Emergencies happen regardless of your employment status. Because of that, it’s important to have enough liquid cash. I recommend people have at least six months’ worth of expenses in their emergency fund. This should not be invested- it should be in cash.  


Create your retirement income plan


There’s not a right or wrong way to create retirement income (which is a challenge in and of itself). What I know for sure is you want your money to last for as long as you need it to. That means you need it to last for as long as you plan on living. Have you ever thought about that? 


If you intend to retire at 65, there’s a really good chance you’ll live for another 30 years. That’s a long time to plan for. If you don’t correctly plan, one of two things commonly happens: either you run out of money, or you’re terrified to spend anything and live hand to mouth. Those are both lousy scenarios. 


The remedy is guaranteed retirement income. Guaranteed retirement income means the money shows up every month and does so until you die. We get this in three ways; Social Security, pension, and annuities. I recommend my clients have at least enough guaranteed lifetime income to cover their fixed expenses (another reason knowing your cash flow and budget is so important). After figuring out how much you’ll have, an annuity could be a great way to make up any shortfall. 


Clarify your future


The only way to have the life you want in retirement is to know how you want your life in retirement to be. 


One of our superpowers as humans is our ability to set goals and make them happen. As you’re thinking about transitioning into retirement, think about how you’re going to spend your time, attention, and money. 


What will you do every day? Who will you do it with? Where will you be? 


I like to think about six key areas for goal setting:


  • Family
  • Community
  • Money and work
  • Wellbeing
  • Personal development
  • Peace of mind


Finally, it’s important to find replacements for all the things work gives to us. Work provides us somewhere to go every day, something to do, prestige and position, community, and a sense of meaning and purpose. The last one is the big one. 


You need to figure out how you’ll matter in retirement. What will you do to find meaning and responsibility? If you fail to do that, I think you’ll struggle more than you need to. 


To help you in your goal setting process, you can access our Goals course for free. 




You’re someone who can have a wonderful and happy retirement. Creating a plan for transitioning from full-time work will go a long way in positioning you for success. 


If you’d like to dig deeper, check out our Retire Happily course


You can also connect with one of our Certified Partners for a no-cost conversation. 


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Check out the LifeBlood podcast.


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