The 5 Stages of Retirement, Diversified Wealth
By: Andrew Rosen, CFP®, CEP®

You are a late 50 to mid-60 year old.  You feel comfortable in your retirement position, having just left your financial professional’s office.  So far, so good, right?  Now the hard part — walking into your boss’s office to utter the words “I’d like to retire.”

Can you relate to this scenario? You’ve dreamt of this day for years, played it out in your mind numerous times.  So, why is it so difficult?  You wonder if these thoughts keeping you up at night will ever subside.

I’m not sure why (maybe it’s something in the water) but, I’ve had an influx of clients looking to retire over the last few months.  All of the questions above are looming in their heads, too.  Rest assured, you are not alone.  To help, I created a “timeline,” of sorts.  As an advisor who has helped 100’s of clients retire, let me share some words of encouragement and walk you through the first 60 days of retirement:

Stage 1: The Thought.

The first stage you’ll go through is simply the thought of retiring.

What will retirement be like?” 

“Is this really happening after 40 years?”

 “I am going to be so bored, aren’t I?”

At this point, the mere thought of retirement seems surreal.  You may compensate by working overtime, or begin to feel ill at the prospect. You’ll think about spending more time with family and friends.  No matter what, thoughts and emotions will be strong during these 30 days leading up to (and 30 days post) retirement.  You can only imagine what this stage of life will bring.

Stage 2: The Prep.

The second stage pushes you past the “thought” of it.  Now, you start getting your financial, mental, and other affairs in order.  You do your farewell tour at work and (for the first time) admit to your colleagues you are turning that symbolic switch to “off.”  You double (then triple) check your finances and start contacting all of the appropriate entities to get the “wheels in motion” — Social Security, health insurance providers, pension company, and so on.

While you are inundated (and overwhelmed) with all this work, you also mentally prepare.  The thought has set in and you day dream about this next step of life.  It’s bitter sweet in a lot of regards, but you’ve put yourself in a position to digest this massive life change.

Stage 3: The Panic.

So, your retirement sails are hoisted.  It’s time to hit the high seas.  Now, you panic as more thoughts run across your mind.

“Holy moly!  What did I just do?  I’m not ready.  I made an enormous mistake. What if I hate retirement? What if I run out of money?” 

Coming to terms with the enormity of what is about to happen is tough.   Most change is hard, but adding doubts to the unknowns involved can bring about a sort of terror.

But, don’t worry; this stage will pass.  At one point the thought of working for the next 40 years set you into a state of depression.  However, you learned to embrace it and take it for what it’s worth.  The panic is real, but take it from someone who’s seen many go through this — the fear is temporary.

Stage 4: The First Day (of the rest of your life).

The time has come. You hand in your keys, badge, and work laptop.  Colleagues give you a retirement lunch filled with goodbyes and handshakes.  Then you walk out that door for the last time, heading home to whatever awaits.

Although exciting, these next 30 days are rough.  Just like starting a new position at work, there is a transition period.  Balancing what to do with your free time and searching for a life of fulfillment is a rocky road.  Many marriages struggle during these first few weeks. Unfortunately, your routine (and that of your spouse’s) are disrupted.  As a past executive, you realize you don’t have anyone to answering to you anymore.

It may even be hard to share your retirement news with friends or family.  I’ve heard many say they are “unemployed” or “figuring it out.”  They hide the news instead of confessing their retirement.

Uncertainty looms large in this stage.  But, soon you will (everyone does) move to stage five!

Stage 5: Euphoria

Now 30 days or so have passed.  You wake up one morning and guess what? You don’t miss working!  Instead, you’ve started filling the days with your passions and hobbies.  Whether that be your grandkids, photography, painting, volunteering, or rediscovering your spouse, you have arrived at euphoria.  You now realize this vacation doesn’t end; you no longer have that sinking “going back to work” feeling.

Once it sinks in, the sun is brighter and the air smells fresher.  You no longer fear admission of retirement.  You’d now rather run to the top of the mountain to scream it aloud!  The panic has passed and the fear is gone. (It might return once in a while.  But not to worry.  It, too, will pass.)  You’ve got your sea legs and are no longer just picturing retirement.  You’re a living testament of it.



Helping my clients retire is one of the most rewarding parts of my job.  Seeing a plan through and watching others achieve life goals inspires me.  I’m truly blessed and honored to have been part of so many of these transformations.  It’s honestly one of life’s most pleasant things to witness.

Although everyone’s journey is different, we all aim for a similar destination.  It takes work, determination, and lots of help.  In my humble experience, the pain is worth the prize.  So, if you are thinking about retirement (or perhaps going through these 60 emotional days) take solace there is a light at the end of the tunnel (and it ain’t the train!)

You’ve earned it, congrats!

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Andrew Rosen

In his role as Financial Planner, Andrew forges lifelong relationships with clients.  He coaches them through all stages of life and guides them to better achieve their life goals.  For more information about Andrew or the other firm partners, Kyle Hill and David Levy, click the link below.

Find out more about Andrew Rosen, CFP®, CEP®
Find out more about Kyle Hill, CFP®
Find out more about David Levy, CFP®

Financial planning and Investment advisory services offered through Diversified Financial Consultants, LLC, a registered investment advisor. Securities offered through Securities Service Network, LLC, Member FINRA, SIPC. Associates of Diversified Financial Consultants are registered representatives of Securities Service Network, LLC, a registered broker/dealer, 9729 Cogdill Road, Knoxville, TN 37932. (800) 264-5499.