I’ve helped many people transition into retirement over the years and when I ask a new retiree how things are going, the response is generally positive.  That said, retirement is a huge transition and there are always unexpected feelings or emotions that crop up.  That doesn’t necessarily mean that there’s something wrong with your retirement.  It just means that you’re normal.  So don’t be surprised if you feel one or more of the following:

The Problem: I feel guilty.

This is surprisingly common and I’ve seen it manifest itself in two ways.  The first is guilt if you’re not doing much or making the most of your time.  You finally have some free time and you struggle with how to use it.  You feel guilty because watching T.V. or running errands doesn’t quite feel like sucking the marrow out of life.

The second is guilt if you’re doing fun stuff that your friends and family aren’t doing because they’re still working.  I’ve actually had clients hesitate before responding to me when I ask “What did you do today?”  The answer is “I went golfing” or “We saw a matinee and then went for a walk” but they are hesitant to say that because they know I spent my day behind a desk.  When prodded, they say they don’t want to make others feel bad or come across as boastful.

The fix

For the first type of guilt, don’t worry!  You’ll get better at it.  You control a much bigger piece of your time in retirement and that takes some getting used to.  Work hard to do things that leave you feeling happy and fulfilled, but keep in mind that not every minute of your day has to be spent bungee jumping or traveling.  Sometimes the best way to spend a day is binge watching House of Cards on Netflix.

For the second type of guilt, just allow it to pass.  Don’t become an insufferable braggart, but don’t feel guilty about enjoying your life either.  You worked hard and made good decisions.  Enjoy your time.

The problem: I’m second guessing my decision.

Buyer’s remorse is a real thing.  Chances are you’ve felt it if you’ve ever bought a house or had to make some similar big decision and feared making the wrong choice.  It can creep up after retirement as well and cause you to question whether you should have retired in the first place.

The fix

I have a client who has been dealing with this lately and she shared something that I thought was really insightful.  She said, “Whenever I second guess my decision, I focus on why I retired in the first place.”  Her choice would have been to work for five more years, but two things happened: Her mom was diagnosed with Alzheimer’s and her grandkids were all at an age when hanging out with grandma was just about the best the thing ever.  If she had stuck to her timeline and worked for five more years, there’s a pretty good chance that her mom may no longer be around and her by then teenage grandkids will have priorities other than grandma.  In other words, she gave something up, but got something far greater in return. There are pros and cons with most decisions in life.  Retirement is no different.  Keep that in mind.

The problem: I feel disappointed.

Most of us have an idealized view of retirement.  Add years of anticipation to the mix or a personality that enjoys the structure and challenge of work and it’s not uncommon to feel a bit underwhelmed after entering retirement.

The fix

The best way to avoid disappointment is to retire TO something rather than FROM something.  If all you do is subtract things—work, obligations, commitments—you simply create a void in your life. That void can open you to self-doubt, regret, lack of purpose and boredom. Nature abhors a vacuum. If you take something out, you need to replace it with something else (e.g. travel, school, a second career, hobby, etc.).  The goal is not to do nothing. That just creates a void. The goal is to do what excites you.

And test those plans out before you retire.  I most often see disappointment arise when a person has prepared for retirement using all lesson and no lab.  In other words, all of their retirement plans are in their head or on a sheet of paper, and they haven’t spent any time actually testing and refining those plans.  Reality can’t compete with 40 years of idealized assumptions.

The problem: I feel like a fish out of water.

No matter how prepared you think you are for retirement, you will probably still struggle.  It’s a huge transition.  The routine you’ve had for the last 40 years is out the window.  That can be a bit disorienting for many people.

The fix

When talking with a client recently, she compared retirement to becoming a parent for the first time.  “Before becoming parents we read books, painted the nursery, sought advice from other parents and bought all the cribs, carriers and countless other things that parents need.  We thought we were totally prepared.  And then we had our first child and all that went out the window.  Retirement is similar.  As prepared as you think you are, you really can’t grasp what it takes or what it will be like until you’re actually living it.  Your experience will be totally different than the guy next door.”  Great advice.  Yes, there are tons of things that you can and should do to prepare, but the battle is always different than basic training.  Don’t get discouraged.  You’ll figure it out and get better at it with practice.  Focus on living the life that you want to live. Imagine your ideal life and then work backwards from there to figure out the most direct path to where you want to be. Focus intently on the things that matter to you and throw yourself into them wholeheartedly. That kind of focus and tactical thinking will help you rapidly flatten your learning curve and smooth your transition into retirement.

Remember that retirement is not a date on the calendar, it’s a life stage that will last for years.  Think back to when you first became an adult.  Were you better at it at 28 than you were at 18?  Of course.  The same will be true with retirement.  It might feel a little awkward at first, but you’ll get better at it over time.

~ Joe