There is something I’ve noticed when people tell me about their first year of retirement.  Occasionally they will mention adjusting to living on a fixed income, but more often it’s the non-financial side of things that occupies their mind. In some instances they sound pleased. For example, they’re eager to talk about new hobbies, interests, or educational pursuits. In other cases, they’re more negative. They’re feeling unsettled in a new home, unmoored without their former routine, or unhappy with how they’re spending their days. The financial services industry has done much to educate Americans about saving for retirement.  Sound fiscal preparation is essential, but we also need to prepare ourselves for the head and heart side of this transition.  Preparing ourselves psychologically is challenging, in part because unlike financial planning, there is very little “hard” data.  Instead, we’re asked to consider subjective factors like beliefs, emotions, values, and the like. There are many things we tell ourselves that prevent us from doing this important psychological work.  Here are five things I hear quite often: I’ll figure it out when the time comes. You’ve never had a hard time deciding what to do on weekends and vacations, and you have a long list of interests you intend to explore once your time is your own. It’s great that you’re able to occupy yourself, but we’re not talking about two days or two weeks here.  Depending on your health your retirement may be measured in decades; you need to plan accordingly.  Similarly, the list of interests you hope to explore could be insufficient if it’s not fully thought through.  For example, becoming fluent in Spanish might be something that you always wanted to do and it might help keep your mind sharp, but are you really willing to put in the effort?  Playing golf several times per week may sound appealing and for some people it’s quite satisfying, but others find after a while that it falls short, failing to fuel their sense of purpose. I’ll become a part time consultant, so I don’t need to think about retirement. People over 50 are more entrepreneurial than is commonly believed.  Rather than retiring, many opt to start a consulting business based on their decades of experience.  On paper it certainly makes sense. They still have industry contacts, their knowledge is encyclopedic, and they’re keen to continue working.  I’ve met lots of people who successfully made this transition late in their career, but I’ve met just as many who struggled. Most of them were talented, decent, and hard-working, but they vastly underestimated the headwinds they would face striking out on their own. True, they had industry contacts, but many no longer wielded the influence they once did.  They counted on known referral sources, but age bias led some of those sources to look elsewhere. They were experts in their field, but it didn’t guarantee that prospective clients would beat a path to their door.  I’m not suggesting that consulting isn’t an option, but it requires an extremely clear-eyed assessment of your strengths, limitations, and the marketplace. I love my work and have no intention of stopping. Good for you, but I respectfully suggest that life has a way of throwing us curveballs as well as unexpected opportunities, so you might want to have a Plan-B.  What if you receive an unsolicited yet compelling offer for your business?  What if the firm you work for is purchased by a competitor that wants to clean house?  What if your health suddenly declines?  The point is, even if you want to keep working you may change your mind or life might change it for you.  Giving some serious thought to how you could enjoy life beyond work can provide you with greater flexibility and help you adapt if your next chapter is different than what you thought it would be. My father retired and within a year he got sick. There is no doubt that our family history can significantly influence the decisions that we make.  Many of my clients have shared how a relative’s experience with retirement affected their own beliefs and feelings about leaving work. Watching a parent or grandparent suffer in retirement can have a profound and lasting impact. That can’t be denied, but it’s important to remember that this doesn’t have to be your mother’s or grandfather’s retirement.  With some thoughtful planning you may have far more options than they did and more time to enjoy them. None of my friends who retired gave it much thought and they seem to be doing just fine. It’s possible that some of your friends moved smoothly into retirement without preparing for it psychologically, but your assertion could be mistaken.  First of all, getting oneself emotionally ready for this transition is typically a private process, so it’s unlikely you can ever really know exactly how much thought your friends put into it.  Secondly, your sense that they are doing fine may be clouded, either by their effort to portray themselves in a good light and/or your desire to see them that way. We tell ourselves these things not just because we believe them, but because they help us avoid the hard work of emotionally preparing ourselves for what could be the biggest transition in our life.  If you want to avoid feeling bored, aimless, unproductive, or dissatisfied, your retirement planning needs to include psychological preparation.