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Plan a Special Vacation to Start Retirement

Updated: Apr 10

If you're about to retire but not really looking forward to it, maybe it's time to schedule something you will look forward to. Kicking off your retirement with a well-deserved vacation can ease you into this complicated transition and give you a small taste of everything you have to look forward to.


Here are two reasons why you should consider plotting a dream vacation right next to retirement on your $Lifeline.


1. Avoid "the Monday morning after."


Many retirees will tell you that the first Monday after retirement is one of the toughest days of their lives. No matter how much you've thought about retirement and planned for it with family, friends, and your advisor, those first couple days without work can be jarring. You might feel a profound loss of identity now that you're no longer a doctor, engineer, or CEO. You might find yourself staring at a blank weekly calendar, wondering how you can possibly fill all that time. And without the drive to execute important work tasks, collaborate with colleagues, and provide for your family, you might feel like you’ve lost your purpose.


Taking a spectacular vacation isn't going to erase all those anxieties. But filling in the first big block on your retirement schedule might lead to you scheduling another big bucket list item, and then another. Planning for the activities ahead will give you something to do; anticipating them will give you more and more to look forward to. Pretty soon you'll be excited about filling in those smaller blocks as well, with things like sports, online learning, volunteer work, or shorter trips to see friends and family.


Taking a big vacation after retirement can also be a great way to unplug from one phase of your life, reflect, and start planning for the future. You might even use some of your travel experiences as cornerstones of your new retirement schedule. If you fall in love with a new cuisine, take some classes when you get home and turn dinner time into its own mini vacation. Explore your destination on foot and you might find you want to make walking or hiking part of your morning routine.


2. Enjoy your best life with the money you have, right now.


We all have things that we want to do "someday" that get pushed off while we're working and raising a family. Some retirees continue to push off "someday" because once they stop earning a paycheck, they worry about running out of money. For too many of those folks, "someday" never comes.


The earlier you switch from a "saving" mindset to a "reward" mindset, the sooner you're going to start making the most out of retirement. It's all too easy for struggling retirees to fall into an unfulfilling routine of puttering around the house until they settle into the couch for the night. A vacation can help you to break that routine before it starts. As you become more comfortable with responsible spending, you'll start to appreciate the possibilities that all your hard work has secured for you in retirement. Hopefully that will inspire you to try new things and visit new places while you're still able.


And once you start to slow down and move into new phases of retirement, your Life-Centered Financial Plan will be there as you explore new ways to keep living the best life possible with the money you have.


In your life and career, you’ve probably found that the best way to get better at something is to work with a coach. Retirement is no exception. If you’re struggling with your transition into retirement, make an appointment to work through our Retirement Coaching tools. Locking down that first bucket list vacation can be the start of a whole new way to think about and enjoy your golden years.


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