Transitioning Into Retirement

The five years before you retire can be a critical period for ensuring a successful, and happy, retirement. In addition to key financial decisions, this window comes with some bigger questions about family and next steps. Here’s a guide to help you prepare to retire.

Ask yourself: Am I ready to retire?

At first glance, this may seem easy to answer: You’ve likely prepared for retirement for decades. But there are layers to the question beyond whether you’re ready to sleep in a bit on weekdays.

First, take a pragmatic look at the question. Do you have enough money set aside to retire? Would retiring within the next five years allow you the retirement lifestyle you hope for? Our article asking “When should I retire?” can help you think through some of these financial considerations.

The second question may be harder to answer: Are you emotionally prepared for retirement? Many people find purpose in their work, have friendships with their coworkers, and enjoy the structure of routine. Take a minute to consider life without these elements, and ask if you’re ready for it. If you’re concerned about the transition, read on.

What will you do in retirement?

It’s easy to think that the lifestyle we’ll live in retirement depends solely on how much wealth we accumulate ahead of time. But what if you flipped the script and thought of retirement income as a tool to do what you want? To answer this question, you need to know what you want to do in retirement. Are you retiring TO something or FROM something?

Many Americans think of retirement in vague terms—as a sort of extended vacation where you can do everything you’ve put off during your working years. And while retirement can certainly be that, the novelty may wear off after the first few months (or years).

Consider making a list of what you want to do with your time in retirement. Include some of those extended vacation items, the hobbies you promised to take up if you only had the time, even key events or people that you want to plan around. Here are a few ideas to get you started.

  • Volunteer: We frequently hear from people that they want to give back to their communities. You might find a volunteer opportunity that takes advantage of your unique skills, like mentoring local teenagers.
  • Head back to school: Retirement can be a great opportunity to learn for the sake of it (versus in preparation for a job). You might consider learning to play an instrument or even working towards a college degree.
  • A second career: If you’ve always dreamed about the career that got away, you might be able to explore a second career in retirement. How you do this may vary depending on your age, energy level, and the size of your nest egg, but if you’ve always wanted to give a different line of work a try, make note of it.
  • Travel: Perhaps you’ve said for years that you want to travel when you retire. This is a good time to get more specific. When you say travel, do you mean driving cross country in an RV, stopping at national parks along the way? Or do you want to see the great museums of Europe?

Once you have some concrete ideas in mind for what you want to do in retirement, give some real thought to how you’re going to spend a typical week, and consider actually writing down a hypothetical schedule.

Having a sense of what you want to accomplish in retirement and how you’ll spend your time can help prepare you for some of the more philosophical questions you might face.

The psychology of retirement

Sometimes, we spend so long preparing for an event that the event itself feels like a bit of a comedown. Thinking about the psychological impact of retirement can help prepare you for potential emotional hurdles.


For many of us, our identity is tied to our profession. It’s how we spend the bulk of our time, after all. If your job is a source of pride and validation, adjusting to life without it may be hard. Knowing this ahead of time can help you with the transition.


If you’re a person who benefits from routine, adjusting to a new schedule may be challenging. You may want to come up with a retirement schedule to help you mentally transition.


If you’re married, you and your partner may have different timelines around retirement or different ideas about what the ideal week looks like. For couples who don’t discuss this ahead of time, finding a new normal can feel challenging.


If retirement is the “end goal” you’ve been planning for, you might worry that retirement is the beginning of the end. Any of the previous issues in this section can exacerbate this feeling. It’s important to realize these feelings are normal.

Sometimes, simply knowing that the transition to retirement may include challenges is enough. We suggest clients prepare for the many joys of retirement—this is what you’ve been working toward after all—while also taking time to mentally prepare for the next phase of life.

If you have questions about retirement planning, or you’re nearing the critical five-year pre-retirement window, reach out to a Bogart Wealth Advisor to discuss.

Please remember that past performance is no guarantee of future results. Different types of investments involve varying degrees of risk, and there can be no assurance that the future performance of any specific investment, investment strategy, or product (including the investments and/or investment strategies recommended or undertaken by Bogart Wealth, LLC [“Bogart Wealth”]), or any non-investment related content, made reference to directly or indirectly in this blog will be profitable, equal any corresponding indicated historical performance level (s), be suitable for your portfolio or individual situation, or prove successful. Due to various factors, including changing market conditions and/or applicable laws, the content may no longer be reflective of current opinions or positions. Moreover, you should not assume that any discussion or information contained in this blog serves as the receipt of, or as a substitute for, personalized investment advice from Bogart Wealth. To the extent that a reader has any questions regarding the applicability of any specific issue discussed above to his/her individual situation, he/she is encouraged to consult with the professional advisor of his/her choosing. Bogart Wealth is neither a law firm nor a certified public accounting firm and no portion of the blog content should be construed as legal or accounting advice. A copy of the Bogart Wealth’s current written disclosure Brochure discussing our advisory services and fees is available for review upon request or at bogartwealth.com

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