The River

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Wishful in Washington - thinking about retirement

May 04, 2024

Dear Tony,

I’m 58 and have been with my current company 27 years. Over the last few years following COVID my mind has shifted to wishful thinking about retirement. I believe I can make it work financially with a few minor adjustments, I’m technically eligible per my company’s requirements for early retirement, and my husband would be delighted if I quit. But in the back of my mind, I keep wondering if it would be a mistake. In addition, I am not sure what I would do with my time. Any advice for how I should be thinking about this?

-Wishful & Wondering in Washington

Dear Wishful and Wondering,

Your instinct to hit the pause button is spot on. Making the decision to retire – when, how, to what, where, etc. is a big-time experience and life event!

The most important advice I can convey to you is that retiring from a professional career carries with it a sense of loss, especially for you with so many years identifying with the same firm. This sense of loss is real and when the time comes you will feel it. However, and this is the most critical aspect, you must realize that retiring does not mean “reduction” or “recession” to a lesser station in life. It is easy to get stuck into thinking that your life’s meaning is getting sucked into a vortex and going down the drain. The reality is life goes on, you continue to grow, your equity continues to build, and life opens up like a flower blooming in the summer sun. You start to see and notice things about life that you most likely didn’t perceive in your busy professional career.

With this in mind, the first piece of advice is to meld together the equity of your career with your current station in life, and take an assessment of all things to date. Review all aspects of life – physical, emotional, spiritual, financial, professional skills, family dynamics, hobbies, relationships, and what you see in your life for personal growth. Take it all in and start to think about the world through the lens of abundance. After you have documented all of these aspects, and maybe iterated a few times on them, it’s time for you to ask the magic question, which is, “What now becomes available to me if I make the decision to retire on XXX date?” Thoughtfully, and with an open mind, contemplate the possibilities this powerful question contains. Write down your thoughts and continue to come back to them over time. This may be good to talk over with your husband, or with other trusted friends or advisers.

It would be best to start this process 5 or so years before you arrive at the potential to retire. But since you are there today, here are a few other pieces of advice I would offer:

  1. If you have a written purpose in life, now would be a good time to revisit it. If not, a quick way to create one is Richard Leider’s napkin test: NapkinTest.indd (
  2. A lot of life is about relationships. If you plan to move, how will this impact your relationships? If you plan on staying put, how can you deepen and create better relationships? In a lot of ways, our relationships create our happiness when we have more time on our hands.
  3. Be ready to adapt to a different structure. Personally, the rising anxiety of Sunday nights as I thought about the week ahead stuck with me more months after I retired. Being around my wife more of the time was also a transition to manage. You will have many of these once you retire, and it would be wise to think about them ahead of time.
  4. You mentioned you are doing well financially, which is great because it put you in this position. It might be wise to invest in a fee only financial planner to get a 3rd opinion. Also, at some point, you will have to start thinking about how to spend the money, instead of accumulate it. I know this sounds weird to think through, but it’s a different mindset in retirement years.
  5. The pressure you are feeling about “not making a mistake” is a gift that will help you bring out your A-game. Honor this feeling, and let it guide you to course corrections as you hone in on making a decision. If it paralyzes you for long periods of time and you end up not being able to make a decision, it may be a signal to hit pause, or it may be a signal to find the courage to make the call. Only you will know the difference. Don’t beat yourself up either way – give yourself some grace as you navigate these decisions.
  6. There are more books on retirement than I can possibly mention here. I’ll only mention that they are there to help you, not make the decision for you. I read a lot of books in the 10 years prior to my retirement, and they were all helpful in their own way. But when it came down to the decision, it was the deliberation between my wife and I that ultimately made the decision.

It’s a great sign that you have some trepidation as retiring early can seem very risky. Being thoughtful, and deliberate, in your decision making will help you make the right decision. No one can make that decision for you, and you will know when the time is right. Take your time, be thoughtful about the above considerations, and know that your life is moving forever forward, upward on onward. It only gets better daily, weekly, and monthly as your life experiences add to your joy and fulfillment.