Knowing When to Quit

Perhaps one of the more under estimated decisions related to your retirement is knowing when you should quit working.  People often just assume that once you have the money you will just instantly leave work the next day.  Often this isn’t the case as money is only one part of your retirement.

Other equally valid factors to consider include:

  • Health: Are you in good health when you retire?  Or is poor health causing your problems at work? Do you have a condition that makes your work benefits especially useful?  Or in the US, do you have affordable health insurance?
  • Friends:  Do you have any retired friends?  Would you be the first to leave work?  Are you ready to make new friends if need be?
  • Family:  Is your spouse ready to retire as well?  Do your children or grandchildren really need your help right now?
  • Career: Are you ready to leave work?  Are you happy with where you will leave things?  Or is there a project you want to see get finished?
  • Hobbies:  Are you starting a new hobby or just doing more of the old ones?  Do you have all the equipment for your hobby?  Do you want to try a few more hobbies before you have a reduced cash flow?

Yet despite all the factors in the world there will be just one question that will matter most: do you feel ready to retire? Notice I didn’t ask what you think, but rather what you feel.  What is your gut telling you about this?  If you feel a little nervous but still excited, it likely is a good choice.  Yet on the other hand if you feel very nervous about it, you might want to wait a little while longer or perhaps cut back on working a slip into retirement more slowly.

Leaving work is a big decision so cut yourself some slack over worrying a bit about things.  You are allowed that as long as you keep it reasonable.  For example, worrying about investment returns for the next 20 years is worthless, but worrying about your asset allocation might be worth a second opinion.  Focus on what you can control and plan for and let go of the rest.

Then one day you will wake up and realize with a fair amount of certainty: it is time to quit.  That is when you know you are making the right choice as the doubt and the guilt vanish and you push into retirement with a big smile on your face.

So how do you think you will know when it is time to quit?  Will you just follow the plan or perhaps just make it up as you go?

2 thoughts on “Knowing When to Quit”

  1. I will address the 5 issues you raised in your post and add a few more of my own. I retired in late 2008 at age 45.

    Health: I am in good health but needed to find a reasonably affordable individual health insurance plan which would fit into my retirement budget. I found one although its premium went up 20% in 2010. Also, I made sure to get some costly dental work done in 2007 and 2008 before I lost that coverage in 2009.

    Friends: I don’t have any retired friends but many people in one of my hobbies are retired, so I fit in just fine with them. I did not hang out much with my coworkers so I don’t miss seeing them.

    Family: I am single and have no children. My ladyfriend lives nearby. So does my dad (my mom is deceased) who has been retired since 1994. Being retired makes it easier to see him.

    Career: I was working part-time for the last 7 years, the last 17 months only 2 days a week. So it was not a big transition to working zero days a week. Working had become a nuisance, getting in the way of the other 5 days I was not working. I was working on one big project in the last 2 years so I wanted to get my part of it done before I left. I made it by 45 minutes on my last day! I had also done some other things to automate some processes better because another coworker who did them had left the company 4 months before I did.

    Hobbies: Being retired enabled me to increase the number of evenings I could do my dancing hobby. It also enabled me to more easily schedule my midday, weekday volunteer work (something you should have listed with Hobbies).


    Just being sick of the long, tiring, awful commute to my office, even as little as 2 days a week, was my biggest reason for retiring. In my last few years of working, I asked myself every day, “Why am I still working here?” The worst two days of the week were those I worked. The worst 2.5 hours of those days was the round-trip commute on the trains.

    I was ready to retire. I couldn’t wait to retire.

  2. yes retirement is not all about money, but when it comes to the money part, I have two ways to figure out if it is time,

    stash away 100% of your employment income in a high interest savings account and see if you can live off your investments,

    if you can get your expenses down to 3% of your net assets:

    if you can do both of these, and you want to quit go for it. Then again, don’t quit, try to get laid off so you can cash in on some severance pay.

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