When I Retire I Will…

I was about three years old and my dad scared the hell out of me. It was the first day of Yellow Duck nursery school. I had never been to school before. I vaguely remember being upset about it. Perhaps crying.

My dad said, “first you’ll have two years of nursery school, then a year of kindergarten, then 12 years of regular school, then 4 years of college, maybe another 4 years of graduate school, then 40 years of work, then when you are old as grandpa you’ll be right back where you are now.”

(and this is all one gets?)

I was thinking, “Holy shit, this sounds pretty bad.”

No I wasn’t. I didn’t know that word then.

But I was thinking something along the lines of “Grandpa is pretty old. This sounds really really unpleasant.” I didn’t cry anymore. I had to go to school. The occasional bad thing happened at nursery school but that can be expected.

But it never escaped me, “wow, it’s a long time until I’m going to be happy again.”

I think my dad might’ve also said something, “in 60 years you can relax again” or something like that. I was three years old but I felt the unbearable burden of what it would take to become an old man. An endlesss array of tomorrows crushing me with their necessities. Even then I couldn’t figure out how I would be able to carry one treacherous burden after another, crushing the music out of me. Because the truth any three year old knows is that old men can’t dance and that you have to be completely insane to work that hard for that many years. I was being pushed out the door into a maze of lies and insanity and it was going to last for sixty years unless I died first. Nights would only be small pauses where cruelties and other insults against my soul and body would add up until finally, retired, I would be a rotted away version of my three year old self.

I decided at three I needed to retire immediately. But when you still shit in your pants, at three or at ninety, other people have control over your life. And they want you out the door, pronto!

I hear a lot of people say, “When I retire I will…”

Then they make their list. Here’s a sample list:

  • “When I retire I will write a novel.”
  • “When I retire I will hang out with friends more. People I like instead of clients or work colleagues.”
  • “When I retire I will do stand-up comedy”
  • “When I retire I will travel more.”
  • “When I retire I will exercise more so I can stay in shape later in life.”
  • “When I retire I will get really good at something – like golf, or piano, or maybe even tango dancing.”
  • “When I retire I will spend more time with my kids.”
  • “When I retire I will meditate and try to find inner peace.”
  • “When I retire I will read more books about the Civil War and really brush up on my history.”
  • “When I retire I’m never going to talk to all of these crappy people again that I have to talk to every day now.”
  • “When I retire I will be happy”


I didn’t have that list when I was three years old, but I definitely thought to myself: “I’m in prison for the next 60 years.” Or maybe my dad said that. I forget.

But I definitely knew that the fairy tales were over. That Santa Claus was dead. That poetry (even Mother Goose) was now silenced, as I climbed in the bus and a Ku Klux Klan of three year old faces in hoods stared back at me.

If I couldn’t retire at three I had to at least pretend. And I’ve pretended ever since.

So I’m going to make my list (it’s very similar to the above list) and I’m going to take out the words “When I retire”.

Now, how can you do it? What if you have a 9-6 job? What if you have to take care of kids before and after (and maybe during).

Well, then its harder.

But let’s think of the things that are NOT on that list that most people do right now that can be easily avoidiable:

  • I didn’t say “When I retire I’m going to watch a lot more prime time TV every night.”
  • Or, “when I retire I’m going to spend a lot of my spare time kissing up to people.”
  • Or, “when I retire I’m going to eat junk food all day long and read three newspapers a day and spend time gossiping with people about Kim Kardashian all day long.”
  • Or, “when I retire I’d really like to get revenge on this list of ten people I hold grudges against”
  • Or, “I really hope when I retire I finally get that promotion I deserved for thirty years.”
  • Or finally, “When I retire I really hope I spend at least an hour a day worried about money”.

(Kim Kardashian takes up too much of my time each day)


Nobody says these things about when they retire.

And yet all of the above things take time. For instance, I’m imagining right now the kind of revenge I’d like to do against a specific person who has wronged me. I see myself following him to work and then bashing him in the crotch with a baseball bat. That took a bit of time and energy to think that. What a waste! Am I going to be sitting around when I’m retired doing all of that imagining while I’m sitting on the Hudson River looking at the trees?

It also takes a lot of time gossiping about Kim Kardashian with co-workers. I have probably spent a half hour in the past day thinking about whether or not her marriage was a fake, should the E channel cancel her shows, why are people so obsessed with her (including me), etc. That takes away quality time.

So here’s the challenge (if you can, do it right now. Take out a little pad, write these things down. Trust me. It will feel good. I just did it myself):

  1. Make the list of things you want to do when you retire. Start each item with “When I retire I will…”
  2. Take away the words “When I retire” from each item.
  3. Now make the list of things you do now that you definitely WILL NOT do when you retire.
  4. Add up how much time you would have per day if you stopped doing the things you list in #3. Obviously some things you can’t avoid: you have to commute. But while you are commuting you don’t have to listen or read the newspaper, for instance.
  5. Start doing, each week, the items on your list of things you would do if you retired right now. Even if you love what you do right now, and you love every minute of it, you can still take out the things you would never do if you were retired and replace them with some of the things you love to do.

In effect, you are practicing retirement. Don’t say you “can’t” do any of these things. If you can do them when you are 70 you can certainly do them when you are 40 (unless you say, “When I retire I will go on dialysis”). There really are no excuses. Time is not an excuse because of #4. The time we spent judging, grudging, gossiping, envying, kissing up, indulging (pop culture, snacks, news, post-work drinking, etc) adds up. Even if it adds up to just two hours a week (by the way, it adds up to much more than that), that’s enough time to take a piano lesson and tuck your kids into bed.

There’s really no excuses.

Then it turns out the word “retirement” is wrong. You aren’t “Re” getting “tired”. You’re not old. You’re getting re-energized.

There’s an added benefit. When you start doing the things that re-energize you, you might find that you don’t want to “retire” anymore. Job and career and health might get better. Passions and work might merge. There’s still some poetry left. There’s still dance in your legs. Not every day is a juicer squeezing away the truth.

You might get those promotions. You might start that business (because you are practicing exploring your passions). You might find your true love (tango classes could do that). Life will get better.

When I “graduated” Yellow Duck Nursery School I remember very clearly the present my parents got me. It was a Hot Wheels toy car. It was colored orange on the outside and purple on the inside. The doors could open and shut and when I ran the car along the floor it went smooth and straight. When I’m 90 years old I’m going to get a car just like it. And I will ride away into the sunset, where my dead grandparents are waiting for me.


See Also, “Ten Reasons You Should Quit Your Job RIGHT NOW”


  • You make a very good point Purvi. The best way to have more money is to spend less of the cash you already have in the bank. Saving money, as well as time, allows you to enjoy the true pleasures in life – exploring your inner happiness, spending time with the people who love you, being there for the people who depend on you. Congrats on your semi-retirement. 

  • One morning just after 5:00 am I was half-asleep while commuting  to work.  Driving past the California Lottery billboard I was jolted back to reality by its neon glow.  I was on the wrong road heading toward the border with Mexico.  How did that happen?

    Later that evening I was sitting on the couch with my wife watching a Seinfeld rerun when the lottery drawing appeared on the screen.  The bobbling balls retriggered that early morning mesmerization and I mindlessly asked her, “What would you want to do if we won the lottery.  If money were no object.”

    She answered the question.  Turns out our answers weren’t all that different. Not surprisingly it involved taking a long drive south.  Once we had a goal, making it a reality was no longer an option.  We began saving like mad, quit our jobs and a few years later headed out on the adventure of a lifetime.  I was 32. 

    That was twelve years ago.  Since then we’ve lived life as if we were retired.  That’s not to say that we haven’t worked.  We have.  Harder than ever before.  But since then we’ve always been the drivers of our own work. 

    And since then we’ve learned that when we are half-asleep and make what at-first-glance appears to be a mindless wrong turn, we should trust the signs. 

    • VW, I like that: you are “drives of our own work”. So many people think that’s impossible.  And yet the tide has come in on corporate America and everyone is standing around naked. Without taking charge of your time, your money, your career, your life, you lose track of what’s important and the next thing you know – the music is gone. 

      You didn’t take the easy way out. You focused on your goals, stuck with it, made them happen. That’s the way to do it. It’s not “Law of Attraction”. It’s committment, confidence, and creation like the gods of our lives that we truly are. 

      • Anonymous

        all very awesome and inspiring, so much so that I linked it to forum.earlyretirementextreme.com an online super early retirement community I’m apart of that’s made me realize it’s possible to retire well before I’m too old to enjoy it. while I squirrel away money, I am indeed “practicing” my retirement. I’ve written a manuscript, I’m getting some short stories published, and I’m working on a webseries. I’m also taking stand up comedy classes!

        when you practice retirement, you also begin to realize that it’s a very good idea to do all this practice (training, prep work, networking…) now when you have the money and energy, so when the time comes you can dive right into your retirement successfully!

    • Anonymous


      thank you for sharing your inspiring story. James, as always thank you for setting the forum for healthy discussion. This is something lacking in our media and daily interactions. I  had success at a young age as an equities trader  and team leader. Every few years I would burn out and have a continual feeling of lack. I then began to meditate, study film, learn a martial art, and volunteer. At 45 I went back to school to earn a second masters; in public policy. I thrived and helped to solve or ameliorate pressing social problems. Now, having just turned 50, with less money and career prospects in public policy dim, I have to reorient myself. I commit myself to “The Practice.” I meditate twice a day and understand that our minds have unlimited potential. There needs to be a shift from a place of lack to one of abundance. Thank you to everyone who contributes. It all seems to come from an authentic place. We are all interconnected in our array of experiences, even though we often feel displaced or isolated. James, I read your blog and books. We need more hope, reality, and compassion. You are fostering a community of truth seekers who have the courage to face the darkness and embrace the light.

    • Roy

      Great website you guys have….you should have a blog as well to update your readers =)

      Also…the link to your book (kindle version) is broken.

      Your site doesnt have a contact link…

      Have fun

    • Anonymous

      Tony Robbins told a story in one of his books about walking along the beach at his Fijian Resort with one of his employees.  He turned to this employee and said something along the lines that it took him “x” amount of years…”x” amount of money…etc, etc… to be able to walk that beach that day in paradise.

      And the employee, who probably did not have a dime to his name, turned and said that he has done this his entire life.  

      Hmmmm…something to be learned by that story.

      I applaud VW and his wife for taking control of their lives…and I applaud you James for continuing to one-up yourself with each and every post.

  • Heyitsminic

    With the situation I m in today, I do not see myself retiring :(

  • I love this, James! Thank you – “An endlesss array of tomorrows crushing me with their necessities.”  That seems to distill the feelings of unwanted obligations!

  • Gezz_wezz

    James… how about writing a post about how do you plan to retire?

  • Anonymous

    James, your writing inspires me daily.  I’m making my lists of ideas, working on my own Daily Practice, and doing a bit of writing of my own again, though this time just for myself, just for the sheer fun of it, no expectations.  No drastic changes in life yet but I definitely feel better inside my own head.  Don’t know from whence within the zeitgeist you have sprung but I sure am glad you did!

  • To be totally honest I never think about retiring, I don’t think it’s in the cards for me. I’m working hard to change how I live and that’s my only goal right now.

    Maybe when all the changes are made, my life might look like retirement to someone else but I can’t imagine not working at something.

    • I think the idea is to slowly eliminate the things you might not like about work and keep adding NOW the things you would do (or previously thought you would do) “if you were to retire”. 

      • Yes, and that is what I am doing in my life right now, (in my case -my life at work and personal life are pretty melded together ), therefore I am working on all aspects concurrently.

        And right now I am at the office to get some work to do tonight because I don’t feel like doing it right now.  :)

  • Telecommuting would be helpful to achieve all that. You would take back 1-2 hours per working day. 

  • Anonymous

    uh oh. the only thing on my retirement list so far is: start using illegal drugs. 

    • why not grow also? ….that way you’ll know it’s organic.

      • Anonymous

        I can’t imagine how difficult it would be to conceal a grove of MDMA trees…

        • lol ..  I was thinking a much simpler garden. 

          I can see your point…. :)

  • busybee2

    “Dance like no ones watching!”  I spend half my waking time plotting out the next fun thing I’m going to do.  I need to make a list of the cool things I have done, because it’s a good one.  My bucket list is long and getting longer each day, because I can always come up with more things I want to do.  I just found your blog a couple days ago and I’ve been enjoying it.  P.S….. You are quite funny and you should go do the stand up comic thing.  Don’t keep putting it off.

  • wsc

    james, hope you are doing well.  i just read the piece on you in Businessweek.  Roben did a good job.  in case i don’t have a chance to comment again soon have a great thanksgiving!

  • I’m laughing…sitting on a company conference call with a plan specialist going through our “retirement plan options” ….and reading your blog. You’d be better giving the talk than this guy on the phone, it’s amazing how many of my colleagues don’t contribute to retirement account (with a great matching program). OH  wait, I know why, the guy talking about “retirement” is talking about re-tiring, not re-energizing. If he framed it the latter way, like you do, I’d bet more people would be engaged in the plan (and his presentation).

  • Mac

    An inspiring post, James. You made a comment in your response to a post above: “…like the Gods of our lives that we truly are.” That’s such an important point that I think most people miss completely — stumbling through life in a comatose state.

    For those people stuck in jobs that they hate — perhaps the majority of people who work for somebody else — it’s easy to feel controlled, trapped, and without any other option in life. I’ve know plenty of these folks — often they’re driving new/recent model cars, have the latest i-gadgets, premium cable channels, and not a penny in the bank. Yes, they are slaves to their jobs and their bosses because they must keep paying those bills. If they would wake the hell up and reduce all their debt (bankruptcy might be a good option, it seems to have worked out for Freddie and Fanny), they might find themselves in a position where they can get up and walk out the door of a job that treats them like the slave that they are agreeing to be.

  • Inspiring post. Just last night I spent all night awake planing my revenge to someone who did me wrong, I usually feel the urge to win all the time in the end it was all a waste of time and energy. Thanks for this, I needed this remainder.

  • Guest

    The way you phrased this really struck a chord, and I have had most of these things go well for me for most of my career (I’ve had my own business for many years, but not currently).  Thanks so much for writing this as a ‘reminder’!  Maybe it’s time for a change.

  • I love this article. This is my story. I started working at 11 years old with a paper route. Went to a hard prep school and then college. Worked my butt off. Then went to law school and worked my butt off again, and worked a 40 plus hour job on the side. Then took the bar (another bar to jump over), then got a job in a big Philadelphia law firm, making tons of money working long hours. That lasted about 3 and one-half years and I was sick of it. Hated it. Hated the law. Hated the big city. Hated everything including myself. So I quit! I literally tossed my wing tips over the Benjamin Franklin Bridge and I drove out west with my then-girlfriend (now wife) and lived in  a tiny town (pop. 502!) growing herbs for a summer. Best summer of my life. (The OJ trial was on TV, I watched all of it). I did go back to the law (legal aid). And I am still a lawyer today. Reasonable hours. I reject a lot of clients. Make a decent buck but not a killing. But quitting taught me that there are alternatives.

    If someone is reading this, and you hate your life, please make a change. Quit. Move on. Try something else. You got one life to live, and before you know it you will be dead. 

    James, thanks for another great article (and say hi to Tasso if you see him).

    John (another lawyer from Scranton, PA).

  • Anonymous

    Ha! You oughta try 12 hour shifts in a factory, throwing 35 pd boxes around all day. Sometimes 60 hrs a week. Then a 40 minute commute each way. I’m stuck until I get this place sold but in the meantime it sucks. The idea of writing a novel or travelling is pure fantasy. I barely have the time or energy to do my dishes. This kind of advice is great for you white collar types, but us working stiffs are usually stuck in place by forces most of you can’t even grasp.

    • Mohammed

      Dear MarkW99,

      some of us have been where you are now.

      but ask yourself….is this all there is…..?

      are there other options in life?

      I believe there are always doors that can open…only if we look…there is always a solution to our “problems”

      I have been reading “The Magic of Thinking Big” by Dr. David Schwartz.

      He talks about how many people suffer from “excusititis” 

      The brain likes to make excuses….because then it doesn’t have to put any effort to come up with solutions.

      So let me ask you….

      1) is it posssible to look for another job? have you looked?
      2)is it possible to move to a different city for a better job? have you looked at other places?
      3) is it possible to use some of your current skill sets to do some freelance work and make the same amount of salary you have now?
      4) Do you have an idea that can be licensed? read stephen key’s book on this: http://amzn.to/utGLUU
      5) Do you have a few like minded people around you where you can start a business…use http://www.meetup.com to find like minded people in your area on any topic
      6) Do you read books or listen to audios that empower you? or do you watch tv? If you think you have no time to read books…try reading on your commute. And I know you are tired on your way back home…so read on your way to work in the morning when you are fresh. Did you know stephen king used to write his first novel on his lunch breaks while working as a school teacher. did you know the director james cameron was a truck driver? my point is no one was born successful….they set a goal….took actions towards it….believe they could do it…and they reached their goal.

      I wish you you nothing but success Mark

    • What are you selling, your home or business? 

      You sound like a person who could start a Cross-Fit gym and make a small fortune. 

      Good luck to you. 

      • Anonymous

        My point was that a lot of advice out there (even James does this) is directed at people with resources, like time or money. Yes, I’ve looked for other employment. They look at your last position and pigeon hole you. VERY important advice nobody gives – don’t take a job that’s a step down or in a field you’re not interested in working in and definitely don’t stay there for 4 years even if it’s all you can find at the time. I have a degree, done some interesting things, even had my name on an office door once and none of that matters now. And I’m actually not completely unhappy at my present job – the pay is tolerable and the benefits quite good. It’s just not going anywhere. Ever. And somewhere along the way I’ve decided it will be my last one come hell or high water. Don’t want or need another in this lifetime. Dunno where I’m going from here, but when this place sells I might walk away with as much as 40k. I’ll sell crack if I have to.

        James’ “There are really no excuses” line just threw me a bit. Yes, actually, there are. I’ve got 2 kids I like to see when I can, a time consuming physically demanding job, an ex wife, child support payments and I’m trying to sell a house. I won’t be learning to tango anytime soon.

        (And I don’t have TV except to watch DVDs on. I’m not here enough to pay $39/mo for crap I don’t have time to watch.)

        • Believe it or not- I understand. 17 years of child support, that was while we were having our own children, plus recently age discrimination for my Husband (that’s another pigeon hole with no escape) and we tried to sell our house for 14 months prior to handing it back to the bank. 

          We had to save our business, instead of the house, because that’s the revenue stream, or trickle, depending on the economy.

          We live in my mother’s basement. I have very little free time, and not much money.  But I still find awesome nuggets of advice on James’s blog.

          I do recognize a relentless reference to money and wealth – but knowing that money is James business and his history, I think that’s to be expected. He has children and child support I am sure..

          I enjoy the honesty in your comments, have a great day!  Or just pretend it’s a great day – that’s what I do sometimes.  :)

  • Roy

    Hi Purvi…

    I am very curious to know what business you bought? =)

    Success stories like yours inspire me…

    • Hi Roy.

      I bought a small web based business. It’s a membership site in a particular niche. I started a bunch of web based dating sites years ago and am a big fan of the recurring revenue model.

      I was trying to start something but most start-ups fail so I thought why not buy something proven and grow it. I’m a marketing exec so that’s what I do anyway for companies.But I was tired of dealing with corporate BS and politics I thought so why not buy something for myself to grow the way I would in a job.

      It’s important to perform a lot of due diligence in a transaction like this. I had several deals on the table that I had to walk away from before I found the right one.

      I think more people should look at buying an established business. Web businesses are great but so are brick and mortar businesses. These more traditional businesses can get bank or owner financing so you can use the cash flow from the business to pay for the asset. Also, I think many local businesses don’t understand the power of the web, blogging, social media, etc to drive revenue. Someone who really understands these things can crush their competition because they simply deliver more value to the market. I’m a big fan of the Inbound Marketing model advocated by HubSpot.

      Hope this helps and good luck to you.

      • Roy

        Thanks awesome….Thanks for sharing =)

  • 23mapper

    This is one of the most practical articles I have ever read in a very long time, thanks.

  • When I retire I am going to:

    Laugh. A lot.

    I think I’m pretty lucky. I’m doing these things now.

  • Today my manager told me I was slacking at work, which I rejected 100% in his face. Please don’t tell me i am slacking after i spent my PTO responding work emails. That’s just total bullshit. For a few hours, I felt I was totally wronged. But he is a good guy, I am very sure he is under a ton of stress, I feel his pain so I let it go. 

    But it made me thinking … this fucking world man, too few people are happy, everybody is stressed out by something, few people knows what they REALLY want, Do people even know what they want to do when they retire? Most people are living as if death does not apply to them, as if they have unlimited amount of time on this planet, and yet everybody is living in fear, everybody is so fucking afraid of something, real or imaginary, that they cannot smell the grass, enjoy the beauty of the world, be creative, and be kind. 

    Work is not getting done on time, what a big fucking deal!

    The disease fucking contagious. It only takes is ONE unhappy person to spread it.

    Thank you for the daily inspiration man, I don’t know how you can pull one out EVERYDAY, you are the best! 

    It’s amazing you can even remember things when you were 3. the earliest i can remember is my 5th birthday :)

  • Excellent website. Lots of useful information here. I am sending it to a few friends ans also sharing in delicious. And obviously, thanks for your effort!

  • Gordonbrown11

    I want this toy car))essays

  • James,
    I discovered this blog by one of your guest posts about a month ago (btw…the guest post idea has really taken off for me! If you hadn’t shared the idea, I never would have researched it. I got my first guest post published today, with two more scheduled in the next two weeks).

    Anyway, it’s weird how signs start showing up all at once. I am not trying to be New Age on everyone, but I have gotten better at noticing when a message just insists on popping up over and over again. This article complements others’ work, like 4-Hour Work Week, which I discovered about six months. It never occurred to me that you can take control of your own life and it actually work.

    I have recently had a big divorce from a horrible boss (a board of elected officials), and i have made up my mind never to live like such a second-rate human being. At first, I feared losing my job, but now it has turned out to be the most liberating thing that has happened to me in a long time.

    I am writing a blog now, and I have a new job with a much better situation. I have decided to build some parameters and boundaries to keep the “crappy people” from influencing my day so much.
    Just thought I would share…Benji Battle http://www.benjibattle.com

  • I am semi-retired now. It came about a few years ago when someone on twitter asked, “What would you do if money was no object?” I wrote down several things and realized – I could afford to do exactly that right now – teach a little, write a lot, travel. So, I quit my job. It takes me about 18 hours of work a month to cover my bills. After that, I just do what I want. I don’t have the biggest house or newest car, but I am writing this in my sunny office, downstairs in a town house by the beach. One of the secrets to retiring early is to cut back on the stuff you think you have to buy.

  • I’m just 24, and might have a different perspective in life than you James; thought I would share. Just graduated from college (sry James!). Just started working. I retweeted this post no 20 nov 2011 and saw it now. I just read it again. This time i made my list (pasted from notepad):

    when i retire i will still love the person i married to, and feel that it was the right decision, that we respect and love each other, that we had similar goals in life and shared passions.

    when i retire i will feel satisfied that i gave as much as i could to my family
    when i retire i will still be happywhen i retire i want to look back at my life and feel satisfied/proud of what i did

    when i retire i will have i met all the goals i had in life: be financially free (not necessarilly super rich), have helped my family in times of troubles (always being there for them), live with peace, and zero negativity.

    when i retire i’d like to look back at the years and know i did all what i proposed myself to do, that I ‘saved a life’ several times, that I gave the most I could to the people around me

    when i retire i will think that i did live my life believing in something, and that every day of my life was worth living.

    • oh i forgot a last one. When i retire i hope i will be able to understand the contents of James’ best bestseller ;)