The Ultimate Guide To Your 20s, 30s, 40s, And 50s

The Twenties

My twenties were the absolute worst.

Everything was supposed to be exciting. I was finally free from the cage. No more parents and teachers. I could take off my clothes in front of other people (with their permission). I could get a job.

I could fulfill all my dreams.

But nothing worked. Because people in their twenties generally are not good at anything.

I learned so little in college (I majored in computer programming but then had to take remedial computer programming classes when I finally got a job) that I suddenly realized how worthless the four years were. Actually they had negative worth because of the debt.

Also, in my twenties I thought I was in a rush. I had to "succeed" and "find my passion."

In my twenties, someone told me, "time is money." That's why missed "opportunity" has a "cost."

"Opportunity cost" is a phrase taught in every Economics class in college. Nobody ever uses Economics ever again after college. I minored in Economics.

Time is not money.

Money I can certainly lose, but I can also make.

I can't make any time. There's no time...machine (I really could not put those two words completely together) that just spits out more time if I put in a five dollar bill.

Money buys me food to put in my mouth. Time is everything else.

In my twenties I was not good at anything. But I thought I was. Because when I was in my twenties I was also stupid.

But that's OK. In my twenties I picked a few things that I did over and over again, thinking I was good at them. Writing, computer programming, and when I had permission - taking off my clothes in front of another person.

I was good at none of these things. But I got a little better maybe at one or two because of blind repetition.


I wish I had just done this: pick three to five things and do them over and over. Only pick things you wouldn't mind doing over and over.

Don't push for any one outcome. Just do things over and over with no expectation.

That's all I had to do.

The Thirties

The thirties really suck.

"Owning a home" is the "college" of the thirties. A 15 trillion dollar mortgage industry hypnotizes society into thinking that "owning a home is a smart investment" or you "need roots."

Owning a home traps you in one place, causes a lot of suicides and takes all of your money.

In my thirties I was getting tired of doing things over and over again.

I felt like I had to be "done." Or "almost there." Or "on the right track."

In my thirties I learned how to fail.

In my twenties I couldn't fail. Everyone else was too "stupid." I just had to try more and more.

But in my thirties I realized I was the common denominator of all the people I thought were stupid.

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In my thirties I finally learned that I was only as good as the people around me. That my value was the added up value of the people around me.

In my thirties I realized there was no such thing as one passion. That you had to pursue many things. That you had to pursue things that created happiness for other people.


If you hung out with good people, and did things that created value for others, and diversified the things you did, then ONE thing will work out.

Sometimes two.

The Forties 

Ugh. The forties suck really bad. They suck shit.

For one thing, you can't eat anymore. And you can't have any stress.

Food + Stress = Aging.

Of course you have to eat. But half of what you used to. And stress will happen. But you have to mostly ignore it or it will kill you.

You eat less by doing what you love. Then you won't sublimate your desires by eating more.

You have less stress by owning fewer things.

In my twenties, thirties, and forties, I have been consistently stupid on relationships, parenting, communication with others, risk-taking, and most other things.

But I don't care anymore. Awareness is better than caring.


In my twenties I thought I knew what I was doing.
In my thirties I would do anything to make money.
In my forties I only do what I love doing.

You find what you love by going back to what you loved in your twenties and keeping expectations low.

The Fifties

A woman once brought her son to Gandhi and said, "Gandhi, can you please tell me son to stop eating sugar."

Gandhi said, "Come back in two weeks."

The woman took her son home, hundreds of miles away. She came back in two weeks.

Gandhi said to her son, "Don't eat sugar."

The woman said. "Gandhi, why did you make me go all the way home and then come back two weeks later. Why didn't you just say that then?"

Gandhi said, "Before I could tell your son to stop eating sugar, I had to stop eating sugar."


The fifties. Come back in two years.

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  • I’m only halfway through my 30s but this is making me feel better about my own life. Not sure that was your intent James…

  • Grant Hall

    Could you elaborate on what you mean by

    “You eat less by doing what you love. Then you won’t sublimate your desires by eating more.”

    It’s a super interesting line. What does it mean exactly?

    • He’s referring to (I think) the idea that by your 40s’ you’ve likely discovered what you love to do- and if you really love to do something, it often takes precedence over filling your stomach…eating too much causes a person to become lazy, a satiated stomach tells the brain that survival is guaranteed and as a result the mind tends to kind of switch off creativity- since we are cognitive misers (as Ramit Sethi puts it). For example, fasting helps neurons in the mind expand, putting us into a slightly survival mode and making us more creative as a result.

    • Diana Matic

      When you do what you love, you stop self-medicating yourself – with food, with alcohol, with drugs, with sex.. whatever it is you default to (learnt behaviours/coping strategies) in times of worry, stress, anxiety, when you dont like yourself, lack of confidence..etc..

    • Southern Man

      I see it as, when people are miserable they do things like overeat or eat junk to make themselves ‘feel better’.

  • Sohel Bhuiyan

    James the incident of sugar eating you have cited, that is of Prophet Muhammad’s, not Gandhi’s.

    • Newbie

      Are you sure because I never heard of that. Anyways, the idea is what matters not the person

      • Sohel Bhuiyan

        Yes, I am sure. I know, what was said matters more than who said it. But established culture says, citing correct reference matters too, because it augments the credibility of what was said. “Brand” matters,
        I guess.

    • Ashfaq Ali Khan

      Sugar (Indian Khaand) was probably not in use in Arabian peninsula in times of Holy Prophet(PBUH). Secondly it doesn’t reflect to be of the Prophet’s personality.

  • jkenn

    So, basically, your life has completely sucked!

  • Newbie

    Enjoyed reading it. Thank you for being honest and trying to transfer your experience to others

  • Finola Howard

    Brilliant – loved it – you’re a year ahead of me – looking forward to finding out how the 50’s work out :)

  • Great article James. I found your book right as I made my shift into being Self-Employed. It spoke to me.

    As of 22 years old I am at this time not working a job.

  • HotmESQ

    I don’t know what you said about 20s-40s (wink), but the end of this article is cluuuuuuutch! LOLLLLLLL

  • Tom Jackson

    Stop eating sugar…

  • Aaron Pearson

    Just hit 26 last week and this was spot on. I think I know what I’m good at, but probably not. However, I do get to do exactly what I want every day and love it!

  • kendisqus

    Look, I really am stupid. What is ‘TL;DR’?

    • “Too long; didn’t read” – in other words, the “TL;DR” version of a story is the summarized version. It’s a relatively new-ish member of abbreviations used on the internet lol

      • Ana Roberta Oliveira

        Thank you, metaliz! I’m glad kendisqus asked,… thought I was the only one to not know what the expression meant.

        • rocoach

          Google search is your friend too

          • Ana Roberta Oliveira

            Rocoach, google is not my friend, it a body part! You see, it was the first time I had hit the expression, but the article was so good I didn’t want to waste the seconds looking for its meaning. Lazy me.

      • Anjana Banerjee

        Got it “Cliffs Notes” I like it.

    • Doski

      Short hand for “Cliff Notes” or “Abridged Version”.

  • Great article as always, James!

  • My fifties sucked big time. It’s when I got a sliding hiatus hernia, fired my CEO and then lost control of my company. But it’s OK because I’ve just been told that my sixties are going to be my best time yet.

    My lovely mum once told me “the most dangerous people in the world are those who think they know what’s best for you”. I haven’t found out if she was right yet.

    I stopped eating chocolate for 2 years in my late fifties. Perhaps that’s also why it sucked.

  • David Allan

    Enjoyed your segment on the Book To Course Summit. You were one of the nagging voices in the back of my mind that drove me give up my “jobs” and hit the road, lead a self-directed career, and start a podcast. Thanks. Would love to have you as a guest sometime from wherever you land that week:)

  • JenSmith

    Holy crapoly. You nailed this at the precise moment this is happening in my life. I was in my 40 ‘ s, I know stuff stage thinking I should share my hard knocks wisdom with the world, when I was hit with the notion, “first, go clean your basement. ” Thanks for being you and sharing so openly. Gives a girl hope.

  • Southern Man

    James, are you sure you’re not slipping toward depression? This sounds very pessimistic.

  • Chris Pillsbury

    The 50s (I am 63):
    Get rid of almost everything you own. If you have debt, sell it and use the money towards your debt. If you have no debt, give it all away. If you own a house, sell it or rent it out. Now you are free. Pick a “developing” country that makes you curious and go there for 3 months. (If you have no money you can teach English.) Now you have the space to begin to realize what you really want for your life. With the medical care coming up, you’re only about half way through. In your 50s you can get rid of all your mental boundaries. You can do anything you want. Really. Be courageous; the hardest part is making the decision.

    • Mia

      Chris just sent you a friend request. I’m 51. Getting rid of stuff and about to rent my house ;D

      • Chris Pillsbury

        G4U! I think you will be glad you did. ;)

    • Chas

      I’ve been thinking about doing just that, living in a “developing” country and teaching English. Most people I’ve said that to think I’m crazy (“WHAT! At YOUR age? You can’t do that! Why would you WANT to?”).

      Thanks for saying it, and helping me to believe I’m not crazy. :)

      • Chris Pillsbury

        It all depends on how you define crazy. Maybe you’d be crazy not to? Maybe they are crazy because they think that what’s right for their life should be right for yours? Or maybe they are just afraid and you are able to imagine. ;)

    • Neal Pritchett

      If you want to teach proper English in a developing country, try the inner city of any large metro area in the US.

      • Chris Pillsbury

        Lol, I hear you. I suggest that someone who just wants to teach English, contact your local literacy council or You won’t get paid, however, so if funding international travel is the goal, teaching in the U.S. is not the solution.

    • This is awesome! I’d no idea how universal these concepts can be. I’m 57, and like James says in the 40’s, “You find what you love by going back to what you loved in your twenties and keeping expectations low.” I’ve totally done that and yet at the same time am kicking myself for not sticking with it through the 30’s and 40’s. I guess that’s the “… keeping expectations low,” part of it. Loving yourself and other from where you are. Forgiving yourself and others. Getting freed up by letting go of material things by letting go of pain and resentment (that can be the biggest part of letting go. The ex … really stretches the ability to forgive!). So, what you wrote about giving it away, I have! Or am constantly in the process. And I have no debt. I drive an old, free car because I don’t care. I don’t care!! Thank you! You’ve got me inspired to keep on going. To do what I love. Artistic endeavors btw. And … to … be … courageous!

  • Wayne Nef

    I just turned fifty in February. Here is my advice: It’s a short blog post.

  • Thank you James for another insightful article I read all of your posts from top to bottom? My 20s was all about graduating from college launching a career but I never thought about buying a home. Still don’t but you’re right it’s time to live free with minimal commitments????

  • John

    You don’t need advice, James, you’re going to be fine. All the comments here show how many people are positively affected by your work. Your 50’s will be your best decade. You show yourself, faults and all, to the whole world, which is both endearing and unprecedented. Your followers won’t let you have a bad decade.

  • Michael

    Your 50’s, the enlightenment decade! Three things to do!
    I found that my desires changed, it use to be high income high wealth, but after a couple of divorces and having to start again, you realize money ain’t it! Quantity of life is OK when you are young, but now my focus is on quality of life, and I agree with Chris Pillsbury, sell everything and go find a developing country. Quality of life is better in developing countries – try Ecuador! That’s the first. The second, learn how to forgive, I mean really forgive, not just lip service, but from the heart! This helps get rid of stress! Third: get rid of the ego! This is probably the biggest enemy stopping you becoming you! The real you! Once you achieve these three steps you will be stress free!

    • Virginia

      Ecuador is on my bucket list for sure especially if things don’t change up here in the far north of Canada.

  • Sean Woodruff

    50’s – people you know and love start dying more frequently. You realize everything they ever worried about doesn’t matter to them anymore. You realize everything you’ve ever worried about shouldn’t matter like you thought it did. Today is really all you have so you might as well think and do fun things while laughing at the absurdity of it all.

  • Virg Lewis

    My 50’s were the least enjoyable time of my life so far (65 now). Health issues, leaving our home of 23 years, losing 2 more houses in bankruptcy, moving to 3 locations we didn’t like, loss of my Mom and second dog, and more. But we got through it and my husband and I are now enjoying our 60’s. Moved somewhere we like, traveling more, I’m publishing ebooks (under Virginia Reeves), Tom works part-time to stay in shape and get cash for our playtime. No matter your age, it’s your attitude and perseverance that keeps you up or down. There are hard times, it’s part of life and learning. But you can be happy with lots of ‘good stuff’ when you choose to be.

  • The 50s. You care less about everything. Friends die. You realize the generation ahead of you (moms and dads) are all dead and next it’s your generation. So you don’t give a shit about stupid stuff and care more about loving worthy humans.

    You spend more time on enjoying life and less time dealing with assholes. You turn into the guy that says whatever he wants and calls out the dopes in front of the whole neighborhood. And you like it.

    And don’t forget your knees — they’re not as young as they used to be so treat them kindly. They have to carry you another 50 years or so.

    • David Coleman

      Awesome 50s summation

    • Tootie Marcs

      exactly…and we are more confident with ourselves. We start to downsize the clutter ,and toxic friends. IMHO it’s family that truly matters. ANd yep we speak our mind and don’t take shit from anyone

    • Anjana Banerjee

      Yes, and don’t forget the hips.

  • Doski

    In your 50’s, assuming your brain is functional, you discover Just how much You DON”T Know and worse Why you don’t. Yup, all them folks you Idolized up through your 40’s were just as ignorant as you are now. It’s not their Fault that they couldn’t teach you that which they themselves didn’t know.

    This is when your Self-Searching and True enlightenment begins as long as you endeavor to Correct / Replace your bad Habits. There is no time left for Apathy or EGO enablement with Retirement on the near horizon. A Quick reflection on the “Accomplishments” of the previous 30 years should Scare the hell out of any sensible person as they recognize that without the Energy wasted in the past won’t be there for them in the future.

  • Ipek Uzpeder

    Thanx James, I loved it. Check this video “Success Stories Asia” and how Jack Ma summarizes 20s, 30s, 40s, 50s and 60s,

  • johnschonegevel

    As someone deep into his 50’s, the best for me has been to reprise the advice you give for people in their 30’s;

    ‘If you hung out with good people, and did things that created value for others, and diversified the things you did, then ONE thing will work out.

    Sometimes two.’

  • Katrina Lewis

    Just leave the past behind, but take away the lessons. LIve life, create wonderful memories, no more buying of “stuff” and revel in the joy of not caring anymore what people think about you, expect of you, learn to say no and play for your own team of you……. be you and surge forth with all the wisdom you have gleaned over the last 3 decades and breathe. Mostly just love and respect yourself and all else falls into place

  • Michael Terwindt

    At my uncles 50th birthday, I asked him what his grand advise was to me, in my 20’s at the time, what had he learned in his half century: he said ‘the older he gets, the less fucks he has to give’. It’s really about letting go. Something I’m trying to get to now, as I approach 30. There’s just not enough time to worry about anything.

    • CT

      Does it make sense to live as if we are 50 when we are 30? I suspect letting go is of benefit to the person who has, rather than person who does not yet have.

      • Michael Terwindt

        I think its almost impossible to ‘live as if I’m 50’. I won’t be able to do that until I’m 50. What I’m saying is that I don’t want to create more baggage in my 20’s, 30’s and 40’s; that I’ll then have to let go of later in life. I’ve got enough shit in my young life that I’m working to let go of now. I don’t want to increase the load over time, but decrease it instead.

        • Josh Harding

          I wonder sometimes if younger generations dont hit these milestones at an increasing rate due to technology and availability of advise online. I’m in my early 30’s and feel like i have the mindset of someone much later advanced. I wonder where we will be 20 years from now..

  • Gretchen Allison

    I think you’ve got this! “Choose yourself”, find something that feeds your soul, and give your time and energy (volunteer) to an organization that resonates with you.

  • Interesting shit

  • Boy I wish I had this list 20 years ago! Great insight and right on target. One of keys is to choose yourself and not rely upon “the man” (or woman) for your ability to create a living/income. Pick something and go! LightSparkMarketing

  • Rebecca Ruby

    I’m 52 now and I thought getting older would REALLY SUCK because of the way my parents and other relatives were aging. However, I’ve taken a different route most of my life (healthy food, no smoking, do things to dial down the stress as much as possible). What I have found, to my surprise is that I, happily don’t give a damn about the things that used to concern me in my 20s and 30s. I have found ways to forgive myself and others for mistakes and crappy behavior plus savor the lessons from those two decades and I now have a level of self worth and confidence that had eluded me until about 4 years ago. It does get better, you just have to grow into yourself and for some of us…it takes a LONG time but, it well worth the journey. Curiosity and a positive attitude are two of my most valuable tools in this life – even when things suck.

  • Dave Kidd

    Jeez, so far my fifties are about finding ways not to give a f@ck, stay independent and freelance, stay chilled, while trying to stay out of the system but earn a living at the same time. Not easy. Money needs pulls you into the system you wanna stay out of. Working on my creativity dreams and my musical dream. Whatever choices I make now (53) will condition my next 20 years. Last chance saloon !

  • jerry wexler

    I’m 72. My knees are getting bad. I still bike(recommendation of my Dr) and do leg extensions at the gym. It keeps me going. Don’t sit down. Ever. In your 50’s you can still do most whatever you have been doing, just a little less. Pretend you are still in your 20’s but don’t injure yourself. Use a hormone cream. Use ED pills. EXERCISE all the time. Eat food that works well for you, lots of veggies. Keep the company of great people and exclude those that make you feel bad. Drink a little craft beer and good wine from time to time. EXERCISE. Write. Read. Love. And above all…DO NOT THINK ABOUT YOUR AGE! (all the time) Read Altucher. He knows shit.

  • All this sounds so very true. 20s are when you look towards a great life ahead, 30s are when you start having doubts whether you will indeed have a great life ahead, 40s are when you are certain you won’t have a great life ahead, 50s are when you comfort yourself that your life has indeed been great, 60s and more are when you are not even sure of the life ahead. Excellent blog post capturing the nuances very beautifully.

  • Russell

    I’m 37 and 6 weeks ago I took redundancy. It wasn’t a huge amount of money around £13k. I worked in IT I sat in a seat staring at a monitor (which I’m sure has damaged the sight in my left eye) occasionally typing some inane data every now again and listening to my boss tell me how bad I was and how I was missing out on opportunities.

    The problem was I just couldn’t keep up the act. The act that Marlon Brando refers to here at 06:25. Marlon was real and he was brave enough to call out the bullshit and be what he believed in. He used his own thoughts and his own insights to question the heavily defended program everyone was following around him.

    At work I’d I’d sit and wait for 9 hours to leave. Throughout my jaw shut tight and tense. They had software that would measure how long it took me to take a piss and I’d be informed by management if I had exceed that allotted time in order for me to correct my behavior. I would look back at them thinking my god we’re bundles of divine conscious energy living on a giant living sphere flying through the universe at a million miles per hour.

    By the end I didn’t speak to people in there anymore I viewed them all as part of the problem. Why weren’t they thinking revolutionary thoughts like me, I viewed their ideas as just supporting the system I found myself in. They were weak and afraid like me and i saw that in them and I started to dislike it. This was bad and I was wrong to think that but I did. I was angry and depressed.

    I was the first out of that door everyday exactly as the second hand hit the hour. The money I earned was OK but it was just too much extra discomfort to consider leaving and finding a ‘new’ job. The problem was the new job wouldn’t be new it would be just the same as the job I was already doing. The job I hated and the job that was in absolute mental and physical terms, killing me. I’d drink lots of alcohol I’d some times take more than alcohol. I was destroying myself, I felt like I was just hanging on. I tested the edge like I wanted something bad to happen to me. It would be a way to get out, to destroy and start again, to let people know I was in a bad way. This wouldn’t be the best way to change things and I knew this so I’d teeter on the edge of a disaster. No way to live.

    The job and my life was like a prison made up of language, rules, and convention. The job itself a place that would take up all of my waking hours so I could never create a way out. I’d pay my taxes, pay my mortgage, have some expendable income to buy junk that provides a short term happy feeling. Alcohol a short term relief, bad food a short term buzz. But long term they make you feel bad or disappointed or unfulfilled. So you turn back to the short term fix again to relieve the pain. The monotonous cycle of destruction.

    Hierarchies of grey, fearfully obedient people ingrained in the program, believing in the program. “If you don’t follow the program bad things will happen” they’d say “keep the house, and spend the money on some new guttering or take a holiday”. “No, No, No! I want to be creative” I’d say and they’re condescending eyes would say “fool, its time to grow up”. Growing up ha! Growing up is getting some heavy debt. That’s all it is. Grown up means being enslaved and dealing with the stress of that. That’s why grown ups don’t smile or laugh as much, they look serious and frown more… don’t they?

    I was a musician from the age of 12 or so. I’d play music with my friends and ebb and flow as one in a sonic sea. The most wonderful feeling in the world. I’d make films and and write and draw. I lost all of this like I was no longer allowed to do that. I had to work I had to pay bills I had to be afraid.

    Now I’m free, well sort of. I’ve sold my house and my possessions and I move out in under a week. I am shooting video, editing and doing motion graphics. I’m a 37 year old intern doing a video animation promoting some new important health care software. I plan to head to India (that idea came from choose yourself) a thriving economy full of opportunities where my money will go further as I train and gain experience. Its still early days but at the very least I can see some hope after being derailed for 20 years. I always knew this is what I loved to do but I denied it. This is what I love and so be it that It took this long to begin again. When I look back over my life I notice everytime I followed what I loved it worked out, sometimes it was pretty good. Everything I knew I disliked but continued with became destructive. Trust what you love and it’ll take care of you.

    Be you, be what you believe in and be brave just like Brando. A real grown up is someone who questions the shackles and finds ways to get their power back. Then condescending eyes will become eyes of awe as you’ll be one of those people that lead and inspire. People see what they wish they had done too but were too afraid and too worn down.

    Don’t let the Authorities or should I say the ‘Authors’ tell you what YOUR story is. Tell your own story, you have wisdom in you and you have power already.

    Listen to yourself and trust yourself. Follow what you love and be brave and the universe will take care of the rest.

    • Russell

      Wow Russell that’s so insightful and amazing. You should listen to LCD Sound System.

      • Russell

        Well actually Russell I’m listening to them right now. And yes they fucking rule.

        • Russell

          Yes they do don’t they. x

    • Josh Harding

      The struggle is real. Its very tough to resist the temptation to take part in the expensive 21st century lifestyle. I’ve resisted buying a new car twice now and have $2500 in the bank due to not doing so. Im trying to keep the willpower up, and this helped!

  • Andrew Buckley

    2015 was the year I hit 50 after a blindsided downsizing in January 2014 and then taking a position from hell that Fall for a bit over a year to replace my income. 2014-the end of 2015 were the worst two years in my life from a happiness standpoint but turning 50 showed me things. I came closer to my family, I learned more in the terrible two years as a result of the difficulty and realized how strong I was. Now, I am thinking about never having those challenges again by ONLY being around the best and most positive people I can come into contact with. I am ready to change everything that I thought was important in my late 30’s and 40’s…and focus on what is truly most rewarding…my family, our experiences with those we love to be around and giving back my time and talent to those I can see will benefit from my experiences and trials of many years. I agree, when one is 20-40 there is so much we are unable to see and even more that we do not appreciate. I plan to help others with advice, show them all the mistakes I have made and hope to prevent them from hitting the same obstacles I encountered in life up to 50. I feel this will be the best for me and my family. Time to get rid of the trophy house for one WHERE we want to be! Time to escape a terrible state and region and it’s tax and redistribute tendencies for a place where a great quality of life can be enjoyed. I hope to help others avoid what has slowed me from attaining true joy and happiness…I am sure it will be pleasurable and emotionally rewarding next 10 years.

  • Jeff Donohue

    In your 50’s you are peaking in the job market and looking at the finish line. I am 63 now. If you are counting on having any money when you retire start getting control of any money in 401K’s and the like. If you can take a buy out, get the wheels rolling so you can get control of it as soon as possible. Learn how to manage your money and make it grow. Don’t give it to a Broker or Money Manager. You spent your whole life to build this pot now learn how to care for it. No one will ever do a better job than you of managing your money. Don’t believe for a second that all your life’s work can’t go to zero overnight. One of my inspirations has been a comment by Steven Spielberg when asked how he knows what kind of movie will be a big hit at the box office. He replied (roughly translated) that he didn’t know what people wanted to see or be a big hit, he only made movies that he would like to see. In your fifties start making the movie you want to see while you still have good health and time to do it.

    • Anjana Banerjee

      Jeff can you recommend something I can read about taking care of my money in my 50s close to 60s, I was just about to had it over just as you say its true. Who will take the best care of me than me.

  • CT

    In my early thirties. I have to say, James, your summation of your 20s dovetails pretty well with my own “lost decade” of wandering in and out of depression, purposelessness, ambition without direction, and coming out of college with a science degree and still feeling like I have no salable skills beyond “communications” (second major in history, though now also learning to program now, at age 31). M.A. from the U of Chicago, where I majored in debt and a useless concentration. Yeah, positive spin and all that, but all the positive spin in the world has yet to take me into a job I want to keep for longer than 10 months, and in the meantime the interest keeps accruing–trapped between hard practicality and the hard-to-kill desire to be more than just a cog in someone else’s machine. I still have academic superstar fantasies, but they’re fading, start-up culture is waxing and academic culture has waned–and there’s a lot of blame heaped on my generation for having dreams.

  • Nimsplayhouse

    I love this post James. I just turned 30. I went to college in my 20’s which for me was a waste of time, and I also believed I was in a rush to find my ‘Passion’. I’ve recently realised that I may never find a single passion, but instead I am making an effort to pursue experiences aligned with my interests. I plan in hanging out with others who make me s better person and I plan on enjoying the simple things in life again and being grateful for the little things I still have.

  • Stan

    Advice about the fifties? Come back in two weeks…..

  • Stan

    Sorry, just realized two weeks is a long time. Looking at my 50’s from a 60’s viewpoint….I’m glad I stopped looking back and started preparing for my 60’s and beyond. Because these decades really need preparing for and planning. If you’re on a great roll and have had the right attitude all along – go right on with it, life’s smiling at you and will continue to do so. And your good Karma will start paying off. But planning is definitely a must. Depending on one’s background and goals, it could mean planning for a huge variety of things – a new diet, how to actually spend your new retirement free time, help the kids and enjoy them helping you now, taking care of your car ’cause there’s no buying new ones anymore, telling it like it anybody you feel like and enjoying the respectful way they look at you because they think you know better, consciously ignoring things you don’t like, but most of all……. planning to feel great about basically everything AND being grateful for it, ALL the time. Going swimming now at a nearby beach – have a great day too!

    • I’m 36 so I’ve got a little ways to go but it’s funny you mentioned diet. I did an overhaul on my diet about 90 days ago (I also made some fairly significant retirement plan changes in terms savings and investments.)

      I’ve been a very lucky man. I’ve never really had to worry about money or health. But it hit me me a few months ago that my health would take major hit in the not-so-distant future if I didn’t change my ways. I’ve got too many things left on my to do list to be burdened by health issues. And while I’ve never had to worry about money, that’s mostly due to being a youthful guy with a lot of energy. That requires good health.

      I love that you mentioned being grateful. There’s just not enough time for all the negativity and stress in the world. It goes by so fast. I’ve really tried to live that way the last couple of years and it’s been two of the best years of my life. Sadly I think it took helping my mother through early onset dementia and then seeing her pass.

  • David Coleman

    50s are very eye opening times for me. 53 my handsome,little son just turned 1. Ido how,that happened but it did. I’ll take any good advice I can,get. BTW your book looks interesting Virginia Reeves

  • Owen Shaw

    The 60’s. That really sucks. Firstly everyone at work notices all of a sudden that you are “the old guy”. Even though you have kept up to date in terms of appearance; tech savvy; fitness and everything else this does not detract from you being “the old guy”.

    Then the economic downturn comes and pressure is put on you to take early retirement “because you can afford it and just think of everything you can do now.” They don’t care that you spent half your life savings putting the kids through college and supplementing your parents frail care, and that the next five years will enable you to top up your savings plan so you can retire at a decent income. You have to go.

    They also don’t care that you have a wealth of knowledge and experience and that you would like to continue to contribute and mentor.

    They chuck you out like a piece of discarded trash.

    What I do like is their turn will come. Then they can see what it’s like being “the old guy”.

    The 60’s suck big time!

  • S. Johnson

    I hit the big 5-0 in 2015, and it was like no other birthday I’ve ever had. I used to laugh at people who would get a “mid-life crisis,” but 50 dumped me right into mine, without much warning. All of a sudden I realized that for the first time in my life, there was considerably less time ahead of me than behind me. You can’t imagine the emotional impact of that realization until you actually live through it.

    I started writing children’s fiction about five years ago. When I turned 50, I realized that I might not have enough time to become successful in this field. Middle-grade and young adult fiction are populated with 20- and 30-something authors. When you’re that age, what does it matter if your first few manuscripts suck? Just throw them in the drawer and start over until you hit the jackpot. Realizing that I didn’t have that luxury of squandering time and/or “doing things over” anymore hit me like a brick.

    With that depressing epiphany came doubts about my marriage: Was this really what I wanted to be doing for the rest of my life? Was this really the person I wanted to spend the next 25-30 years with? Did I really want to make all the compromises I had to make for 15+ years in the future… until I DIED? Was my relationship stagnating? Was my husband holding me back from living the kind of life I really wanted?

    This is also the time where both men and women look at a 25-year-old beauty and realize they will never again be with someone like that. I think it’s even harder for the guys; it’s probably what drives them over the edge and makes them look for red sports cars and extramarital sex. :)

    I’d say 50 is the hardest birthday of all. Hopefully, by 60 I’ll be wise and relaxed enough to have settled into this “new normal.” I’ll report back in nine years.

  • Totally true, in my Thirties!

  • I did nothing in my 20s. Trying to make a difference in my 30s. It’s a slow process, but I’ve started with a website… Baby steps to helping a million people

  • Chas

    Here are two things I’ve read that have helped me a lot. (I’m in my mid-fifties):

    […] “Your youth evaporates in your early 40s when you look in the mirror. And then it becomes a full-time job pretending you’re not going to die, and then you accept that you’ll die. Then in your 50s everything is very thin. And then suddenly you’ve got this huge new territory inside you, which is the past, which wasn’t there before. A new source of strength. Then that may not be so gratifying to you as the 60s begin [Amis is 62], but then I find that in your 60s, everything begins to look sort of slightly magical again. And it’s imbued with a kind of leave-taking resonance, that it’s not going to be around very long, this world, so it begins to look poignant and fascinating.” […]


    This also is very true for me:

    […] At midlife, we find ourselves experiencing a discrepancy between who we thought we were and who we actually are now.

    To make matters worse, while the person we thought we were seems to be dissolving, the person we hoped we weren’t begins to show up more and more.

    This clash of images can leave us feeling sad, depressed, angry and very alone. We might feel a sense of profound loss that we cannot really explain to ourselves.

    Midlife transformative forces can push us deeply into our fear. Then we see its real nature. Behind our fear is a sadness that is an expression of a tender heart. This tender heart is an important source of compassion and concern for others as well as of awe and wonder about the mystery of life.

    When we connect with our tender heart, we no longer have to be embarrassed about who we are.

    There is an art and science to making a midlife transformation. First we need to recognize that the turmoil we feel represents life working on us rather than evidence that we are sick or other than we should be.

    At midlife our soul makes a grab for the steering wheel, it wants to drive. Ego’s dress rehearsal is over.

    Death is no longer hidden on the horizon. We need to face the task writing a script for the second half of our lives, so we can live with conviction and real intent.

    As we give up our concepts of who we are and what we “should” be, we can then become sensitive to a kind of internal guidance.

    Our psyche, at first, frightens us by shaking up our world entirely. It then stimulates us by pointing to some of life’s most interesting possibilities. Our task is listening and attending to what our soul is telling us.”


    I’m experiencing all of this. I feel now is time to reassess and change direction, to get new priorities and be more true to myself. Reading James’s “Choose Yourself’ has been part of that process.

    Lot’s of good comments in this thread. Thank you everyone.

  • dean53

    My 50’s: In the aftermath of divorce at 48, I lost my home and my kids. I incurred $100,000 credit card debt with a personal income (not counting X’s) of $8,000/year. Homeless. Crashed with friends. Did housekeeping in exchange for room and board. Transitioned into a 28-foot 5th wheel for 1 year. Then into an apartment. Got 2 kids back. Lived with them in 1 bedroom apartment for 3 years. Severe depression for a decade.

    Rescued by another crashed-and-burned, barely surviving fellow struggler whom I married and then he died. Finally semi-recovered in my early 60’s, mostly through time, my kids grew up, and financial support from late husband and new husband #3.

    Glad it’s over.

    • Anjana Banerjee

      You did love Hubby #1 at one time as well. At least you believed in sharing your life with another person and believed in it even thought you had to go through some failures. Sticking to something you believe in eventually brought you the stability and success in your life. God bless you.

  • José Baquero

    Yo estoy en los 40… eso es 20 + 20 …. NOOOOOOO

  • Alex Dubois

    My thirties were interesting. I worked hard, started and ran a couple of businesses, but confused action with progress. I got rid of a belief structure that I had determined was not correct and was not serving me any longer. That would be religion if you are interested. My forties were much better. I moved away from Dallas, which was the hottest/coldest wettest/driest place in the country. I moved by to the SE to start over, to reinvent myself, where I wanted to follow my passion rather than just make money. Now that I’m in my 50’s, I’m once again trending upward. My wife and I started another company, this time with the accumulated knowledge of both of our lives. We haven’t done everything right, but we are way ahead of many of our peers and are a lot happier. I have discovered the pleasure associated with the ingestion of certain chemicals, both natural and manmade and am working to expand my horizons and my consciousness. Both are going well. I have a real desire to live now and work toward the future. Starting to think about what happens next. I’m not sure what it will be, but I’m pretty sure it will be exciting.

  • Such a good sprightly read! My take on The 50s: You’re suddenly the oldest one in the room, you can’t read menus, and your lower back aches. Everyone under 30 looks the same age. You don’t give a rats ass what any one thinks anymore, like a switch has been thrown in your head. You don’t care about being right anymore, your perspective and kindness widen immensely. You grow to loathe movies.

  • Yinka Taiwo

    I am fifty three years old , I wrote seven things I learnt in my years of existence on my blog. It is short if you care to read.

  • JohntheHunter

    I’m 26… reading these comments… kinda scary… but also encouraging. Thanks old-timers haha ;)

    • Virginia

      HaHa young-man John! You should be scared. Hope you are working on getting your own biz going.

    • VF

      I’m 42. I wish I would read it when I was 26. It is your great opportunity to plan ahead.

  • John W Johnson

    great post James…
    My version…
    20’s, freed myself from the trajectory that was set by society/parents. Found out that what i went to college for a vocation had nothing to do with my own skills and talents (engineering).
    Traveled, worked at tons of different jobs, got in to therapy, performed in a theater group off off broadway, trained guard dogs, was in a PhD program at NYU. When someone asked me how i got so much done, i told them “it’s amazing how much you can do when you aren’t married!”
    30’s Moved from NYC to Venice Beach California, started my journey as a Somatics professional ( body work, psychotherapist), continued my performing, focusing on dance, got married, started my entrepreneurial journey. Fell in love with rock climbing.
    40’s more of the same, got good enough as a rock climber to kill myself, gave it up so i could continue my dance career. Moved to Oregon, couldn’t afford anything in California and my wife loved the NW.
    50’s, more of the same, went bankrupt because my staff was stealing from me and i had no good inventory control in place. Wife passed away.
    60’s, made millions on line, recession and google panda happened. Lost it all keeping the business going.
    70’s persistence, still doing everything, healthy as a horse. Life is good.
    Owning a home has been one of my good plays, easy money, as well as doing short term vacation rental, such easy money.