When is Enough Enough?

How do you know when you have enough to retire early?  When is enough enough?  In a rare guest post, the Early Retirement Dude pays a visit to Root of Good to share his thoughts.  

Relatively new to the FIRE blog scene, the Early Retirement Dude is no stranger to the refined art of Early Retirement.  Now 47, he retired over a decade ago at the ripe young age of 36 (ha ha I beat him by 3 years but it’s not really a contest, is it?!).  I had the pleasure of hosting ER Dude at my house several weeks back, and can confirm he’s a legitimate ER Dude, scraggly two week beard and all.




It’s May of 2005 and I’m officially quitting my job this morning—or, technically, I’m being laid off because I’ve turned down a directed transfer—and part of the process is an exit interview with our divisional president.

I’ve just turned thirty-six.

Cliff is a good guy, and for a couple more hours I’m two tiers down from him on the org chart. I report directly to a woman who reports directly to him, so he and I have gotten to know one another and become friends. He’s also helped me out career-wise; involved me in higher-level meetings, invited me to the right cocktail parties, and been solicitous of my opinion.

So at the appointed time I show up in his office, him in his charcoal Brooks Brothers and me in my Grateful Dead t-shirt and cargo shorts and running shoes. I mean, what the hell, right? Truckin’…got my chips cashed in, etc.

Cliff checks out my outfit and grins. “I guess you’re serious.”

I chuckle. “Yeah.”

“OK. Can’t say I didn’t try. Have a seat.”

On the far side of his office he’s got two couches and two easy chairs arranged into a conversation pit. I take a couch and he comes over and sinks into a chair.

“Right,” he sighs. “Uh, Rachael filled me in somewhat. Said you were leaving the industry.”

Rachel’s an HR rep. “Sort of,” I say. “I’m getting completely out of corporate America. I’m done.”




He shifts his gaze to the big plate-glass windows. He’s got the blinds open; it’s a bright spring day. “You know,” he muses, “I’ve heard a lot of people talk about doing what you’re doing, but nobody ever does.”

Now: Cliff is a a guy whose net worth is easily ten million dollars. I’m guesstimating, but I’d once seen the standard executive-level contract, blank, and between the perks and the stock options and the bonus floor and the wide wide empty salary line with plenty of room for zeroes; and of course his slice of the phantom equity the company originally distributed when it was a startup, I know he’s done and is still doing well for himself.

So I call him on it. “Man, I don’t get it. I mean, you. You’re worth, what, ten million bucks? And I know you’re burned out, so why are you still here?”

He replies a little too quickly, as if he often asks himself this question. “Because,” he tells me, “you get the big house and the nice cars and the toys, and your kids are in private schools and your wife gets used to the lifestyle, and that’s it.”

I nod. “OK.”

And that’s pretty much it for the personal side of the discussion. The rest of the interview is the usual formulaic bullshit about my satisfaction with career development, how I feel the company can improve employee retention, whether I have any concerns about discrimination or sexual harassment, and so forth, and within twenty minutes we’ve got the whole thing wrapped up. We stand up and shake hands, he directs me to the HR VP’s office, I sign off on my severance contract, and I’m on the train home before noon.

I never see Cliff again.

A few years later I hear through the grapevine that the company axed him after a regulatory agency found his division guilty of violating the agency’s operational standards. Not anything criminal, but sketchy enough nonetheless. The agency’s finding cost the company an eight-figure settlement, which of course resulted in several public and bloody decapitations, including Cliff’s.

Which triggered his severance agreement. And that meant he’d just thrown however many million dollars his package was worth onto his already Kilimanjaro-sized pile of money—not to mention however much that mountain had grown in the years since I’d left.


These days I don’t think about Cliff much, but I wonder if that layoff was the point at which he left the industry. I hope so, because how much is enough?

Maybe he started consulting, or maybe he moved on to a different field. He’s not on Facebook, or at least not the last time I checked, and I guess I could google him or search LinkedIn, but I haven’t bothered.


That exit interview was eleven years ago. I’m forty-seven, now, and as I write this I’m sitting alone on the beach on Cape Lookout, a barrier island off the North Carolina coast. This is an undeveloped beach, a national seashore that stretches on and on for fifty miles, and at this time of year it’s deserted. I’d be surprised if there are twenty other people sharing the island with me.

When I drove off the ferry eight days ago I hit the beach and drove south through the sand for I don’t know how many miles until I got seized by The Thirst…so I pulled over onto a nice flat spot in the shelter of the dunes, cracked a beer, and set up camp.


I’ve been sun-basking and surf-fishing and beer-cracking ever since. I’ve gone running along the tideline, picked up a million seashells, watched the lighthouse’s beam endlessly circle around and around, counted shooting stars, and of course I’ve been doing some heavy thinking. You can’t help but think in places like this.

And so I thought of Cliff. I don’t know where he is; what he’s doing; how his life is going…but he’s certainly not sun-basking or surf-fishing or beer-cracking or even soul-searching on Cape Lookout.

This must be an allegory for Cliff – stuck on the hook and unsure how to free himself.

That thing he said about the house and cars and private schools and such. I think taking a job you hate and getting addicted to the paycheck is one of the worst ways you can screw up your life. Money can’t buy you happiness, but I guess it makes misery more enjoyable…as the old saying goes, or ought to.

So wherever Cliff is, I hope it’s someplace he wants to be. He’d be in his early fifties now, so maybe he DID get out.
Whatever the case, I wish him well.


Don’t forget to visit Early Retirement Dude!



Any Cliffs out there willing to admit it?  If so, when will you call it quits?  How do you persuade yourself that enough is in fact enough when there’s always the fear of running out of money in early retirement



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  1. What a depressing story! For Cliff, I mean – Early Retirement Dude, you sound like you are doing great. But Cliff’s story illustrates something I find really puzzling: how can you have enough self-awareness to say something like “you get the big house and the nice cars and the toys, and your kids are in private schools and your wife gets used to the lifestyle, and that’s it”, but then not do anything about it? I think it would be really tough to live knowing your life could be so much better, and then take no action…

    This isn’t the first story I’ve heard along those lines, but the apparent feelings of helplessness over something so clearly within one’s control is still really confusing.

    1. It’s confusing to me, too. But too common it seems. Hard to imagine all those nice mansions on the hill filled with rich but unfulfilled people.

    2. Definitely doing great. thanks for the good word. Weird how good people get at pretending they’re happy. The better I got to know him, the more I saw that Cliff was definitely one of those guys.

    3. It isn’t confusing to me because it really isn’t about having enough as much as it’s likely more that he doesn’t really know what else to do or have a real plan on what he wants. How many people are initially driven, work hard, go hard, keep that nose to grindstone and barrel forward, then after years they finally look up one day and realize they’ve actually accomplished all the life goals they shot for. Career, Family, material possessions, savings, etc. all pretty much done. You made it, you are a success, you ticked off all the boxes! Way to go! Now what?

      Say you’re in your mid 40’s, but you have no killer career ambitions to pursue beyond what you have now? You don’t have any “calling” demanding you switch to a new career but any action you take to shift gears from your current position seems like a massive step backwards only to do what? Achieve again what you have now? That seems totally useless when what you have is what you have spent 20 plus years working towards. Life is good, but maybe no longer exciting, but it also has momentum. That momentum has inertia that is hard to suddenly change. The resistance comes from inside you, but it also comes from a spouse used to a certain status and standard of living, kids who expect certain things, deep seated moral values and ideas. Maybe you can’t see yourself “retiring” because your hung up on the word and only “old” people retire and you aren’t “old”. Maybe you have an internal script of your parents yelling at you to be a success and part of that is that you have to be working to “support” a family. Whatever it is, unless the person makes the change or the change is forced on them (e.g. his layoff) there’s no reason to upset the apple cart. This happens to people in mediocre or bad relationships they don’t leave until forced, then wonder why they ever stayed. I think it happens more often than folks think.

    1. Actually it is more taxable in terms of offsetting SS benefits. I think I am right on this – just started checking out how to max benefits.

  2. Very nice story ERE Dude. It reminds me of the following quote by Nassim Taleb:

    “The three most harmful addictions are heroin, carbohydrates, and a monthly salary.”

    I would check out your site and your story to see what you inspired you to retire so many years ago.

  3. I think what give you confidence is the ability of visualizing your next life with some practical details, your dreams and aspirations. When you approach 40, you realize that some people close to you don’t live longer. You feel confident to focus on what is important for you and your loved ones. We are in our way to early retirement. Right now, we need three more years. We will be 42 and 43 years old with a 5 years old child.

  4. Great points ERE – “Money can’t buy you happiness, but I guess it makes misery more enjoyable” – so true. I’m getting out June 30th at 50 years of age. I went an extra year – but it solidified our finances and my emotions about really being able to leave early. Many people I work with are miserable (or pretty unhappy…) but they drive fancy cars and live in houses that cost 2-3 times what my house cost. We’ll be on the beaches like you come fall. Can’t wait!

    1. Nothing wrong with working an extra year beyond your goal for the sake of peace of mind. Otherwise you might end up fretting over every penny spent and actually decrease your overall enjoyment of life vs. while you were still working.

  5. Wait, you can just drive on the beach, camp on the beach, have a fire on the beach, and drink a beer on the beach. That sounds absolutely perfect.

    Thanks for the post, one phrase really hit home for me: “taking a job you hate and getting addicted to the paycheck is one of the worst ways you can screw up your life.” I have been living this for quite a while now. It’s time to find something to do that I love.

    1. I´ve done that for several years. By that time i did not know about about the FIRE movement, i was blind and stuck. If you´re living like that you´re luckier than me, because you can use that monthly paycheck to build your ER and do what the ERE dude did. Also, i fell into that situation because i wanted to find something to do that i loved. Working for someone else is a difficult way to find that.

    2. That deserted beach vacation set up sounds so cool, doesn’t it? ER Dude admitted he was left eating only fresh fish, quinoa, and oatmeal by the end of the two weeks there. However he also showed up at my house with a cooler full of beer, so I’m assuming he didn’t go thirsty on that deserted island, if you know what I’m saying 😉

  6. I think this sort of reflection is a healthy way to evaluate your choices. I am also on the path to retire early, but I may continue working afterwards. Not because I hope to amass more than “enough,” but simply because I believe in the work that I do. Cliff’s response does give evidence of his addiction and slavery to consumption. Cheers to you for finding freedom at a young age, and to benefiting others by sharing your story.

  7. Awesome read, ERD. You’ve definitely got a style. It’s so sad, but there’re Cliffs everywhere around us. People who make good money but instead of using ’em right, the money use ’em. Slaves in nice houses, driving nice cars and taking nice vacations…
    Thanks a lot for this post, another motivation for staying on track

  8. Nice story. I once had a big house with a pool that consumed most of my paycheck. I decided to turn my life around and left of that inflated lifestyle behind.
    Now we’re financially independent and getting ready to retire in 2 years. I set a personal deadline of end of 2019, not a day more. Justin, please, please punch me in the face if you see me posting a deadline past that on the blog! Enough is enough. 🙂

  9. Dude, fishing and cracking beers is my MO! I left work almost a year ago at 34. It doesn’t cost much to enjoy some good beer and nature. I’m hoping to sway my friends to join me enjoying life. Some are turning around, others are dead set on buying new cars and “living it up.” I just don’t see stressing about deadlines, sitting in traffic with my new car, or spending most of my waking hours in a cubicle as “living it up.” At least it leaves more deserted beaches for us to enjoy 🙂

    Keep living the dream, and Cheers!

    1. That’s true. I’d hate to see the roads, trails, and pools full of retired people in the middle of the week. No way could I enjoy an olympic size swimming pool with other people swimming in it. There would be ripples! And maybe splashing!

    2. You know, one thing I didn’t realize before we ER’d was that since my fiends…er, “friends”…were still working, the only time I’d be seeing them during the day was when they were on vacation. And what do many people want to do when they’re on vacation? Get bombed, that’s what. So you have to be careful: imagine that once or twice a month you’ve got friends vacationing with you for a couple of days. Gets to be a liver hazard.

  10. Cliff reminds me a lot of my boss (although he doesn’t have a $10m net worth). He grew up in a single parent household on government assistance and now makes many multiple hundreds of thousands of dollars a year. Lives in a swanky suburb of the big city. Has a summer house a block from the beach. When we get together and a bottle or two of wine gets drank, we start to talk money. I poke a little on if “if it’s all worth it” and obviously he wouldn’t tell me “no” but he doesn’t really say “yes” either. The new life becomes the norm, when the family would of been plenty happy on a scaled back version which is now believed to be too late to go back to. Lifestyle inflation is a bad, bad thing.

    1. Of course a lot of those kind of guys know deep down they’d be almost as happy without the luxury car or beach house (or whatever big expensive luxury item they own). I’ve talked to a ton of them in my ER lifestyle consulting hustle and through this blog (hi you guys if you’re reading!). It’s often the spouse or the kids they don’t want to disappoint. It all boils down to “your money or your life”. Work longer for more stuff or make do with less and have more free time to enjoy life outside of work.

      1. Exactly. Don’t discount the spouse, or especially the kids. If you’ve got a core belief that your children will be happier with fancier things, it’s hard to let those go.

    1. Man, we were raised to think like that. To fight for bigger or fancier as if it was simply better. It’s so difficult to get rid of that mindset, or even to realize that we’re trapped in it.

  11. I came from a different mindset in the sense that I never expected to work ANY regular 9-5 job. My goals from an early age were to work in the entertainment or sports industry, make a bunch of money and never work a “real” job. This actually worked for a few years, but what a shock when I woke up one day and had to take a job that paid 12 months a year. I was miserable from day one at the straight job, so it was never an option of staying longer than I had to, but more of when is the absolute earliest possible day I can get out. As I’ve gotten older I’ve been surprised to find so many people who either liked working no matter how bad the job seemed to me, or felt the security of the job was too important to throw away on something as frivolous as early retirement.
    I don’t judge those people too harshly. First of all I respect any one who is willing to work hard and pay their own way. I don’t care how bad or low level the job is, if you’re willing to work hard you deserve respect. There are way too many people walking around today who COULD work, but choose not to for a variety of reasons – none of which include they retired early.
    Second, many people worked very hard in school or thru apprenticeships to make themselves valuable to a company. This in turn gave them a job and a salary that has given them self respect, independence and the ability to have a family. These are no small feats. It takes a ton of effort to make all these things happen. All too often the media and elites look down on the average guy who figures out how to make it in the world. I don’t.
    Lastly, early retirement has it’s ups and downs – it’s not all sitting on the beach fishing for blowfish…esp if you have a family. Sometimes making a couple million dollars and retiring early can be just as complicated as sitting at a desk 8 hours a day – in fact it can be MORE complicated.

    For some of us getting out of the rat race is a no brainer, but for those who happily (or even not so happily) choose to slip on their track shoes day after day…I get why you do it.

    Maybe having the best of both of those worlds or some percentage of each is just as satisfying as going all in on one.

    1. Great points, and I agree re: the benefits and value of work. Hey, it’s a steady paycheck and if you’re half way competent you generally don’t have to worry about losing it (you can always find a new McJob in general).

      I think I’ve found a nice compromise between retirement and work. I spend some effort on this blog, do 1-2 hours of my Early Retirement Lifestyle consulting per week, show up at various civic and volunteer engagements to benefit the community, and I’m good. I have a generally laid back lifestyle punctuated by brief spurts of productivity.

  12. Nice story for sure!
    I am still 5+ years away from FI. I don’t anticipate become a Cliff since I don’t think I am or will be that addicted to a fat paycheck. What I do see happening perhaps, is staying 1, 2, or 3 years to long trying to increase my safety margin for early retirement. I guess getting laid off at that point wouldn’t be a bad thing 🙂

    1. That’s probably what I would have done if I didn’t get fired. I considered going back to work to top off the portfolio. Even applied to many jobs while drawing unemployment. No luck! I’ve since turned down many job offers, since my finances seem to be doing just fine.

      1. I had a decent job the first five years then it changed on me. The last year has been stressful with no signs of changing.

        I’m glad I am getting out a few years earlier to keep my sanity. I asked to be fired, so in that sense I’m a bit peculiar. Much to my delight it worked and I’m going into ER with severance and unemployment. I don’t have an end date yet but I will soon.

  13. I love the story. Very personal yet relateable. I often wonder what it’s like to be super rich. But maybe rich people have their down dilemmas they can’t solve themselves. Thanks for sharing this great post! 🙂

    1. The super rich still have plenty of worries and stress. They still have to make decisions. It’s just that their decisions tend to have more zeroes on the end of them. I was just reading some posts on a forum about a guy that has a net worth well into eight figures (and gets a massive pension on top of that). He still has to think about investments, manage his managers that manage his properties. Make decisions about which new luxury car to buy. Deal with contractors at his 2nd, 3rd, and 4th properties, etc. Honestly, his life sounds more stressful than mine! Though his pool is WAAAAY nicer than my non-existent pool, and he has a service that cleans it.

  14. “I think taking a job you hate and getting addicted to the paycheck is one of the worst ways you can screw up your life.” I think you hit the nail right on the head there. Great read. I’m thankful not to be miserable at work by any stretch, but that still doesn’t deter me from thinking about early retirement. Gotta weigh the pros and cons I suppose!

  15. I liked the story and the message as well. I’m really one of the exceptions in the FI crowd who doesn’t really want to retire early. But unlike cliff it’s more because I like my job. I agree wholeheartedly with your ending about getting addicted to your paycheck. I will call it quits when I turn fifty five or when someone ticks me off too far to bear. Why 55? The other things I’d do with my time after retirement require more flexibility and kids to be adults.

    1. For most of us, it’s those things we really want to do in life that encourage us to quit working. I just can’t recall many moments while working when I was like “woah, this is so cool! I’m glad I get to do this instead of playing with my kids, killing bad guys in a video game, standing atop a mountain looking at the world around me, etc”.

      1. Those jobs ARE out there though. I had a helicopter trip out to a platform for a day last week, toured shipyards in the Far East (watching cruise ships be fabricated is just as cool as being on one, at least for an enginerd like me). My wife is (soon to be was) a special-ed teacher and her job was cool in a different way – and it doesn’t hurt that she was paid to do something she was previously doing voluntarily, but with less influence.

        We both started our careers in crappy jobs that made us miserable, but once you get to FI the world is your oyster. I guess those ‘big wigs’ feel trapped by golden handcuffs and didn’t develop their plan for what to do after FI. It’s sad when the cage-door swings open and the animal is too complacent to run to freedom…

  16. Great post – I had a similar talk with my old mentor who had told me he was worth over $10mil. When I asked him why he was still working he told me he was honestly scared of running out of money. Even on a $500k a year salary he was living paycheck to paycheck – mainly because his wife was a little too free with the Amex and regularly ran up $20-30k a month charges on god knows what. Lucky for him he really did/does love the job – but I can’t help but think he’d be happier giving up all the stuff and cracking open a brew with you on the beach.

    1. As a non-married guy, I have to admit this scares me the most. I have a friend whose wife has a taste for the finer things in life, to the point where he actively hides investment accounts from her because she can’t be trusted to know that they have some money. However much his raise is, she can spend it. Before he met her, he spent years telling me something like that would be a dealbreaker.

      They’re on vacation in Paris. He wanted to just rent an RV and roadtrip to Florida.

      I can’t wait until I can crack a beer with all the other early retirees on that beach.

      1. I don’t know – those RV rentals can be expensive! 😉

        This is something you want to figure out early in the relationship though, and not find out about someone’s unlimited capacity to spend money AFTER you marry them. Recipe for disaster.

    1. Really depends on your expenses. Cashback Pal has good advice. 25-33x expenses which would allow a 3-4% withdrawal rate from your portfolio. For $40000/yr expenses that equates to $1.0 to $1.3 million investments (need the higher end of that if you’re 30- or 40-something).

  17. Nice story guys, thanks for sharing it. The ‘moral’ of the story is true too. Getting too attached to a luxurious lifestyle is a great way to screw-up your life.

    There’s extremes in both directions of course. A person could just give up money and head out into nature for the rest of their life. Who’s going to be the happier person?

    I’ve seen arguments for both sides.

  18. Money is not a goal, but a tool. It is useful to accumulate some to enable a different life. The way I think of it, it may not buy happiness, but it prevents a lot of misery. It is also a quick way to solve problems, though maybe not the most efficient.

  19. For each their own. Many people would never give up a life of luxury and are content with it. The sad part of this story however, is that it lingers through that Cliff clearly isn’t. Also makes me realize how important it is to keep on pursuing the things you love, no matter what that is.

    Thanks for sharing.

    1. Cliff will never be satisfied with his material wealth since for those type people, more is always better. Hit $10 million and you feel inadequate till you hit $100 million.

  20. Great story. Reminds me of a senior colleague from 10 years ago who was a sweet guy I met in that company, who had like 50 people report into him. But his wife wanted an ever increasing luxurious lifestyle that even his fat salary couldn’t keep up with. Some time after I left, I heard from former colleagues he was fired for starting a shell company and getting fake invoices paid through our company that he was signing off on. Pressure of keeping up appearances can be too much even for otherwise smart and rational managers.

    1. That’s crazy. But I guess more and more money is addictive, and like an addict, you’re willing to do ANYTHING for the next fix. Including setting up a shell company. One day I’ll have to share the story about Mrs. Root of Good’s coworker who stole $100 million from their employer. 🙂 Fun times…

  21. Excellent story on how lifestyle can hook you up forever.

    We are so lucky to have never done that. We have reached quite soon a lifestyle that is enough for us. As a result, we now feel liberated from pushing ourselves in our job and career. When we do it (like I do still), it ois because we want not, not because we have to do it!

    1. That’s what it’s about – getting to a point you are comfortable with. Doesn’t necessary equal quitting a job immediately once you hit your FIRE number.

  22. I’ve discovered your site today and I have been ravenously digesting all your posts 🙂 You have a great site, with immense personal financial detail being covered. The one thing I could not locate in your posts was your investment asset allocation. I would love to see how you spread your money.

    Your “Zero To Millionaire in Ten Years” post was almost an exact match to my road to a million. What’s funny is that we have nearly the same portfolio total of 1.7mill, but I’m 4 years older DOH!!! I just don’t have the courage to take the final plunge. My wife wants to quit now to home school our 3 children and I’m on the fence about letting her. So I’ve been seriously diving into the options to at least allow her the freedom. Honestly, my insecurity comes from having a crazy life where at one point I was homeless.

    Your site is actually making me think it’s possible for both of us to take the plunge into retirement now, not later!!!

    1. Might be time for you to quit. Maybe not. Really depends on your monthly expenses. We spend $30-40k most years so $1.7 million makes that kind of spending easy.

      1. We spend roughly 50k at the moment. One of my main problems is that we still owe 190k on the mortgage. I’ve actually decided to pay that down as fast as possible to take that out of the equation.

        The other problem I struggle with is that we finally got into very high incomes, and I would hate to loose the income from these peak earning years. The downside is that tax time sucks. We don’t qualify for child tax credits, and can no longer add to the Roth IRA’s. Conversions are out of the question at the high tax bracket.

        1. Take the mortgage out of the equation and maybe you’re spending a lot less per year? One idea is to treat your investment portfolio at two pots of money. One is worth $1.5 million and that’s what you’re going to rely on for early retirement. The other is $190,000 and that’s to cover the mortgage liability (whether you pay it off immediately or keep the investments and pay it off over time out of that $190,000 pot of money).

          If your annual expenses drop to $40,000 after taking the mortgage out, then you’re only looking at a 2.7% withdrawal rate from the $1.5 million main pot of money in your portfolio. 2.7% withdrawal rate is very low, and will likely allow you to withdraw that amount indefinitely.

    2. ITSB – I’m basically where you are. Almost exactly identical net worth and in high earning years. I’m 37 years old, and I don’t want to be in this job a day past 40 years old. But we have 5 kids and I want to make sure I have their college educations solidified. So we’re focusing on getting those 529 plans established and fully funded before we FIRE. I’m targeting $200K and I’ve got $55K funded. But we’re aggressively adding to those now.

      1. I think planning for the kids’ college BEFORE leaving work is important if that’s part of your financial plan. It’s the guys that are just running up the score because they don’t have anything better to do that make me wonder when will enough ever be enough.

  23. I recently read Your Money and Your Brain by Jason Zweig and one of his statements sums up exactly what you are talking about here:

    How good our money makes us feel depends partly on how much money the people around us have.

    No one wins when we do comparisons because there will also be someone out there that is smarter, wealthier, more attractive, etc. Measuring our own happiness is a much better metric because for one thing we feel happier when we think about our happiness. But for another thing, when we start thinking about what truly makes us happy we may start to realize that it often isn’t material possessions.

    As part of my Sustainably Happy Project that I started in 2017 I’m currently evaluating whether I have enough to either take a sabbatical or a semi-retirement. I recently took a week off of work and will take another 3 months off within the next year to test things out. My biggest concern has been getting comfortable with the paychecks and benefits and continuously putting off making the changes in my life that will truly boost my happiness.

  24. “I think taking a job you hate and getting addicted to the paycheck is one of the worst ways you can screw up your life”

    Well said! Cliff reminds me a lot of my ex-boss. I have no idea what happened to him either, but when I left he was working so much he nearly died of a blood clot. So not worth it.

  25. Yesterday I saw a post in FB that showed one of my classmates from both grade and high school passed away suddenly at 64. From his obit it appeared he never stopped working. When you see real world examples close to yourself it does make you sit up and take notice. Very thankful my wife checked out of the workforce at 57, and I did at 60. Best wishes to ER Dude and all on this post.

    1. Yeah, it’s crazy. I’ve seen a couple guys in the neighborhood kick the bucket in their early 50’s. No way I’d want to keep working into my 50’s if I could afford to pull the trigger in my 30’s or 40’s!

  26. I can’t imagine having $10 m and working a job I hated. My family would have to change the lifestyle, because hating your life is terrible for the family’s happiness.

  27. Great story. At my last job I worked with several people who were 70 or older and none of them were planning or able to retire. One 72 year old had $40,000 in credit card debt. I kept explaining to the younger workers that unless they wanted to work forever they needed to save for retirement. The business matched up to 5% of their contribution and began making retirement savings mandatory the year I retired. I did talk a few into increasing their contributions but not sure if it stuck after I left. I put their reluctance down to a lack of imagination. You have to be able to envision retirement life in order to save for it.

    1. Most folks where I used to work at a small engineering consulting firm contributed at least enough to get the 4-6% match. Of course we were mostly math-minded spreadsheet jockeys without big lifestyles so that probably helps. And there was an investing culture at the firm too, which helped a ton. At least one other guy basically got to FI in his 40’s not long after I left. Not sure if he quit his full time job there, but he had built up his Amazon sales biz on the side to net enough to live on, and he was saving and investing his whole career too.

  28. An all too familiar story for most of the people out in corporate America. It’s amazing what a little lifestyle inflation does and how people let it drive them instead of letting their money work for them. Great life lesson on perspective and what can happen even with the largest paychecks.

  29. Interesting post.

    I wonder whether its always so black and white? It isn’t for me.

    I have a very well paid job ($500k plus) and my feeling about the job varies from hateful stress where I just want to walk away right there and then to a kind to a feeling of deep satisfaction when I feel I’ve made a positive difference to a client or team member.

    Periodically the balance between the positive and the negative changes and makes me feel less or more inclined to retire early. The fact that there is a (big) paycheck hitting the bank account each month makes any permanent decision less urgent. So while I moan about work, there are many positives and I expect a lot of people find themselves in that halfway house which I wouldn’t call indecision, its more that there isn’t the screaming imperative to change.

    At 52 and the work situation is not changing but now I find thoughts of mortality creeping in and as the children have now left home the pull to RE has increased so I’ll be leaving work in 56 days. At the end of the day the buffer is now at the level where the risk of running out of money has almost certainly gone and I’m not so naiive as to think that people will thank me if I drop dead at my desk. But I will leave with mixed feelings.

    1. Yeah, I totally get that. I look at some of the cool projects I’ve worked on during my short career and think “hey that’s pretty neat – this will probably be here in 100 years for my grandkids to see!”.

      But at the end of the day, I always knew I would enjoy doing something more fun than what I did professionally. Work was just a source for a paycheck.

  30. I can’t imagine how many Cliffs there are out there. It makes you wonder if fear really is the main driver for why people can’t leave. That or there is too much social pressure. Either way I think that this story also is a good allegory for how your stuff can own you. Gotta be careful of that.

    1. I think it’s getting stuck in a rut and never thinking hard enough about what your options are to escape the comfort of a paycheck.

  31. This is quite an interesting post.

    Our “enough” is 3 million which to a lot of people (even in the PF community) sound absurd but I can’t forgo leaving my children empty handed. In a way I do see a bit of Cliff in my husband. We don’t want to go down that route so I guess it’s good at age 25 I’m reading about it now. Thankfully hubby doesn’t detest his job and we’re good savers. Those lifestyles are so easy to get addicted to…

    1. The fact that you’re here at an early retirement blog attests to the fact that you’re aware of the issue of when enough is enough. Maybe your 3 million is higher than most of our numbers, but I don’t even think Cliff has a number. He wouldn’t know when he hit FI since he (or maybe his wife/kids) spend it faster than he can make it.

  32. I seriously want to retire early but need a basic roadmap of what I can do to get there and what to do. We don’t make big money but have always saved in our 401(k)s. Saving $1 million seems very unattainable. We are debt-free but have one child that is a senior in college with a year and a half to go. We live pretty frugal with no car payments at this time. I’m not very experienced in investing. My son graduates in a year and a half then I will have more money to invest. My company does not match in my 401(k) at all and my husband and I invest 15% each right now. What is your best advice for me at the age of 48.

    1. I have been doing my job for 26 years and I’m feeling burned out. Since my son turned 21 his father is no longer helping with any expenses, I also struggle with whether to have my son get any loans, I do have a college account for tuition but am paying for room & board out of my income.

      1. Not a bad idea to let your son take out some loans to fund college. The whole idea of college is to boost your earnings potential so there is nothing wrong with taking on temporary debt to fund the education. Like an investment in one’s future.

        And considering that there are no loans for retirement, you should take the loans where you can get it.

    2. Once you have a good source of money to invest (like when your son is off the payroll!) then focus on low cost investments. I like index funds, usually from Vanguard. Check out the FAQ’s at Bogleheads.org for some basic investing advice.

  33. My brother told me of an old fisherman he’d met on a Florida pier who said, “All I need is osters (sic) and beer.”. Life is really pretty simple. Sometimes all you need is oysters and beer.

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