Should You Plan to Retire?


“I’m not planning to retire.”

This came up in a conversation with a friend of mine. He gets paid upwards of a few thousand dollars per hour to speak, often being flown into exotic locations to run workshops for corporate clients. On top of that he recently self-published a book, with the proceeds going to charity.

He was commenting on how, as he gets closer to the age where most people plan for retirement, he couldn’t be happier with his career and level of success. Why would he want to give it all up?

He even wondered whether he made the right choice putting his savings in a tax-deferred retirement plan (as opposed to a normal investment account), because as his income and tax bracket are much higher now than when he was doing most of his saving.

I can’t say whether my friend made the right investment decision. But his story does raise an interesting question: Should you be planning to retire? Or should you be trying to build a career that’s so intrinsically rewarding you’d never want to leave?

Why Retire?

Before retirement and pensions became an expectation for the workforce, people basically worked themselves until they died. I can remember my grandfather telling me stories of his father, working until he was seventy-five.

Retirement was a luxury, and most people couldn’t afford it. If you didn’t retire, it was because you couldn’t, not because you didn’t want to.

For many people today, retirement is still a luxury. With pension plans folding, massive debt and unforeseen obligations, many people who want to retire, can’t. My case for planning not to retire isn’t a justification for those tragedies, nor is it a call to return to my great-grandfather’s day of a work-until-death necessity.

Rather I’d like to ask a question for the smart, talented and accomplished minority. If you can truly design a career and lifestyle that is deeply fulfilling, would you want to give it up, just because you’ve reached a particular age?

I’m a bit young to be in a position to assess my desire to continue working in 35 or 40 years. But I admire my friend’s situation. He’s spent his life doing what I hope to achieve—meaningful work with meaningful rewards. If I could achieve that, I’d want to continue working as long as I’m physically able.

Planning For, Versus Planning To

Although I’m not planning to retire, I’m definitely planning for retirement. When people say planning for retirement, they mean having enough money so that they aren’t forced to work.

I’d rather avoid the pains of destitution than enjoy the excesses of wealth, so I’m definitely saving and investing my money. The fact that I may never retire is irrelevant. The goal of having financial abundance is freedom—to choose where to work, whether to work and how to live.

In this last ten months I’ve earned a little under $40,000, but I’ve saved almost half of that. Not simply to wait for the day I’ll stop working, but to create freedom far earlier in my life. If we consider it punitive to forbid someone from retiring after 65, why should it be any different at 45 or 35?

Planning for retirement, in the forms of creating enough wealth to give yourself options is a worthwhile goal regardless of whether you actually plan to stop working.

Does Work Fulfill Your Life or Drain It?

My friend clearly sees work as a fulfilling part of his life. Although it can be difficult, and occasionally exhausting, the net rewards give him more satisfaction and energy for life than without it.

I contrast my friend to the majority of people I see nearing the age of retirement. Work at least appears to them to be a constant drain on their energy. They are noticeably happier during vacations and dislike the constant demands of their job.

If you’re in the latter situation, retirement only makes sense. It gives you something to look forward to after your years of toil. Work is a necessity of living, but it creates a personal cost.

But if you’re defining your ambitions, should you really be looking to the latter group as a role model? Why instead of planning for your life under the assumption that all work is toil, wouldn’t you strive to create a career that adds value to your life?

“If You Don’t Want to Retire, You Must Be a Workaholic”

Donald Trump once said something along the lines of, “You should have a job you like so much that you don’t want to take vacations.”

I remember I read this quote in an online forum, where immediately after it were dozens of comments crying out that Trump and people who follow this advice are workaholics. The theory is that if you prefer work to vacations, or plan to work your entire life, there must be a deficit in your personal life or you have an unhealthy obsession with work.

I think this is merely a poor rationalization from people who hate their jobs. They can’t imagine what it’s like to do work they really love, so any desire to work more than is necessary must be a psychological defect.

I don’t see it that way. I love running this online business, and despite my lack of years of experience, I could foresee myself doing something like this forever.

That doesn’t make me a workaholic. I love Tarantino movies, old books and I probably drank far too much wine during my last year in France. But if I go more than a few weeks without working, I get that itch to start writing or dreaming up a new project again. Work can be good even without obsession.

My friend responds similarly. He speaks about his profession with enthusiasm, including the new projects he’s undertaking. But he also takes time to go on vacations with his wife and watch his son’s sports games.

An Alternate Life Plan?

My big question is, if you don’t plan to retire, how does that change your perspective on life?

Tim Ferriss explored a similar question, arguing against the “deferred life plan” which so many of us are attached to. If you didn’t plan to retire, that might mean that all those things you plan on doing someday, you’ll start taking action on today. It might mean you’d engineer work that’s fulfilling instead of merely bearable.

At this point, I still believe many people will want to retire. Not everyone can work in ideal careers, and sometimes work is a necessity. But as I’m speaking to many young, ambitious people who have the talent and means to do almost anything with their lives, should they be basing their ambitions on that assumption?

Image courtesy of Kris Haamer

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  • Stefan

    Awesome Scott.

    Recently I was at a ‘Healthy Ageing’ Debate at my University. Full of ‘grown-ups’ and one started with saying something like: ‘The new young people only want to work for a couple of years for a employer, take a vacation and then they are going to change jobs where they can learn more’.

    As one of the only ‘young people’ over there I was obligated (to myself) to respond. And my response is totally in line with your post.

    I told him: ‘Of course we are taking vacation during our working life. We see our parents and grandparents working their ass off, until they are completely burned out by the working life. Then they are going to retire, and get so bored they get sick from the boredom! (This is scientifically proven, retirement is bad for you)

    I don’t want to have a burn-out before my 65th and I don’t want to have a bore-out after my 65th. I am going to have such a nice job that I want to work till my 90th or something! I won’t retire, I will start to work less. And during my life I will enjoy a mini-retirement every once in a while. Why wait until you are so old that you have problem with your back to explore the world? I want to explore the world RIGHT NOW. Live with the experience of seeing the world and enjoying little things (for instance: grandchildren) when I am older.’

    I hope I never want to retire.

  • Jen Gresham

    Scott, one of the most important sentences in this post is here: Not everyone can work in ideal careers, and sometimes work is a necessity.

    The reason this post is so important for your readership is that this sentence probably doesn’t apply to them. Smart, ambitious people with talent are in short supply. Believe me, as a former senior-level manager, I know.

    What I would say is that if you’re talented, ambitious and willing to take a leap, there’s absolutely no reason you can’t have an ideal career. What holds most people back is fear, not lack of opportunity.

    I’ve written about this extensively on my blog in my career design series, which talks about why I gave up my cushy government job to create one I really would enjoy until my dying day. I also started raiding my savings account at the age of 38. You save money so you can spend it when you need it. What better time than right now–to enable a fulfilling life.

    You’re on the right track, Scott. I predict with confidence you’ll never have to retire. Keep spreading the word.

  • Wendy Irene

    I think saving to give yourself a buffer to have the freedom to choose when and what to work on is a great idea! Happiness doesn’t really come from spending. Having freedom to not worry as much about having periods of working less I think sounds far more peaceful. I love the idea of keeping at what you are doing until your heart tells you otherwise, if it does.

  • Stanley Lee


    Where should I begin…IMHO, retirement is either a luxury of not having to work in a soul-sucking career anymore (although there are arguments about why this process can’t start earlier), or a result of tragedies that disables you to work anymore.

    Planning for retirement is important, I agree whole-heartedly. You can eventually work without being financially forced to, i.e. securing freedom for yourself. Steve Pavlina talks a lot about the psychology of abundance vs. scarcity. Too often, naive people believe that someone (i.e. their children or the government through the next generation) will take care of them since their retirement at age 65, despite folding pension plans, massive debt, and unforeseen obligation. Longer life expectancy also adds to the problem (not that I’m against people living longer). I’m currently writing a guest post pitch mythbusting the notion of being taken care of by pensions and social security.

    My 2 cents.


  • Stanley Lee

    On another note, although I’m very far detached from my workaholic days due to excessive demands from the high-tech sweatshop mentality of my previous college major (electrical engineering), I still find myself working a lot…with the goal of accelerating my path to personal freedom lifestyle. Just want to throw it in there before I forget.

  • Scott Young


    I agree. But I find my personal ramblings or advice to the select minority of readers here are often misinterpreted as a call for a new world order. I realize, of course, that retirement is a good system for most people. Except we aren’t most people.


    Planning financially for your future is a whole other subject. I personally lean towards a robust approach that emphasizes freedom over spending, but I’m also cheap and disinterested in owning a lot of crap. To each their own, I suppose.


    Mini-retirements are part of the “alternate” life plan. Of course they may not be suitable in every position, but sabbaticals and periodically shifting the tempo of life ensures it stays fresh and you don’t sit in a rut where nothing changes for decades.

  • A.H.A.

    Here’s something else to consider: life extension technology might be invented in the next 40-50 years. Check out the Immortality Institute.

  • Jay

    Hi Scott,

    Interesting post. I think that once I can support myself with a job I love (like blogging or writing in some other medium) I want to continue working in that way as long as I am capable. The rewards of writing are so great–it connects me with like-minded, interesting people and I also find it intrinsically rewarding. I think that I would want to continue that as long as possible.

  • Anass

    I see retirement as the fact of been free to do what i want whenever I want. I’m more with the 4 hour work week approach and the lifestyle design concept, living a life with mini-retirement, a period of work (working on something I like to do) and a period of learning or doing some great activities (photography journey, yoga, or surf).
    So I don’t think myself planning for retirement because normally I will be living the retired person life 😀


  • Chris


    I look at retirement from a value stand point. When we’re young, we extract a lot of value from the system. When we’re older, we usually add value.

    Retirement doesn’t mean stopping to add value. Old people sometimes have the most precious thing in society … WISDOM.

    Value only matters when it’s shared.

  • Joe King

    Find something you love and you will never work a day again!

  • Travis Webster-Booth

    Hey Scott,

    The key to this question, particularly at our age, is flexibility. When in 40-50 years I round the corner of 60 and then 70, I am sure that I will want to have the flexibility to work when I want and how I want. I think we build flexibility in numerous ways, from having a large enough cash flow to not be “locked in” to choosing work that we scale forward or backward.

    So long as you plan for the future, as you say, then you give yourself options. And the older we get, the more that matters.

  • Life Exceptional

    This is a topic I have thought about a lot actually.

    I would say that retring at 65 because thats what society expects is a bad idea – it shows far to clear a distinction between “work” and “life”. If you enjoy your work, and you should, then the distinction doesn’t get made. Why would you even want to stop working at 65 if you enjoyed it?

    But equally, I think it is a bit risky to assume that you will always want to do what you are doing now. In ten or fifteen years you might want a change and start something new. So rather than planning for retirement, you should plan for a change, a put aside some money and resources to make sure you can make that change when you want to.

  • NuViewIRA

    Especially in this day and age, it seems like young adults change their mind quite a lot, even in careers. Moving between jobs and not having the opportunity to consistently save, which means not having a solid retirement plan, could end up hurting them in the future. Having the freedom to not worry about finances should anything happen is worth the effort to plan ahead.