Rethinking Retirement

(The following is a guest post by Nick at – another site dedicated to the art of financial independence)


Over at my site,, we talk a lot about “Pretirement” as a new — or at least newly recognized — stage of life. We touch on all the same issues as Justin here at Root of Good and, like Justin, my goal is to get people to think differently about their lives.

One of the interesting things I’ve discovered since I began blogging was how much of a struggle it is for most people to grasp the concept. To be fair, America’s puritanical history doesn’t prepare us well for adopting this new mindset.


We’re steeped in the “Protestant work ethic”, we don’t get dessert until we eat our dinner and the grasshopper will starve this winter because he didn’t spend the winter preparing unlike the industrious ant. Keep your nose to the grindstone, young man, and someday you’ll get to “retire” and slow down America’s roadways in your very own RV! One of our political parties has even taken to insulting poor people by demanding they enjoy the “dignity of work” — while THEY live off their investments, of course.

Paradoxically, while Americans feel you should work an entire hard lifetime before getting your reward, we are also simultaneously some of the shortest-term thinkers on the planet. Drenched in easy credit and TV commercials, we can have nearly anything we want at very close to the exact moment we want to have it. Cars, electronics, toys, fancy food, you name it. With a swipe of a card, it can be yours.

Those of us on a different path are all very aware of those folks who haven’t learned to resist the siren call of “stuff” and have buried themselves in debt. It’s understandable given the culture in which we’ve been saturated. What we’re less able to understand is how very responsible, hard-working and well-paid Americans find themselves close to retirement with virtually nothing to show for all their decades of labor.

That’s why I began writing over at I wanted to convince people that there is another life path available. If the goal is a long, happy life, then the strategy should be to reach financial independence as early in life as possible — even if you choose to keep working.

Because there’s another aspect of the American mindset that actually works for us: our concept of personal freedom. No, I’m not talking about your “freedom” to shoot your own nuts off with a firearm. I’m talking about the ability to live life the way you want. To spend each hour of each day living with intention. Are you doing what you really WANT to be doing right now?

For some what they WANT to be doing is work. Entrepreneurs, physicians, engineers, artists, farmers: these are some of the occupations we think of when we think about people who enjoy their work. But even some cubicle dwellers love what they do. They love the interactions with people and they like feeling as if they’ve contributed to something each day. While they probably wouldn’t keep heading into work each day if there wasn’t a paycheck attached, they’re happy at work and it’s something they want to keep doing.

Others, however, grit their teeth and suffer through each depressing day just to reach that next direct deposit. Years go by. Decades. Bodies become hunched and broken. Eventually they’ll find themselves used-up 50-somethings struggling to keep up with the latest technology and fearing the next layoff will include them. And there’s always some Millennial ready to do the same job for peanuts.

Which is why I hope Americans will begin rethinking retirement. The reason I use the word “pretirement” is that I want to open minds to the idea of a life stage in-between your working career and traditional retirement. The main difference being that “retirement” begins when you begin to draw a pension (ha ha!) or social security. Pretirement begins when you reach financial freedom. When your core bills are covered by your income from your investments, say around $2,000/month, you can declare yourself “pretired.” If you’re able to reach that stage in, say, your 40s, you can enjoy life for 20 years or more before giving yourself a raise when you decide to retire.

What will you do with all those years? Maybe you’ll focus on your kids. That’s what I’m doing right now, although I’ll need something to fill my time when he goes off to school. Like the aforementioned cubicle-dweller, you might want to keep working. But you won’t have to take any crap anymore. You’ll feel like you’re walking an inch above the ground as all the petty infighting and corporate politics seem smaller and smaller. You can finally be honest in meetings!

Or maybe a second career is in your future? What have you always dreamed of doing? Others will devote themselves to their communities, volunteering for a favorite organization.

The point is that it’s up to you. End the mindless spending, invest well and stay focused. Once you’re there, you’ll find it is so worth it.


Root of Good’s comments: Excellent article, Nick!  I feel like I could have written this myself, as it echoes my sentiments very closely.  “Freedom” is really what you are buying when you stick your hard earned money into a 401k or IRA.  Tiny shares of freedom.  Maybe you find yourself loving your job, or the concept of a job, but having a sizable investment portfolio makes you a little more bulletproof in your job.  

After accumulating a sufficiently sized nest egg, you can afford to take risks and speak your mind.  After all, the worst thing that can happen to you (losing your job) won’t impact your daily life one bit (other than creating a gaping hole in your Monday-Friday schedule that you’ll have to fill with something interesting).  

Another key point in Nick’s piece is living intentionally.  Life is of a finite length, and comes with an expiration date unknown to all until it has passed.  This can be a sad and depressing thought, but only if you fail to take action and live your life with intention.  You are the only one that can make positive changes to get you into a position you want to be in.  It could be a different job, a higher paying job, or a different career altogether.  

You may want to work forever because you enjoy your job.  That is okay too, but remember it should be an intentional choice, and not a “choice” forced upon you by decades of indecision and failure to get your finances in order.  


I wanted to thank Nick for writing this guest post.  If you like what he wrote, he’s just a click away at

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  1. As you already know, we share very similar ideas on pretirement/financial freedom Nick. I’m thinking of writing a similar post soon that details why the American view of retirement is so off tilt. Why is life divided in parts – being a student, running the rat race, then finally enjoying life in retirement after you’ve spent your best years doing something that you hate?
    Makes no sense, and I think many people could avoid the whole thing if they’d be exposed to sites like this, and ours, at a young age.

    1. Thanks for saying so, Jacob! I sure wish we’d had an internet around when I was younger. I always had a general idea of how I wanted to structure my life, but it took me a long time to figure out exactly how to get there.

      1. Sites like these have also helped me really clarify my mission and purpose with money and “pretirement” (love the definition and word, by the way Nick). Thanks!

        1. I don’t think I ever really thought through the fact that if you are 60-80% of the way to retirement, you can really cut back your working to “just get by” for 5-10 years while your portfolio grows. Maybe after a couple of years of doing something easy or less stressful, you might want to head back to your old rat race for a year or three to make the big bucks once again to finish the race (more like marathon!) to retirement.

          1. Justin, one of the things that really horrifies me is how so many people will take the FLIP side of your point here and get self-trapped into working fulltime “one more year” so as to overpad their retirement stash. Some people repeat this OMY syndrome over and over, staying chained to the job MMY (many more years) for the sake of budgeting in a new car every 5 years or some such. And totally ignoring the fact that every OMY year they put in is ONE LESS YEAR of life left to them to enjoy in freedom.

            1. Absolutely correct. I have a post to write on “One More Year Syndrome” at some point. It is real, and I suffer from it too. I know I can get a regular full time job for a year or two and make enough to 3-6 years of living expenses without working too hard. Maybe after some time off it will be a smart decision.

              But the point you illustrate, that working 1 more year = 1 less year of life to live, is a great way of presenting the situation in stark terms. My rebuttal would be “enjoy life as much as you can while you are working”, which means don’t get a job that requires working more than 40 hours per week. Part time is even better.

    2. Unfortunately, none of us have multi-million dollar marketing budgets like big corporations have, so it can be hard to get the word out there.

      Convincing people to spend money on crap they don’t need (and didn’t even realize they wanted) ain’t cheap.

  2. I struggle with that too. Lately, I’m thinking of it more as a lifestyle design process. We figured out how to live the life we want and there is no right word to call it. It’s an uncommon path, but it’s great so we want to share it.
    We have choices now. We don’t have to work all our life if we don’t want too. It’s too bad more people aren’t willing to have an open mind.

    1. Absolutely! And what’s the worst that can happen by picking the early retirement/financial independence path? You get bored and go back to work! I don’t see a downside.

  3. You nailed it, Joe. So many people are locked in a mental box and all day it’s spend, spend, spend, then work, work, work to pay for it all. Hopefully this will change a little bit now that there is more access to countering views via the internet.

  4. The more people can be exposed to the concept of financial freedom and having options, the more we’ll see such actions being taken. Many people really can use a paradigm shift, but are so busy working hard day in, day out, that they don’t pause to consider that there are other alternatives. We can actually work hard to give ourselves a choice, instead of working hard just to do so or to get by day-to-day. Posts like this are great for raising awareness.

  5. I’m a huge fan of freedom. Call it whatever you want. The day that you can walk away from a toxic job or a situation you hate, you are truly free!

  6. Great post. As someone who is very close to pretirement at age 45, I can’t tell you how much better I feel even though I am still dealing with the day-to-day BS of corporate life. My biggest regret? That I held too much savings as cash over the last 20 years. The Fed has made sure that those who save in the form of cash will be punished. If you are young, don’t be afraid to be investing your savings in broad, low-cost index funds such as those offered by Vanguard.

  7. Hi.. i recently came across your website and have begun reading your posts from the beginning.. awesome stuff!! Quick question.. are you pulling any of your investment income from your 401k or IRA Accounts? Dont you have to wait until the age of 59 or pay penalties?


    1. For the next 10-15 years we’ll be spending down our taxable investments. During that 10-15 year period, we will convert Traditional IRA assets to Roth IRA assets. There is an exception to paying the penalty for Roth IRA conversions. Just wait 5 years after the conversion, and you can withdraw those amounts converted penalty free.

  8. A bit late to the party here guys however loving the article.. For me “retirement” is all about having the opportunity or choice to spend time as I’d like to rather than needing to rely on someone else for income & then being able to give back in a massive way 🙂

    Loving the site and going to smash through the articles

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