So You Say You Want To Work Forever?

Which coworker is eating their lunch on the toilet?
Which coworker is eating their lunch on the toilet?
Which coworker is eating their lunch on the toilet?

I was on the phone with a good buddy of mine last week and we got to talking about money. He’s doing all the right things with regard to his finances—solid 401(k) deferment, maxing Roth IRAs, living below his means, risk averse and diversified in his investments, and continuing to achieve greater things (see: salary) at the office.

He’s a true picture of financial security and is a perfect candidate for some extremely early retirement (I reckon early 40’s). I’m supremely confident he’ll be a multi-millionaire in well under ten years.

Given his financial security, and my penchant for wanting to leave the corporate world as soon as humanly possible, I was floored when he expressed an interest to continue working into his early-to-mid fifties. For sake of privacy, let’s call him “Grasshopper.” The conversation went thusly:


Eric: “Grasshopper, you must be kidding. You could retire way before that. Given your pension and the projected millions you’ll have saved, you could retire quite comfortably at 43 or 44 years old.”

Grasshopper: “Yeah, but I’m very risk averse. I don’t want to take any chances. Plus, I think I would get really bored if I wasn’t working.”

Eric: “So, do you like your job?”

Grasshopper: “Absolutely, I couldn’t imagine doing anything else.”

This, quite honestly, it outside my abilities of comprehension. As somebody who is entirely horrified at the prospect of working past 35, working into my fifties would seem, frankly, like a waste of life.

I’m unique, though, so not everyone will feel that way. So today, I want to address those that want to work forever.

What are Your Reasons? 

Maybe you have no desire to retire early (much less retire extremely early). An obvious reason to keep working late in life is that you need the money. But, what would be the reasons to stay at a job when you don’t need the money? I’ll list ten reasons, from good to bad, for you to keep working past when you have to. You might:

  1. Find meaning/fulfillment in your work
  2. Love your coworkers, interaction with others
  3. Love your work
  4. Love your company
  5. Be otherwise bored or purposeless without your job
  6. Lose your identity without your job
  7. Be addicted to the money
  8. Be addicted to the lifestyle
  9. Lose your sense of self-worth
  10. Greater and greater financial security

There are some good reasons in there, and then there are some sad and bad reasons. Personally, I can think of a lot of things I’d rather do than work. Also, using my own dad as a precedent—who left a job he’d identified with for over three decades—I believe that you quickly adopt a new identity once you leave the workforce.

Should You Keep Working?

Among the reasons I gave above for continue to work due to choice, rather than necessity, some were good (Nos. 1-4) but most are pretty bad. So, here’s a little graphic to determine if you should continue to work past when you have to.

The Work Voluntarily Rubric

The way I see it, if you job offers you a fair compensation, adequate freedom to do other things, meaning to the world, and day-to-day enjoyment, then I say “Go For It” and work until you die at your desk. I think having a job that accomplishes all four of these things is a true blessing. I’m confident the only job, for me, that accomplishes these ends is blogging and writing about finance. It provides me tremendous enjoyment and is a captivating and compelling subject (i.e. “it doesn’t feel like work”). I’d like to think that it has meaning. Ideally, I’m getting others to look at life differently and hopefully inspire them to improve their financial situation. Writing gives me total freedom over my time and efforts. I took the past week off—how cool is that? And compensation. This is a tricky one. Writing does not provide adequate compensation currently. But, as I increase streams of passive income, I could swing writing as an occupation probably even earlier than my 2019 goal.

Have you ever heard the term, “Find something you enjoy and you’ll never work a day in your life?” Let me be the first to say that that piece of advice is A.) Awful, and B.) Borderline dangerous.

Why is that advice awful? Well, I’ve enjoyed many jobs. Fun coworkers, pretty easy work, comfortable working environment. These jobs paid well and some even offered me the freedom to pursue other endeavors. However, looking at the rubric above, I’ve only hit three of four criteria. These jobs had very little meaning. I wasn’t saving lives or helping people. I was middle-office, doing generally mundane stuff.

I see people today, at my current job, that are very passionate about their work. They love what they do and the pay is handsome. Some would even say there’s meaning (making millionaires even more millions). But, the job lacks any freedom to do anything else. It’s like being in the military but without the camaraderie. Their life is the job. Without a doubt, they are living to work. Most jobs fit one or more criteria, but it’s tough to find a job that fits in the intersection meeting all four criteria:

Work Voluntarily Rubric with Jobs

So, why is that “find a job you enjoy” advice dangerous? Because it implies that enjoyment is the only (or at least the biggest) key to finding a job that works for you. It’s a key, but not the only key. Bronnie Ware, an Australian palliative nurse summed up the biggest and most common regrets of those facing death. First on her list was living a life true to one’s self. In her words:

“When people realize that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honored even a half of their dreams and had to die knowing that it was due to choices they had made, or not made.”

Finding meaning and fulfillment in your work is truly essential. Coasting through life in a job that is enjoyable, pays well, and gives you lots of vacation is great, but it leaves you liable to have a deathbed confession that your life’s work had little or no meaning in truly helping the world.

It’s very comforting to know that this blog, as scant and pithy as it might be, is something only I could do. Every bit of it is original work that will live on long after I’m gone. Right now I’m touching 30-40 people a day—if only for a few minutes each. Maybe that number will increase in time, maybe not. But, I’m happy knowing that what I’m doing has true meaning, even if just a little bit.

You Still Want to Reach Financial Independence

Even if you have a job that falls at the elusive intersection of meaning, money, enjoyment, and freedom, it still behooves you to seek financial independence as soon as possible if for no other reason than “people change.” You may love your job today, but can you say the same for how you’ll feel working the same or similar job in twenty years? Going back to Bronnie Ware’s deathbed confessionals, many had expressed regret over working so hard. In her words:

“This [regret] came from every male patient that I nursed. They missed their children’s youth and their partner’s companionship…All of the men I nursed deeply regretted spending so much of their lives on the treadmill of a work existence.”

Your job might not feel like “work” today, but it might later on. When it does, when the day comes and you wake up and it’s not “fun” anymore, wouldn’t it be great to have the freedom to just call it quits?

I might work past the age of 34. If I love my job, it’s enjoyable every day, it pays well, it gives me the freedom to do other things, and it has meaning to the world, then sure, I might stick around. But, I’m realistic. One day, I’m not sure when, I’ll be pulling into the office and I’ll have a moment of utter clarity…”what the heck am I doing here?”

I’d like to have a resignation letter in the glovebox ready to drop on the boss’s desk.

That’s the kind of freedom that only financial independence can bring.

Take Care,




  1. I stared at the work rubric for a good 10 minutes (of company time!) trying to assess where I would position my job. I had difficulty because my perspective always changes with regards to the things I like and dislike, and I suspect there are a lot of other people like this.
    I consistently imagine what it would be like to wake up without having earn money (financial independence) and sometimes I’m going out for runs in the morning, visiting with family/friends and volunteering and other times I’m sitting in my underwear on the couch watching reruns of Maury all day. It’s the Maury scenario of early retirement that scares me to death (“you are the father!”…
    I’m sure I could enjoy my job a lot more if I became more engaged and made more of an effort to socialize, but my mentality is geared towards early retirement, so it can be difficult to stay motivated.
    Really enjoyed the post and all the thought you put into it

    • Jommy,
      Thanks for stopping by and commenting. I hear you about motivation at work; my thoughts are often geared toward FI while I work–I think that pervasive mindset, though, is what will push us to FI sooner than we expect.

      And there’s nothin wrong with killin’ a few hours with Maury–whatever makes you happy.

  2. For me it is just too early to say exactly when I would like to, or will be able to retire. I know I definitely do not want to work forever, or really past 50-60, circumstances depending of course.

    I like my current job, certainly above others I have had and it is an entry-level position into what I hope to be a good future in Financial planning where I can actually help people.(fingers crossed)

    So for now, I am just building up my portfolio and passive income to give me the option and extra breathing room of being able to eventually choose when to retire.

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