Why Are You Still Working?

A man puts his hand on his chin and has a questioning expression.

(Image credit: Getty Images)

I am going to take you down a rabbit hole here, so I apologize in advance. I’ve been doing a lot of reading and thinking about work-life balance and happiness these days, so my topic du jour is: Why are you still working? I’ll set up a handful of categories of people and how they respond to that question, and then I’ll address my epiphany. (As an aside, I recently read a good book, for those looking, called From Strength to Strength by Arthur C. Brooks.)

Category 1: I must keep working.

I put myself in this category. I’m 42 years old and have three children, two dogs, one wife and endless expenses. Although I’m doing a good job saving for the future, I am far from financially able to walk away. Guess one could argue I could move to a farm and live off the land, but let’s be honest here: I wouldn’t last two weeks.

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The reality is that the majority of people probably fall into this category of why they are still working. Now, I consider myself one of the lucky ones who loves what he does and finds it mentally challenging, engaging and extremely rewarding.

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My only comment to this group is to do a real soul search and make sure you find yourself fulfilled at work, rather than wasting away behind some desk.

Category 2: I probably should keep working.

In this group are individuals and couples who could find a way to retire now. Perhaps they are in their early to mid-50s but still have three kids they want to put through college. Or maybe they spend a ton of money on passions, and thus they aren’t quite there financially, and/or there is too much risk for them to pull the plug today.

We run these financial models all the time where we say if you are content, then working another five to 10 years is going to really pay dividends.

Category 3: I want to keep working.

Are you in a great position financially but still working because you love your work? I certainly see this plenty where 60-year-olds can easily retire, yet still grind away 40, 50 or 60 hours a week. Lots of times, I see this with our professional clients (doctors or lawyers) or business owners.

There is something they are getting from this work that they need or love (or so they tell themselves). Could be power, money, fulfillment or a sense of being.

Regardless, this group has no end in sight and might pass away at their desk. Many of you reading this are nodding your heads in agreement, I assure you.

Category 4: I’m afraid to retire.

We see individuals all the time who are afraid to retire. Heck, we get hired to solve this exact issue. These people are afraid of not receiving a paycheck anymore, or worry about how they’ll turn their life’s savings into a consistent income stream.

What if the markets have another 20% down year, or someone they don’t like gets elected? This group has a million and one reasons not to retire. The question is: Are any of them good ones?

Category 5: I don’t know why I’m still working.

When asked why they are still working, these people say something like, “I don’t know,” or “What else would I do?” Or, even worse, “I really don’t have any hobbies or passions, so I figure I might as well work.”

I run into this group a fair amount, and it takes some real pushing to convince them otherwise.

The first principle

Now bear with me as as I tell you about the first principle, which dates back to good old Aristotle over 2,000 years ago and is defined “as the first basis from which a thing is known.” It is a concept that top industry leaders like Elon Musk use on a regular occurrence. At its core, it breaks down a thought process to the beginning, instead of building on what is known.

Let me give an example: Let’s say you want to create the next great dinner table. One way of thinking is, “Well, let’s find the best table on the market and have a think tank figure out all the tiny flaws, then come up with creative ways to fix them. Like, we should add a built-in ridge to hold cups so they don’t spill — that would make this table much better.”

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The way a first principle thinker would attack it, would be to say, “Forget the traditional table of four legs and a square or circle shape. What are we trying to solve here? Is it a place for people to eat meals and put their stuff down? Maybe we can get rid of the entire tabletop and simply have small floating orbs that have no restrictions and you have barely any tabletop.”

Break it down

So, instead of building on what you know or are told, we would do the opposite — break things down to their most basic form and then address the same question.

Now, how is this relevant to our question — why are you still working? — and categories three, four and five above (the people who want to keep working, who are afraid to retire and who don’t know why they’re still working)? Let’s do the same first principle concept and ask, Why are you working in the first place? You must ask yourself this, and don’t take into consideration what TV, newspapers, your country club friends or anyone else has to say about it. Also, don’t accept what you have been conditioned to believe is the answer.

If I asked you to define your ideal day, week, month and year, what would they look like? Where does waking up at six in the morning and working eight, nine, 10 hours a day fall? Seriously, if you had no agenda and nothing you “had” to do, what would those days look like?

Your ideal week

Here I’ll help, as I just took a week’s vacation. I’d wake up around eight a.m. and go do some form of exercise, ideally tennis, as I love competition. I’d then go for a walk with my wife and dogs and grab a nice late brunch or lunch. Then I’d go do some nice reading in the warm weather and wait for my kids to come home from school. I’d hang out with them for a while until dinner with friends and family. I’d do a lot of traveling and volunteering and learn some new hobbies. So what would you do?

Here is the fun part: If work isn’t part of your ideal week and you fall into category three, four or five above after some real soul searching, then… WHY ARE YOU STILL WORKING? Work is not optimizing your happiness, and newsflash, you are not getting any younger.

Honestly, do you want to wake up five years from now and say, “Crap, life is great now that I’m retired. Wish I’d done that five years ago.”

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Remember: You can’t get that time back, no matter how hard you try, and I’ve tried, trust me.

Thus, it is up to you and only you to do this soul searching and break things down to the first principle of happiness. Once you do so, I have just one question for you: WHY ARE YOU STILL WORKING?

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In March 2010, Andrew Rosen joined Diversified, bringing with him nine years of financial industry experience. As a financial planner, Andrew forges lifelong relationships with clients, coaching them through all stages of life. He has obtained his Series 6, 7 and 63, along with property/casualty and health/life insurance licenses. Andrew consistently delivers high-level, concierge service to all clients.