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Deathbed Regrets: I Should Have Spent More Time at the Office

Have you ever heard the phrase “No one says on their deathbed, ‘I should have spent more time at the office’”?

Well, maybe that’s because, distracted by the emotional needs of distraught family members,  their own final death throes, as well as regular doses of heavy opioids, perhaps they are simply not thinking clearly.

As the morphine drip clouds their judgement, they may fail to recognize that the hours they did spend at the office are paying for this private room, excellent end of life care, not to mention the down payments of the homes of their children, currently surrounding them, wishing Dad had spent more time at their soccer games.

Am I advocating a Don Draper like existence, putting career ahead of everything, treating family as an inconvenient appendage, recoiling from love or human connection?

Hardly (although those are all valid choices). Just that we need to be more honest when we make major financial or career decisions.

Let’s talk about a popular trend right now: re-evaluating life choices, particularly career choices, to make sure they are truly making you “happy” (which in itself is a scam).  A recent New York Times article focused on this very thing, and countless other personal finance pieces advocate a similar approach.

My problem is this: why is it that when doing a serious life evaluation (often prompted by a major “wow, life is so short” event like the untimely death of someone close), people always seem to choose a career that makes them LESS money? No one ever says “My best friend was a corporate lawyer and keeled over from a heart attack at 45. With my mortality staring me in the face, I did some serious thinking, and decided to… work twice as hard to get that promotion”?

So, being the Contrarian that I am, please let me advocate for a thoughtfully considered career path that takes you away from love, family, and your true calling, and towards filthy lucre.

IMCO (In My Contrarian Opinion), there are several good rationales for this choice:

  1. You can’t afford your true calling. As I have pointed out before, I support a life following your true passion, but only after you have achieved FI to do it. Otherwise you may end up suffering through years (or decades) of financial stress, affecting both you and your loved ones, as you get up and running with that jewelry design/children’s book author/psychotherapist career.
  2. Your family doesn’t need you (as much as you might think): I look back at the time in the 90s when working women seized on every study showing that the kids of working Moms were just as healthy, smart, well adjusted, etc. as stay at home Moms. How cute. Little did they know that not only should they be working full time, they should avoid spending time with those kids even at off-work hours! I think we are realizing that the pendulum has swung way too far in the other direction, and that most kids need less helicoptering, more independence, and a little more “laissez fare” parenting (OK, to a point).
  3. Yes your family needs you, but they also need your money: let’s face it, at some point, most kids would gladly trade “quality time” with parents for tuition assistance, a first car, a first home down payment, or free rent for a few years as they get their graphic arts career under way in a high priced urban market. Some may resent the hours you spent working for all this, that took you away from their soccer games. But I’ll bet that just as many will someday appreciate the sacrifices you made so that they didn’t need to go into $200k debt to get a college education.
  4. Maybe you’re just lazy: and I’m not saying this to judge you – with a four hour daily work day, I am the king of laziness. But let’s be honest: why is it that, when re-evaluating their life and career choices to focus on what’s “really” important, people always choose a path that’s easier and more fun?  I’m just advocating that you examine, and accept without judgement, your true motivations: are you really leaving accounting/law/medicine/ corporate executive-dom for your family and “true bliss”, or are you just over it all and looking for an excuse to get out?

With all that said, I don’t necessarily think it’s wrong to abandon the pursuit of money in order to spend more time with your family, pursue your passion, or any of the other stated reasons for a major career (down)shift. I just think it’s healthier to be honest about the true motivations, and accepting of the financial consequences. In other words, do what you want, just stay financially woke while doing it.

Has a major event caused you to re-evaluate your choices? Did you regret it? Tell me about it in the comments below!

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