Career Decisions & The 5 Dying Regrets


Career changes & the four last things: death and judgement, heaven and hell

A recent article “Top Five Regrets of the Dying” written by Australian songwriter Bronnie Ware struck me because most of the factors were paramount in my decision to choose self-employment over conventional 9-to-5 work.

Let’s review the five regrets:


1) I wish I’d had the courage to live a life true to myself, not the life others expected of me.

The expectation others tend to give is a “one-size-fits-all” approach to work, and that size fits neatly in a Monday thru Friday, 9-to-5 box, with an appropriate benefits package of insurance, vacation time and 3 percent annual raises. That’s fine if you like the work, but what if you working in that environment leaves you feeling as though your talents are suppressed, that your capable of more and you can handle the challenge of self-motivation?

That’s the way I felt, and it was time to ask if the conventional career model offered up really was in my best interest.

And if it wasn’t in my best interest, what was the issue with changing? There are a lot of factors that have to be in place to make a career change the right thing to do, but those factors become more manageable once you shed the expectations of others.


2) I wish I didn’t work so hard.

This one’s a little tougher call. In choosing self-employment, I’m not naïve about the amount of work it takes to be successful (and in fact, I’m typing this piece on a Saturday night after a family get-together).

But in discussing my venture with relatives, the point came out that there’s good stress and there’s bad stress. In working for myself, I feel the motivation to create and to generate activity, whereas in a conventional job the stress came from constantly trying to please a management that couldn’t always (or ever) be kept happy.

Keeping work in a healthy perspective is still going to be a very hard challenge, but I believe I have a better chance in an environment where I’m the one with final accountability.


 3) I wish I’d had the courage to express my feelings.

I can’t say this one had anything to do with my decision on a professional level. The personal side is another matter entirely, but that’s a subject for another time.


4) I wish I had stayed in touch with my friends.
This was a huge factor choosing the path I did. I live far away from my friends and family. It wasn’t possible to see them all working a conventional job. There wasn’t enough vacation time and I felt like I was buried. Now my job is where my laptop is and that opens the freedom to keep up with the people who matter most. True friends are all you have in your pocket when trouble hits (at least in purely worldly terms) and it’s imperative to do whatever is possible to keep those bonds strong.


5) I wish that I let myself be happier
Letting myself be happier is a byproduct of being true to myself, having better work balance and staying in touch with friends. When you add to that I’m doing the work I love the most, you have a good formula for contentment.

Here again, there’s the challenge of making sure I allow myself to be happy, but the framework is in place. What it all boils down to is that work, like any other decision in life has to be done with the Four Last Things in mind: death and judgement, heaven and hell. And while one absolutely must consider the practical factors—finance, insurance, etc.,— they do have to be subordinate to the things we’ll really worry about when dying.


So where does that leave you, CatholicMatch members? What regrets do you have—in work or in your personal life? What are you doing this New Year to eliminate them?




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