The Illusion of Wishing You Worked Less

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You’ve probably heard the refrain that as people are facing death no one says, “I wish I spent more time at work.” In her book Regrets of the Dying palliative care nurse Bronnie Ware lists the five most common regrets she’s heard in her career, one of which is, “I wish I hadn’t worked so hard.” (You can see all five regrets on her website.)

This seems obvious. Our families and friends can love us, your job won’t (see “Love Your Work, but Remember—It Won’t Love You Back”). I don’t disagree that for most people who have healthy relationships, those relationships will be more fulfilling than a job.

Last week I wrote “Money Can’t Buy Happiness, or Can It?” But that’s only one side of the coin; life isn’t only about fulfillment or even being happy. As humans we want to be happy, but we also want to avoid pain. Pain can be in many forms, including physical pain, emotional trauma like stress and fear, and lack of basic resources like food and shelter. Humans have a well-documented loss aversion. In experiments, people saw the loss of $100 as bigger than the equivalent gain of $100. While I haven’t come across versions of the study that are more philosophical (as opposed to quantitative, using measurable amounts like money), presumably people would more highly avoid a certain amount of pain over the gain of an equivalent amount of happiness (however such experiences can be measured).

Even without detailed research it should be obvious that if you take the average household income in the US of $80,000 in 2023 (source: Federal Reserve Bank of St. Louis) and looked at the extra happiness of $40,000 more per year versus the pain of $40,000 less, the downside is much more significant than the upside. The upside is a bigger house or more vacations, and less financial worry. The downside is nothing but worry and hardship; it directly impacts the most basic of Maslow’s hierarchy of needs: food, shelter, and safety.

The challenge of human perspective is that it’s temporally unidirectional. We have clarity on our past, but not our future. There’s the old joke that your last check should bounce, meaning that you should spend every dollar you make on your needs and happiness, dying bankrupt. From an economic optimization standpoint that is ideal. Practically speaking, however, you don’t want to run out of money and live penniless the last few years of your life. That’s the key point; your risk aversion to living penniless from lack of certainty as to the future (i.e., your financial needs for an unknown number of years at the end of life) is why don’t try to do that.

How does this connect back to spending time at work? It’s easy to be on your deathbed and think, “In my forties I wish I had spent more time with my kids.” It’s a common sentiment as Ware has observed. But what about the alternative? Suppose in your forties you didn’t work quite so hard. Unfortunately, things got tough for the company due to a recession, and your company did have layoffs. Instead of being ranked in the top half of workers, you were in the bottom half, maybe bottom quarter. Consequently, you were one of the people let go and with the recession you were out of work for a year or more. You had to move to a smaller house, and your kids hated it because they moved away from friends at school. The stress of being unemployed harmed your health. Instead of building retirement savings, you took money from it, making your retirement all the harder. The question is, should you have worked harder to avoid that or not?

Of course, we can’t know if you would have been laid off if you didn’t work as much. Maybe you wouldn’t have, or maybe you would have. Even if you were laid off, perhaps being able to spend more time with your tween kids for a year was better for them and you, even if, say, the stress of that period caused you to die two years earlier. One year of spending lots of time with your kids at that important point in their life may have been better for them and/or for you over two years of end of life when you would have been sick and your now-adult kids may have lived far away from you. But we can’t know that either. Alternatively, maybe working harder would have caused you to miss so much family time that your kids would have resented you and the stress of the extra work coupled with the increased strain of family dynamics may have harmed your physical or emotional health, not to mention your long-term relationships with your spouse and children. Again, this is only a what-if we can’t easily answer.

We don’t know, during our working years, whether we need to work marginally harder or not. We don’t know what tomorrow will bring. We don’t know about recessions, global pandemics, the amount of social security we may actually get, or how much our health care costs will be in the future. Most of us don’t want to gamble with that.

At the end of your life, you can look back and say, “Oh, I had X extra dollars left, so I could have worked less;” but you didn’t know that a priori. What we get is a survivorship bias. Someone who winds up with excess money may say, “I wish I spent more time with my family in my 40s and 50s.” Someone who at the end of life is suffering financial trouble, or really anyone, is less likely to say, “I wish I spent less time with my family and more time at work.” Even if they wish they worked harder, it’s unlikely this is what they want to be commenting on in their final days; and if they do, most people probably don’t note it as remorsefully as someone saying they wish they had spent more time with their families.

It’s not unlike what we see with startup founders. For every rags to riches story of a founder who worked hard and became a billionaire, there are thousands more of people who worked hard and never made it, meaning it would have been financially better off working in some corporate job than wasting a few years for little or no pay. But no one writes about Bob who decided not to start a company and instead stay in middle management for the next twenty years. We hear about the exciting, successful founder stories, but only after we know they’ve been a successful founder. Likewise, we hear about the people with regrets for spending too much time at work only after they’re assured at the end of their lives that they did have enough money and could have done with less money and more family time.

I am not saying you shouldn’t try to maximize your time with your family. However, knowing how to maximize it in light of the uncertainty of future income and financial needs is very, very difficult. It’s why most of us don’t bounce our last check or do the time equivalent of working just hard enough, but not more, such that we get laid off exactly on the day we planned to retire. Yes, spend as much time with your family as you can, but there’s a reason you’re working hard, and maybe not spending as much time on your family and hobbies as you’d like. It’s not because you don’t love your family; quite the opposite, it’s because you do love them and want them to have financial safety and in an uncertain world.

In a world of stress and burnout, it’s hard to say, “you should be working more” (especially as an executive who has people working for me). To be clear, I’m not saying you need to work more (or that you need to work less). I can’t tell you the right amount of work for you. I’m only saying that if you sometimes worry that you’re working too much and may regret it later, to be kind and understanding to yourself; you’re working this hard to make sure there’s a big cushion between you and the bounced check. Make the best judgement call you can and know that in an uncertain world, optimization is traded off against risk.

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