I'm a naturally competitive individual and I like to out-compete my peers at work - in other words, to win. I don't think this part of human nature will ever lessen no matter how far technology advances.
You should re-calibrate your winning condition to "spends the most time relaxing" instead of "makes the most money".
Really, you should do whatever you like, but part of the problem is that our collective winning condition is based on a number that has, after a certain point, little relation to happiness.
Personally, I try to optimize my happiness. I'm not doing that great a job though because I still spend more than 40 hours working a week. I think my ideal would be to spend 25-ish hours at work and the rest on "leisure"[1] activities.
The nobel economist who invented the GNP (predecessor to GDP) even warned that "the welfare of a nation can...scarcely be inferred from a measure of national income"[2]. Yet here we are 80 some odd years later and it seems the only thing that matters for a nation is GDP growth and the only thing that matters for a person is salary.
Those are nice things to track, but they don't tell you anything about the welfare and happiness of people. Trying to optimize GDP/earnings growth is almost entirely the reason the US doesn't have universal health care, or a higher minimum wage, or mandated child-care leave or vacation leave, etc. We're too scared that it might impact a number without any regard to the actual humans who have to slave away in misery* to attain it. We need to recalibrate our winning conditions to something more, well, humane.
* - misery is mostly hyperbole, fwiw
[1] - leisure activities for me would be a side business, cycling, hiking, gardening/farming, but they could really be anything.
[2] - http://en.wikipedia.org/wiki/Simon_Kuznets
Jonathan Haidt's "The Happiness Hypothesis" makes the point that very few things actually long-term moves the needle when it comes to happiness:
Meditation does. As does therapy. And drugs.
These can move our "normal range" of happiness. Most other things, Haidt argues, will temporarily bump our happiness up or down, but we quickly revert to our normal range.
Some things that generally don't affect our happiness in the long term according to Haidt: The amount of time we work or spend on leisure activities. Major health problems that are not degenerative (heart attack, losing your legs). Winning the lottery. Getting that big raise at work.
The reason, it seems, is that we adapt very quickly. Winning the lottery will make us very happy for a short while, but without a lot of discipline we've shortly adapted to our new-found wealth and the needle goes back down to our "normal range". Losing your legs will make you depressed for a while, but soon we adapt and the needle springs back up. Getting a raise is great for a month or three, but then we're used to it and looking forward to the next one.
As long as things are steadily getting better, we are mostly happy. If they are steadily getting worse, we are mostly unhappy. Even seemingly earth-shattering events that totally changes our lives only tends to affect most people for a while.
This does explain some of the obsession with GDP: It is a proxy for growth, and ongoing growth is associated with happiness. But as point out, optimizing for GDP can happen at the cost of negatively affecting other things that are also associated with happiness, and the net result is not necessarily all that great.
An interesting aspect of Haidt's claims is that we should not aim for a too rapid improvement if they make further improvements harder. That is, it's better to get a steady 3% increase in salary, than 50% now, and then nothing for many years. If you do get that 50% raise (or a huge exit), it is better not just for your finances but for your happiness to invest most of it, and slowly increase your spending over time.
My guess is the freedom to try new things would be a way to maintain or improve ones happiness. There are a ton of things I wish I had time to do/learn/experience, but the general trend of society is to chase the dollar through "steady" work.
