I think the answer is more about who you are than what you do or did. It's about your attitude toward whatever you are doing. A person can always find some pretty good reasons to be unhappy or to be happy with whatever the circumstances.
I look back at my short stint in the Navy, for instance, and remember those years fondly. I remember lots of excitement shooting 5" guns, ASW weapons, war exercises and all manner of manly things. I recall conning the destroyers I rode alongside replenishment ships, among ships in formation, and into new berths after being at sea. Boy was that fun. What I DON"T seem to remember as well is the tedium, the anxiety, the fear, and the lack of sleep that went along with it.
I've thought about this question before, and the answer is to do as many things as you can fit into your life and still get by comfortably. Early on, money did not drive my actions. I've worked as a laborer, a plumber's helper, an auto worker, a musician, a surveyor, a teacher, a researcher, a design engineer, a manufacturing engineer, and a corporate manager to name some. Most of these I did before getting married. The beauty of having done so many things is that you don't have to wonder "what if" so much when you're putting in the 25-30 years to support the family you created.
But, to answer the original question, what other path would have been more enjoyable? I can only compare what I've known. Here would be my perfect occupation: Teach a class until noon, survey land in the afternoon, play in a band until mid-night, and be a tour guide to somewhere new on the weekend. Of course someone else would have to prepare for class and grade papers; do something with all the data I collected in the afternoon; put in all the hours of practice necessary to perform well at night; and take care of the chores and maintenance that are needed that I would normally take care of over the weekend.