Oregon Trail. If you recollect the name of this captivating educational computer game from the original Macintosh Apple II computers, you are definitely the generation that I am speaking to with this article. The Oregon Trail computer game was developed to engage elementary students in rousing navigation while embarking on the journey of settling across the open Prairie in the late 1800s. Along this journey, if you are female, you make life-altering decisions about how many children you will birth, your profession, and the number of oxen, chickens, sheep, and goats that you wish you carry in your entourage.
Seems simple, right? Wrong. As it may appear that the ideal early settler would have a larger brood, many times as you navigated the game, it was exactly the opposite. Little Johnny is ill with cholera and you are set back in your prewinter travels by three weeks, thus, you miss the open pass to the nearby mountain range you needed to reach by Spring. The popular phrase, “You have died of dysentery,” became a threat amongst you and your fourth-grade peers.
The tactics of the Oregon Trail game were evaluated on four platforms: hunting, death, scoring, and legacy. Sounds a lot like your life managing 8 a.m. board meetings, heels on icy pavement, blind dates, or a bikini wax, right?
Never once did it occur to me to check “single settler,” as I began my riveting Oregon Trail experience. In fact, I highly doubt that in 1988, that they even offered such a choice.
What does the word settling mean to you? Does it mean selling yourself short? Growing accustomed to a certain situation? Giving in? Putting yourself last? Or, does it mean simply loving where you are and accepting your life?
My point is that this one small word can mean so many things to many different people. I was reminded of this while having coffee with a dear girlfriend of mine just this morning. She and I feel similarly about settling, in that we are both enjoying our late twenties, we’re both single, hold successful careers, and we have both have dated hosts of men. Some young, some old(er), some rich, some poor, and some still “finding themselves.”
To us, settling is a term that we have coined for women who have succumbed to the pressure and mostly Midwestern mentality of marrying at a young age, and straddling the fine line of wife, mother, career woman, and socialite. None of these titles are light orders, and many come with strings attached.
While the Oregon Trail female settler is a far cry from women of the twenty-first century, I believe that we can learn something from women of each generation. Early settlers endured pain, struggle, triumph, and pleasure, but they were not given the options or choices that we are blessed with today. Are you taking advantage of the opportunities given to you, or are you settling—resting on your laurels?
Once your journey came to a conclusion on the OT, the measure of your life was weighted upon the profession that you had chosen amidst your travels, the health of you and the family members survived in your brood, in-pocket dollars saved, and remaining possessions. This is not unlike the judgment cast on the measure of a woman in today’s society. As you evaluate how you have “lived your dash” (in between your birth date and the date that you leave this earth), what truly matters?
If today’s women settlers could be measured by the mark of their character, elevation of their morals, purity of gumption, understanding of their roots, and passion to make the world a better place, perhaps we would all reach the end of our Oregon Trail with successful bounty.




