A little personal story ahead also sorry for the long post...
Three years back my life was a disaster, I was as far away from Dhamma as possible, I was into the dark side of modern life. Drowned into money, greed, sex, addictions which inevitably rolled me into stress and depression, but I still had my job. At the time, I was reading one of the books by Thich Nhat Hanh and one evening as I left my office, I sat on a fountain-side watching all the people coming out of the high-rise buildings rushing to catch the tide back home. I had kind of epiphanies moment where I asked what am I doing with this? where is my life going? I felt that I definitely did not want to spend my life climbing the corporate ladder...it was like a terribly dreadful feeling I can't put into words...
So very next day I quit my high paying job, in a few days moved out of the big city and into my parent's house. From there I started seriously reading Buddhism. In a years time, I was way over my addictions at least the alcohol was out. From there I did a couple of 10 day- vipassana retreats and also did a month-long retreat at a Zen monastery. At the end of last year, I was over my anti-depressants tablets and stopped going to a psychiatrist.
This whole year I spent meditating in Zazen and Vipassana, I have finally to my satisfaction finished reading books. Now I have come to the point that I have known that the Theravada tradition is best suited to me and I am reading Ajahn Brahm's book on Jnanas the third time.
My life has been changed for better, I don't have a job for three years but I don't have any financial worries or family concerns. I have narrowed down to bare minimum needs and I can possibly live like this till I die.
But now it seems I want to live in a better way, in the right way according to Dhamma. Instead of getting back to rat race I can live some other kind of way to make money, go find a girl (again), basically get into Samsara. Life seems to have gotten a new meaning if I choose to give it. It will be a repeat of the cycle, just better this time.
I have made some good progress in meditation. If I continue with current focus for this coming year(2019) I am hoping to progress till a nimitta. Also, I have met a normal guy online who has attained Enlightenment, (from his words and actions he looks genuine) so following his example, Nirvana seems like an achievable goal within a human lifetime.
The problem is that the idea that if I get Nirvana I will not be reborn again seems discouraging. Now life seems like worth living again, although I am very much well versed with suffering.
So, in the end, my real question is how should I make a choice between Samsara(going back to make money and lay life) and Nirvana(single minded focus on meditation)?