By keeping your options open and working hard at what you decide to do you will CREATE YOUR OWN LUCK. I would encourage you to work hard for what it is you want to do - but be very realistic about opportunities and do not rely on luck for your future. Most of the lucky people you know of have done a lot of work behind the scenes to put themselves in that position. In other words they created their own luck.
You should always pursue what it is you want to do, but you should also have a realistic back up plan as well.
Example: You want to be a professional athlete, so you will need to work hard for that goal. That does not mean that you stop working in other areas. When you are young, you should be working on more than one path. You will more than likely change careers multiple times when you are older.
Long answer: Start with that dream but be open to what comes your way. When I was in college, my goal was to be a comic book writer and possibly illustrator. I even ended up getting an internship at a pretty prestigious comic book publisher, but no paying job came from that.
I'm now starting in a field that I never knew existed when I was in college. I'm happy, doing fulfilling and creative work, and it's my dream job that I never knew I wanted.
Luck may get you some things, but persistence will take you the rest of the way. Keep trying and take the opportinities you find.
Truly a great question on multiple levels!
Dream job? Wow! I'd love to hear more about all it entails. For now, the operative words from your question that really stood out are "luck" and "safe." With that in mind, let's peel back some layers of your sense of risk in your career, let alone life. Every moment of life is a risk. Haven't we all experienced that through a magnified lens this past year!?!?! Since risk implies loss, it begs the query, "What are you afraid of losing?"
Viable career advancement path?
Sense of accomplishment?
Or, like many of us, it could be a combination of these and other factors. In my case, it was all of these, plus triggers to past loss. And then there was this internal force -- my refusal to someday find myself on that proverbial deathbed with this regret, that ultimately overshadowed my shadows. I went for the gusto.
As for you, Derrick, or anyone out there, only you can assess your level of risk tolerance. In doing so, you need to turn the question around on its head. What is the risk of you NOT pursuing your dream job doing what you perceive as requiring significant luck? What happens to you if you take the secure, more sure route?
Finally, isn't it possible that this dream job -- regardless of how it actually turns out, may lead to something else even dreamier? I can't tell you how many times I've seen that occur throughout people's careers. It's always so heartwarming to see people discover what derives passion and fulfillment internally while at the same time, providing a greater good externally. In other words, this may appear as a dream job right now from this viewpoint. Yet, your career is an emergence, just like you. Stay open to possibilities while learning about yourself along the way.
In your life, you will not always find the good job where you feel in your place.
Most important is that you perform something that you like to do, i.e. when you wake up in the morning, you look forward for your journey.
Of course, it will be difficult days like in every job, but if you remain motivated by what you do, then you have chosen the right orientation.
One other criteria is the work-life balance, don't forget that ! If you just live for working, you will keep up.
Also be cautious in well remunerated functions upfront, sometimes it looks nice, but it asked to invest so much of your person, with high expected objectives, that you will be stressed.