Yeah, I've had similar anxiety recently choosing a new place for my family to live. I think keep in mind that if both choices seem like good options you're likely to get some good outcomes either way. My wife put it like this,

What's nice is the way the human brain works, down the road we'll be thinking, "I'm glad we made this choice because then X happened."

I'll be the Oracle from Matrix. "Because you didn't come here to make the choice, you've already made it. You're here to try to understand why you made it."

I must have seen that movie a hundred times, but I didn't really understand this until I got older. Every time I seemed to be paralyzed by the choices, it turned out I was just afraid to commit to what I really wanted to do.

Not sure if knowing more about your career path, skillset, and planned change could help in giving you better advice... all I can say is: I was in a similar spot once. And tell you a story.

Once upon a time... I had to choose between going to college, or jumping into a job offer and leaving college for maybe later. Had about 4h to decide, but I took inventory of all I knew, asked some people, and based on my skills, career and abilities, everyone told me to ditch the job, college was more important and would get me more doors to open. I kind of knew that was "supposed to be" the answer too, "learn to fish" and all that, and was eager to take that path... so I did that, passed on the job, went to college.

Some time later, life happened, it became harder and harder to stay in college, so I dropped out and jumped into some jobs. As it turned out, none were like the one I had passed on. Then life happened again, and working became harder... life happened again, and forced me to switch and twist my career... and life kept happening, and messing things over and over, up until right now. It hasn't really stopped yet.

Had I picked not to go to college that year, things would have been different. Hard to say whether for the better or worse... even if I'm 99% convinced it would've been better, and I could've gone back to college at any point.

...or maybe not, maybe life would have kept happening, just in some other ways, messing up things in that other path I didn't take.

In hindsight, I know I took a bad path, but I can't know whether the other would've been necessarily better. Thinking back to that moment, all the data I had back then, pointed to the choice I did make, so I don't think I really made a mistake, even if it didn't pan out nearly as planned.

Turns out, life has its ways to really mess up a lot of plans... but you don't really have a choice, you make some plans, to the best of your knowledge and abilities, and then... who knows, maybe they pan out, maybe they don't.

So my advice would be: make your plans, to the best of your knowledge and abilities... make a pro/con list, weigh the probabilities, ask people for input... but if the anxiety is too much, just stop thinking about it, toss a coin, whatever.

You can't know what the future will hold, can't know whether the best of your decision making will pick a good, or even a better path, not even in hindsight... so just make a decision, see how life unfolds, and don't worry too much, it will be whatever it will be.

Good luck.

I was, multiple times. I always decided for the path I can justify the easiest to myself. Almost always, the lazy way was the one I didn't choose. I know I'll be still me in 10, 20, 50 years and I really don't want to look back to a time when I was younger but didn't do what'd give me the best position at older age. Yes, this even included not trying to find a girlfriend because I rather spend that time learning, self reflecting and pursuing a career. And I personally believe this was always the best decision. A lot of decisions can be made really easy if you look up stoicism and meditate about what truly is in your hand and what is totally chance of luck.

At the end of the day, you know deep inside what the right choice for you is. The unknown is scary, but the future is always unknown, no matter what you choose.

I went the route of going back to school for a fresh start, after my first career attempt didn't work out. It was absolutely the right choice. I went from feeling stuck in a bad situation and absolutely miserable, to a career that allows me to live my best life and I am infinitely more happy.

I didn't know what was going to come out of the change. I knew I couldn't keep doing what I was doing. When I went back to school, I did as many different internships as I could, since I knew what I didn't want to do, but I didn't know what I wanted to do anymore. I ended up falling into a career field I never even knew existed, but matches up to my strengths perfectly. Bonus points for being paid more than I ever imagined I could make (I basically tripled my income from my old job when I started my current one).

Life's short. Change is constant, no matter what you choose. Do what makes you happy, even if it's scary. We all end up as worm food, do you want to live your life as a series of "What ifs?" Or do you want to take a chance and try new things?

When in doubt I choose change. This hasn't always worked out, but it has been interesting.

get a coin. heads = school; tails = wait. flip the coin.

you're not actually seeking an answer from the coin, but rather to see your gut reaction to what the coin says. maybe it's excitement, relief, calm, or acceptance. maybe it's sadness or dread or disappointment. maybe it's still confusion. in any case, it can help shine a light on what you're feeling, which can be useful when you're overwhelmed by thinking. don't be afraid to trust your gut.

I feel for you. This is something I always dread, big decisions that can have a huge impact on your life. All kinds of obstacles seem to pop up, things that could go wrong. I tend to agonize over them, letting those obstacles grow bigger with every thought. But, looking back, I don’t think I’ve ever regretted one of those decisions in the end.
Anyway, in the end I take a devil-may-care attitude (something very unlike me) and just go for the choice that put me in those crossroads in the first place. I tell myself that I’ll deal with the consequences when they get there.
Thankfully, it turns out I’m much harder on myself than reality really is :)

TL:DR; Been there. Ask yourself what it is you really want out of this struggle. If obtaining it would make it worth it and $ isn't a pressing issue, go for it.

How have you felt so far? How close do you feel, any closer in any way than when you first finished school (or whatever marked the start of your journey) looking for the next opportunity? How are your finances?

Do you still in your heart believe that this is the direction you would want to go? If you manage to obtain it before the end of the year or next year, would you look back and say to yourself, the struggle and the wait was worth it for this?

If you feel like you're going through what you're doing just because of sunk-cost, probably be a good idea to change your course. If your desire to take this path, even if it wavers a little, and the passion you had going into this journey remains, then keep going and keep trying.

I'd consider myself fortunate in the circumstances of my life, but I've been there a couple times, where as I finish the program I've been doing, the railroad track I've been following in my life seems to disappear in a dense fog of unknown, quickly approaching and it sometimes appearing like a cliff.

You never know what the future will hold, trying to predict every single possibility before deciding will only make your head spin (it did mine). What will happen will happen, but what you have control over is what you yourself would do about it. No matter what path you take, acknowledge 'possibility' but focus less on the unknown and focus more on how you can best prepare to reach your goal.

Yep, I just spent months agonizing over choosing a school program. I think our bodies tell us what we need if we listen. I was set on the "safe" choice, but as the registration deadline got closer I got more and more depressed and wasn't sure why. I came home one day and just collapsed on my bed and started sobbing because it didn't feel like "me" and I couldn't see myself being happy doing that for the rest of my life. But I didn't even realize how much I didn't want to do the program until it got so bad I couldn't control my emotions. I was trying really hard to force myself to be excited about the safe route but I just couldn't do it. I think our bodies tell us what we need. I was ignoring the twist in the pit of my stomach, ignoring how drained I felt learning the subject, ignoring the subconscious procrastination and lack of focus. I switched my program to what I really wanted to do and p much immediately felt relief. I feel aligned with myself, excited to start classes, feeling good about the job prospects and the types of people I'll get to be around. I literally feel lighter.

Some other people have made really good comments and suggestions about how to figure out what your gut is telling you. It's a bit morbid, but I like to pretend I'm old and on my death bed looking back at my life. How would I feel about the decisions I'm making right now? Will I regret not going for the harder thing I want more? Will I be happy to take the safe route? Did I waste my precious time that's now ending? Etc etc

Figure out your deepest, ground-level goal/motivation.

Let’s pretend your most profound goal is “stability.” That may mean staying where you are, or it could mean taking the risk on school for the greater stability it offers in the future.

Identify your life’s motivation and then apply it to your options. Simplify to one word if you can. Bare bones.

Damn I'm basically at the same spot as you