You have run the numbers a hundred times in your head, and they never come out the same way twice. Some nights the safe path looks like wisdom. Other nights it looks like the slow version of giving up. You are not confused about the facts. You are confused about which fear to trust: losing what you have, or never finding out what you could have had.
Most people around you will hand you their own risk tolerance and call it advice. Three thinkers on the Consilium roster would refuse to do that. They would ask you to look at how you are calculating, not just what you decide.
Franklin: put it on paper
Benjamin Franklin would not tell you whether to play it safe. He would tell you that you are trying to solve this in your head, which is exactly why it will not resolve. His method was to draw a line down a sheet of paper, list every reason for and against, then weigh each one rather than just counting them, until what remains is a balance you can actually see.
Though the weight of reasons cannot be taken with the precision of algebraic quantities, yet when each is thus considered, separately and comparatively, and the whole lies before me, I think I can judge better, and am less liable to make a rash step.
He would push you past the vague dread of "it's risky" and ask what specifically you are afraid of losing, and how likely that loss actually is. Franklin ran his own life as a series of small, trackable experiments rather than one irreversible leap, worth noticing since the safe path and the risky path are rarely the only two options once you break a decision into steps you can test.
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Kahneman: your fear is not measuring what you think it is
Daniel Kahneman would say the real problem is not the decision, it is the instrument you are using to make it. His research showed that losses feel roughly twice as painful as equivalent gains feel good, which means your brain is not weighing the two paths fairly. It is overweighting the loss by default, every time, without telling you it is doing so.
Nothing in life is as important as you think it is while you are thinking about it.
He would ask you to take the outside view: forget your particular hopes and fears for a moment, and ask what happens, on average, to people who take the risky path in situations structurally like yours, not what could happen to you specifically. He would also point out that vivid, imagined disasters feel more probable than they are simply because they are easy to picture. That ease of imagination is not evidence.
Ellis: you are catastrophizing, and you know it
Albert Ellis would skip the spreadsheets and go straight for the sentence running underneath your hesitation: "I must not fail at this, and if I do, it will be unbearable." That sentence is doing more damage than the actual risk. It is not the possibility of failure paralyzing you, it is the demand that failure be impossible.
There are three musts that hold us back: I must do well. You must treat me well. And the world must be easy.
He would ask you to separate the practical odds, which Kahneman can help you estimate, from the emotional verdict you have already attached to a bad outcome. Losing the safe option would be uncomfortable. Ellis would insist it would not be catastrophic, and that the word "catastrophic" is doing dishonest work in your head. Dispute it directly: what would actually happen if the risk did not pay off, in specific, unglamorous detail?
Where they disagree
Franklin would say: this is solvable with structure. List it, weigh it, test it in pieces before you commit to the whole thing.
Kahneman would say: structure will not save you if the inputs are distorted. Fix how you are perceiving the odds before you trust any list you make.
Ellis would say: the odds barely matter next to the story you are telling yourself about what failure would mean. Fix the story first, and the decision gets much easier to see clearly.
None of them would tell you what to do. Franklin trusts a good process. Kahneman trusts corrected math. Ellis trusts a mind that has stopped lying to itself about the stakes. Notice that none of the three simply says "be careful."
The question you came here to avoid
You did not search this question to learn how to calculate risk. You searched it because some part of you has already chosen the risky path and is looking for permission, or has already chosen the safe path and is looking for an excuse to stop feeling guilty about it. Either way, the calculation was never really the point.
So ask yourself what Franklin, Kahneman, and Ellis would ask together: if you strip away the fear of regret and the fear of loss, and you strip away the story about what failure would say about you, what does the actual evidence say you should do, and why haven't you done it yet?