When I’m mulling over some kind of new opportunity, relationship dynamic, career change, or other deviation to my existing lifestyle structure I work through a series of questions, including:
Will this increase or decrease the number of options and opportunities I have in the future?
From where I’m standing today, does this seem likely to make me more or less fulfilled, more or less challenged and growth-oriented, more or less generally satisfied on a day-to-day basis?
Could the time, energy, and resources I would spend on this be better spent on something else (for some value of “better”)?
Does this align with my values?
Do I have any ethical problems with this choice, where it puts me, who and what it associates me with, or the things I might be required to do as a consequence of choosing it?
Is this a decision I would be comfortable having other people know I made? Would I be proud of it?
What are my other options, both obvious and less-obvious? What does the exact opposite choice look like? Are there any positives to that opposite choice I’d be missing out on?
What will this cost me (in terms of money, energy, time, relationships, opportunities, preferences, priorities, reputation) daily? Weekly? Monthly? Yearly? Over the course of my life?
What are the downsides and how might I reduce their impact?
Is this a stepping-stone to something else? If so: how might I skip it, how might I get stuck and fail to make the next jump, and how might I convert the opportunity into more than just a vehicle for getting from point A to point B?
What is the very first thing I’ll need to do once the decision is made? The first big, effortful thing? The first expensive thing (in terms of time or money)?
What unknowns are associated with this decision, and how might I make them known before deciding?
Is there another way to accomplish the same intended outcome?
Are there other outcomes that would also be acceptable to me?
Who might I talk to if I want to be more certain about this decision? What might I ask them and what might they say that would make me more or less sure of my decision?
Who and where do I want to be in five years? What do I want to be doing with my life at that point? Does this get me closer to that desired outcome?
What’s the best argument for this decision?
What’s the best argument against it?
Will the future version of me thank the current version for making this decision?
I often come up with other questions that are more specific to the decision I’m facing, too, and many of these questions lead to other, more granular ones.
But I find that interrogating the issue in this way casts light on previously unseen dimensions of the opportunity, makes me more aware of possible consequences for choosing one way or another, and allows me to address niggling or substantial qualms, quibbles, and quagmires—which in turn allows me to feel more satisfied and confident with whichever direction I ultimately choose.
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