Facing A Difficult Personal Finance Decision (Or Other Major Decision)? Try These Seven Techniques

As I mentioned a while back, I’m in the midst of making a pretty significant life decision: do I make the leap to being a writer, or do I keep doing things as I currently am? I’m turning the whole matter over very slowly and analyzing from a lot of different angles.

Since I’m taking this decision so slowly, I’m trying a wide assortment of different techniques for making my decision to see where they point me. Here are the ones I’ve tried that have provided some revelations to me.

Make a giant list of pros and cons I shared the highlights of this list earlier, but since then I’ve kept it around, growing both the pros and cons of the decision to almost absurd lengths and often rewriting and clarifying specific points.

This constant revision has started really breaking the decision down into the true pros and cons of the situation. In truth, the pros are about what my heart wants and the cons are about what my mind understands. On paper, I shouldn’t even consider making this move. In my heart, though, I have a sense that if I don’t do it now, when the pump is relatively primed, I never will.

Prioritize your options The Prioritizer does a very good job of helping you rank a list of items based on your personal priority. I disassembled the various pieces of the puzzle (children, intellectual curiosity, etc.) and ranked them using the tool.

I found out that my children are my highest priority, which is a vague indicator that I should play the safer route as it provides a greater security net for them. What I did find, though, is that control and freedom over my work are things that I value very highly – I don’t like work where I have limited control over what I’m doing and what I’m producing.

Call a trusted friend for a long, heartfelt talk Often, there are aspects of your situation that are intrinsically tied to who you are as a person. As a result, there is significant added value in talking to someone who knows who you are and can include things like your personality and a more detached view of your skills and talents into account, things that you can’t judge accurately for yourself.

Once you’ve initiated the conversation, lay it all on the table – everything you’re thinking both ways on the issue. Hopefully, you’re talking to a friend close enough to you to provide their most honest assessment of the situation, even if it might not be the one that you want to hear.

Look at the “big three” scenarios Sketch out in as much detail as possible the best case scenario, the worst case scenario, and the average scenario that would result from making the decision that you’re debating. The best case scenario reveals the things that compel you the most, the worst case reveals the things that worry you the most, and the average case indicates your authentic hopes for what will happen.

The more you detail those scenarios, the better your understanding of the actual dilemma becomes because you begin to actually see the secondary and tertiary effects of that decision on your life. Quite often, these secondary and tertiary effects are the ones that make or break your plans. For me, I’ve found these secondary and tertiary effects to be quite fascinating. Would this move make me less social? Would it improve my children’s intellectual development? Interesting issues to think about.

Collect advice from as many sources as you can While it may not have the value of a deep conversation with a trusted friend, running a two minute drill of your dilemma past a lot of people can provide a lot of insight. Submitting your concern to a large group can reveal countless angles that you never considered and it can stress certain areas that you glossed over before.

By merely writing about my decision on this blog, I threw my dilemma out there to 100,000 eyeballs – and I collected a lot of advice from a lot of people. I’ve also threw the dilemma out there to almost everyone in my life to see what they thought about it – and collected their ideas, too. What does all of this data mean? It’s a serious gut check – in my case, the biggest one was about the quality of my writing, something which underlies all of my plans. People are very honest about their concerns, often revealing angles that I never even conceived of on my own.

Tuck it away for a while Many major decisions, like this one, don’t have to be made immediately. You can gather information, then tuck the information away in your subconscious mind to work slowly over time. This is actually the place I’m at now with my decision – I’ve postponed further thinking and deliberation for a month to let it all settle and allow my subconscious mind to work away at it for a while.

This has been very beneficial to me many times in the past. I basically stopped deliberating my choice about college (I had a handful of strong options) for a month and let the choices settle in my mind. When I picked up the decision again, the right answer revealed itself very clearly and quickly.

Take the road less traveled In the end, one big piece of the puzzle that keeps most of us from making the move that we feel is right is a fear that it’s not the socially acceptable thing to do. Lately, I’ve been thinking aboutgroupthink” quite a lot and I’ve come to the conclusion that quite often it prevents you from making the best decision.

My conclusion? Don’t worry about what “society” might think of your choice. Quite often, they point towards a path of conformity in some fashion or another. While conformity might help people get along in social situations, it’s rarely a healthy indicator of how you should live your life. Discard those worries and take the road less traveled.

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I –
I took the one less traveled by,
And that has made all the difference.
– Robert Frost, “The Road Not Taken”