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Anyone who knows me, knows that I tend to overthink things. I'll research even the smallest decision. Major decisions can take forever. I like to joke that I do my buyer's remorse before I make the purchase: I'll already know what the potential disappointments are, or trade-offs I've made, before I hand over the credit card. No surprises!

On the one hand, I know that this is how I'm comfortable making decisions. If I haven't mulled something over long enough, I'm just not comfortable choosing. On the other hand, I sometimes feel that the time I spent researching an item is inordinately long. Or worse, that it is wasted. I remember when my husband saw a particular computer and told me it's what I should buy. I spent days reading every piece of available information about it and all the comparable models. In the end, I bought the one he suggested. That result begs the question, is my research worth it?

Maybe you can help me answer that question. Look at these three situations. What do you think I should have done in each one? Do you agree with final analysis of each one? And what stories of your own do these bring to mind?

Situation #1

A close relative has had some serious health problems. She was put on a new medication for her heart, and she needed to check her heart rate and her blood pressure at least once a day – more often if she was experiencing symptoms. Right after the doctor's appointment, I ran over to a store where I knew they would have a blood pressure monitor at a decent price and bought it. Later, my husband looked that model up online and told me about the reviews. They were horrible! Almost every single person either said the monitor gave readings that were much higher than the ones at their doctor's office, or – even worse – that the results were erratic.

What do you think I should have done here? What would you have done?

My final analysis: Looking back, I think the issue here is that this is a pretty high stakes decision. If my relative can't accurately track her heart rate and blood pressure, it could have serious consequences. Yes, I wish I'd done my research before I bought it. I need to bite the bullet and just buy one of the highly rated models, whether or not my original purchase can be returned. If it wasn't so urgent & important, I could wait until we could get her doctor's office to check its results. But I don't think that's an option.

Situation #2

And then there's the shrub that I bought. A friend gave me a gift card she hoped I'd use for my garden. I decided to purchase a nice plant, so that I could take a picture of it and send it to her. I went to buy the plant on a day when I didn't have a lot of time. I had kind of an idea of where I was going to put this plant, so I'm trying to quickly read labels and find some that might work. I finally pick one and dash to the checkout line. That was a six or eight weeks ago. The plant is still sitting in its pot waiting to be set out, because it isn't quite right for that spot.

What do you think I should have done here? What would you have done?

My final analysis: I should probably just get over this perfection complex, stick it in the ground, and see if it's happy. And if it makes me happy. I can always move it in a year or two if it doesn't work out. It's not an irreversible decision!

Situation #3

Then there is this major financial decision that another person and I have to make together. We've been talking about this for a quite a while. There isn't really a deadline for the decision, but thinking about it for so long has worn me out. One night, the other person and I had a conversation about the newest info that had surfaced. We came to a decision. I was so ready for it to be done that I didn't listen to the little voice that said, "Sleep on it first." Instead, I fired off an email as soon as we got off the phone. By the next morning, my gut told me that I shouldn't have done that. I ended up writing another email, asking the party to ignore my late-night message and give me more time.

What do you think I should have done here? What would you have done?

My final analysis: Since there's a lot at stake here financially and we don't have to make a decision right now, I'm trying to tame my desire to wrap it up. We took a step back and are getting advice from a couple of different types of professionals. With their help, I hope that the right choice will emerge before too much longer. If not, I may have to accept that there will always be more unknowns here than I'm comfortable with. I'll have to remind myself that, at some point, you have to do the best you can do and move on. And not blame yourself if you didn't make the optimal choices.

Final thoughts - from me and from you

I suppose the fact that I wrote a blog post about these decisions and how I approached them is confirmation of what I said at the beginning: I overthink things!

I'm interested in hearing about your decision-making style and how it's worked for you in different situations. Please take a second to tell me about that in the comment box below.