Updated on 10.20.11

Some Thoughts on Handling Life’s Crossroads

Trent Hamm

Every so often, we’re met with a situation in our lives that represents a seriously life alteration. If we go one way, our whole life is going to go down a different path than if we chose the other option.

These can take a lot of forms. The choice to marry someone. The choice to divorce someone. The choice to change career paths. The choice to sign a long-term contract. The choice to retire.

When we’re faced with one of these moments in our lives, it can be an incredible challenge. Often, both directions offer some positives and some negatives.

The usual advice in situations like this is to make a list of pros and cons. That’s often a powerful first step, but it’s just that – a first step.

The real challenge comes in when you’re looking at those pros and cons and you’re trying to figure out which set comes out on top. Here are some of my thoughts on the issue.

Maintaining things the way they are now isn’t really much of a positive. If the way things are was satisfying you, you likely wouldn’t be at this crossroads thinking about this decision.

Keeping things the same is often very tempting because, as humans, we’re creatures of habit. However, if you’re keeping things on a path that led you to these crossroads, it’s not really much of a positive.

If you can maintain an extremely basic standard of living, choose the path with the most upside. Often, a crossroads is a choice between a “safe” path with less risk and a “risky” path with the greatest positive potential outcome. If the risky path offers at least a minimal standard of living as the worst case scenario, the risky path should be strongly considered.

Why? Almost always, when we choose the more challenging path, we never regret not choosing the easy path. However, when we choose the easy path, we often find ourselves regretting not taking that more challenging path.

Set yourself a firm deadline. More often than we’d like, a difficult decision at a crossroads is decided by indecision. We sit on it and hem and haw until the decision is essentially made for us – and that usually takes us down the safe path.

Instead, set yourself a tight deadline for resolving this crossroads and hold yourself to it. One effective way to do this is to inform interested parties of your self-imposed deadline by telling them that you’ll have a decision by that date. This puts some additional pressure on you to actually move forward with a decision.

Talk to people with experience at this same crossroads. Internet forums can be perfect for this as it allows you to anonymize yourself, but there’s also incredible value in talking to trusted friends about such things, too.

Simply put, you’re looking for advice from people who have gone through something like what you’re going through. This advice can be incredibly useful, but you also need to filter it a little. Make sure that people are being genuine, and ignore advice from people who seem to have an axe to grind. Usually, their anger has little or nothing to do with what you’re saying or what your situation is.

Crossroads can be difficult places. Good luck on whatever path you follow from here.

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  1. valleycat1 says:

    Once you’ve got the list of pro’s and con’s, you need to weight and/or rank the various items. You could have a lot of what you consider minor entries in one column and one much weightier entry in the other – sheer length of one column’s list isn’t the sole deciding factor. And sometimes by writing a pro or con down you realize it isn’t that big a deal, or is a much bigger deal than you’d thought.

  2. Gal @ Equally Happy says:

    This is well timed for me Brent. I’m considering leaving my current job and starting my own business. I’ve been putting this off because I’m scared of the risk but the truth is that I dislike my job. Starting my own business would be a lot of fun, I have the savings to do it and if I fail I can always find another job in my field. I have no downside and all the upside.

    Thank you,

  3. Squirrelers says:

    Good thoughts here. I absolutely agree that conversations with those experienced in the same type of crossroads can be invaluable. Sometimes, there’s nothing like actual experience to be able to guide or advise someone through the finer points of different choices.

  4. kc says:

    You can find a lot of good tips on reddit.

  5. Karla says:

    Well timed for me, as well. I have to decide between an amazing work opportunity that would take me overseas and a new but promising relationship. Two long time dreams in direct conflict, ugh. Maybe there’s a blog for that so I can read it and know the right answer? :)

  6. Andrea says:

    I recently heard someone on the radio talking about how they made a big life altering decision. For 1-2 days they decided that they would act as if they were going with option A, particularly related to self-talk. Then for another couple of days doing the same with option B. You can start to see and sense your true opinion of things like, oh I wont be at this park anymore or eat at this little corner restaurant when I live 2,000 miles away. Are those evoking positive or negative feelings about the decision. At least for the person talking on the radio it gave them clarity and helped them make their decision.

  7. Georgia says:

    Karla – I had the same decision to make over 48 years ago. I had an absolutely fabulous, well paying job that would also send me overseas to work. I met a wonderful man. The man won. My mother was afraid I would regret my decision, as I had always wanted to travel. But, I read what a very wise man said about regret – If you had taken the path you regret not doing, what guarantee have you that it would have worked out? No guarantees in life, so good luck making your decision and sticking to it. Regrets are too negative to allow into your life.

  8. Matt says:

    Crossroads is a restaurant in our area that shut down within 6 months of opening. Just saying :-P

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