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A good friend of mine is having a really tough week. She has a clear Feeling preference, so I am constantly thinking of how best I can reach out to her for help. I've never experienced what she's going through and quite honestly am out of my comfort zone as an ISTJ when trying to comfort someone in pain.
This got me thinking...is that the hardest thing for me to do based on my type? Is trying to figure out someone else's emotional need one of the greatest "out of preference" challenges I face as an ISTJ?
If I'm being entirely honest the answer is no. As an ISTJ I work my way around doing the whole shoulder-to-cry-on thing by providing tangible support. If a coworker has to be out of the office to deal with an emergency, I'm a billion times better at taking care of their to-do list than I am at the Chicken Soup for the Soul stuff.
Basically, I use my ISTJ preferences to help in other ways, which is exactly the message Greg Huszczo talked about in Making a Difference by Being Yourself.
The honest truth, though, is that my biggest challenge is asking for help. I have a tendency to over-commit and burn out because I refuse to fail at any task, deadline, or commitment. I also prefer to get things done on my own, so my lack of delegation ability compounds the original problem. This is definitely on my areas for development list.
What about you? What is your greatest challenge based on your personality type?

Wow. Great post. This has me thinking about a training course I took on working in teams. Everyone in the class took the Myers Briggs evaluation. The evaluation indicated that my personality type was ENTJ. The interesting point was that my score for "J" - the Judging part - was off the charts. This means that I can tend to be a very structured person that plans things out.
The course facilitator pulled me to the side and said that I will have to work hard to tone down my "J". I have had instances at work and in my social life where I found it very difficult to be spontaneous. The tricky part is that people often suggest that I "lighten up" and act more spontaneous. I really don't feel that me trying to be like everyone else is the answer. It is very tough for me to navigate through this because I even try to "plan" being spontaneous.
I'm an ENFP. I have two big challenges that are probably due to my type.
The first is that I want to do EVERYTHING. NOW. I always feel like "If I don't do this now it'll be too late! I'll miss my chance!" It's just not realistic for me to pursue all of the things I want to, and I'm often challenged when I have to decide what I'm going to do now and what I'm going to hold off on for the time being. I love having options and I hate "closing doors" so I can be very, very indecisive.
The second is that ENFPs are introverted Feelers. That means as open as I am, I struggle to express things like affection, and I will almost never let people know when I am struggling or feeling angry/sad. If I do give people a hint at how I'm really feeling, it rarely demonstrates the full depth of the emotion.
I'm working on both of these. The first requires faith in myself to get around to things further down on the list, and to trust that even if opportunity A is no longer available, something else equally interesting will be. The second requires opening myself up to vulnerability. So far I can pretty much do this just with my S.O. (and I still struggle to show him my affection.) But I'm trying.

Keith- as someone who also scores 5 (very clear) on all J facets, I can totally understand what you experience.
Nicole- great example! I'm fascinated by ENFP's because they are the opposite of me. Your comment about when you do show emotion it is still rarely reflects the depth of the emotion was really insightful and something I will keep in mind when I interact with my ENFP friends.

@Breanne
How do you handle being a strong "J"?
Hm, where can you take this personality test? I have no idea what type I am, but I can say that I too have a problem with wanting to do everything I can possibly do. I tend to take on too many things and once I commit to something, I feel horrible backing out. At the same time, I sometimes never have the time or energy to complete everything I've set out for myself!