I’m not a natural planner. It’s difficult for me to plan out my weeks to a tee, I cringe when people tell me the details of their life plans, and I get overwhelmed when having to manage a calendar. Needless to say, I’m not having fun with wedding planning.

While I’ve gotten better at planning (it’s still my least favorite thing about being a professional), I think my overall aversion to it is because I like the flexibility of possibilities. Also, I realized at a young age when I put so much stock into a plan or dream, I’m more likely to be let down. I prefer loose plans. Plus, I enjoy my freedom too much. My life approach is somewhere between be wise and YOLO.

But I’m quickly realizing the value of planning and staying organized. Especially when trying to convince people to hire me. For example, today I had an interview that was really going great. They asked that annoying question, “What’s your biggest weakness?” I felt the interview was going well to be completely honest, so I said something like, “I’m not great at planning and staying organized.” Of course, their pens scribbled away and when I asked what qualities they’re looking for in an ideal candidate, planning, organizing and prioritizing were all among the answers.

I hope that one response didn’t discount all my other great attributes and charm. Of course, I did round out my silly response with the truth that I’ve learned the value of staying organized and having a plan, and I’m learning to prioritize tasks and goals right away rather than taking on too much and needing a breather; but like everyone and everything else, I’m still a process.

The tradeoff with my improving planning skills is that I’m flexible when things need a sudden shift. This is the biggest reason why I’ve not prioritized planning skills because I know that life happens and needs change rapidly. I may not be happy about sudden changes (is anyone?), but I’m able to switch gears quickly and find creative solutions.

However, when it comes to wedding planning, I really am struggling. There are too many possibilities and it’s all expensive. I’m this close to going to the courthouse tomorrow.

Interactive blog questions: 

• Are you a planner or an improviser? 

• How do you find a good medium ground? 

• What wedding planning tips do you have for me?

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A look at my (very empty) calendar for March. Part of my learning-to-be-a-better-planner action steps is taking time to fill this out at the end of the previous month with solid dates like birthdays, events, bills, meetings, etc. My next baby step is to start filling it out with to-do’s each week. Ugh…