As I wrote the title to this post, I automatically realized the errors in that statement.  How about when planning a vacation?  I spend many hours planning vacations, comparing flight options, accommodations, and activities.  I find it to be a fun challenge to try and put the most fun into the available time for the best value.

So where does the emotion expressed in the title come from?  It comes from when I think about planning financial success.  When I think about trying to make a plan to achieve financial independence, my stomach starts to go into knots.  I start to think about balance sheets, assets, investments, interest rates.  I face a similar challenge when requested to develop a plan for work using MS Project and I'm supposed to say what will happen over the next few months, where I feel like I don't know.

How can I be a successful financial and work project planner?  I can start by asking questions just like that one, and also:  Why am I a good at planning?  Why do I enjoy planning?  Who can I ask help me improve my planning skills?  What plans can I copy?

Another idea is to stop focusing on planning and instead thing about strategies.  What strategies do I have to achieve my goals?  I really like the idea of throwing spagetthi against the wall and seeing what sticks.  In that way, I enjoy thinking up many strategies to achieve my goals, and trying many of them out and seeing what works.

Here are some strategies to improve any skill, including planning:

1. Motivation - Ask "Why am I a good planner" or similar questions.  If the "Why" is big enough the "How will figure itself out"
2. Ask others - Ask other people for assistance.  Including mentoring
3. Copy - Find out what others do by observations and try and do the same.
4. Learn - Take classes, and/or research about the topic, for example using Google

I know I am a good planner because when it is something "fun" then I plan for hours.  Why is "work" "fun"?  How about that?  Vacations are fun because there is no downside.  If my vacation plan doesn't work out exactly as I expected, it's no big deal.  When it comes to "work" there is a fear that if the plan doesn't work out that I will have some negative result like someone saying I did a bad job or getting fired.  In reality, the worst that has happened is that someone says something negative about my work, I can handle that.

Why do I enjoy planning?  I enjoy planning because I love research.  I like looking at possibilities.  I like comparing different options and using my knowledge and experience to pick the one that suits the situation best.  I also like the challenge of trying to get the most for the least.  I like the defined nature of plans because they have a start and end.