Planning Things Precisely vs. Absolute Spontaneity

We should all plan for our financial futures because planning is free. The question is, whether planning things precisely is the way to go for maximum happiness.

It occurred to me that when it comes to money, I like to plan.  I have a spreadsheet that contains conservative pro forma estimates over the next 20 years with every line item you can imagine possible.  I've calculated monthly expenses 30 items deep and a revenue stream which already looks outdated because the economy has come back.

For everything else, be it a weekend or a vacation getaway, I don't plan at all.  I'm totally spontaneous and decide what to do the night before or the morning of.  If I'm honest with myself, I attribute much of the reason to my lack of planning to laziness.  I just can't be bothered to put work into fun, because planning ain't no fun!  Earlier this year, I decided to go for a week long getaway to Hawaii just a couple days before Valentines Day.  My lack of planning cost me probably an extra $350 in airline ticket costs.  Meanwhile, I miss event after event on the weekends because I don't bother looking at the upcoming calendar.  That's not good, especially when N'Sync and the Bacstreet Boys are in town.  Oh yeah!

Not planning leisurely events can be expensive, we all know that.  But, I guess the reason why I don't plan for fun events is because they are in essence already fun to do.  Being pleasantly surprised on the upside is always a nice feeling.  Who needs planning?  However, when it comes to money, it's often the medium which allows for great experiences without worry.  Hence, I plan and plan some more.

What about you guys?  Are you meticulous planners or do you do many things on a whim?


Finances For Couples – A Guide To Starting Off Right by RJ Weiss.  Some really good viewpoints from various bloggers on whether or not to combine or separate their finances.

How Inflation Screws The Poor The Most by Darwin discussing a very important topic which may come in the future given so much money printing by the Fed.  Buy real assets!

The Only Six Personal Finance Blogs You Will Ever Need by Financially Poor highlights an eclectic list of blogs.  What I like about the post is that Kevin actually picked out three good posts from each.

24 Free On-line Resources To Help Increase Your Personal and Financial Wealth by Barbara Friedberg.  Great aggregation of resources Barb!

What Are You Putting Off? asks the Wealth Artisan, which is quite pertinent to today's post.  I'm putting off getting 6-pack abs until the next life.  How about you?

What To Do If You Lose Your Job is a great post by the Amateur Financier who went through a job loss himself earlier this year and knows what to do.

Do I Think About Money Too Much? asks Evan from My Journey To Millions.  It definitely sounds like it E-dog!  Perhaps cut it down by 90%.  One the money is automated then just sit back and rake it in!

The 25 Most Influential Finance Bloggers you Should Know by Jason from Redeeming Riches.  Jason himself has a wonderful site and is a Twitter machine with a very generous heart!

Related: To Be Happy You Must Constantly Forecast Your Misery



19 thoughts on “Planning Things Precisely vs. Absolute Spontaneity”

  1. I really liked this article. If I can be so bold, WOW you are even more obsessive than I am about your finances :). I tend to be really planful in general and of course with my finances as well. On the week ends I usually just relax, exercise, and watch movies, so not much planning there :)

  2. I like to plan the basics out way in advance for vacations. Once I get the dates set, I can’t really relax until I have the flights and hotel booked. The competition for good vacation dates at my work is a big part of my sense of urgency when it comes to planning since my boss is very strict about how many people can be out at once (and my direct colleagues also plan way in advance). I also like doing a lot of research on the places I’m going so that I can figure out the logistics of what I want to do and when since time is usually tight when I travel.

  3. BSB and NSync? You missed out :)

    I like planning, for the big ticket items (like planning a trip) and doing my research. Once I get there though, I’m pretty low key about things and let things go with the flow.

    Sometimes spontaneity is fun and a great spark for the good ol’ marriage :) (Not that I am married myself, but you get the gist).

  4. Planning is really needed to make sure that you are ready for everyday happenings. I think you can say not to ready for a small thing but if you know that it is important I am sure that you will be in a hurry always to get ready. I am glad that I am one kind of person that let things be prepared always even if it is not so important or what.

  5. harvestwages

    Hey Sam,
    Planning is not my thing. i often plan over night, i don’t entertain plans in my head before.

  6. Planning ahead of time is good, because we will be able to calculate how much we should need to explore on our journey. Although, we also have to bring some extra cash for in case an unexpected expenses occurs we have something to depend on, to be sure.

  7. Definitely build your real asset portfolio. It’s a no brainer in an inflationary environment. Job income, side income, dividend income, online income, rental income, and so forth.

    If there’s massive inflation, take on as much debt as you can!

  8. I do a lot of fun stuff without any kind of plan but I don’t do anything big without planning! But I am sure you could have guessed that lol.

    Thanks for the mention!

  9. I like to plan things when I go on vacation. At least I book the place to stay and plan out a few things to do in each location. We don’t always stick to the plan and go with whatever we feel like at the time.
    Financially, I think planning helps a lot and our finance became more and more structured overtime. See my latest post, money flowchart. :) We don’t track every last pennies, but lump things into bigger categories like fixed cost, credit card charges, and cash allowance.
    I don’t know why my comluv doesn’t work on your site.

    1. Micro focusing on finances I think is debilitating. Chunk in big categories is better.

      Sorry the commentluv doesn’t work. It’s finicky, as it works for some. Perhaps you have to “unban” your URL at their site? Donno

  10. I am a mixture. My life is very planned because the 3 teens in my life have plenty of commitments that keep me going. However, with my spare time, I am very spontaneous. I will just get the kids in the car and go. We might end up in Canada, grabbing hot chocolate and looking at Christmas lights, putt putt golfing, who knows. I love the ‘spur of the moment’ events!

  11. I suppose it depends on if one is vacationing on a stringent budget or not. For example, if one only has $1500 planned for a trip, you better believe that he or she will try to maximize the fun by getting their flights and N’Sync tickets way away of schedule. Clearly, you vacationed with way more money than you had to spend, so at this point in your life, you can vacation as a free-spiriter.


    1. Romeo, sorry, not following you. Why do you think I vacationed with way more money than I had to spend? To know this, you’d have to know how much I have and how much I spent no?

  12. Hey Sam,

    I’m pretty much the same when it comes to planning for fun. When people ask what I’m doing for the weekend, I usually reply with “I don’t know, it plans itself.” When it comes to an actual vacation, I can usually sit down with pen and paper, but it is tough. Thanks for the link and I hope your Thanksgiving was great!


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