More Experience = Less Complexity?

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When we had our first child, it seems like we were prepared for the apocalypse whenever we stepped out the door. Below is a visualization taken from Pinterest, while we actually had this $60 SkipHop diaper bag filled to the brim.


Compare that with what I grabbed as my “diaper bag” for our youngest baby this morning:


If I am going to be out for no more than a few hours, this is all I really need.

– 99 cent reusable grocery bag
butt everything wipes
– two diapers
– poop bags (also used for dogs)
– food/drink (if breast milk unavailable)

If you aren’t experienced, then you want to be prepared for every possible situation. Over time, you realize what you really need and leave everything else at home. Instead of more stuff, you are instead mentally prepared with the various improvisations you can perform in unexpected situations. (I also keep a bag in the car with an extra change of clothes for everyone.)

A similar example is packing luggage. What used to just be for “backpackers” is now for everyone. Websites about packing light abound. My first few trips, I packed myself a huge, cheap Wal-Mart suitcase at maximum-weight along with another maximum-size carry-on. Something like this:


After many flights (and an experience with delayed luggage), like many others I found myself with just a carry-on travel backpack for a month-long trip (or even longer).


I feel like this trend should apply to investing as well, but it seems like the ultra-wealthy tend to have a more complex mix of investments. Perhaps the very wealthy like to spread their money across various asset classes like real estate, private equity, and hedge funds because it reduces the chance of catastrophic loss. For example, sometimes I want to buy a rental property as it seems it would offer additional diversification to a stock and bond portfolio, but I really don’t want to deal with bad tenants or mediocre property managers.

I do like the idea of simply transferring over some of my bond interest payments and stock dividends to my checking account every month in retirement. However, a part of me is uncomfortable having so much of my net worth in investments where the only tangible evidence is paper and ink via monthly statements.


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  1. I had a hard time believing my friends on their 4th and 5th that traveling with the kids could be that simple, but I’m starting to come around on the idea ourselves. We toss the diaper pack, the clothes pack, and a food / drink pack in a tote and are good to go. It’d be less complicated than that but we just went out for a one hour errand and got stuck in traffic for hours, getting home after four hours, so we’re still leaving the house a little over prepared. No one wants to face our kid without enough snacks in a bad traffic situation! ?

    I have the same issues with wanting to simplify our finances but I need to spread out risk across investments too. Right now I manage our tax-deferred retirement investing, a brokerage account, and a rental property but it feels like any major shifts in the economy that significantly impacts the market will likewise bring down our entire portfolio because it’s all connected. Not sure how to crack that nut, yet!

  2. Understand you wanting to spread the risk across real estate for the tangible benefit and increased diversification but dealing with bad tenants and mediocre property managers is a real risk. Enjoy not having to deal with it. Index funds don’t need new roofs.

  3. As I get older, I’m drawn more and more to minimalism. It’s the ultimate form of sophistication. Only bring what you need. Only buy the house that you need. Anything in excess of what you need is a waste of money and time.

  4. I agree with Frugal Professor as I’m down that path also. I found less stuff=less headaches

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