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AUTHOR: Doug C on 3/30/2026

I have found, especially as I get older, that there is a real benefit to simplifying many aspects of my life.  For me the reasons include:

  • Saving time
  • Easing decision making
  • Limiting behavioral mistakes, including thrashing or freezing, due to complexity 
  • Preparing for cognitive decline or physical incapacity
  • Preparing for ease of transferring responsibilities to spouse or children

Do you find that simplification helps you and if so what things have you done to simplify your financial situation and other aspects of your life?

Below I have listed some of the areas in my life I have tried to simplify and specific things that have helped me.

Financial Investments

  • Simplification of financial investments
    • Use of an “all in one” fund. Its attributes include:
      • High diversification
      • Low Cost
      • Automatic Rebalancing
      • Hands off
  • Consolidation of similar accounts (multiple IRAs, Roth, Checking)
  • Minimization of number of companies used (Vanguard, Fidelity, Schwab)

I have it easy as the bulk of our investments are in tax deferred (IRA) and tax free (Roth) accounts.  So it has been easy for me to make simplification changes without tax consequences.  I have decided that an appropriately chosen “all in one” fund is good enough for our financial needs. I specifically use Vanguard LifeStrategy Funds, and have chosen for myself to invest all of our IRA and Roth funds in the LifeStrategy Moderate Growth Fund (VSMGX). 

The bulk of our investments are at Vanguard and we will likely keep them there.  I also have a Fidelity account as my past employer had made use of it for certain financial accounts they set up for me.  I do prefer several aspects of Fidelity’s interactive web site, so I have opened and retain Cash Management, HSA and 529 accounts there.

Automate Payments

I have all bills automatically paid using a credit card, and where not possible use ACH transfers from a cash management account.

Create On-Line Calendar Reminders and Record of Events

I have super charged the use of an electronic calendar and the search capabilities within them. 

  • I create electronic entries for everything  so I don’t have to remember anything and always get timely reminders.
  • When activities need to reoccur, I create automatic recurring reminders.
  • I make sure to make use of the “Notes” section in a calendar entry item to facilitate detailed documentation and ease of search in the future.
  • My spouse and I share calendars with each other so we both know what the other is doing and can easily coordinate plans 
  • Items I create calendar entries for include:
    • All appointments
    • Auto and home maintenance reminders
    • Reminders to review something in advance of an automatic renewal (insurance, ISP contract, cell phone carrier)
    • When something significant happens that I want to remember with its details, I create a calendar entry item for it for easy search in the future.

Use of Cloud Based Password Manager

If you are like me, you have accounts for hundreds of different online resources. Without a password manger it would be impossible for me to remember or manually document all of the associated information for all of these accounts.

With a password manager, I never have to remember my id or password, am able to automatically fill those fields when needed, and can store all kinds of other associated information related to the account.

In addition, certain password managers (like the one I use named BitWarden) allow you to store generated “Passkeys” that can be used on compatible websites, further eliminating the need for password and id input.

Consolidated Tracking Of Financial Resources

I find it useful to have a consolidated view of all of my financial resources.  This includes:

  • Net worth tracking
  • Asset evaluation (allocation, performance)
  • Transactional view (view, search, by category, by time )
  • Retirement planning (scenario projections based on various criteria)

I use a couple of sites that have overlapping capabilities, with each more useful for certain aspects:

  • Empower (Free)
  • Fidelity Full View (Free for people with a Fidelity account)

For more heavy duty retirement planning I use a few different resources including:

  • Boldin (Paid)
  • TPAW Planner (Free)

Setup Privileges, Authority and Access In Advance

For online resources such as financial and medical, as appropriate, I and my spouse have both set up accounts and grant full access to one another’s accounts. Doing this in advance will prevent difficulty and delays in a situation where one loses capabilities.

What things have you done to simplify your financial situation and other aspects of  your life?

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kristinehayes2014
13 days ago

I’m a huge fan of simplification.

All of our bills are on auto-pay. We have also set up auto-shipment subscriptions for a multitude of items–the most important shipment is the dog food (at least according to our dogs).

We also have an “Instacart” subscription that allows us to have items we purchase from Costco delivered to us for a small fee. That feels like a real luxury. I used to enjoy going to Costco and walking the aisles. No more. Now I love that I can just pay someone to go and pick up the regular items we need. I’m sure it saves us money on impulse purchases too.

Edwin Belen
14 days ago

I can tell you are a process person. The one thing I would highly recommend to others is to get your wives or significant others comfortable with a password manager. By combining all of our passwords into one password manager and organizing them by subject it has made both of our lives much easier. It also makes it easier if one of us passes so that she can share with our children if needed. I would also say if you use a Mac as an example to make sure that you turn off apple‘s password manager so that everything resides in one password manager. You can also use apples if you don’t want to use a separate one, but I am very comfortable with the LastPass.

John D.
15 days ago

Great article. As I approach 80, I’ve done almost all of the things that you’ve done. The main thing that I’ve purposely not done is to commit my passwords to an online secure site. I have four 8×10 pages of sites/passwords that are roughly categorized and updated about 3 times a year. Call me paranoid or overly cautious, but with all the compromised (once secure) websites that I’ve noted over the last two dozen years, I sleep well. I also switched everything to an Apple computer in 2012 after having used Microsoft stuff since 1991.

Michael1
14 days ago
Reply to  Doug C

If it’s offline, I assume it automatically fills credentials to sites visited on the Mac but not across other Apple devices? If that’s the case, then I guess one just has to remember them when using iPhone for example?

John D.
15 days ago
Reply to  Doug C

Doug,
Thanks for the suggestion. I use about 50 different passwords and don’t use qwerty+digits anymore. All of them conform to: upper, lower, special character and number, but are rarely longer than 9 or 10 keystrokes. What do you think of using those google Chrome recommended multi-character passwords that show up every once in a while when I go to some new site? (I use Chrome, Firefox, Opera, and Safari for various sites…do you recommend one more than another?)

Randy Dobkin
15 days ago
Reply to  John D.

I only use browser (in my case Microsoft Edge) generated passwords now. The longer they are, the harder they are to crack.

William Dorner
16 days ago

Excellent article Doug. I continue to simplify as best I can. Overall, I have done all of the above. In addition my wife and I simplified our housing by moving into Independent Living. Maintenance, meals, paying bills is totally automated as you get a single bill each month. I can even get haircuts and other services right where I live. If needed or wanted meals can be delivered to my apartment. Yes, at 80 years old this is the way to go. I too wanted to live in my home until we passed away, but my wonderful wife made this great suggestion. In addition, entertainment, interesting speakers, just about any activity is available along with a fitness center. I just tell people I am on a permanent cruise with the ship always in port, and no waves. More interesting people here than anywhere, kind and helpful. Happy retirement sailing to all. Just keep it simple.

Mike Lynch
17 days ago

Doug:

We are of like mind. I have instituted many, if not all, of your mentioned simplifications, except for spousal access and mutual digital calendars.

While my wife has 100% access to all of our assets and accounts, she is NOT a “techie person,” as she calls it, and would be hard-pressed to do anything online, other than buying craft stuff on eBay and getting recipes from the Food Network. Previous attempts to “train her” to use the financial aspects of the computer have been “less than. enthusiastically embraced.”

Same for the calendar. I keep a digital calendar, but we also have a wall calendar we both share. I add my stuff to her’s on the calendar as needed, so we each know when we can schedule things.

As far as financial records, I have a document that is both a “hard copy” and digital, with the digital version kept on the desktop of my computer. My wife keeps the “hard copy” in her stand-up jewelry case, and she has the password to open my computer.

The document is basically a step-by-step guide instructing her what to do if I don’t wake up tomorrow. All banking and financial accounts, passwords, assets, and addresses for accounts, advisors, and our attorney are listed in the document. It is updated monthly and/or when anything major occurs, such as my recently discovered veteran’s benefit of $2004 doillars for funeral expenses. I discovered this benefit, which only came into existence in October 2025, when arranging for my father’s inurnment later this month. Although he is not eligible for it, because he died in 2018, when I die, my beneficiaries will enjoy that benefit.

Admittedly, my document is “old school,” but it suits my wife. Our daughter, who is our executrix, also receives a copy of the document when it is updated, without account numbers or passwords.

normr60189
19 days ago

My preferred grocer has an online shopping app. When G and I do our weekly inventory or discuss a shopping list I open the app and add the items to the shopping cart. I can use this list when shopping at any grocery. It also provides the total cost of items in the cart. It’s a convenient way of managing groceries and I think we purchase less.

Mike Lynch
17 days ago
Reply to  normr60189

We have started doing that as well…at Food Lion, Walmart, and Carlie C’s…the stores we shop at the most.

I really like the notes on the aisle location.

Winston Smith
20 days ago

We put most of our bills on autopay.

We still do check our credit cards by hand though.

William Dorner
16 days ago
Reply to  Doug C

Doug, I use Quicken for that, and all accounts update at once. Over my 80 years I have found very few bank errors, I think 3, but the most unusual one was, my bank credit card bill was paid automatically and then immediately indicated late payment, that took some real up the bank ladder to get that software error fixed. I have everything automated.

C Boyce
20 days ago

This post is a keeper and one that I will go back over in detail many times and send along to others.

Here’s my addition: Don’t stop at providing your partner (or child or whoever is first up to provide support as you age) passwords and a letter of intent. Explain everything to your support person even if you have written it down for them AND periodically engage with them on your financial situation with details. Multiple times. Regular engagement over time is an opportunity to communicate updates and repetition increases your support person’s knowledge base, comfort level, understanding of your intent and how to carry it out. If that person is not financially savvy because they don’t have the time or inclination to learn, discuss with them potential supports they can use in your absence, temporary or permanent. I’m thankful that my husband and I have reviewed our portfolio quarterly for years-even more so after recently watching a friend whose husband died unexpectedly grapple with her finances.

Jerry Pinkard
19 days ago
Reply to  Doug C

I was warned by Fidelity that if I ever shared my logon credentials with anyone, that would void their guarantee to me to restore any losses to my account by fraudsters. When I had a hacking attempt, the very first question my rep asked was “have you shared your logon credentials with anyone?”. Be aware of this important Fidelity requirement.

Luvgov
20 days ago

I like the idea of using an electronic calendar. Is there one you would recommend for ease of use?

DrLefty
20 days ago

This is a great list. I’m learning to lean heavily into calendar reminders as well. As you said, you can even use them to find details from a previous event. For example, some friends invited us to dinner recently. We had only been to their home once, in 2019, and I wasn’t sure I knew the address. But when I went to add the dinner to my calendar, the previous time popped up, and there was the address!

I’ve also found that my Notes app has turned into an extension of my brain, especially since it saves across all of my Apple devices. Need the settings for a Peloton bike in a hotel gym? It’s there in a note. The new building entry codes for our condo, which just changed? There, too. My weekly meal plan with recipe links for when I’m in the grocery store? Yep.

1PF
16 days ago
Reply to  DrLefty

Here’s a handy use for the Google Keep notes app that’s in the right edge panel of the web Gmail window.

Say you have a group of people you occasionally need to email, and you don’t want them in your contacts, nor do you want the complication of a Google group just for this.

I create a note and title it with the group name. In the note I list the email addresses separated by commas. Then to address the email, I simply open that note, do a quick copy of the batch of addresses, and paste them all at once into the To: (or Bcc:) field.

Dan Smith
20 days ago

Doug, I love this subject, and have written a related post or two. In my first year in the tax prep business, I had a retired client with about a dozen funky partnership K1s and a duplex that he and his wife lived in. My first thought was, how will his widow deal with all this? 
About one year ago, I consolidated most of our accounts into Fidelity, including IRAs, brokerage, checking, and credit card. I also use BitWarden for passwords, and Full View to keep an eye on investments, credit cards, and net worth. I do keep an IRA and brokerage account with an advisor friend of mine, for the purpose of not having all our eggs in the same basket. 
There is one area where I am a step behind you. I still own a handful of funds that require occasional re-balancing. I don’t personally have a problem with this chore, however, Chris doesn’t share my interest in such things. Also, if I survive Chris, will there come a time when I’m no longer up to the task?
I have my eye on the same Vanguard Life Strategy Funds, as well as some similar I-Shares funds. Capital Group has a managed balanced ETF, CGBL, that I like a lot. I would consider using it, along with one of the passive funds, due to low correlation. It has not been around too long, but is a near clone of the American Balanced Fund (ABALX), established in 1975. That fund has only suffered rolling three year losses in about three or four percent of all such periods since its inception. Unlike ABALX, CBGL has a .33% expense ratio and no front end load. I would argue that the expense ratio is well earned.

David Lancaster
20 days ago
Reply to  Dan Smith

Just beware that when you only have a fund with both bonds and stocks that when you take a withdrawl both are taken at the allocation set by the fund. In a situation like we have today or any other time with significant drops in equities some of the withdrawl is coming from the depressed stocks. If you have separate funds for equities and bonds you are able to take from the stronger sector. I plan on utilizing this procedure until I no longer have the mental capacity then I will probably use Vanguard’s advisors to continue this plan unless they can explain why that doesn’t make sense.

Dan Smith
20 days ago

Yes, on it. I’m using a Fidelity Money Market (SPAXX) with over 12 months worth of cushion, and a CD ladder that’s good for about another ten years.

William Dorner
16 days ago
Reply to  Doug C

Sorry, I have no faith in Password systems like those. I use only my MacBook, iPhone and a well guarded spreadsheet for all passwords. I especially like my finger touch, or facial recognition for passwords use.

David Lancaster
20 days ago

I have one suggestion, but it is to simplify for your children. We set up a trust. Now with our children nearing or at 40 they are named as successive trustees as of our last passing. Having all of our non retirement assets in the trust allow our children, who have always gotten along well with each other, to decide how to divvy up our assets between them, without having to go through probate. It also allows our assets at death to remain private. We decided to pay this significant expense after seeing all the hoops that my sister, my parents’s executor, had to jump through going through the probate process in NH.

Last edited 20 days ago by David Lancaster
William Dorner
16 days ago
Reply to  Doug C

I highly recommend using a Trust. My parents had that and I was able to handle all items with no Attorney and no Probate.

Dan Smith
20 days ago
Reply to  Doug C

In the meantime, Doug, just make sure you have beneficiaries properly named on everything, including your home. This will also avoid probate.

Kurt Yokum
16 days ago
Reply to  Doug C

Some states don’t have TOD for your home, but they do have “Lady Bird” deeds (or enhanced life estate deeds). Those essentially do the same thing as TOD. I would check with an expert for your state, because the internet is all over the place on which states allow those deeds.

Dan Smith
20 days ago
Reply to  Doug C

 It varies state to state. In Ohio it’s called a  ‘transfer on death affidavit’. It’s filed with the county auditor/recorder. I used WillMaker software to prepare mine; it has the proper form for each  state. There may be some states where this can’t be done.

Jerry Pinkard
20 days ago

How much time does it take to do all this? It seems like it would take an inordinate amount of time to organize and track everything.

I do auto payments and deposits. I also have a tax Excel spreadsheet that I use to estimate my current year taxes. I use this to do estimated tax payments, Roth conversion planning, QCDs, etc. I use Fidelity for all investments. I had CDs at different CUs, but have consolidated all of that as they matured. I have a limited number of low cost index funds/etfs. I do not obsess over having the perfect fortfolio, just one that is good enough.

I also have a letter of final instructions which is quite detailed with all my business, banking and investment accounts plus everything else my executor will need. I originally did that for my wife, but she passed away last year, so it is now for my kids. I have all my estate documents.

All of this has taken time to setup, but it does not require much time to manage.

Mike Gaynes
20 days ago
Reply to  Doug C

I’ve explored password managers in the past but never used one. How does it work to change over your existing passwords? And do all the new ones simply autofill?

Last edited 20 days ago by Mike Gaynes
Mike Gaynes
20 days ago
Reply to  Doug C

Thank you for that thorough reply, Doug. All my passwords are offline on a Word document (I’m something of a technical Troglodyte) and moving to BitWarden does indeed sound onerous.

Maybe I’ll just try to get somebody there on the line and ask them.

Thanks again.

Michael1
21 days ago

Wow. That’s quite a list. I don’t think I can add anything. 

All our bills are paid automatically, and we both have access to each other’s accounts. Converting investments to cash is not automatic yet, but I agree it’s a good thing to do at some point. Have to get on that password manager too. 

Though I profess to simplify, I am still tempted to add little complexities here and there, like the occasional individual stock. Also there are some things I’m not prepared to do. Shifting everything to a target date fund is one of them. I realize it can be a great solution for many, just not for me, at least right now. 

We’re thinking of settling in Ireland for a while, which if we do it is going to add plenty of financial complexity.

Ken Tyrrell
16 days ago
Reply to  Michael1

Noticed that you’re considering moving to Ireland. We recently returned from a 3-year stint for work. We loved it but there are subtleties to be aware of.

cautions:
-cost of living is high esp rents,while salaries are lower. The government is working to increase housing stock and they are making progress but still do your homework re rents.
-the USD was strong when we moved but more recently the USD is much weaker to the tune of about 15% less.
-some US financial institutions are very difficult to deal with for example they are not allowed to offer financial advice while living in the EU. Put your investments on auto drive before moving.
-making financial management worse are the time zone differences if you need to talk to someone, about 8 hours
-Irish weather, yikes, I kept waiting for sunny and 20C to play golf, nope, ain’t gonna happen. Get Goretex gear and play like an Irishman.
-medical and dental and insurance are different. Patient pays direct then submit receipts to ins co. There are different levels of med insurance, again do your homework.

Dont miss:
-Irish butchers are entertaining plus their beef is far superior to anything in the US. My favorite is Higgins in Sutton, near Dublin, I often stop in for the good Craic (enjoyable convo)
-Government Post Office (GPO) museum in Dublin. Wonderful displays and short video about the revolution v England.
-New Grange prehistoric monument/tombs – wow!

we relied on public transportation and didn’t have a car. We lived in Howth at the north end of the DART line. We’d rent occasionally for weekend trips and have been all over the island.

my wife has excellent advice about visiting Ireland, DM me for more advice!

greg_j_tomamichel
21 days ago

Thanks for a great article. We have done 2 key things:

– Moved to a small, simple house that should be easy to maintain and navigate for many years.
– Consolidated all our accounts with the help of a fee-for-service financial planner.

Both of these have been really positive changes.

greg_j_tomamichel
21 days ago
Reply to  Doug C

Thanks Doug. We’re the opposite – I quite like change, but my dear wife had made it clear she would gladly never move again!

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