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The other evening I looked at the clock for the fifth time: 3:26am. I just couldn’t get to sleep. My mind was like a merry-go-round with different payment obligations occupying the funfair horses: wedding dress 1, wedding dress 2, vacation home property tax, a $10,000 down payment for a wedding reception here, an upcoming $6,000 payment for a summer trip there. They all revolved around my mind, and they all had one thing in common—an end of January payment date.
I’ve been retired for nearly a year, and up to now I’ve had no substantial expenses beyond the everyday costs of living a pretty frugal lifestyle. The specter of spending nearly $30,000 in a few days had really unsettled my normally sound sleeping pattern. It feels different than spending large sums when I was working, with a steady stream of monthly income getting deposited into the checking account.
Intellectually I knew I was worrying over nothing. More than enough cash is sitting in a combination of money market and immediate access savings accounts, but it’s the high hurdle of pulling the spending trigger that robbed me of my ugly sleep. I even went as far as logging into my accounts the next morning to check the balances, like a child reaching for a comfort blanket and seeking reassurance.
I’ve learned something about my retirement self: I find large lumpy expenses disturbing, and I’m doubling down on keeping more cash than strictly necessary available for such situations. It might be a drag on my total returns, but it’s a price I’m happy to pay for peace of mind. I can’t imagine the stress some people must experience on a daily basis if they’re constantly juggling payments and wondering if their nest egg is sufficient for the challenges ahead.
I’m grateful that throughout my career I prioritized saving for my future self and didn’t commit to retirement until I had more than enough. A retirement living on just enough is definitely not for me. Now I just need to take a deep breath, gather my strength and get started paying the bills!
Another perspective on paying out a big lump of cash is celebrating your ability to do it without negatively impacting your life in any way. You’ve worked hard and invested properly just so you could do this. So don’t sweat it… savor it. Even strut a bit. You deserve to.
Would the love birds consider eloping if their wedding gift from you would be 1/2 the cost of a wedding that you would otherwise pay for?
It would be a much more practical use of money in my opinion and experience.
I was the lone voice lobbying for small, intimate weddings on foreign soil—preferably at a beach so I could wear shorts instead of a suit! Both couples turned down my suggestion. They all have a cherished desire for their elderly grandparents to be at the ceremonies.
A wise man once said this: “I think the most important lens for viewing a one-off purchase is what percentage it represents of your total wealth. For example, if it’s 0.1% of your net worth, it’s barely worth the mental energy to deliberate over. If it’s 1%, you should probably think more delebritly before pulling the trigger.”
Well, what can I say… guilty as charged. But I have a perfectly good defense that I always used when my children were young: do as I say, not as I do 😂
I hope that the act of writing this article helped to put the expenditures in the right perspective, and will enable you to sleep soundly tonight.
Those that juggle in retirement probably had plenty of practice juggling during their working years, and likely sleep pretty well.
I opened my chromebook a few minutes ago to a reminder that our largest semi-annual expenditure, property taxes, were being debited from the Fidelity Money Management Account today. I’m grateful that having such an account is necessary. It’s taken me a bit longer to get to my happy place, but the work and sacrifice were sure worth the effort.
I took the bull by the horns this morning and sorted all the payments out, it’s far less intimidating during daylight hours. I tried having a proper moan to Suzie while I was at it, but unfortunately she was too preoccupied with the latest wedding drama: finding a seamstress with availability before next January. My financial anxieties didn’t stand a chance against the Great Seamstress Crisis of 2026/27.
I looked at the clock for the fifth time: 3:26am.
This is what has worked for me now that I’m retired: Since I don’t need a morning alarm, if I wake in the middle of the night I’ve trained myself NOT to look at the clock. Instead, I push off the covers for a few minutes, just until I cool down and get drowsy again.
If my mind is really racing, I do controlled breathing (e.g., 4-7-8 or 4-4). Before I retired, I would silently count backwards from, say, 500 by 7s (just enough to take my mind off the worry).
Some people find it helpful to get up, go to a different room, and do reading or something; that didn’t help me.
And yes, I think this is important financially: it is nearly impossible to make good decisions the next day if so low on sleep!
Sending you good sleep wishes! 🥱
Thanks for the sleeping tips, though I have a feeling if I started counting backwards by 7s, I’d trip myself up and have to start again… repeatedly. Which would probably keep me awake even longer knowing my luck.
When that happens to me I just keep repeating to myself the word calm. It really works.
Be thankful your lack of a peaceful sleep is only about money, Mark. There are worse things over which you have no control. Last week in addition to chemo treatment, I took Connie to three different doctors. This week isn’t any better.
I do realize I’m blessed in many ways at this point in life. Even so, the mind still plays its games. I hope Connie is tolerating the chemo without major side effects—I know the constant worry you must be feeling. My youngest daughter’s cancer has returned and she’s preparing for more radiotherapy soon.
Dick,
Keeping you and Connie in my thoughts.
Sounds like you need to make the payments without scheduling them in advance!