Optimization Is Stealing Your Joy

You ran the numbers three times before you booked the flight. Then you booked it. You are still not sure.

The trip is good. Your wife is excited, the dates work, the grandparents are in. But two browser tabs ago the fare was forty dollars cheaper, and some part of your brain has decided to keep that case file open indefinitely.

There is a kind of man I hear from who has done everything the books told him to do. He budgets, invests, knows his marginal tax rate, and can tell you the MER on every fund he owns to the second decimal. And he is miserable.

Optimization is a good servant and a cruel master. This is a piece about the moment it changes jobs.

Why the Ledger in Your Head Never Closes

Every purchase gets a full trial. The $60 dinner out comes with a second bill attached: the $500 it could have become in an index fund by retirement, and both numbers sit on the table next to the bread basket. He knows the math because he has run it. He has run all of it.

Every decision gets re-litigated. The car he bought two years ago still comes up for review on long drives: should have gone used, should have waited for rates. The mortgage he locked in gets re-scored every time the Bank of Canada announces anything. Even wins get audited. He made the right RRSP move last February and has since found two blog posts describing a slightly better one.

And underneath all of it hums a single dreadful metric: opportunity cost. Once you train yourself to see it, you see it everywhere. Every latte is a lost contribution. Every generous impulse has an asterisk on it, because the same money, invested for thirty years, would be so much more.

The scorecard promised peace and handed you a job, one with no days off and a performance review that runs all day in the back of your head.

I want to say this carefully, as a man who went to school for financial services and genuinely loves this material. Stewardship was never supposed to feel like a debt you can never quite service. When the planning starts producing dread, something has taken the wheel, and it deserves a name. Its name is anxiety.

I Help Run the Scoreboard, So Let Me Own That

A confession before we go further. This site publishes calculators. There is a tool here that will show you, to the dollar, what a daily spending habit compounds into over thirty years, and I stand by it.

I also like spreadsheets entirely too much. I have put hours and hours into them, and I have even paid a few dollars online for good templates.

I have played with the numbers just to make it all look nicer. Past a certain point, a spreadsheet is there to make you feel something. A little hit of control. A little sense that if you look one more time, the future will hold still.

It never does.

And I will go further, since we are confessing. I once caught myself in the shower, hot water running, working out how I would calculate what each minute in there was costing me. I have done the same with the fireplace in January and the air conditioning in July. It left me more consumed by the captive thoughts of money.

The way out, for me, was realizing it was ridiculous. Some things just need to be enjoyed, and some are bare necessities of life. Everyone technically pays to shower, and mine are short anyway. Just enjoy it.

A calculator answers a question. You bring it a real decision and it gives you a real number. You decide and close the tab.

Anxiety asks the same question again tomorrow. If the tab never closes, the tool is managing your feelings now, and it is doing that job badly. No spreadsheet has ever once produced peace.

Run the numbers. Then be done running them.

The "Well Done" Was Word for Word the Same

In Matthew 25, a master entrusts his property to three servants: five talents to one, two to another, one to the last. The five-talent servant doubles his money. So does the two-talent servant. And when the master returns, he says the identical sentence to both of them: "Well done, good and faithful servant!"

Word for word. The man who presented ten talents and the man who presented four heard the same commendation and received the same promotion. In Matthew's telling, the master's praise does not rank them. He does not ask the two-talent servant why his absolute return was smaller. And, this is the part I want you to sit with, he does not ask the five-talent servant whether a sharper allocation might have produced eleven.

The grade Scripture cares about is faithful, and faithful has a finish line. You can reach it and know you handled what you were given. The theoretical best is a horizon, and horizons move when you walk toward them.

The servant who got condemned was the one who buried the money in the ground, and the master's verdict is "You wicked, lazy servant!" (v. 26). That verse gets used to push cautious men into the stock market, and there is something to it. But listen to the servant's own words: "I was afraid." And listen to what the master says would have satisfied him: money left with the bankers, earning a little interest (v. 27). The dullest option on the table would have been enough.

Which means the over-optimizer and the man who never invests at all have more in common than either would like to admit. Both are being driven by fear. One buries the talent in the backyard. The other buries himself in the ledger. Neither one is free.

You Keep Refusing the Gift

Ecclesiastes is the Bible's book for men who think too much.

The Teacher, the book's narrator, has run the full experiment. Wealth, work, houses, vineyards, everything a man can accumulate and measure. His conclusion lands in chapter 5, and it is stranger and kinder than you would expect. To eat and drink and find satisfaction in your work, he says, is your lot. And then this, about the people who accept it: "God keeps them occupied with gladness of heart."

Enjoyment, in Ecclesiastes, is God's gift. Which casts the man at the restaurant, the one mentally converting the bill into foregone compound growth while his kid colours the placemat, in a light he has probably never considered. He is being handed a gift, at that table, by God. And he is leaving it wrapped.

Jesus asked a question in the Sermon on the Mount that every optimizer should tape to his monitor: "Can any one of you by worrying add a single hour to your life?" The mental ledger has the same yield. Worry is the one line item with a guaranteed return of nothing.

And here the Sabbath comes in. God built stopping into the structure of creation before anything had gone wrong. Six days, then rest, and the rest was called holy. Whatever else the Sabbath teaches, it teaches this: stopping is godly. There is a day whose whole assignment is to not improve anything.

A fully optimized life has no room for the things God says make it good. Contentment reads as settling. Rest looks like idle capital.

And generosity fails the efficiency screen outright. The tax credit hands part of each gift back (in Ontario, about 40 cents of each dollar past the first $200 a year), and the rest leaves the portfolio for good. The optimizer knows it, which is why his giving tends to shrink to whatever survives the model. Maybe you want to give more and cannot get the desire past your own spreadsheet.

Run the optimization far enough and it will, with perfect logic, strip out most of what Scripture calls the good life.

If your worth rides on the scoreboard, the goalposts move every time you reach them. I have written elsewhere about learning to mean the word enough, and underneath both essays sits the same anchor: a man whose treasure is already secure in Christ can afford a suboptimal February. The optimizer's ledger is, at bottom, a way of earning your standing, and a brutal one. Tim Keller summed up the difference: religion runs on "I obey, therefore I am accepted," and the gospel runs on "I am accepted, therefore I obey." Your money decisions live downstream of which of those two sentences you actually believe.

Good Enough Is Faithful

So what does a man do with this? Because the answer had better not be "stop planning." Proverbs is unsparing about the sluggard, and trusting God has never meant ignoring your bank account. Trust God and be wise. Both.

The question is how to plan without the planning eating you.

Start by deciding once. Take the recurring decisions that keep reopening themselves and close them, in writing if you have to. What percentage you invest. Which boring fund it goes into (a single all-in-one index ETF or a target-date fund is a complete answer, and if that surprises you, good). What you give and what the vacation budget is.

A decision made once, prayerfully, with real numbers in front of you, is allowed to stay made.

Groceries are one of mine, and that one has stayed made. We are going to spend money on good groceries, because food is fuel. I shop smart, with a ceiling and a floor. I skip the high-end brands and I don't go to Farm Boy just for the sake of it, and I don't go super cheap either. I buy what I know is good for us and what we will actually eat, with an eye on quality and our taste. If I grab something only because it is on sale and we don't even like it, it goes to waste.

Then automate the follow-through. Your TFSA contribution leaves chequing the morning after payday. Your giving goes out the same way.

We automate everything, the tithe included. It's freed my mind so much.

For the optimizer, automation works like a spiritual discipline: it moves your good decisions out of reach of your 11 p.m. second thoughts. Set it and forget it, and mean the second half.

Last, give optimization a budget. My wife and I hold one money meeting a year. The timing is different every year, and it is mostly review and some dreaming.

Pick your own window, and in yours, audit everything with a clear conscience: rates, fees, allocations, insurance. Dream a little, then close the books until next year. Outside the window, new information goes on a list for the next review. It does not get to convene an emergency session of your brain at bedtime.

Leave Room You Never Optimize

Everything else is slack, and the slack is deliberate. The unoptimized dinner out. The fare you paid without checking a second site. The groceries you actually like. The cash that sits in a savings account earning slightly too little because the buffer buys your wife peace of mind, and her peace is worth more than the spread.

Slack is where the enjoying happens, and we have already established who the enjoying comes from.

When I mow, I aim at a point at the far end. You cannot mow a straight line staring at your feet; every bump becomes a correction, and the corrections wander. Fix your eyes on that point and the line takes care of itself.

A man checking his portfolio daily is mowing while staring at his boots. I have been that man. During COVID I checked my investing account a dozen times a day or more, hoping to see it go up.

For a Christian man, the point at the far end is the household he is trying to provide for and the open-handed man he is trying to become. Aim there.

Will a man living this way leave a few basis points on the table? Almost certainly. Count it as what it is: the cost of sleep, and a bargain at the price. The two-talent servant came back with four, heard the same sentence as the man who came back with ten, and was invited to share his master's happiness.

You Can Close the Ledger This Week

One assignment. Sit down this week for thirty minutes and take an index card.

First: the money decisions you keep reopening. The fund you second-guess. The refinance question that resurfaces every month. Name them. There will be fewer than you think; the same four cases keep coming back to court.

Second: next to each one, write the decision. Actually decide. Use real numbers, and pray over it. Then write the date beside it. That date matters; it marks the moment the file closed.

Third: book the reopening. One calendar appointment, a year out, or six months if a year is too long. Until that date, those decisions are made, and when the second thoughts come at 11 p.m., as they will, you get to tell them, truthfully, that the matter is settled and the hearing is scheduled.

Then delete the tracking app from your phone's home screen (it can live one folder deeper, where opening it takes a decision), and go take your wife out for the kind of dinner that fails a spreadsheet audit.

I mean that last line, and it doubles as the test. If you can sit through that meal without converting it to its thirty-year future value, the ledger is closing, and the airfare file can close with it. The habit took years to build. Conviction is patient with a man while he changes. Be that patient with yourself.

The men in the parable who heard "well done" heard it from a master they trusted. The servant who buried his talent said it himself: he was afraid of his master. The one watching your money is a Father, and the audit you keep bracing for already ended at the cross.

God keeps a man occupied with gladness of heart. Let him.