Insights - Transcend Wealth - Cleveland, OH

Save Until It Hurts

Written by Dennis Coon | Aug 19, 2026, 7:04:36 PM

For years, I've had a saying that I would occasionally use with clients:

Save until it hurts. I have to admit, that probably needs some explanation.

I'm not suggesting that people should make themselves miserable today in hopes that they'll finally get to enjoy their money 20 or 30 years from now. I don't think you need to stop going out to dinner, cancel every vacation, or feel guilty every time you buy something you don't absolutely need.

Quite the opposite. What I mean is that if you know you aren't saving enough, push yourself just a little beyond what feels comfortable, then give yourself some time to get used to it.

The January Gym Problem

Think about what happens at gyms every January.

Someone who hasn't exercised regularly in years decides this is finally the year. They're going to work out six days a week. They're going to wake up at 5:00 every morning. They're going to completely change the way they eat.

The motivation is real and their intentions are good. But a few weeks later, they're done. Not because getting healthier was a bad goal, but because they tried to change too much, too fast.

Sometimes the first step toward developing a new exercise habit is to simply join the gym. Then maybe you commit to going twice a week. You get comfortable with that, then add a third day.

Heck, for someone who has spent years avoiding exercise, maybe the first victory is simply driving to the gym and walking through the front door.

Saving can work the same way. Suppose you're currently contributing 6% of your salary to your 401(k). You run a retirement projection and discover you really ought to be saving considerably more. The mathematically correct answer might be to increase your contribution to 15%, but there's a problem: 15% feels impossible.

So instead of jumping from 6% to 15%, what if you went from 6% to 8%? You'd notice it. Your paycheck would be a little smaller. You might have to make a few adjustments. It might even hurt a little. And that's the idea.

Then Wait Until It Doesn't

Something interesting happens when we make relatively small changes to our finances: we adapt.

The paycheck that initially felt a little smaller eventually starts to feel normal. Spending adjusts. Maybe you eat out one fewer time each month. Maybe you keep your car another year. Maybe you discover a subscription or two you don't particularly care about.

Or maybe you don't know exactly where the money goes. You simply get used to having a little less available to spend. Then perhaps you increase your savings again. Eight percent becomes 10%. Ten becomes 12%.

A raise can make this even easier. Instead of allowing every dollar of a raise to become additional spending, increase your retirement contribution at the same time. Your paycheck still goes up, just not quite as much.

Over time, something that initially felt difficult becomes routine. So maybe the complete saying should be:

Save until it hurts. Wait until it doesn't. Then save a little more.

This Isn't About Giving Up Everything You Enjoy

There's a strain of financial advice that seems determined to convince people that enjoying money is some sort of character flaw.

Buy the coffee and you're irresponsible. Go out to dinner and you're sabotaging your retirement. Buy the nicer car and apparently, you'll be working until you're 87.

I've never found that particularly helpful. Money is supposed to support your life. And part of the reason we work and save in the first place is so we can enjoy some of it along the way.

But I also think most of us have spending in our lives that contributes less to our happiness than we imagine. There's a difference between cutting something you genuinely value and cutting something you barely notice.

Maybe it's going out to eat one fewer time each month. Maybe it's choosing a slightly less expensive version of the next car. Maybe it's keeping the current one another year. Maybe it's simply becoming more intentional about purchases that have gradually become automatic.

None of those decisions are going to transform your finances overnight. But that's exactly the point. Building financial independence usually isn't about finding one enormous sacrifice. It's about making relatively small decisions repeatedly for a very long time.

Time Can Do More Than We Think

We tend to overestimate what we can change in a short period of time and underestimate what can happen over a decade or two. Retirement saving is a good example.

Increasing your savings by a few percentage points this year may not feel particularly significant. Your retirement account probably isn't going to look dramatically different next month or even next year. But continue doing it for 10, 15, or 20 years and you're no longer talking about a small difference.

You're giving those additional dollars years to accumulate and compound. And every time you increase your savings rate again, you're adding a little more fuel.

That's why I would rather see someone develop a sustainable habit than chase a theoretically perfect savings rate they can't maintain. Consistency isn't exciting, but it works.

The Same Idea Can Apply in Retirement

This principle doesn't disappear once you retire.

Sometimes retirees discover they're spending more than they anticipated. Or inflation has pushed expenses higher. Or life simply turned out differently than the retirement projection suggested.

The natural reaction can be to think something dramatic needs to change. Often, it doesn't. Sometimes you simply need a small course correction.

Maybe you spend a little less on travel next year. Maybe you replace the car a year later than planned. Maybe you find a few hundred dollars a month of spending that isn't adding much to your life.

The goal isn't to make retirement less enjoyable. It's to make relatively small adjustments while they're still small.

Think about steering a ship across the ocean. A tiny course correction made early can dramatically change where the ship eventually ends up. Wait until you're miles off course, and getting back where you intended to go requires a much sharper turn.

Financial planning works much the same way.

Push Just Beyond Comfortable

When I tell someone to save until it hurts, I'm not telling them to make themselves miserable. I'm suggesting they find the edge of what feels comfortable and push just slightly beyond it, then live there for a while.

Eventually, the smaller paycheck becomes normal. The restaurant meal you skipped isn't particularly missed. The car you kept another year still gets you where you're going.

Meanwhile, something is quietly happening in the background: you're buying yourself more choices in the future.

And when the sacrifice doesn't feel like much of a sacrifice anymore, push a little further.

Retirement usually isn't built through one heroic financial decision. It's built through hundreds of relatively small decisions, repeated over many years, that don't feel particularly heroic at all.

Save until it hurts. Wait until it doesn't. Then save a little more.