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These Are the Things You Should Never Feel Bad About Spending Money On

No matter how old you are, dropping a thousand bucks on anything feels horrible. That mostly means it’s easy to put off long-term investments and make Future You, the sucker who has to deal with Present You’s laziness and bad ideas, deal with it. After all, Future You has dealt with your crap before, and he’ll do it again. But according to financial experts, although intimidating, some big investments really pay off in the long run.

For Your Health

A Real Vacation: Contrary to what you probably thought, taking a vacation is one thing many of the financial experts we talked to agreed is a great investment. “You should never regret spending money on a vacation,” says Andrew Fiebert, co-owner of Listen Money Matters. “Vacations often get written off, having nothing tangible to show for all of the money invested, but the long-term benefits of taking a vacation shouldn’t be underestimated. Along with lowering your risk for all kinds of nasty health problems including heart disease, depression, weight gain and strokes, it can be a great way to revitalize yourself and actually increase motivation to accomplish your ‘real-life’ endeavors.”

Kerri Moriarty, co-founder of Cinch Financial in Boston, agrees. “If you’re going on vacation, go all out,” she says, adding that penny-pinching on vacations can ruin the whole point of going on vacation in the first place. “I’m not saying book first-class tickets to the penthouse suite you can’t afford, but don’t skimp on the smaller things that result in small savings but huge inconvenience.” Case in point: A flight with a layover might save you $200, but can add hours of frustration to the trip. “You’ll stop looking forward to your destination, and instead be focused on all the misery that comes with getting there.”

Hiring a Personal Trainer: This seems like a big step beyond the already-considerable expense of a gym membership, but Tal Frank, president of PhysicianLoans, argues that a personal trainer — even if only for a year — is a great investment. “Just as spending $1,000 on a bathroom remodel pays dividends in the future, so does working out with a trainer,” Tal says. “At least, this holds true for those of us who lack the self-discipline to do the work without a trainer.”

As well as motivating you to go to the gym more often, a personal trainer can craft a workout catered to your personal health. “I only learned good training advice after my back went out for no good reason,” Tal explains. “An honest personal trainer set me straight about what I needed to do after spending way too much on insurance copays three times a week. To me, it’s pay the money now on a trainer, or pay it later on medical bills and a personal trainer.”

A Security System: Rigging your home with an alarm system might be expensive for a purely precautionary measure, but Benjamin S. Offit of Clear Path Advisory argues it’s not the matter of preventing theft where the savings lie (although this can happen), but rather the peace of mind that comes with it. “An excellent alarm system, one that can be monitored and controlled by phone or tablet, is a great thing,” he says. “It allows you to lock doors, turn off lights, adjust the thermostat, have a camera, etc. These things may cost a bit more, but they allow you to feel at ease when going away from your home for the night or a long vacation.”

Buying Decent Clothes: Following the “buy once, cry once” mantra of spending more upfront for quality goods that will last, Moriarty also advises investing in a sturdy winter coat. “Yes, spending $400 on a puffy arctic North Face parka may sound asinine at first, but six years later when you’re still wearing it and it’s just like new — and has actually kept you warm winter after winter — you’ll be glad you did!” she says.

The same idea goes beyond just winter coats. Reddit’s Buy It For Life crowd follows the same philosophy: From $400 Wolverine 1000 Mile Boots to pots and pans for your new apartment, the subreddit aims to “fill a niche for only high quality and durable products.” It might suck to drop $400 on boots now, but after five years, either you’ll be wearing $400 boots that are good as new, or you’ll be on your fifth pair of $60 boots.

For the Home

Installing a New HVAC System: “One expensive item that pays off in the long run is something my family recently purchased — a new HVAC [Heating Ventilation Air Conditioning] system,” says Danny Kofke, personal finance author of A Simple Book of Financial Wisdom: Teach Yourself (and Your Kids) How to Live Wealthy with Little Money. An HVAC system is a lofty expense — they can run between $6,000 and $12,000 for a 1,000-square-foot home — but it will provide a monthly savings on your electric bill.

“It was painful to part with that amount of money, but we’ve saved around $25 a month so far on our electric bill,” Kofke says. “In fact, when it was replaced, we were told how lucky we were because our air handler was leaking a lot and was close to overflowing the pan that was under it. We could’ve come home one day and faced a collapsed ceiling in our kitchen! That would have really cost some money.”

Putting in New Windows: Sacha Ferrandi, founder of Source Capital Funding, says that updating your windows is another cheap upgrade that provides long-term value, both in the bill department and tax department. “Not only do new dual-pane windows come with a tax break for energy efficiency, they also help reduce energy usage by controlling heat distribution in the summer and winter months,” he explains. Beyond upgrading those rickety old window panes, being smart about your windows can cut down on A/C costs as well — e.g., installing “a retractable shade on the outside of new windows diverts direct sunlight to keep the space cool in the summer months.” Double-paned window replacement can set you back $600 to $,1000 per window, but at least you won’t be providing heat for the whole neighborhood anymore.

Upgrading Your Shower: Simple upgrades to your bathroom can have significant impact on the resale or renting value, but it needs to be more than just hanging pretty pictures of shells, explains Ferrandi. “An important point to remember is that permanent amenities are the only upgrades that increase home value. If space allows, a separate bathtub completely changes the design and value of a bathroom. If space is an issue, adding a bathtub and upgrading the shower amenities is a great alternative,” he says. Simply upgrading your existing shower with a trustworthy contractor also can be a cheaper alternative. “Consider adding separate body/foot jets to improve the shower experience. With the right contractor, this project can be completed for only a few hundred dollars.”

Investing in a place to take long, lavish baths might not sound like the best use of your money, but that time spent soaking pays dividends, too. Because if you’re long-dead of a stress-induced heart attack by the time those more concrete investments pay off, what the hell was the point of it all in the first place?