The Secret to a Longer Lasting Paint Job

Most people think painting an old house is as simple as picking a color, grabbing a brush, and cracking a cold beer when the last stroke dries. The truth? That’s how you end up with peeling paint, warped siding, and a project that looks worse after two years than it did before you started.

Painting an old house isn’t just about slapping on color—it’s about chemistry, history, moisture, and patience. Done right, paint can protect your home for decades. Done wrong, it becomes a money pit (hello Tom Hanks) with flakes for days.

I’ve recently put together a one-day hands-on Paint It Right Workshop to teach you the secrets to achieve a paint job that lasts 20+ years compared to the 10 years most painters deliver. Since not everyone can make it to the workshop in person I’ve summed up the whole day in this one blog post in the interest of helping the most people.

The Ghosts of Paint Jobs Past

Every historic home has its own archaeological dig site hidden under those layers of paint. Peel back the coats and you’re reading history. For centuries, linseed oil paint was king. It soaked into the wood fibers, hardened from within, and stayed flexible enough to breathe with the seasons. That’s why so many 19th-century houses still wear their original coats. The downside? You need the patience of a monk, because each coat takes a full day—or more—to dry.

Then came the alkyd revolution of the 1920s. Suddenly paint dried faster, looked glossier, and cost less. By the mid-century, it was on every door and baseboard in America. Alkyds were tough but not forgiving. They yellowed indoors and peeled outdoors when trapped moisture tried to escape.

By the 1970s, acrylic (water based) paints took over. Water cleanup, quick dry times, no harsh smells—contractors and homeowners were hooked. Acrylics are flexible and colorful, but they form a film on the surface instead of sinking into the wood. On modern materials, that’s fine. On old houses, it can be a recipe for peeling if you don’t prep properly.

The point is: paint isn’t just paint. It’s a chemical relationship between your house and the coating you choose. If you don’t know the backstory, you’ll never understand why some paint jobs last fifty years while others don’t survive a Florida summer.

When Paint Fails, It’s Telling a Story

Alligatoring: If your siding looks like a reptile hide, congratulations—you’ve met “alligatoring.” That happens when a stiff alkyd topcoat is layered over softer oils. The rigid film can’t flex, so it cracks into scales.

Bubbling: If you’ve got bubbles, that’s trapped moisture trying to escape like steam from a kettle and it’s almost certainly poorly applied acrylic paint.

Peeling: Large sheets peeling off? That’s what happens when someone painted over dust, chalk, or damp wood. If it’s peeling back to bare wood it’s a sure sign of moisture problems in the wood.

Chalking: And that chalky residue that rubs off on your hand? Cheap paint, or it’s just too darn old and needs a repaint because it’s been baked too long in the sun.

None of these failures are random. They’re the house trying to tell you what went wrong. Once you know how to read the signs, you stop guessing and start fixing the system instead of just the symptoms. Read here to learn how to deal with common paint problems.

The Lead Paint Reality

If your house was built before 1978, assume there’s lead somewhere in those layers. The danger isn’t the paint itself—it’s the dust created when you sand, grind, or burn it. That dust is invisible, and it doesn’t just vanish. It rides home on your clothes, settles in the carpet, and ends up where your kids play.

The good news is you don’t need to panic—you just need a plan. Test before you scrape. Contain the workspace like a mini operating room with plastic, tape, and zipper doors. Wear proper gear. And use methods that don’t turn paint into dust clouds, like an IR Paint Stripper, wet scraping, or HEPA-captured sanding.

Skip those steps and you’re not just doing a bad paint job—you’re putting your health at risk. Learn more about lead safe work practices here.

Prep: Where the Magic Actually Happens

Here’s the hard truth: ninety percent of a good paint job happens before a brush even hits the wall. The painting itself is the easy part.

If you attack your siding with a high-powered pressure washer, you’re not prepping—you’re shredding. Old wood only needs a gentle wash with low pressure and time to dry. Once the wood is clean and dry, you scrape off anything loose.

The trick is to use a pull-style scraper that cuts with the grain. Those five-in-one tools most homeowners grab? They’re like butter knives on soft old wood—you’ll spend hours sanding out the gouges.

After scraping comes sanding. Feather the edges until your hand can glide over them without catching. Repair rotten spots with epoxy—Abatron’s LiquidWood and WoodEpox are my go-to combo—and never leave gray, weathered wood exposed. Gray wood is dead wood; paint won’t stick to it.

It’s a sequence: clean, dry, scrape, repair, sand, pre-treat if necessary, caulk only where water sneaks in (never where it needs to drain), and then prime. Skip a step, and you’re rolling the dice.

Primer: The Invisible Hero

Primer isn’t glamorous, but it’s the foundation your paint job stands on. Without it, paint peels, stains bleed through, and moisture has its way.

Linseed oil primers soak in deep, feeding thirsty old wood. Oil/alkyd primers bond well and lock down chalky surfaces. Acrylic primers are fine for new or stable surfaces but not enough for weathered wood. And shellac? That’s the scalpel—perfect for spot-blocking stains but brittle in the sun.

The secret weapon is always priming the end grain. Those cut ends act like straws, pulling in moisture. Seal them, and you’ve just added years to your paint’s life.

Choosing Paint Like a Pro

So, what do you actually put on the house? For repainting most exteriors, a high-quality acrylic is the safe play. Use oils or enamels on high-wear spots like doors and windows. If you want authenticity and have patience and bare wood, linseed oil paints are still the gold standard. Stucco loves elastomeric coatings, and porches demand tough urethanes.

And don’t overlook sheen. Flat hides imperfections but can’t handle scrubbing. Satin is the sweet spot outdoors—durable without looking plasticky. Semi-gloss makes trim pop but shows every flaw, while gloss demands near-perfect prep.

Hint: If you’re working with linseed oil paint, you don’t even get a choice—it naturally cures to a soft semi-gloss that ages beautifully over time.

Why Tools Matter More Than You Think

A good brush isn’t just a stick with bristles—it’s a precision instrument. Natural bristles for oils, synthetics for latex, angled sash brushes for trim, flats for siding. Cheap brushes leave streaks, shed bristles, and make the work miserable.

The same goes for rollers and sprayers. Match the roller nap to the surface texture. If you spray, you’d better know what you’re doing. Sprayers can make a job look flawless or like you painted your neighbor’s car by accident. Either way, always back-brush or back-roll to work the paint into the surface.

Don’t Be “That Guy”

I’ve seen the hall of shame more times than I can count: painting brick (ahem!) (moisture pops the face right off), skipping primer, painting in full sun, recoating too soon, ignoring end grain, or using the cheapest brush on the shelf. Every one of those mistakes shortens the life of the job—and your patience.

The Bottom Line

Painting an old house isn’t just cosmetic—it’s preservation. Done right, paint becomes armor, shielding your siding and trim for decades. Done wrong, it’s just expensive wallpaper that peels off in sheets.

If you’ve ever felt overwhelmed standing in the paint aisle, or if you’re tired of repainting every few years, I built something just for you.

The Paint It Right Workshop takes everything I’ve learned about paint chemistry, prep, lead safety, primers, and application, and puts it into a hands-on, step-by-step system. You’ll learn the exact methods pros use to get a 20+ year paint job, and you’ll leave knowing exactly what to do (and what not to do) on your own house.

Sign up for the Paint It Right Workshop today and stop wasting money on paint jobs that don’t last.