My nephew Jake basically harassed me for six months straight about getting a skateboard. Every family dinner. Every phone call. ‘Uncle, when can we go look at boards?’ Kid’s relentless. Half my friends who never touched a skateboard are suddenly like ‘hey maybe I should try that.’ Must be something in the water. Or maybe everyone’s just having a midlife crisis at the same time.
Point is, skateboarding’s having this moment again. Brands are reissuing all these old 90s graphics I remember from high school. Makes me feel ancient but whatever. If you’re thinking about starting — whether you’re buying for your kid or you’re an adult wondering if you’re too old (you’re not) — it’s honestly way simpler than people make it seem. Everyone acts like you need a master’s degree in skateboard engineering. You don’t.
I started skating around 13. Maybe 14? Somewhere in there. Skated pretty regularly until I was like 18, then life happened. Jobs, college, bills. The board ended up collecting dust in my parents’ garage for over a decade. Then last year at 32 I randomly decided to start again. Honestly can’t remember why. Saw some kid cruising past, felt nostalgic, went and dug out my old board. Except it was completely trashed. Bearings were seized, grip tape was peeling off, trucks were rusted. Had to start fresh.
Skating as a teenager was 100% about looking cool. That was the entire point. Trying to impress people, not wanting to fall in front of anyone, very concerned about image. Skating at 32? Whole different vibe. Now I’m just thinking ‘please don’t let me break something because explaining a skateboard injury to my boss would be mortifying.’ Way less pressure though, which makes it more fun. Although I gotta say, falling hurts way more now. My body does not bounce back like it used to.
Quick History Lesson
Skateboarding started in the 50s. California surfers needed something for days when the ocean was flat — which apparently happened more than you’d think. Someone bolted roller skate wheels onto a wooden plank. Sidewalk surfing was born. Pretty genius if you think about it.
Fast forward and now you’ve got skateparks everywhere, street skating in cities, kids doing it in driveways. It’s even in the Olympics now which feels super weird. Like skateboarding was always this rebel counterculture thing and now it’s… official? Times change I guess.
Different styles developed. Street skating is stairs, rails, ledges — using the city as your playground basically. Park skating is bowls and ramps at actual skateparks. Vert is those massive halfpipes you see on TV that look absolutely terrifying. Then there’s cruising, which is just riding around because it feels good. I mostly cruise now. Occasionally I’ll try an ollie when nobody’s looking. Usually fail but that’s fine.
Board Components Explained
The deck is what you stand on. Seems obvious but width actually matters. Wider decks are more stable — good if you’ve got big feet like me. I wear size 11s and anything under 8 inches feels cramped. Narrower decks are easier to flip for tricks. Most people ride something between 7.5 and 8.5 inches. Don’t overthink concave and shapes when you’re starting. That stuff you figure out later.
Trucks are those metal T-shaped pieces that attach your wheels and let you turn. These are worth spending money on. I learned this the hard way. Cheap trucks feel sketchy and break. Good trucks last forever — I’m still using ones I bought like 6 years ago through three different decks. They’ve outlasted everything else.
Wheels come in different hardnesses. Softer ones (around 78a-87a) are smoother for cruising on rough streets. They absorb all the bumps and cracks. Harder wheels (99a-101a) are faster and better for tricks but you feel every single pebble. I’ve got two setups now — soft wheels for just cruising to the store, hard wheels for when I actually practice at the park.
Bearings make your wheels spin. Cheap bearings are miserable — like pushing through mud. Get decent ones. Trust me on this.
Buying Your First Board
Just buy a complete. Everything’s already assembled and matched. You can get fancy with custom builds later once you know what you like. Starting out you just need something functional that won’t fall apart.
Skip department store boards. I know they’re like $30 and tempting but they’re genuinely dangerous. I bought Jake one from Target thinking we’d test if he was serious about skating. Truck literally snapped after two months. He nearly broke his ankle. Felt horrible. Bought him a real board from a skate shop, suddenly he was landing tricks and actually having fun. A proper complete costs around $100-150 but your body will thank you.
The Helmet Conversation
Wear a helmet. Yeah I know. Nobody thinks helmets look cool. When I was a teenager literally nobody wore them. Now I always do. I’ve seen too many bad head injuries at parks. This one guy fell backwards on a ramp, smacked his head on concrete, concussion, out of work for two months. Another friend hit his head during a simple fall, same deal. This stuff happens more than you think.
Modern helmets don’t even look that bad anymore. Not like those mushroom things from the 90s. Get knee pads and wrist guards too when you’re learning. Falling on your hands is instinct — guards save you from sprains and fractures. Some people ditch the pads eventually but keep the helmet. Broken bones heal. Brain injuries don’t.
Where to Shop
Go to actual skate shops. Places like Skate Warehouse where employees actually skate. They know setups, can answer real questions, won’t sell you garbage. Big sporting goods stores have skateboards but the staff usually knows nothing. I’ve watched them give terrible advice to beginners.
Don’t be embarrassed asking beginner questions. Shop employees hear the same ones constantly. They’d rather help you get it right than have you quit three weeks in.
Learning to Actually Ride
First figure out your stance. Regular is left foot forward, goofy is right foot forward. Just stand on the board naturally and see what feels better. Do this on grass first — safer if you lose balance.
Practice balancing before you try moving. I know it’s boring but it matters. Then work on pushing — one foot stays on the board, other foot pushes. Took me weeks to get smooth. I looked ridiculous. Like a baby deer learning to walk. Stopping is just dragging your back foot. Turning is leaning. Start somewhere smooth and flat. Empty parking lots work great. Or tennis courts if you can access them.
Basic Upkeep
Trucks need tightening sometimes when they feel loose. Bearings need cleaning when they sound crunchy. Check your deck for cracks near the bolts. Replace grip tape when it gets slippery. Store your board somewhere dry. I left one in my garage during a wet winter once and it warped into this ridiculous banana shape. Completely unusable. Learned that lesson.
Skateparks and Progress
Parks seem intimidating at first. All these good skaters flying around doing tricks. But honestly most people are pretty chill with beginners. Everyone started somewhere. They remember. Just follow basic etiquette — don’t cut people off, wait your turn, pay attention.
Progress is inconsistent. Some days everything clicks. Other days you can’t land anything and you wonder why you even bother. That’s normal. Everyone experiences this. Set small goals. Ride confidently first, then turn well, then stop smoothly, then maybe try tricks. Film yourself if you can — super helpful even though watching yourself is humbling.
Don’t compare yourself to kids at the park doing perfect kickflips. They probably started skating at age 6. You’re an adult with a job and responsibilities. Different situation entirely. Last month I saw this guy who looked about 55 learning to drop in. Took him like forty attempts but he finally got it. Huge smile on his face. Made my day watching him. If someone can start at 55, anyone can start. Just wear the helmet.
