30 Lessons Learned from Motorcycling

I bought my first motorcycle (a 2013 Triumph Boneville T100 Black) on June 11th,
2015. Since then I’ve ridden ~10,000 miles, dropped my bike 3 times, lost 1
helmet and spent far more money than than I expected prior to the purchase.

In Hindsight, would I do it again? Without a doubt.

Here are the top 30 things learned for anyone looking to buy a bike.

  1. It takes ~800 miles before you start feeling comfortable riding.
  2. It takes ~2,500 miles before you start feeling confident in your riding. Once
    you’re confident, you’ll start driving like an idiot and almost get into an
    accident. This quickly humbles away your confidence.
  3. Everyone recommends that you buy a small (sub 500cc engine size) motorcycle to
    start. All of the bikes that I liked were well over 500cc though. At this point,
    you need to decide: do I buy the bike I want that everyone says is too big to
    start with or buy a bike I’m not really into that’s a good “starter-bike?”
    Choose the bike you actually like. My Triumph is 865cc and it’s been no problem.
  4. Trying to buy a motorcycle from a dealership is hell. All of the classic sleazy
    car salesman stories you’ve heard apply fully to motorcycles. Check out
    Craigslist instead. Great deals can be found.
  5. Buying a used motorcycle when you’ve never ridden a motorcycle before is an
    awkward situation. You can’t test ride the bike and don’t really know how to
    make sure you’re not being screwed. Bring your dad (thanks pop) or a friend that
    rides with you.
  6. There are two questions everyone will ask you when they hear you have a
    motorcycle. “Do you own a leather jacket” and “aren’t you scared?” Regardless of
    the truth, you should answer yes to both. Any other answer upsets the masses.
  7. People always talk about “dropping your bike” but I never knew how it could
    happen. The answer is…driving at slow speeds. I dropped my bike 3 times in my
    first year and each time I was going less than 2mph. The slower you’re going the
    less momentum you have and the easier it is for the bike to fall. How bad is it
    when the bike falls? Not horrible…it’s simply lifting what’s effectively a 500
    pound weight that’s lying on topof your body.
  8. There’s one other way to drop the bike…don’t forget to put your kickstand down
    when you park!!
  9. After ~200 miles of riding you’ll inevitably start taking longer rides. For some
    of these rides it makes sense to take a highway versus backroads. However,
    you’ll likely still feel reluctant to take the bike out on the highway at that
    point. Get over your hesitation and get on the highway. It has to start
    sometime…the sooner the better.
  10. Wear earplugs! It makes driving on highways so much more fun while also
    preventing deafness. Your classic win-win situation.
  11. Don’t cheap out on your gear. Especially the helmet. My mom actually came with
    me when I went to buy gear for the first time and graciously purchased my helmet
    for me, knowing that I’d likely skimp. She was right (as usual) — don’t skimp on
    your gear!
  12. You’ll only get better once you start riding consistently. For the first ~6
    months with my bike, I kept my motorcycle at my parents’ house in New Jersey
    even though I live in NYC. I’d go home on weekends to ride and get in 3–4 hours
    in a day of riding. During those 3–4 hours, I’d improve pretty rapidly. For
    instance, if I started at a 20/100 I’d end the day at a 26/100. Good progress!
    However, I’d spend the next 2 weeks in NYC not driving regressing my skills back
    to a 20.5/100. Fast forward to today where I’m motorcycling in the city to and
    from work everyday. In any given day I’m only riding ~40 minutes but I’m riding
    consistently. I can see on a week to week basis myself improving. The only way
    to get better is to ride consistently.
  13. Cracks / seals on the road are scary when you start. You think you’re going to
    fall over when you ride over them, especially diagonal ones. You won’t. Just
    keep riding.
  14. When you start riding you’ll notice that motorcyclists driving towards you will
    quickly raise and lower their hand as you pass. At first you won’t realize what
    this is. After ~20 of these, you’ll learn that this is the unofficial motorcycle
    to motorcycle hello. You’re going to try to wave back but won’t feel comfortable
    enough taking your hand off the handlebar. Keep your hands on the handles! At
    least until 800 miles…
  15. Sign up for the American Motorcyclist Association (AMA). $50 a year and free
    towing!
  16. Your bike will break. Your breaks will go out. Your shifter will fall of when
    you drop the bike. Your battery will die and you’ll be stranded on the street
    with no way to start the bike. It’s fun to think back to in hindsight…not as
    much fun in the moment. Get an AMA membership!
  17. Owning a motorcycle will cost you more money than expected. Just accept it…cost
    of doing business.
  18. One day afterwork you’ll be riding home. Halfway through the ride your bike’s
    engine will just die. You’ll continue to cruise until the bike comes to a full
    stop at which point you’re going to try to start the bike again. The bike will
    kind of start, get going and then quickly die. This’ll happen over and over
    again until you realize it’s time to call the AMA (tow truck time)! While you’re
    waiting for the tow truck you’ll ask yourself “maybe I’m out of gas? the light
    was on after all…”. At this point, you’ll walk to the nearby gas station, fill
    up a plastic container, refill your bike, turn on the engine and everything will
    be working (except for your bruised ego).
  19. You’re able to ride a lot in one day. A 9 hour ride from NYC to Acadia national
    park in one day is fully doable if you take a lot of breaks. Doing it in 9 hours
    and 30 minutes is also doable if you’re ok lying on your couch for the next 3
    hours in pain.
  20. Parking your motorcycle is one of the great joys in life. Being able to find
    that perfect spot between two cars right in front of your building is a little
    nugget of joy you can look forward to every night on your ride home.
  21. If you ever walk to where you parked your motorcycle and notice it’s missing,
    just breath. Yes, there’s a good chance it was stolen. There’s also a good
    chance it just got towed.
  22. Speaking of getting your bike towed, in case no one told you, you need to get
    your bike inspected once a year. The inspection is amazingly quick (all they do
    is check that your lights and breaks work) and cheap ($6). However, if you fail
    to get your bike inspected in time and it gets toed, you’ll be on the hook for
    $200 in towing fees $65 for the ticket. All because you forgot a $6 inspection.
  23. Parking in NYC? Get a disc lock!
  24. When you park your bike, you take off your gloves, put them in your helmet, place
    your helmet on the car next to you and proceed to put on your disc lock. You’re
    in a rush so you quickly run to get into your apartment. It’ll be 12 hours
    before you realize you forgot to take your helmet off the car the day before.
    Don’t get your hopes up…the helmet is gone.
  25. Riding in the rain is scary. At first. After awhile, it’s kind of fun. But still
    mostly scary. But fun too. Except if you’re riding really fast…then it kind of
    hurts. But is still fun. And scary.
  26. Random people will talk to you when you have a motorcycle. People will stop you
    on the street when you’re carrying your helmet to ask what kind of bike you
    have. Truck drivers will pull down their windows to ask how long you’ve had your
    bike for at red lights. Random women on the sidewalk will ask if you’re riding
    to Harlem and if you can give them a ride. Little kids will ask you about your
    bike. It’s fun.
  27. All your friends imagine your bike will help you with women. It hasn’t yet but
    who knows.
  28. No one will understand why you got a motorcycle. There’s no point in trying to
    explain because there isn’t really any one answer.
  29. Riding a motorcycle is not always convenient. It takes longer to get moving when
    you have to put on all of your gear. It’s sweaty and uncomfortable wearing lots
    of gear on a hot day. Your tank only has 3.5 gallons so you have to fill up a
    lot more often than everyone else. On the other hand, “driving through traffic”
    (that is, going between cars that are stuck) is a blast
  30. Riding a motorcycle is great. It’s one of the few times in life when you’re
    fully alone. There’s no one to talk to. You can’t check your cellphone. You
    can’t focus on anything else but riding unless you’re cool with dying. To top it
    off, the act of riding is fun as hell. On a motorcycle you’re nimble. You’re
    going fast and you have the wind in your face. Enjoy it.

So should you get a motorcycle? Yes!

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Hi, I’m Ron Jacobson. I'm the CEO of Rockerbox, lifelong fan of the Spurs, Startups, Israel and Tomatoes. Follow me at @rjjacobson

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