Cruising down the road at 45 miles per hour you spot a guy wearing a purple shirt, a genuine smile and a thumb jutting out standing confidently on the side of the road with a bright sign that reads “NYC”.

You have heard of hitchhikers before, but never actually seen one. Your altruistic gut is telling you to slowly pull over and offer this stranger a ride in your car. You never pick up hitchhikers you think, but this guy doesn’t seem like the horror stories you’ve heard.

You make decisions every day, sometimes life changing, in mere seconds; this is your subconscious mind guiding your decision making well before you can consciously articulate “why”.

I am hitchhiking across America for two weeks and I will be writing about my experiences and the invaluable wisdom gained from talks with hitchhikers and internet research. Look out for the next article post-hitchhike on my experience and overview on what worked and didn’t work. Most importantly, I’ll write about the people who will fill my sails on this journey and reaffirm my notion that there are many kind people in this nation.

Every person I asked before this trip about hitchhiking fell on two sides. One type has never had a first or second hand experience with hitchhiking and was very concerned for my safety, and many thought it was reckless. The other camp has had personal experience with hitchhiking and told me of the great stories and character building nature of accepting the ebb and flow nature of hitchhiking. The only people I met who had a significantly bad experience were women who traveled alone, who nonetheless learned to prevent those situations in future.

A large portion of population in the United States have no experience with hitchhiking and are more familiar with the horror stories rather than beauty of helping others and sharing resources. Getting a ride as a hitchhiker in today’s fear soaked society requires a few things to insure a speedy trip and great stories.

Hitchhiking is Like Sailing

Hitchhiking reminds me of the art of sailing. My first experience sailing was at midnight in the middle of the ocean. I experienced a very visceral feeling of connectedness to nature within the interplay of animals, air and sea. The wind was gently blowing and the boat was silently cutting through the waves as I could see glowing phosphorescent trails from dolphins and hear sharp bursts of air from hidden whales. Harnessing the force of the wind to travel seemed so natural and effortless, which was in stark contrast to when the roaring engine forced us through the ocean unconcerned with the natural forces around us.

Hitchhiking also involves harnessing the existing forces already in motion. You go with the flow instead of pushing through on your path alone.

In sailing you have to be knowledgeable about wind and have hope the wind will blow again when it is calm. The wind will not always blow, or even in the direction you would like, but you can always redirect that energy to to push you forward.

Hitchhiking requires knowledge in the rhythms of travel: knowing the subtleties of car refueling patterns and the telltale signs of a good pickup spot. Like the wind, the person who picks you up has no monetary incentive to help you on your path. To sit on the side of the road waiting for the kindness of another human to pick you up can be a test of will and faith in humanity.


Smile, it increases your face value.

In the many seemingly awkward social experiments I have forced on myself, one of the most interesting truths I discovered was walking down the street; if you smile at people, most will smile back regardless of their current emotional state. After experiencing this firsthand I always remembered you can make someone feel better just by offering a smile. Scientific people explain it with the fact we have mirror neurons in our brain that propagate this, some simply say smiling is contagious.

A smile can instantly show a potential ride that you are currently in a positive state of being, that sets you apart from the down and out vagrants that many people associate with hitchhiking. Who doesn’t want the happy guy in their group?

You want to make sure you give a genuine smile to make sure you radiate the most positive energy as possible.

Eye Contact

Eyes are windows into the soul. When hitchhiking it is best to make direct eye contact with the driver as they approach. If you avoid eye contact it is easy for the driver to dismiss you as they are unable to gain a sense of your current mental state.

Mark Snyder and his coworkers found that hitchhikers doubled the number of ride offers by looking drivers straight in the eye. A personal approach, as my partner knew, makes one feel less anonymous, more responsible. – “Social Psychology, Myers p.503 Social Relations”

Approachable Appearance

A genuine smile and good eye contact go a long way in assuring your ride you are friendly and safe.

Your appearance is a close second. A big scruffy beard, all black attire and face tattoos is a direct stereotypes people have of their nightmare hitchhiker.

Take a second to visualize in your mind what your nightmare hitchhiker looks like. Now take that image and present yourself in a manner that is the opposite of that. You are on a job interview every time you are on the side of the road with your thumb out. First impressions are everything and you are walking into the interview with no resume and only a few seconds. Looks are everything.

Some say clean cut works better than hairy. Hair is reminiscient of primal urges and clean cut brings to mind logic, manners and orderliness. Another viewpoint to keep in mind is that some people only want to pick up experienced travelers not a clean cut business man.

Color Theory In Hitchhiking

You only have a couple seconds in this drive by interview. Think about wearing colors and accessories that are bright and light rather than dark and saturated. Dark may be easier to keep looking clean while traveling, but light colors have a better emotional appeal. Wearing lighter colors also show that you have not been rolling around in the dirt on the side of the road dirtying your potential rides car. Dressing in a bright yellow shirt and orange pants may be the perfect way in catching attention, but be careful of looking too weird.

Before Getting in the Car

Consider the following points to proactively prevent unwanted situations.

  • After they pull over, first ask them, “Where are you going?”

This allows you many strategic advantages

  • How are they communicating with you? Are they impatient, slurring their words, stuttering, reaking of alcohol.
  • If any signs indicate a potentially dangerous ride, you can tell them you are only looking for a long ride and you will wait for another car.
  • You should always keep your most valuable possessions on you at all times. Your main bag should be in constant reach and preferably not in the trunk.

Good Conversation For a Good Ride

One reason people pick up hitchhikers is to have a conversation to stay awake or to keep boredom at bay. Stay clear from any controversial topics like politics or religion, unless you are ready to get in a heated, and possibly very uncomfortable situation in a small space. Instead, ask questions about their destination and what awaits them there. Where are they from? Be aware some just want to lend a helping hand and are content being a shy introvert during your ride.

Share Music

I find road trips are the ideal environment to share and be exposed to new music. I will be bringing my phone and an audio cable to plug into their car radio, most modern cars have this built in, but if not I also have an FM transmitter. People open to picking up strangers are also more likely to be open to new music. Hopefully I will be able to expose a driver to new music they never knew they liked.

Leaving the Vehicle

As you enter the car you should know where they are heading and how far they can take you before they drop you off. If you have internet access on your phone you can check out Yelp or Google Maps for gas stations and rest stops. Look up the best location and see if the driver can drop you off at the best possible spot you can find. It is better to get dropped off early and have a better shot at getting another long ride.

Leave the door open until all of your belongings are out of the car.

Of course after you exit thank them for their kindness and generosity.

Exiting The Vehicle Prematurely

I hope I never encounter the situation where I need to leave the vehicle due to mental instability or weird actions by the driver, but it is best to be prepared.

If you feel uncomfortable and need to leave you can pretend to get sick and tell the driver he needs to pull over because you are about to vomit.

Leave a Positive Impression About Hitchhikers

Most people have a negative impression about hitchikers.

I live by a central tenet that I strive to have people be better off in life having me in their life, let it be a brief interaction at a coffee shop, a car ride together or a long term relationship. By being a net positive, people want to be around people that bring them up.

I plan on leaving no trace of my presence in the cars I hitch a ride in. No trash will be left, lists of artists they enjoyed listening to with me will be.

My friend gave me a bunch of thank you cards written out in envelops to give out to my rides. It touched me, that she knows the type of hitchhiker I want to be. I am excited to see my rides faces when I hand them a thank you card as I leave their car.

Hopefully, I will have reached a small portion of people who would normally not have picked up a hitchhiker and make it a bit easier for future hitchhikers to get a ride.

A Great Sign

Some hitchhikers swear by having a sign in hand, others find it prevents people from picking them up because they may not be going directly to that location.

I designed a reversible and reusable sign green on one side and yellow on the other. Both are highly visible and the colors have good associations with happiness and nature.

Destination Signs

You can create a sign based on a destination. It is best to choose a decent sized city in the direction you are going. This can increase your chance of having someone stop, on the flip side it can limit people who aren’t going to that city or only going a short distance.

A second approach is to just write a cardinal direction like East or West. This is broad and can be helpful in getting a short ride if you are stuck in a place for too long.

Funny Signs

Humor can be a great ally in getting someone to stop for you. There are many things you can write on your sign to get that next ride. You can try “I got cookies”, “Freshly Showered” or “Won’t Kill You”. Having a funny sign can be polarizing. Some drivers would only stop because you made them laugh and feel good. Others may be more likely to pick you up if you had a destination on your sign rather than a witty comment.

“How to Win Friends and Influence People”, one of my favorite books and the oldest book on personal development was written by John D. Rockefeller who said, “The ability to deal with people is as purchasable as a commodity as sugar or coffee and I will pay more for that ability than for any other thing under the sun.” Hitchhiking, unlike a class on self improvement, is free but I hope it will improve my ability to communicate with people, be it from the side of the road or communicating through my clothes, sign and trustworthy smile.

Hitchhiking Packing List

I am posting my packing list here to help you in packing for your trip. Some items are season/climate unnecessary in the places you may travel.

General Items

  1. Backpack
  2. 1 Good Book – You can always trade it in for another
  3. Phone number list stored in shoe
    1. If I lose everything I still need to get a hold of someone. Sadly with the advent of cell phones I don’t remember anyones phone number.
  4. Reusable sign that can be written on with dry erase markers.
  5. Dry Erase Marker For Sign
  6. Sharpie
  7. Pen
  8. Journal
  9. iPhone
  10. USB ciggarette charger, maybe have an extra usb slot to charge multiple phones or an inverter to power a laptop charger
    1. PowerGen Dual USB Port 2A – Heavy Duty Ouput Car Charger
  11. Head Torch
  12. Camel Back
  13. Sunglasses (Don’t wear when hitching on the side of the road)
  14. Money
    1. Do not put your whole amount in one place. Keep some in your shoes, backpack, or jacket, just not all in one place.


  1. 2 Pairs of Jeans
  2. Three Shirts
  3. 4 Underwear
  4. 4 Socks
  5. Shoes
  6. Zipper Jacket
  7. Long Sleeve Shirt
  8. Poncho
  9. Beanie
  10. Sandals
  11. Shorts
  12. Nice Long Sleeve Shirt

Personal Hygeine

  1. Deodorant
  2. Toothbrush
  3. Toothpaste
  4. Toilet Paper (Wrap 1/6 roll around some flat cardboard)
  5. Bar Soap – Bar soap does not leak
  6. Sunscreen
  7. Lotion
  8. Lip Balm
  9. Low Absorbtion Towel

Digital Nomad Items

  1. Camera
  2. Camera Battery and Charger
  3. Laptop & Case
  4. Laptop Power Adaptor
  5. Gorilla Pod Tripod
  6. Earphones
  7. Auxiliary audio cable
  8. FM transmitter (For older cars without a way to directly connect my iPhone)

McGuyver Items

  1. 4 Safety Pins
  2. Zip Lock Bags
  3. Zip Ties
  4. 50’ Paracord
  5. ½ Roll Duct Tape wrapped around some cardboard
  6. Floss With Sewing Needle inside
  7. Spork

Items For Comfort and Ease

  1. Swim Shorts
  2. $5 Assorted Change For Public Transportation

Lookout for my second post after I get back from my travels.