149. Hitchhiking — an unexpected way to do job hunting

This story isn’t one of mine. It doesn’t even belong to someone I know, but it’s so great that I wanted to tell it anyway. Suffice to say that the details aren’t super important, but the rationales and insights are.

Now, I guess that you’re now thinking one of three things.

  1. Bullshit. I don’t buy it, and nothing you say can convince me.
  2. Interesting. I’d never thought of that. Tell me more.
  3. Of course! I don’t need to read on. It’s self-evident why.

Now, there are plenty of legitimate reasons to be in the #1 group. Maybe you live in a place where hitchhiking is dangerous (lots of those around!). Maybe hitchhiking is especially dangerous for someone like you (also very possible). Maybe hitchhiking just isn’t a thing where you are, which makes it pretty damn hard to do this. Thanks to Raquel, Liselle and Nicole for sharing thoughts.

That said, when I heard the story the first time, I fell squarely into the #2 category. My curiosity was piqued, and I wanted to hear more. If you’re like me, read on!

But before you get into a car with a stranger with dreams of solving your unemployment situation, here are some things you should know.

The premises: Don’t try this at home if this isn’t you

Premise #1: You need to have job skills that are easy to understand

If you design the snazziest web pages south of Svalbard, you’re good to go. Being a skilled photographer, an experienced project leader or a performance coach also works. Doing something extremely specialised that is hard to explain is less optimal. Having a Master’s Degree in Biology is great, but to most people it’s not clear what that makes you able to actually DO.

But if you can explain what you’re good at to someone over the course of a minute or two in a casual conversation, you’re golden. Especially if it’s a slightly unusual skill or you’re extremely good at it.

Premise #2: You need to like talking to strangers

If you’re going to go hitchhiking, you are going to spend a lot of time talking to people you’ve never met. If that makes you uncomfortable this is not for you. Also, if you’re the pushy type, who thinks you sell yourself by selling yourself in every situation, this is also not for you.

If you like getting to know people and are a good conversationalist, then you’ll be like a fish in water.

Premise #3: You play the long game

There’s no guarantee that this strategy will work, but that’s true of any strategy. The thing about hitchhiking as a job hunting strategy is that it will take quite a bit of time. No one knows whether it’s trip #1 or #44 that leads to your next job, so if you’re out for a fast solution, this isn’t for you. Sure, it might work, but it’s a bit of a numbers game.

Ok, premises understood — go on…

Now you need to forget about yourself for a moment, and put yourself in someone else’s shoes. Let’s talk a bit about your ride. Because you obviously don’t want to ride with just anyone. No, you’re hitchhiking tactically, and getting from A to B is the least of your worries.

Families are out. They may pick up a stray dog like you out of pity or altruism or nostalgia, but they’ll not really have time and energy to talk. If there are kids in the car, this truth becomes 10x’ed. Families that pick up hitchhikers are great (all power to them!), but they’re not who you’re looking for.

Cars with multiple occupants are likewise out. They might contain interesting people, but you’re playing the game of odds here. While there’s a chance that a car with 2–4 people can fit an extra in, there’s not that good a chance that the conversation will be one in which you get afforded a lot of room. Joining a couple of friends on their way somewhere is great fun, but we’re not just looking at fun here.

The same goes for low-end cars. It’s harsh and ugly, but it’s true. Just because someone drives an expensive (or at least semi-expensive) car doesn’t mean that they’re your ticket to a job, but it does mean that the odds of them knowing others in the same economic bracket are higher. It may leave a sour taste in your mouth, but it’s true nonetheless. A high-class Mercedes simply has a better chance of containing a CEO than a banged-up Opel Cadet does.

Your optimal ride has the following characteristics:

  • The driver is somewhere in the 40-55 range and is alone.
  • The car is a nice one. Not necessarily flashy, but definitely not cheap.
  • Someone in a suit scores higher than someone in gym pants.
  • You need to have chemistry the moment the door opens.

The reasons for this are quite simple.

While there are plenty of people in this world with power, money and influence, there’s an overweight of them in the 40-55 segment. Likewise, there are millionaires who drive old Volvos, but there are more who drive Audis and BMWs. The same goes for clothes. Casual clothes don’t mean that you’ve got a rich hobo on your hands, but few people drive alone in a suit (or something similar) unless they’re business professionals dressed for work. Finally, if you are offered a ride by someone where you feel that it’ll be strictly hitchhiking but with no conversation, then pass on the offer.

And here’s the kicker. The group I’ve just described are prime hitchhiking ride material. Many of them have a long drive to work that they do all too often. They feel safe and secure and aren’t too worried about you being a crazy car-thief (which might be different in you try for someone in a Bentley or a Ferrari). And they’re bored out of their skull by the prospect of yet another lonely drive, listening to car radio, podcasts, or whatever.

Once you’re in the car, don’t talk about what you do

I know, I know. I’ve said that this is about job hunting, and it is. But it’s also about people, and while you can fake interest in people, it’s a lousy thing to do and a lot of sharp operators will see right through you.

You’re in a car with a stranger. You’re going somewhere that makes sense to both of you, and a certain spirit of generosity has already been established. Don’t try to sell the poor (wo)man the vacuum cleaner right away!

No, instead, talk about life and the weather and the road and society and travel and all those things people talk about when they meet for the first time. Don’t rush it. If you provide interesting conversation, sooner or later the question will come:

And this is where things get interesting. Because the worst thing you can do now is to try to sell yourself. Don’t. Just tell what you do as if you were at a party and someone asked you while waiting in line for the toilets. It shouldn’t be a long and detailed answer. It should just be enough to make the other person want to know more.

“I’m a photographer. I just did a series of portraits of dogs with disabilities, but mostly I do commercial photography.”

“I’m a consultant, and yeah, I know, that doesn’t really say anything these days. I help organisations figure out how to optimise production processes and use more digital tools.”

“I build handmade furniture using recycled materials. So I guess you could call me a carpenter-artist if you wanted to.”

And THAT is when you talk about what you do

If you’ve served it right, the response should be a slightly raised eyebrow and a “That’s interesting. How does THAT work?” or “That sounds interesting.”

Chances are that this will lead to an honest and casual conversation about what you do, why you do it, and so on. Again, just like if you’d met somebody at a party, except that there’s no loud music, the driver is (hopefully!) sober and you have a lot of time to kill together.

Now, there are several (good) ways it can go from there.

Option 1: “Well, that was interesting. Thanks for telling me about your job. Have you ever been to Barcelona, by the way? It’s a great city.” and then the conversation moves on.

Option 2: “Huh… that sounds like exactly what my friend Louisa needs! She runs a shoe company, and they’re looking for somebody with exactly those skills. Should I hook you up with her?”

Option 3: “Damn. We’re actually looking for someone like that at my company! Let me get your number and let’s talk more next week. I guess this was a lucky ride for both of us, no?”

Needless to say, it can also end with Option 4 (You bored the poor person to death and they just want to get rid of you), Option 5 (It turns out you’re a competitor and they kill you and dump your body by the road) or even more exotic outcomes.

But the three first ones are very real possibilities.

Rome wasn’t built in one day, though

Chances of you landing a job by hitchhiking once are low.

I’ve talked with plenty of people who have been job hunting for months (or even years) with little success. At least this way, even if it doesn’t lead to a job, you get to have new experiences and meet (probably interesting) people. Searching through job index websites and writing unanswered applications is a lot less fun, I’d wager.

The key here is perseverance and not getting mechanistic about it. In a sense, it’s like going to a string of network events, except the setting is very different. Once you start operating off a script and become robotic about it, you’re lost (unless you’re incredibly talented at that sort of thing!). So do it until you don’t feel like doing it anymore, and see where it takes you.

My five cents say that it will beat most traditional job hunting in both how your time is spent and the results you get. And who knows? Maybe it won’t bring in something right now, but a few months (or years) down the line, someone will say “Hey, you know, I once picked up a hitchhiker who could do the thing you need done. How about I give you her number?”.

And just to give a personal example of how hitchhiking stories work, I’ll share a tale of two fathers and a one-liner that’s hard to beat.

In 2002 some friends and I were going to a pirate larp adventure in another part of Denmark, and we’d hitched a ride with a work contact of my stepfather (Eric) who had both a car and the space to spare. The drive took less than two hours, but we got to talk a lot about larp — we were, after all, a couple of 20-somethings dressed as pirates, and this friend (who was in his late 40’s if I recall) had never heard of larp before.

That journey was pretty unremarkable, aside from the fact that it was mighty nice of him to drive us buccaneers to where we needed to go. The interesting episode came some months later, when this person was in a meeting of some kind with my father. They were — for whatever reason — talking about how larp was becoming more and more fashionable, and this guy (our driver) shares the pirate transport story, telling how he’d driven us from Copenhagen to Odense.

He then turns to my father (Anders), who has been keeping unusually quiet during this conversation and says “Hey, Anders, one of those larpers was actually Eric Jul’s son. You know Eric. Did you know his son was into that larp thing?”.

At this point my father — and I love him for this — smiles broadly and says:

General hilarity ensues, as the people in the conversation discover that Eric Jul’s (step)son is Anders Raasted’s (biological) son. But the reason they found out about the parental circumstances was because the guy was relating a story about larpers who had hitched a ride with him. Sure, it was through a friend and not on-the-road-thumbs-up-hitchhiking, but that’s just details.

The key takeaway from the story isn’t that my two father figures get along great or that my father has a wonderful sense of humor. No, it’s that this guy mentioned the larp hitchhikers in a random conversation about larp BEFORE remembering that there might be a personal connection to someone in the room. People talk about people they meet — especially if there’s a reason to.

Hell, I find it interesting enough that I’m writing about it, and I didn’t even get the story first hand. I got it through my brother David (Eric’s son, not Anders’), who’d talked with a friend who’d gotten gigs by hitchhiking.

So let that work in your favour.

Be interesting.

And hit the road.

If you like my writing, and want to free up my time, to write more, you can do exactly that, by supporting me via Patreon.


If you want to get into contact, I can be reached at claus.raasted@gmail.com.

Director at The College of Extraordinary Experiences, Coach at McKinsey & Founding Partner at The Global Institute For Thought Leadership. Author of 31 books.

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