Today, I want to share how you can win this lottery called life.

I’ve been reading and writing about the notion that you can make your own luck for over five years now. And for the past year or so, I’ve been praising the power of collaboration.

I say, for instance, that my work nowadays (such as it is) seems to be meeting and chatting with like-minded folks from all walks of life. They email me to say, “Want to have lunch?” and I say, “Of course!” We talk about podcasts or libraries or bicycling or comic books. Whatever strikes our fancy. And when we’ve finished our tea or our Thai noodles, nothing major seems to have happened.

What’s happened, however, is that we’ve both just received lottery tickets. By meeting and chatting and sharing ideas, we’ve been granted a ticket in the lottery of life.

And there are other ways to get lottery tickets too. Any time I try something new, I get a lottery ticket. Since I make it a point to try new things all of the time, I get a lot of lottery tickets.

  • When I learn to drink coffee, I get a lottery ticket.
  • When I learn to drink beer, I get a lottery ticket.
  • When I learn to shoot a gun, I get a lottery ticket.
  • When I learn to ride a motorcycle, I get a lottery ticket.
  • When I learn to speak Spanish, I get a lottery ticket.

I’ve found another way to get these lottery tickets, too: I say “yes” things that seem scary or difficult. For instance, when I agree to speak on stage in front of one thousand people, I get a lottery ticket. When I fly to Ecuador to help people learn about financial and personal independence, I get a lottery ticket. When I spend six weeks locked in my office writing an e-book about money, I get a lottery ticket.

In short, any time I do something — especially something new — I get a lottery ticket.

But what do I win? Great question. Turns out, the prizes are pretty fucking awesome.

When I learned to speak Spanish, for example, I hit the jackpot. I made new friends (my tutor, my English student), traveled new places (Perú, Bolivia, Argentina, Chile, Ecuador), read new authors (Neruda, García Marquez), tried new food, watched new movies, and more.

Today in Quito, I walked about ten miles across the city — up and down, up and down, up and down since Quito is nowhere near flat — spending part of my time on the teleférico, which is the cable-car that transports visitors up the mountainside from 9000-foot elevation to 13000-foot elevation.

During the steep fifteen-minute ride to the top of Pichincha Vulcano, I sat with two couples. They spoke only Spanish. If I didn’t know Spanish, I couldn’t have understood them, much less conversed. (Hell, I wouldn’t even be here in Ecuador if I couldn’t speak Spanish.) But I do speak Spanish, so I enjoyed a pleasant chat about one couple’s life in Venezuela and the other couple’s life here in Quito. Yet another small prize to add to the mountain of booty that I’ve obtained just because I spent some time learning another language.

Kim is awesome at playing this lottery. That gal gets tickets all the time. Because she’s a friendly and fun dental hygienist, her patients are constantly giving her things. In the eighteen months I’ve known her, she’s been given eggs, tickets to the country fair, tickets to a historical museum, tips on travel, and much much more. Remember how I recently sold my comics for a ton of money? (Wait, you can’t remember that because that article won’t go up at Get Rich Slowly until this Thursday!) Well, several thousand dollars of that came because we used one of Kim’s lottery tickets; one of her patients introduced us to a couple of folks who were interested in buying them.

To me, the best part is that one good thing often leads to another. Luck begets luck. When I win once, I get another winning ticket. I’ve reached the point where my entire life seems to be a series of fortunate events.

Note: Often just doing the thing that earned me the ticket is a sort of prize. Meeting certain people can be so delightful that even if nothing else came of it, the meeting itself was a tiny jackpot. Learning to drink coffee provided a small reward, not to mention the ongoing payouts involved in the fun morning ritual I get to share with Kim.

You know what doesn’t give you lottery tickets? Watching TV, for one. Also, playing videogames. Sorry, but there’s no payout for playing another round of Angry Birds. You don’t get lottery tickets for being a picky eater, being afraid to take calculated risks, and refusing to do the things that scare you.

Not every meeting and not every experience pays off. But many do provide a reward, and some of those rewards are enormous. Winning lottery tickets are so common and so fruitful, in fact, that I’ve almost become addicted to playing this lottery called life. I relish making new acquaintances, going new places, and trying new things.

So, get off your butt and go do something new today. Talk to a stranger. Try a new cuisine. There are still lots of prizes left in this lottery, but you have to be in it to win it.

24 Replies to “How to Win the Lottery Called Life”

  1. I love what you are saying here. So true. I wish watching just one more episode of my latest TV obsession got me a lottery ticket, but unfortunately it doesn’t! I wish I had the mind for languages, if I did, I’d probably learn Italian or Spanish, never know I might give it a try. You’ve inspired me.

    • Alek Hartog says:

      I honestly don’t mean to seem judgmental or condescending in this reply but your post seems remarkably non-committal. Like you’ve given up before you’ve even tried to start. It reminds me of the lifehacker post I saw today, of how people WANT to be skinny without working out and giving up dessert. Of how people WANT to start a business without hardship and strain. Stating that you don’t have the mind for languages…what does that even mean? It most likely means there’s an alternate method you could try to use and learn! Go try it out!

      Again, I’m no paragon of success or commitment, but you struck a bit of a chord.

      Best of luck,

  2. Josh says:

    Is there any chance of you setting up another event on financial independence in your home town of Portland? It would be a really great opportunity for those of us just starting out our journey towards FI.

    • jdroth says:

      Yes, there is a chance. In fact, a good chance.

      I’d been hatching a plot for some sort of retreat here in Portland, and this just solidified the idea. I have some other obligations to get through before I do any serious planning, but look for some more concrete info early next year.

  3. Ivan says:

    What a fascinating read, J.D.! You’re absolutely right. The only way to win in life is to get some skin in the game and play. It’s tempting to stay on the sidelines and play critic. But that rarely – if ever – gets you anywhere.

    Sure, you’ll never know if what you do today is going to pay off tomorrow. That’s the “lottery” part of it. But as long as you keep an open mind, you’ll find that things work out more often than not. It’s just that sometimes it does so in ways we have never expected it.

    My approach to the lottery of life is this: the more I fear something, the more I push myself towards it. Every now and then, my fears are justified and they save me from doing something stupid. But more often than not, my fears are telling me exactly where I need to grow my life. So that’s where I go.

    And it’s been a fun journey so far!

  4. Here I am with my girlfriend on one of the America’s Cup chase boats, racing around the San Francisco Bay at 60 knots, just for fun. Why? Because I happened to talk to the guy with the keys to the boat. I was actually talking to him about another boat of his, that we were taking out sailing. This boat was parked next to it. My girlfriend said, “I want to take that one out.” basically as a joke, but his reaction was “hmm, alright, let’s go”. We actually took both boats out, just because we asked. Nothing ventured, nothing gained, and sometimes all you have to do is ask.

    J.D.’s right though. You “make your own luck” (I really don’t like that phrase because if you make it, it’s work, not luck) by trying new things. My brother has been talking about trips he wants to take for years, but since he’s never done a big international trip like the ones he wants to do, he’s too hesitant to actually try and plan one. Meanwhile, I’ve done similar trips simply by deciding to say, “Hell, I’m buying plane tickets. At that point, there’s no turning back and we’ll have to arrange the rest of the trip!” I guess the whole thing largely comes down to saying “seize the day”, but it’s so much *easier* not to take advantage of all the opportunities that are sitting right in front of us, and instead watch another episode of Breaking Bad.

  5. PawPrint says:

    Just want to say that it’s never too old to start doing something new. I’m in my 60s and decided last year that I didn’t want to be afraid to try new things. My challenges started off small (taking a car through the car wash) and have become bigger (teaching a reading/writing class to ESL and ABE students–teaching was not my profession). Moving from Boise to Seattle to live in an urban apartment was a biggie–leaving a couple of kids (they’re 40 and 35, but still kids to me), my friends, my activities. Essentially starting over. My rewards have been intrinsic (reconnecting with school friends, meeting new people), although putting more money in the retirement fund is always nice. I like Ivan’s comment” my fears are telling me exactly where I need to grow my life.” I do watch TV at night, though. Walking everywhere and working out daily, I get pretty tired and like to veg out and be entertained by “Midsomer Murders.”

  6. Marge says:

    Thanks for the reminder to keep playing the game! Love the picture, too!

  7. Martin says:

    Oh man, I probably talk to too many strangers, I might have to slow down on that front.

    I love the Spanish stories because I have been learning Spanish this whole year. Now it’s time to do something. I’m planning a trip to Argentina for November. Any suggestions? I’m 25, single, and not opposed to anything.

  8. Chris says:


    I just ran into you via Jlcollins site. You have some neat ideas. I would love to help make the next one happen…perhaps in the Gorge? I live in White Salmon.

    Consider this an invitation to discuss your ideas over a trip while rock hoping up one of the most incredible waterfall gorges that you have ever seen…and I’ll bet ya a beer you have never been there !

    Email if interested JD

  9. Leah says:

    One of my college professors used to tell the story of a student who lamented her decision as a child to not play piano. She loved the music others played. He told her “start tomorrow. In five years, you’d have been playing for five years rather than further lamenting more lost opportunities.”

    That said, watch the judgment call — the fact that I play video games (on occasion, and not all the darn time) has helped me get along with my students, make some friends, and be a great babysitter over the years. Nothing like being able to play some MarioKart with my charges. Anything that can result in a common interest can do that. Singular focus is perhaps not good, but most activities aren’t inherently bad. It’s about how one uses those “lottery tickets” one is receiving that results in the gain.

  10. chacha1 says:

    I do feel like I’ve won several big lotteries in life. I “won” good parents and godparents through no effort of my own, but applying for the scholarship = free college, just for starters.

    Moving to California without ever having visited before was a big chance, but it paid off in many ways. Taking dance lessons meant meeting the love of my life (plus finding a sport for life). Not being afraid to leave a crappy job meant finding a better situation down the road.

    I think the key to the “lottery” approach to life is to be able to recognize the opportunities that open up because of a chance taken. A lot of people take chances, but not all recognize the opportunities that result. You have to have an open heart & mind, a sense of adventure, and the willingness to faceplant once in a while.

  11. KSK says:

    I’ve taken a lot of chances this year, and have been saying “yes” to things that scare me. It’s been the most fulfilling year of my life.

  12. Matt Ainslie says:

    Reminds me of what William Hutchinson Murray once wrote:

    “We had definitely committed ourselves and were halfway out of our ruts. We had put down our passage money— booked a sailing to Bombay. This may sound too simple, but is great in consequence. Until one is committed, there is hesitancy, the chance to draw back, always ineffectiveness. Concerning all acts of initiative (and creation), there is one elementary truth, the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then Providence moves too. All sorts of things occur to help one that would never otherwise have occurred. A whole stream of events issues from the decision, raising in one’s favour all manner of unforeseen incidents and meetings and material assistance, which no man could have dreamt would have come his way.”

  13. Mike Crassweller says:

    Thank you for helping me finally find the words to describe my general outlook on life. The lottery ticket analogy is PERFECT and I think my friends and family will understand and accept it more than me telling them “You make your own luck. Good things happen because you make them happen” (I’m usually met with a very grumpy response because folks think life happens TO them). This is a much more positive message I think people will be more receptive to.

    One point of disagreement though on your article (well… sorta…): Videogames being a time-wasting thing that doesn’t give you “lottery tickets”

    My wife and I met and got to know each other through talking about World of Warcraft, a game we both played at the time.

    My love of games and gaming led me to a career in the video game industry. My job has allowed me to move to Michigan, Texas, and later this year the Netherlands. I’ve met amazing & smart people and been positioned to take advantage of great opportunities.

    All because I play video games 🙂

  14. Great post…funny how the harder you push yourself out of the ol’ safety zone, the more rewarding it is. My husband and I sold our business to our employees and ‘retired’. He was 39 and I was 36. That was 17 years ago.
    Sometimes, when we see something that’s clearly out of our budget, we have a standing joke, “Should have worked for two more years.”
    But it IS a joke; I would never give back the time we’ve had to travel, spend time with friends and generally pick up ‘lottery tickets’ every morning when the alarm does NOT go off.
    Going against the social norm is scary, yet exhilarating. I had no idea when we quit that I’d become a travel writer. But, because I had the time and space in my life, previously unimagined possibilities presented themselves. I’ve jumped into South African gorges, zip lined in S. Africa and Wales, done walking holidays in England, celebrated day of the dead in Mexico, cycled the Velodrome in Glasgow, lived a couple of months in France…all in the last 15 months.
    Making connections with new people/ideas/destinations/cultures/art means daring to be open and vulnerable, but oh my…what a great ride.
    Thanks again for your inspiring website. If you’re ever in Vancouver, I’m available for coffee (we have a few of those places here!).

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