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Win two roundtrip tickets anywhere in the USA

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I’m writing you from my apartment in San Francisco today. Normally, I live in New York, but I also have an apartment in SF. I know it’s a little ridiculous, but to me, it’s part of living a rich life.

I’ve asked you before: What does “rich” mean to you?

For some people it means fancy shoes. Let’s call this GOODS.

(As opposed to patronizing personal-finance “experts” who tell you all materialistic things are bad, my take is half of them WISH they could afford $500 shoes. Buying nice things is not evil — if you want them, and you can earn enough and automate your money to afford them, do it.)

For other people, it’s having 6 months of an emergency fund. Let’s call this SAFETY.

For some, it’s donating 10% to their local church or charity. Let’s call this CHARITY.

For other people, it’s being able to take a 3-week vacation to Asia…or take a pay cut to work at a job they love instead of chasing money. Let’s call this FREEDOM.

You’ve heard me talk about what rich means to me, like waking up and deciding I want to go to SF for a week and hang out with my friends there. Or see my parents for a weekend. I call this being FLEXIBLE.

You can see there are TONS of definitions of a rich life. And none of them make you feel guilty for using your money to do what you love.

But today, as I sit here in my second apartment (something I never thought I’d say…ever), I want to focus on one. I love the idea of being able to fly somewhere on a whim.

So I’m doing a new giveaway. This one is really simple:

I’m giving away two roundtrip tickets to anywhere in the USA.

All I ask is that you tell me where you’d fly and who you’d bring in the comments below.

I’ve done a few of these giveaways, but nothing like this. As long as you keep spreading the word about IWT, I’ll keep doing these. I want us to all share the idea that living a rich life doesn’t have to mean scrimping and cutting back on everything. That it’s OK to want more — and to craft your life around achieving it.

This ends 9/24.

Here’s the 10-second signup:


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  1. I would bring a girl I’m interested in dating to Las Vegas. She’s Canadian.

  2. I would bring my husband and newborn to visit family in Seattle.

  3. I would bring my little brother who just started college.

  4. My husband wants to go to Maine. We live in Los Angeles. We don’t really know what is in Maine but it seems like it would be great to fly there and rent a car and go exploring.

  5. I would fly to Omaha, Nebraska. Sounds exciting, I know, but hear me out. I want to go there to discover my past.

    I’ve been researching my family history recently and discovered that many of my relatives come from a little town north of Omaha. I looked up the town and what I learned reminds me much of the place I grew up in Idaho. I don’t know much about my family history other than a few facts and I want to go to this place and discover who these people were, what did they do there, how did they contribute to their community, etc.

    I’d like to take my wife as my traveling companion during some time off between semesters in her law school studies. She compiled research on her own family and is very good finding information. I need to have my research assistant with me to help find that information that will help me identify with my past and how it shapes me today.

  6. I’d like to take my soon-to-be fiance to New Orleans for a nice getaway. It’s one of her dreams to wander around the French Quarter all day and eat beignets. Needless to say, I fully support her wanting to travel cross-country for some fancy French doughnuts.

  7. I would either go to California, not sure what city, or to NYC. I would take my mom. She has taken me on so many trips through my life and it has made my life so much more interesting and enriched. It would be up to her whether we went and relaxed, more like explored, somewhere in California, or if we went to NYC and visited one of my lovely cousins who lives there and we both miss.

    I hope I win it, because my mom has been through so much this year and deserves someone else paying for the flight, finally.

  8. I’d go to Chicago with my husband! We recently talked about how we want to explore different places while we have the excitement and relative flexibility (pre-children).

  9. I would go Florida with my girlfriend because she’s been dying to swim with manatees.

  10. Since I haven’t yet been to Chicago, the only major city which I haven’t visited, I think I would travel there with my photographer friend. I want to improve my skills and it would be awesome to travel with him to take photographs of Chicago for a few days or week!