The May Rewind
News, notes and 16 highlights from my birthday month
The Point is a smart, thoughtful dispatch on elevated travel with points and miles. The Point has been featured in The New York Times, New York Magazine, Condé Nast and more and is a top ~40 bestseller in travel.
The Hyatt devaluation was somehow not THAT bad. If you booked trips in advance and any rates went down, you should see the refund in your account. If the rates went up (many did but just not by as much as we thought!) then you’re lucky to have booked ahead. This was a good reminder that things change but we can always adapt!
We launched a new series called Good Points to give paid subscribers (thank you!) easy to follow, digestible points and miles tips — and answer readers’ questions. More to come — I love this series because I think short easy to read newsletters (of which the one you are reading is not) are very helpful ;) I hope you do too!
Many of you used my links to apply for cards this month and I just want to say thank you. Each time you click the card links and get approved for a card, you’re not only earning yourself welcome bonus points, but you’re helping a small business grow. It means a lot. You can always find card links here - or DM/email me for any you don’t see. Thank you!

The premium version of the #1 card for travel has an elevated offer of 150,000 welcome bonus points that is ending soon. Remember, the annual fee is always worth it for the first year. If you’ve been waiting for a high welcome bonus to justify getting this premium card, the time is now. You can read more about it here. Don’t miss this!
This is one of the top business cards I’m recommending right now. Even if you have other cards from this bank, you are likely still eligible for this bonus. Please use this link here to apply and feel free to reach out to me if you need any help! This card can earn you 100,000 of my favorite points with a very low annual fee. Enough said!
Rove (not a credit card!) is a great way to earn points. Click here and sign up to earn 1,500 transferable points (for new sign-ups). Do it today — takes 3 seconds.
Get a free mini-wallet edit. New here? Ready to level up? This is the best and easiest way to know you’re going in the right direction with points. Click here, it’s free. Use this form and get in touch as many times as you’d like!
“Deeply serious about points, deeply kind about people. You trust her advice because she’s clearly done the work and actually wants it to help.”
- Ally Jane Ayers of Money Changes Everything
Some past features…
Condé Nast asked how we booked our spring break trip for our family of four to Eastern Europe on points. I broke it all down in a full feature! Read it here.
The New York Times: It was such an honor to speak with the New York Times about loyalty and credit cards!
Bloomberg Travel: I talked to Bloomberg News about home swapping — one of my favorite ways to travel!
New York Magazine: I shared my thoughts with New York Magazine on how to save on travel.
My friend Rebecca Soffer wrote a beautiful piece for Time Magazine about the end of the Late Show as well as this beautiful piece for her newsletter Modern Loss ❤️
I convinced my friend Brenda Bergen | Wink Design to join substack and I am obsessed with her travel color pallettes.
Check out this article Finding beauty in the everyday by Blue Balloon Songwriting (my first baby) and Six Pics I Clicked.
The answer to You really want to raise a kid in New York? by Alexis Benveniste is YES!
Air France Promo fares: If you’re heading to Europe, check out the promo fares on Air France! Look for 18,750 economy fares one way — and don’t forget kids 11 and under get 25% off award fares! Here’s a bunch of available flights from NY to Copenhagen (as of the time of publishing). This article will tell you how to find these fares!
There is also a 25% transfer bonus from this bank which means you can potentially fly to Europe for 15,000 points with this bonus + the promo fare. A tip: to figure out how many points to transfer, take the points needed and divide by 1.25!
May started with a trip to the Berkshires for a business and wellness retreat hosted by Shira Gill. Things didn’t go as planned back at home (a story for another day) but I met so many amazing women and it was nice to get out of the city!



I got to hang in Nolita with some other substack friends and I will say it again that it is truly the best that Substack friends can actually turn into real life friends.
Afterwards, I headed to The Knockdown Center in Bushwick/Ridgewood to see Bill Callahan of Smog! He was one of my favorites growing up and it was amazing to see him perform after all these years.
Leah Wiseman Fink and Allyson Stone had a beautiful luncheon at 12 Chairs Café in Williamsburg. We all got to leave with the prettiest bodega flowers. The best.
I couldn’t do my usual staycation this year for Mother’s Day but I did get away for a few hours to see The Devil Wears Prada with Jennifer Cook of Mom Friend followed by drinks at Hotel Delmano (reliving the early 2000s in every way).




Gina Hamadey invited me to a talk at Emma Straub’s Books are Magic to see the incredible Roxane Gay and Isaac Fitzgerald. Very inspiring!
I saw Bruce Springsteen for the first time. WHAT A SHOW that guy can still put on. At 76 he can still put his whole self into a three hour show meanwhile I had to sit a few times just watching!
My 10 year old flew to Detroit on his own to spend a long weekend with my parents. I am so blown away by his independence and bravery! The flight was delayed over 5 hours coming home and he handled it like a total champ (while I was sweating the whole time).
I got to try out the new Bathhouse on Atlantic Ave in Brooklyn with my friend Lesley. I will go anywhere there are thermal baths. I’ve already gone back twice!
I did an enneagram session with my friend Ali Dunn and I learned so much about myself and my natural tendencies. It turns out, I am a perfectionist, creative AND visionary! Apparently it’s a rare combo but maybe explains a lot about my life choices?!
Kamali and I saw Belle and Sebastian at Pier 17 for their 30 year reunion show that made us feel old and young at the same time. I saw so many old friends and somehow still knew all the words to their songs!
My brother in law and his family came to town and we had the best weekend. wish we lived closer to family!






We had such a lovely evening hosting friends for drinks and conversation over Memorial Day weekend. It was the kind of night I didn’t know I needed.
My birthday came and went with a night at the Park Hyatt New York that needs a redo! We got a call at the end of watching Ragtime on Broadway that one of the kids broke out in hives and we headed home that night to make sure he was ok (he’s ok but they are not totally gone - tips??).



Henry’s baseball coach surprised the team with a stretch limo to take them from practice to a Cyclone’s game. The parents all chipped in and it was one of those core memories I don’t think he’ll ever forget.
My songwriting school had our 17th annual showcase at City Winery next to Little Island with over 120 kids performing over the course of the weekend. I am still recovering from the two day event but wow was it amazing. Six Pics I Clicked // Ana Gambuto took so many gorgeous photos of the show. Thank you Ana!




The 17th Annual Blue Balloon Showcase!


Love reading your messages 🖤
Ps - The Costa Rica edit is here and here!
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