Rachel Lipson's Inspiring Advice on Overcoming Impostor Syndrome and Self-Doubt
The entrepreneur tells us about her sought-after songwriting school, favorite dishes for entertaining, and the joys of a lively neighborhood playground.
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Hi! How are you doing? We’re visiting family in New England this week and soaking up the cozy fireplace, snowy walks, and meals that remind us of our childhood. We even found a couple mixed CDs with hits from our high school days. Speaking of music…
Today, I’m thrilled to feature Rachel Lipson, who has been called the “matriarch of modern music education.” Rachel is the ultimate multi-hyphenate: songwriter-performer-educator-business consultant-(multi)instrumentalist-entrepreneur. In 2008, she started Blue Balloon Songwriting School as a one-woman music school in her Brooklyn studio apartment, and now, she oversees a national network of 75+ instructors who teach over 400 students per week all over the country.
Rachel is also a mom, a master at traveling with points and miles, and an admin for the popular Park Slope Moms Facebook group. “It’s a fun way to be connected to the community and to help bring people together, which is something I care a lot about,” she told me.
Here, Rachel shares excellent travel advice, a beautiful customizable gift you can buy in Park Slope, her favorite local restaurants, and more.
Hi Rachel! We have a lot to chat about, but I have to admit, I’m fascinated with the world of traveling with points and miles, so let’s start there. When and how did your passion for traveling with points and miles take off?
I didn't get on an airplane until I was 16. I didn’t go very many places as a child. I’ve mentioned this vaguely before, but I grew up agoraphobic. I was scared to leave my house. I was scared to be in my house. It was a big part of my childhood and my teens and 20s. Actually, part of my decision [to move from Detroit to NYC was] if I was going to be scared to leave the comfort of my home and the area around my home, I might as well live someplace that’s really interesting and exciting. I was able to get past this and over time I overcame my agoraphobia. Not that it never presents itself at times, but I'm not agoraphobic anymore. But, my biggest fears were always around travel; my anxiety was around travel. But I want to see the world. So, when I finally had some time for myself, which was after years of working 15-plus hour days, seven days a week to get my business to run without me in the weeds every moment, I was like, I want to travel with my family!
We started to travel and got really into it and then I was like, oh, how am I going to pay for this? I started learning more about traveling with points and miles and did so many deep dives. I went down all the rabbit holes [laughs]. I learned as much as I possibly could, which is very much my personality, and it's paid off. We’ve traveled to dozens of places with points and miles and figured out ways to leverage our everyday spending to turn it into trips and memories with our family.
Now, you’re sharing all this knowledge on social media and through a new online class, right?
Yes, Brooklyn Family Travelers is an amazing community and resource for families looking for trip ideas and travel recommendations. It's all the things that are so great about online communities. I really want to help families have these experiences without having to, you know, take out a second mortgage on their house.
The Getting Started with Points and Miles 101 class is for anybody interested in dabbling in the world of points and miles. Anybody who has no idea how to get started, or maybe you’ve done a little bit but aren’t quite sure the best way to use points and when to not use points, this class is for you.
It seems like there’s so much to learn. What’s a tip you share with someone who’s just getting started with points and miles?
This is the big one —