I’ve been doing a lot of things in the last six months that by previous standards, would have been considered unreasonable in my book.

I say no a lot. First I started by saying no to meetings, at least the kind that don’t have an agenda or some type of pre-written document to go with it. Then I started saying no to social engagements, projects, and the frequent, “Can I pick your brain over coffee?” meeting. More recently, I started saying no to alcohol, caffeine, grains, dairy, and soy.

I started putting myself first. I can’t remember the last time I pulled an all-nighter or worked through a weekend. I stopped telling myself that being “always on” was a good thing and started incorporating things like gym time in the middle of the work day.

I let vulnerability and spontaneity into my life in big ways. I stopped judging myself for the things I was or wasn’t doing. I stopped censoring my emotions. I learned to incorporate travel into my life in a way that fuels creativity and productivity. I spent 161 days away from New York this year and covered nearly 160K miles.

In short I learned that there’s a difference between selfishness and self-care. As I’ve become more unreasonable, I’ve found myself happier, healthier, and more fulfilled than I’ve ever been.


30 Things I Learned Before I Turned 30

I turned 30 a few weeks ago and spent the last few weeks reflecting on who I am and what’s changed over the last decade. I revisited a private blog I started in college and the author was full of naiveté and plenty of insecurities. Although there are still lingering bits of that here and there, I feel like a much wiser, more confidant woman (and every bit as obsessed with the Internet as I was back then).

As I launch into my thirties, I’m grateful for the following lessons I’m taking along with me:

  1. Sleep is important. I didn’t get much of it in college and my sleep habits didn’t improve when I started working. In fact, I used to be one of those people who said stupid things like, “I’ll sleep when I’m dead.” What I’ve come to learn is that I function at my best when I’m well rested – my mood, productivity, and overall wellness hinges on a solid 7 hours of sleep each night.
  2. Happiness is a state of mind. I used to think that if I achieved certain goals or whisked my way off to distant places, it would somehow fix or change something about my state of being. It turns out that every variable in my life – money, relationships, location, etc. have negligible affects on my happiness. I feel the greatest sense of joy when my why is clear.
  3. You can leave New York City and it will always forgive you when you return. I’ve left the city twice now, first for Boston from 2008-2009 and then for Washington D.C. in 2013. I think I’m going to leave it again, but I’m not sure for where or when.
  4. Cooking is soul-feeding. Food has always been such an integral part of my life, from family holidays to exploring new cuisines across my many travels. Learning how to cook has been one of the more gratifying skills I’ve picked up over the years. There’s still so much improvement I can do in this area, but I relish the opportunity to prepare food for myself and for other people.
  5. Lean towards yes. I need to work on saying no more, but saying yes has served me well on so many different levels. Although I do think setting boundaries and not being overcommitted is a good thing, I’ve had the most gratifying, serendipitous moments of my life by being open, giving, and adventurous.
  6. Surround yourself with incredible women. I chose to attend Barnard College in 2004 and that’s where I fell in love with sisterhood. I learned what it was like to be loved and supported by smart, curious, and passionate women and that’s stayed with me ever since. Because I work in tech, which is so male-dominated, it’s that much more important to me to find women I can draw energy and inspiration from.
  7. Find your mentors and champions. So much of my professional growth is fueled by the wide net of individuals who have been both coaches and advocates for me. I don’t think it’s enough to just have mentors. Their empathy and advice will only take you so far. It’s equally important to find your allies, people who will fight for your cause no matter what that is.
  8. Laugh often and out loud. My laugh might be one of the more distinct aspects of my personality. It’s loud and uncensored and comes from deep within. My dad, the ultimate jokester, said this to me when I was little and it just stuck: “It doesn’t matter if no one else is laughing with you. Just own it.”
  9. Give to get. Any time I’ve embarked on an endeavor with the phrase, “What’s in it for me?” the outcome has always been lackluster. 9 times out of 10, I get out what I give. Generosity and abundant thinking are two guiding principles that have served me well.
  10. See the world. I must have inherited my wanderlust from my mom, a former flight attendant, immigrant, and globetrotter. I know airline travel stresses people out, but I love being on planes and in airports. It makes me feel like every corner of the world is somehow accessible to me. In so many ways, it actually is.
  11. Learn to see your parents as peers. My relationship with my parents changed dramatically once I started recognizing that once upon a time, they were just like me – two young people trying to figure things out. It’s been great getting to know them as an adult and to actually have them not just as parents, but friends too.
  12. Recognize others and how much they mean to you. I’ve recently come to appreciate how important words of affirmation are, not just in personal relationships, but work ones too. It’s so easy to take people for granted or to focus on what’s wrong instead of what’s right or good. I’m trying to do a better job at letting people know that they’re appreciated.
  13. Fail often and fast. It’s such a startup cliche to say this, but I do think that your 20’s are a time for experimentation and iteration. I’ve only ever experienced growth when I’ve pushed myself outside of my comfort zone. Although I feel much more risk averse than I did at 22 or 25, I still create mini challenges for myself or experiments that help me learn and grow.
  14. Think in 3’s. One of my first mentors, an ex-McKinsey guy, gave this one to me during my first job. He said, “Alexa, you have to break it down so people understand you. 1, 2, 3. A, B, C. Beginning, Middle, End. No more, no less.” It was this type of structured thinking that’s made me a more effective communicator and story teller.
  15. Know thyself. Introspection is something that I hold sacred. You can’t possibly know where you’re going if you don’t have a sense of who you are. I think my dad gave me my first diary when I was 10 or 11 and I kept maybe 5 of them as a teenager. I’ve since started and stopped various Xangas, Bloggers, LiveJournals, and WordPress instances all chronicling different aspects of my life. I might not always share these thoughts publicly, but the act of writing my thoughts down and having them for posterity is something I deeply cherish.

There’s a part 2 to this list that’s much more akin to lifehacks I’ve acquired along the way (e.g. airline miles, productivity tips, etc.). If I get ambitious, I won’t let 2+ years pass in between this post and my next one.

Til next time, sayonara!

Teaching Myself How to Code on a Saturday and Founder FOMO

I’m starting this post at 10:38 on a Saturday night and the FOMO is starting to set in. Industry colleagues are drowning my Twitter feed in SXSW selfies and photos of BBQ and cookie and milk shots (!!!). Friends are scattered across the city urging me to come out and play.

There’s this immediate FOMO I feel about not being out tonight, but what’s even more persistent is this other type of FOMO — fear of missed opportunities.


I’m tuning everything out and sitting in my Upper West Side apartment because I’ve committed to a night of code. I’m learning Ruby on Rails because I’m desperate to build a custom CMS and take my baby off of WordPress (I love you WordPress, but I need something more flexible beyond the world of posts and pages). After attending this panel at Columbia on Thursday with Jessica Livingston of YCombinator and 3 YC alum, I came home and immediately started a Ruby tutorial on CodeAcademy. I’m at the halfway point of the class and feel like I have some basic fundamentals under my belt – arrays, loops, booleans, and blocks (oh my).

I’ve had a lot of responses like, “Why don’t you just hire someone to do it?” but the reality is developers are expensive and that elusive technical cofounder is MIA. Time to take matters into my own hands (**but please world, send any developers my way who can help**).


I started Dipsology.com about a year and half ago with my co-founder and fellow Barnard alum/a cappella nerd Adrienne. We started the site to help connect and educate a growing community of cocktail enthusiasts. We’ve carved out a really nice lifestyle business in a niche market, but we’ve always seen the opportunity to be something bigger. What if we could create a platform to transform the ways in which liquor brands connect/engage consumers and on-premise accounts?

The visions are grand, but like most nontechnical entrepreneurs, I’ve struggled to find a partner to collaborate with on the site. It’s that elusive technical co-founder that’s missing. I’ve had several calls in the past few weeks with developers in Bangladesh, the Philippines, and India and weighed the pros and cons of outsourcing. I’ve sent feelers out to different friends and colleagues who might have developer friends to moonlight on the project. At the end of the day, it just feels like wasted time.

And so here I am, on a Saturday night, cozied up in sweatpants at my kitchen table about to tackle another lesson on CodeAcademy. Perhaps we’ll reunite again SXSW. Until then, wish me luck!