30 Things I'm Happy I Tried and Learned Before 30

Woman walking on dock over lake with arms outstretched
Woman walking on dock over lake with arms outstretched

This article was originally published on Levo.com

This could be a list where I look back and regret all of the moments that were difficult and frustrating and painful, but instead, before my 30th birthday, I'm going to look back at these moments with gratitude and grace, as these moments helped me get to 30. I don't think everyone should go through these moments for growth -- and I can assure you I was not enjoying myself during them -- but looking back, I'm happy I went through them.

30. I had my heart ripped out of my chest. Heartbreak sucks, but there are moments when it saves you. My heartbreak came in the form of a stone that gathered moss. It was a small tear in my heart that brought up things in my life I still needed to work on. Things like my relationship with my family, myself, my self-worth, and my job. Without this heartbreak, I wouldn't have done the work to do the work.

29. I pushed myself to the point of total exhaustion. I was a workaholic; I worked myself to the point of an emotional breakdown: anger, resentment and physical and mental exhaustion. Why? Because of fear. Because I never thought I would make it. Because I thought that was the only way to work. If it wasn't for this lesson, I would never know what my boundaries are. I would never be able to identify this fear that sneaks up on me relentlessly; I now can see it from a mile away, and not let it define me.

28. I failed, learned, and failed again. In my first job out of college, I made a lot of mistakes. I felt misguided and like I had no mentorship or support, so I spoke up. I spoke up after three months and received a little help putting me in a much better direction than I would have been otherwise. When you fail, you learn about what you need in the process of failing to succeed.

27. I acted like a mean girl, and apologized. When I was growing up, I was made fun of and bullied. Then my braces were removed, I learned how to straighten my hair, and there I was, on the other side of the coin. I became a mean girl because I thought that was what would keep me popular, and what would keep me "safe." I learned a lot of hard lessons, and even after apologizing to those I had wronged, I came upon mean girls in my life years later. Because I was a mean girl at 16, I now can spot the mean girls as being hurt, confused, sad women who are alone and afraid. I am no longer afraid of the mean girls, and now I can help them.

26. I moved. This is literal and figurative. I moved three times in high school, and it was a painful and difficult process for me. I talk about this a little more in my TEDx talk. Moving to all different schools and embracing who I am was the biggest gift I could have asked for. Looking back, I don't know if I would be so willing to step into new places and meet new people if it weren't for those moments of sitting alone in the library for lunch. Moving moved me never to settle for what's comfortable, and to reach for what is new and maybe a little scary.

25. I drank, ate, drank, repeat. I was in a sorority, went to a state school and then worked in nightlife and hospitality. The amount of alcohol I consumed over 10 years, and the amount of food I ate mindlessly, changed the way I now look at consumption. I am so grateful I was safe enough and smart enough that nothing happened to me or to anyone else besides my own poor body. By after over-indulging in things that took me out of my reality, I now have a lot of self-control and connection to what I consume.

24. I lived in NYC. Although I was born 20 minutes outside of NYC, my families on both sides are three generations of New Yorkers, so NYC is literally running through my blood stream. I lived in NYC for five years, and during those years I fell in and out of love with NYC and myself. Every single person should live in NYC, even for a little bit, if you have the opportunity to. It will harden you and soften you and straighten you out while also tearing you apart.

23. I lived in California. If anyone graduated high school or college around 2000, you should know the "sunscreen song": a song that epitomizes all of the lessons learned in life. One of which is, "live in New York and leave before it makes you too hard, live in California and leave before it makes you too soft." It has been a very cathartic three years living in LA. I have found a comfort zone there that feels like a womb. I have found caring, loving, considerate friends who are my family. I have found pieces of myself that I was too busy to look for when living in NYC.

22. I committed to anything. For years, I ran around like a chicken with its head cut off. I sprinted from friend group to friend group, barely catching up with myself. I then started to make little commitments. Commitments to friends I refused to break, commitments to myself that I made a priority -- and as I stood true by these commitments, I also realized how important it is to follow through with things that are important to you.

21. I set boundaries. I have definitely allowed for people to take advantage of me. I was the type of person for years who offered my services, connections, brain and heart to anyone that would ask. Guess what? No one likes a martyr. This leads to resentment, heartache and frustration. I started to see how important it was to set boundaries after I hadn't for so long. It gave me enough me for me.

20. I ignored the gossip about myself. Ever deal with a situation where you hear what people say about you when they actually have nothing to do with the situation? One of the biggest lessons I learned before 30 was to never defend yourself against a lie. By doing so, you are dragging yourself into the lie. In circumstances like this, I learned to say nothing, stay calm and rise above it.

19. I chose my people. For so long, I didn't think I had to choose the people who have access to my deepest darkest fears, secrets and emotions -- and that they would either choose me, or I could just make everyone that person. This is an important one. Not everyone has the capacity to hold space for you. You have to be selective with who you let in close and who you let show up for you.

18. I broke someone's heart. This one is harder than having your heart broken. When you hurt someone you love, it feels like you are dying inside, but what's worse than not letting someone go is holding onto them for your own benefit. I still remember really hurting someone, only to see them find all of the happiness they deserved and more and remembering they would have never had that if I held onto them because I was afraid to be alone.

17. I learned how to love being alone. Alone doesn't mean lonely. For so long I refused to be alone. I am an extrovert and wanted to always be around people, until I realized I didn't know myself. By giving myself the time and energy I had been giving everyone else, I was finally able to learn more about myself.

16. I. Slowed. The. F. Down. I go a million miles per minute. I totaled a car, broke my foot, hurt a lot of people and myself by moving too fast for my own good. By slowing my physical body down through yoga and breathing, and slowing my mind down through meditation, I have learned the practice of listening to myself. My natural tendency is to be fast, so learning the lessons on how to slow down has been crucial for me.

15. I trusted myself. The worst thing I have done over the years is to have not listened to my gut or intuition. That little feeling that says "this guy isn't going to treat you right" or "don't hire this person" has been squashed by my need to get things done quickly. This is NOT OK. It is so important to listen to that part of yourself whispering for your attention. This part has saved me from some really bad mistakes that could have continued for a lot longer than they should have.

14. I cried. A lot. For years, I thought crying in public was wrong. I didn't cry in public for four years because I was told it was weak and unacceptable. To cry is to show strength. If you can show your deepest emotions in public, that's pretty incredible. I learned my vulnerability and empathy are gifts that I refuse to keep for myself.

13. I fell in love with a truly good human. I was super into guys who just didn't like me, for years. These guys would judge me, put me on a pedestal but not date me -- among many other things that just didn't feel good. I finally made a choice to fall in love with someone who loves me unconditionally, who is a considerate, genuine man who works on himself and can own up to his wrongs and give me the space to do the same.

12. I opened up to my family. I did serious work to have an open, honest and loving relationship with my family. Everyone thinks they have this, until the holidays, when your parent says one tiny thing and you feel like throwing a temper tantrum. I confronted my parents about little things that I'd buried from years of my life that had very little to do with them, so that I could forgive them and learn more about myself in the process.

11. I faced my demons. Four years ago, I pulled out a journal to start to write. I hadn't written in five years, but finally was giving myself some time to express myself. I opened up my journal and wrote: "Would you date you?" And then answered, "No, maybe in two years." This shed so much light on the self-hatred I had. I didn't love myself enough to be with me, so who else would want to be with me? I took the time and energy to find as many ways of support as I could to do the work of facing my demons. I took responsibility for things holding me back; I went deep inside and asked myself what really made me happy, and I removed everything that didn't.

10. I said yes. Five years ago, I was asked by a friend to work a conference called Summit Series. I took 10 vacation days from work and used them to work on a cruise ship. Then I met my current partner, Tony Hsieh, at Summit Series, and when he asked a group to come to Vegas, I said yes. An inspiring conversation and a few phone calls later, I left my job and started a company across the country, in a city I had only been to once before. Taking risks leads to unexpected transformations you can't possibly imagine until you say yes and jump in.

9. I dreamed big. Five years ago, I woke up at 3:00 a.m. and had a vision for a non-profit music festival in Central Park. I had never been to a festival, and yet I created a huge PowerPoint presentation with meticulous analysis of what it would take. I was then introduced to Ryan Gall and Hugh Evans through a big dreamer, Bobby Bailey, who were working on something very similar. I ended up being one of the first few people who worked on the Global Citizen Festival in 2012, and watched it become a reality. Now as a proud board member, I look back realizing I never would have become involved if I didn't push myself to dream big and then follow through on those dreams.

8. I gave up. I have had SO many ideas for businesses. They weren't just ideas, though. I would create case studies, research reports, extensive business plans, go after investors and identify partners -- until I realized this just wasn't what I wanted to be doing. As Elizabeth Gilbert brilliantly writes in her book Big Magic, sometimes you have to let go of ideas that are not yours so they can travel to someone else who will implement them. I have seen so many ideas I have attempted to birth over the years come back to me fully fleshed out by others, and I know by letting go of something that's not my dream, I open the door to someone whose dream it is.

7. I educated myself. I realized that if I don't continually educate myself, then I won't grow. There is nothing worse than a know-it-all, so this is not what I mean. I realized I can never know it all, as the world is constantly moving and growing, and the only thing I can do is attempt to gather data and knowledge as much as I can.

6. I maintained a state of gratitude. There are times when I am about to complain, and I stop myself and remind myself how much I do have. It's so easy as an entrepreneur to compare myself to everyone else and use their social media pages as an example of what I want. It's a lot harder, but more fulfilling, to be grateful for what is and has come to you.

5. I forgave myself. I made tons of mistakes. I have definitely hurt myself and others, as I mentioned, but it was so important for me to realize that it's OK to forgive myself. There is nothing more poisonous than swallowing self-resentment every day of your life.

4. I forgave others. I realized that it was OK to forgive others, but not necessarily let them back in. Forgiving someone does not mean they have to be your best friend or even acquaintance, but it means you are setting yourself free from the torture that holding grudges creates.

3. I shared with others. Over the years, I've shared my house, my learnings, my failures and my pain with others. I've opened up and taught others through my stories; I've been unabashed with my writing and have received notes of gratitude because I haven't been afraid or selfish with sharing.

2. I learned the power of vulnerability. There is absolutely nothing more powerful, when it comes to connection, than vulnerability. When I share a story that is deep within my core, or cry or ask for help, I give others around me permission to do the same. This is the greatest gift I could ever ask for.

1. I learned to love myself no matter what. Turning 30 is scary. I haven't accomplished all I want to accomplish, I haven't done all I have set out to do, and who cares? Life is about embracing where you are, loving the tiny beautiful things about yourself and the world -- as Cheryl Strayed talks about in her incredible book -- and not letting anyone ever convince you otherwise.