Ajay Relan's Advice on Heartbreak and Vulnerability


Team Mend

Ajay is a co-founder of #HashtagLunchbag, an organization that distributes meals and love letters to those in need. Its rapid growth led to the formation of the Living Through Giving Foundation, a non-profit dedicated to celebrating charitable initiatives. He also runs Hilltop Coffee and Kitchen in Los Angeles and invests through On Purpose VC, an intentional capital firm.You can follow him on Instagram @ajayfresh.


“I think the first time I got my heart broken was junior or senior year of high school. The girl was a year older than me, and before she went off to college, we had this whole summer of just hanging out everyday and it was really fun. I was super attracted to her. When she asked me out I got really really excited, even though I was actually dating someone else at the time. I just sort of kicked the other person to the curb to pursue it and I didn't even think twice. But when she went away to school it just abruptly ended. It fucked me up pretty badly. I haven’t really talked about it or thought about it until now but it probably has affected my relationships since then. I can count on two fingers how many real relationships I’ve had since. I have not been broken up with since that time in high school.”


“I feel like a lot of my relationships had glass ceilings in place, whether I put them there or not. I know for a fact that I broke some hearts because of it. As I got to know myself a little bit more, I would give little disclaimers upfront about my track record. It was the same cycle over and over and I started to become more aware. I’m an entrepreneur and I'm an only child, so background plays into it. I was raised by a single mom, with no dad around, so I never had that example of what it means to be in a committed relationship where you have someone else’s back, and only that person’s back.”


“I’ve had the opportunity to meet and date some really amazing women. The majority of them - all of them, actually - are still friends to a certain extent because we had a friendship first. It was like, ‘lets go out, let’s go to dinner, let’s get some wine and enjoy getting to know each other.’ That would go on as long as they would let it without me having to commit. But eventually it’s the case of ‘hey dude, what are we doing? We’ve been doing this for months now,’ and in some cases that goes on for years, until eventually someone leaves or moves away or gets married or something.”


“The way I learned how to be a man was by watching television shows like Full House and Family Matters. I was constantly looking for what it really meant to be a man. My mom worked a million hours a day and no one was really watching me and I overcompensated in a lot of ways. I kind of shaped myself to be like who I was around or whoever they wanted me to be. So I hit this wall and realized that I couldn’t keep going like that, for myself or for anyone else. It wasn’t just in my romantic life but my professional life as well. I was constantly starting things and they would achieve a certain level of success, enough to pass it on, but I’d get bored. I just wanted more and more and more. It was never enough.”


“I eventually came to this conclusion that I wasn’t enough. It had nothing to do with other people, it just had to do with how I felt about myself. Anytime I would get into anything a little more than casual I would find myself reflecting on who I was, and the more I looked at myself, the more I didn’t like myself, for no particular reason. I had been going through life becoming close with people and creating all these memories and then just stopping it and cutting it off. And it wasn’t that I didn’t want a deeper connection, I just didn’t feel like I deserved it. If you ask my friends, they think I’m a good guy, which I genuinely believe. But what people say about you and how you feel about yourself are two completely different things. I saw a TED Talk by Brene Brown about vulnerability, which made me read her book and led me down a path to seeing a therapist. I started doing a lot of work on myself. I started reading a lot of different books and blogs. This was in 2012, when I was 28.”


“Then one day I was hanging out with some people that I honestly didn't know very well, and somehow families came up and they started asking me about my mom, and it was like, “Oh, my mom’s awesome,” and “Oh, I’ve never met my dad.” They started asking me all these questions about it and it didn’t irk me, but something clicked that I needed to meet this guy, so I went searching. That was heartbreaking in itself. It’s rejection from birth. You have this constant rejection and then you finally meet the guy and he doesn’t give a shit. I got to put a face to a name, got to see what he looked like and got to know that I don’t have any brothers or sisters. And then I just continued on. I don't think I really all the way dealt with it. I did as much as any of us deal with anything. You internalize some of it, talk to a few people about it, but life goes on.”


“When I met my father for the first time, I was in a relationship - a few months into it at that point. She was great and super supportive, but then it got to a point where all the fun stuff was over and things started to get dark again for me. I was learning a lot about myself. I was doing erratic things. I left a startup that I had built because my partners weren’t getting along and I was sick of it. I got into the restaurant business because I thought it made sense. I thought, I like sports, I like to drink. I’ll open a sports bar. There were highs but then there were lows and they were very low. It's easy to start something. It's easy to meet someone. It's easy to get to know somebody. It's easy to be intimate with somebody physically, but maintaining it and sustaining it is difficult. It’s just like a startup. It’s just like a business, where you think, Oh I have this great idea, let me put together a business plan. And then let me do this everyday and let me wake up everyday and be excited about it. She was great and she just loved the shit out of me every single day. I just didn’t grow up with that kind of love, so when someone is giving it to me, it’s hard for me to accept it because I don’t feel like I deserve it. And eventually it got to a point where that had to end. Not because anything was wrong but because it was killing me psychologically that I didn’t feel like I deserved it. I had this beautiful, smart, driven, incredible woman who just wanted to love me and I was saying, ‘Get away, I don’t deserve this!’ It was almost weighing me down. I was asking myself, what’s wrong with me? This isn’t normal, this isn’t right, I shouldn’t feel this way.


"So I go to a therapist and they tell me that I’m depressed, that it’s chemical, and they send me to a psychiatrist. He looks at me for two seconds, doesn't even make eye contact and writes me a prescription. And I’m thinking, no, that is not how I want to mend my situation. I know a lot of people that are depressed and who cope that way, and they are still in a pretty shitty place. So I’d rather feel the way I feel now than feel that way. The only other thing she prescribed to me was to go volunteer and I thought that was the most ridiculous thing I’d ever heard. It went from this pharmaceutical solution, to, 'go spend some time cleaning the beach.' But I put it on my to do list."


“I looked for a way to volunteer, but everything was really disconnected. I remembered a friend of mine used to make bag lunches, walk around the pier and pass them out and share. So I woke up one morning pretty early and set the goal of making 100 meals - the kind of lunch that you’d be really happy your mom packed. My roommates wake up and we start really inefficiently making these meals. Our friends ask us what we are doing and we tell them we are making some meals and are going to drive around and hand them out - nothing crazy, nothing revolutionary. We made it fun because we are fun guys. We listened to music and we added some libations. We jokingly decided to share it on social media and we spelled out the word hashtag, because we kind of hate hashtags, and went about our day."

"When we looked back at our phones we had an abnormally large number of likes, calls, texts, and emails from friends saying, ‘I’ve been looking for something to do and I can’t find anything. Let me know the next time you do this.’ We had had no intention at the time of doing it again, it was just a spontaneous act. But we decided to do it again in January of 2013, and this time there were 10 of us, and it was much more streamlined. Same deal: made the meals, passed them out, felt awesome, put it up on social media and a week later my friend uploaded the video he'd made on a GoPro. I used to work at a talent agency and one of the actresses that was represented there retweeted the video saying 'This is awesome.' So we decided to build a website. None of us had ever built a website but we wanted to share our story: that we wanted to give back and didn't know how, that we couldn't find anything that spoke to us, so this was what we did, and here are some easy tips so you can do the same."

"The following month was my birthday and usually I have a big party, but that year I decided I wanted to do this instead. We had 100 people show up! We got a huge age range and diversity, and everyone was having fun dancing and connecting. A lot of people had never done anything like this before, just like me and my friends the first time. So we all went down to Skid Row and did the sharing experience, and then everyone shared it on their social media. Ever since then it’s just continued to grow, now to over 100 cities all over the world. We’ve been around for 2 and a half years now and we have some amazing corporate partners. We eventually asked ourselves, why are we doing this? The food is really just the vessel, so we started incorporating love notes to recognize the humanity of those we’re serving. That’s what these individuals are taking with them for inspiration. It’s really about being open, vulnerable and watching the world around you become a better place. We are making it fun and cool for people to give back, and then let them reap the psychological benefits on their own."


“You know it’s over when they unfollow you on social media. That’s the definitive end of a relationship these days. I will say that I don't go out of my way to unfollow anyone but if they unfollow me, I’ll unfollow back.”


“The lesson that I’ve learned on this journey, which I’m still on, is that you have to see yourself in a certain way, hold yourself in a certain regard and esteem, and really own and like who you are, where you’ve come from, and how far you’ve come to be able to even entertain the idea of giving that [love] to someone else. This is a lesson that I’ve learned fairly recently on my path of self discovery. Now more than ever, people have this responsibility to themselves. I think it is really beautiful that many more people now are more self aware, but the vast majority of people just go about their lives, rather than trying to explore a little bit more of what makes them lovable.”


“What I used to do was not a sustainable solution. I used to go out of my way to get everyone to like me. I would blow them away with what I thought they wanted to hear. It wasn't that I was lying, I would just play to a different crowd every time. Now I’m very selective about who I spend my time with, where I go, what I watch, what I listen to, and what I read. I’ve been exercising a lot and trying new things. Getting out of my comfort zone, physically and emotionally. Being a lot more vulnerable than I’ve ever been. Vulnerability without any intention is kind of a slippery slope because it is something that is meant to bring people together, so if it’s not matched on both sides then it can kind of be disastrous. Meditation is something that I started recently and I find it very helpful. I would say I’m in my optimal place right now. I’ve realized when I’m writing, sharing or creating, that is when I’m at my best.”


“When I Was Your Man by Bruno Mars. That song would get stuck in my head all the time. I think it just got stuck now!”


“The last few years I have embraced being creative. Being creative is something that has always been within me, but I’ve never wanted to own it because it puts you in a very vulnerable space with potential to be rejected. But at the end of the day that’s why we’re all here. We are all gods in our own right and we all have the ability to create and inspire and keep the momentum going.”

Photographed by Ellen Huerta in Los Angeles.

Related posts