On mourning, my time at a startup, and how my faith in online communities was restored

This is a story about loss and grief, and how one tragic event became the catalyst for a new beginning.

This past May, I closed doors on two chapters of my life — two very different chapters, but whose timing was inextricably intertwined. It’s only with a little distance that I have begun to realize that there’s an almost poetic, uncanny parallel to the timing that can’t be ignored; both stories begin and end at the same time.

Change. Sometimes we welcome it and sometimes we fear it. There are times when change occurs gradually and goes virtually unnoticed until one day you suddenly realize you’re in a different place. Other times you’re cornered into submission; we change because there is simply no other option. I had been mulling over a career change for years, having grown tired of design and desperately wanting something new after having worked as an Art Director for 16 years. Ironically, the fear of change — the very thing that I craved—would form a wall of self doubt that would hold me back from acting on those desires. But two years ago I suffered a tragic loss when my only sibling committed suicide. This is the type of thing that turns your life upside down and makes you question everything because life no longer makes sense.

Mourning a death feels like you’re moving through a dream. Dealing with the aftermath of a suicide layers on additional feelings of guilt and regret. There are a ton of questions and what-ifs that will never be answered. Grief makes your body numb and time feels weirdly suspended. Your fears, however, along with every other emotion can also get dulled down. This is how I was able to take a leap of faith. That line between what’s rational and irrational, what’s risky and what’s safe becomes fuzzy when you’re in a period of grieving. It’s what prompted me to leave design behind and join my friend’s startup. My life had changed after my brother’s death and the only thing that made sense was starting something completely new.

Old friends, a new beginning

Tarikh and I met at ITP, a graduate program at NYU, 18 years ago. Neither of us had gone the path of typical 9–5 jobs after we earned our masters degree like many of our classmates. We both freelanced, started companies, and consulted, but never had the opportunity to work together on a project. When I came back to NYC from a trip to California to try and find some answers around the circumstances of my brother’s death, Tarikh encouraged me to come into the office that week after a few initial meetings about working at his startup earlier that Spring. I felt like it was too soon, but two days after I landed I found myself sitting in an office.

Whatever foresight my friend had, going into an office a few days a week proved to be cathartic. I hadn’t worked an office job in years, having been a freelancer since both my children were born, so office life and working with a team was novel and new. Apparently, it was also what I needed to create some semblance of a routine and order in my life. While I wasn’t exactly sure what my role at the company would be, I continued to go in a few days a week that summer because I welcomed the distraction. It got me out of the house even though what I really wanted to do was hide from the world. I was probably still in denial— our brains have a way of shutting down after trauma to protect our minds and hearts from shock —but burying myself in work was the way I chose to cope.

The summer of mourning, and startup life

Our first office in West Soho on the 18th floor had these incredible 270 degree, uninterrupted views of the city from floor to ceiling windows. I got lost in that view everyday and watched as summer gradually transitioned to fall, the light changing over the city incrementally week by week. Some of the pain was starting to lessen as my family and I adjusted to this new normal. By October 2014, the start up succeeded in raising a seed round and I officially came on board as an employee. It was my first staff job in 12 years. In that same month, I unexpectedly found myself embroiled in a lawsuit relating to my brother’s death that opened up wounds that didn’t even have time to heal. Life had become surreal at that point.

Startup life was not without its challenges, obviously. We had a tiny team — 6 at the the time — and I was the only woman. “This is your entire diversity team right here” I would joke to Tarikh. “I’m a woman, a person of color, AND over 40.” Being the only woman wasn’t really ever an issue on our team, but gender stuff did rear its head at times. It didn’t help that my role was fluid and I was trying to find my place in a company that was still trying to figure out what exactly its product was. Having freelanced for so long, I had forgotten how challenging work relationships and communication between team members could be. This was hard stuff! I was used to getting hired for a project, getting the design work done, and invoicing the client with clear tasks and deliverables. The emotional energy and mental head space required in getting a team in sync wasn’t something I was used to.

We languished those first 6 months as we struggled to find product market fit, but one fateful day last year in March, Josh, our engineer, worked on a hack to save live Meerkat broadcasts just a few days after the app exploded at SXSW. Katch was born, and we decided to pivot into the video space.

Those early days of katching Meerkats and Periscopes were pretty exciting. We spent our evenings late into the night hanging out on Slack long after we left the office, monitoring our Twitter feed and watching new users sign up, one after the other. We cheered when we nabbed our first celebrity and major brand, and slogged through some of the early tech glitches and setbacks (which always seemed to happen over weekends when the team was apart, by the way). But we had users! And traction! And press! We were rapidly growing and people seemed to really like us. As my role grew into managing our growing community of users and curating video content, I dove into livestreaming even though the idea of live video made me highly uncomfortable. But if I was going to work in this space, I needed to use the products and see how it worked from a user perspective. What happened when I went all in was a bit of a surprise.

Livestream restored my faith in online communities

I’ve had a long presence on the internet. I designed my first website in 1998, and co-founded an Asian American webzine in 2000 before web communities really crystallized. I started an on-line journal before blogging become a thing, and then launched a series of product blogs in 2004 with another grad school friend just when monetization on blogs were becoming realized. In 2008 I started a bakery business with my husband and started yet another blog to document the launch of our new venture. But things really started connecting for me when I jumped onto Flickr in 2006, and then Twitter in 2008.

Those early days of Twitter were fun and I met fellow designers, bloggers and other small business owners, many of whom I’m still friends with today. We would follow each other on every new platform that rolled out (Instagram, Pinterest) and would eventually abandon those platforms that failed to hold traction for us (Vine, Ello). But for whatever reason, this community was slow to adopt live video and I found myself connecting with a whole new base of users when I started streaming. My world on the internet expanded and became so much more diverse, and I met people that I probably would never normally meet. It was different from the early days of Twitter and Flickr when you were attracted to like-minded folks. Now, I was just meeting interesting people, our only common thread perhaps being that we were early adopters of live video.

I’m no stranger to online sharing. I’ve always prided myself on authenticity in blogging and wrote from the heart, often without any filters. But when my brother died, two things happened that made me pull back from social media. I’ve had my fair share of negative blog comments over the years and can differentiate between criticism and trolling. While I did blog about my brother’s death when it happened, I didn’t disclose any details, but sometimes it just takes one cruel, judgemental comment that aims straight for the heart that makes us question why we share things online. Around the same time, I also experienced online harassment that went on for months. It was racially charged and I found myself the target of someone’s misogynistic agenda. I wanted to give up on all social media, at least in sharing things from the heart. I didn’t see the point anymore when my words could be twisted and used against me.

It was the livestream community that helped me feel comfortable sharing again. While I never streamed anything particularly personal (I wasn’t ready to go there yet), I watched countless videos of people baring their souls on every topic imaginable, pulling support from the viewers who interacted with them. I saw communities of people come together and do great things. Even though it was my job at Katch to connect with these people, I also formed friendships because I started to genuinely care about them. It was through intimate musical performances that I found the most comfort and a direct connection when I felt the most alone and overwhelmed. Sometimes my new Periscope friends played songs just for me — all this through a little phone screen. This was the power of live video.

I knew that in time I would talk about my brother’s suicide, if only because I do believe we need to remove the stigma and allow it to become part of our discourse in mental health issues. I didn’t, however, think I was going to do it first on live video — I had always assumed that it would be through writing as I am doing here now. But there is an immediacy in feedback and support on live video that encourages people to tell their story. It makes you feel more exposed than any other medium, but with a close knit community, it also feels intimate and safe. Sometimes it’s also easier to bare your soul to strangers than to those really close to you. Words are powerful, but hearing someone’s voice, the inflection in their words, and seeing their vulnerability worn on their face can be even more so. I realized that I had more stories to tell and I wasn’t done sharing them.

The death of a product

In late April, my team made the announcement on Periscope and Medium that Katch was shutting down. If the news seemed sudden to our users, it was equally sudden to our team. We experienced steady, organic growth — incredible growth! — month over month and our numbers were better than ever. In the end, however, we failed to secure our next round in what would become an increasingly difficult funding landscape.

I didn’t expect that shutting down a company would feel like mourning another death, but it did. To shut the lights off on something that you worked so hard on, a product that you built from basically nothing, was incredibly difficult. The timing also coincided with the settlement on what ended up being a very emotional lawsuit which resulted in the return of my brother’s remains back to our family. While there never really is any closure after a suicide, I felt like I was finally able to deal with this loss, something that I was not able to fully do while the details of his death were still being scrutinized by lawyers. So while I can’t speak for my teammates, the shut down of our startup was emotionally intertwined with this particular chapter in my life. Maybe that’s why I took it so hard.

So, what now?

It’s been two months since we closed our company. I admit that I feel no more certain of what I want to do career-wise than when I first jumped into the startup game. There is this fear that I’m back to where I started and this career change away from design, which I set into motion, has come to a pause. An interesting thing happened, however, during this time. As I was meeting new people through my job, most who knew nothing about my previous work history, I realized that I began to feel lost about my identity and I was no longer sure of who I was, professionally at least. I had always been a designer and a creative person, but when our jobs and careers are so often tied to our identity, who was I now? I guess I now have the time to find out.

One thing that I’ve taken away from my brother’s life is that it’s too short to be working all the time. His career as an Emergency Critical Care Veterinarian consumed his life; my brother was always working. Up until recently, I was holding down 3 jobs myself (I still maintained some freelance work and helped run our bakery business while working full time at the startup). Right now, I think I just need time.

I don’t want to have any regrets about working too much and not spending enough time with my girls, who are rapidly growing into teenagers. You never get lost time back. So much has happened in these past two years that I’m currently in decompression mode. I have no idea what’s next, but I’m giving myself the space to feel lost, relieved, confused and all the other emotions that flash through me daily. I also feel this obligation to take the time to figure out what I really want out of life.

I want to see and do things out in the world and to enjoy this life more intently than I have in the past—certainly for myself, but also for my brother because he never gave himself permission to fully live his life. I feel like this is the best way to honor his memory. Based on the painful conversations that we had before he ended his life on his 38th birthday, I think it’s what he would have wanted for the family that he left behind.

Jenna is a designer, photographer and a small business owner. Life is a continuous journey. Follow hers here and on Instagram and Twitter.

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