#13. Confessions of a Job Seeker – Oct. 2012
This series is based on a design journal that I kept between 09/12 – 02/13. New? Start here.

As I pulled together my job search materials, I was thinking a lot about language and storytelling. A friend had just shared an exercise where you ask different people in your life to send you the top three words that come to mind when they think of you. This exercise was a bit out of my comfort zone, but I understood that the people around us can sometimes know us in ways that we might not know ourselves. I decided to go for it and sent out an email to ~ 45 people from different areas and phases of my life. I heard back from most of them almost immediately and their responses were informative.

In order to learn more I put each word on a post-it note and then clustered them into buckets. This enabled me to identify my top three words: Adventurous, Creative, and Thoughtful. It also prompted me to ask questions, like which of the words were most reflective of how I was currently living and which of the words did I maybe want to be embodying more. It was revealing to see which words came from people in different parts of my life and surprising to see how certain words showed up more strongly than I realized I was conveying. Overall, the exercise was simple, easy and fun and I’d definitely recommend it to others.

#14. Confessions of a Job Seeker – Nov. 2012
This series is based on a design journal that I kept between 09/12 – 02/13. New? Start here.

As I continued with my job search, I began to focus on cultural fit. Unfortunately, this is not something that you can easily search for (believe me, I’ve tried). I was willing to put in the legwork though, and knew that this would mean connecting with lots of different people. In the beginning I reached out to friends and former colleagues, but soon I was following up on random intros, going to events and saying ‘yes’ to pretty much everything.

For a while, coffee meetings became a way of life. There were days when I’d leave meetings with the sense that I was floating in career purgatory. There were also many occasions though, when I’d walk away from conversations completely energized and inspired. During this time I got to meet a lot of very cool and interesting people and even made some new friends. Having an open mindset and genuine curiosity for others led to events that have since unraveled into a whole chain of possibilities. I knew that my efforts would not necessarily result in short-term gains, but that was not the point. I believe in seeding serendipity and am in it for the long run anyway.

#15. Confessions of a Job Seeker – Nov. 2012
This series is based on a design journal that I kept between 09/12 – 02/13. New? Start here.

Over coffee one day, a friend and former colleague explained her take on ‘authentic networking’. She said it’s really all about asking ‘Who do you want on your team?’ This made a lot of sense to me, especially given the ways that the workforce is changing. Very few people spend their entire careers at one or two companies anymore. Most people now will have many jobs and multiple careers in one lifetime. I think this shift reveals an important truth – careers today are built around people, not around companies.

When it comes to asking who I want on my own team, I think about it broadly. I try to surround myself with people, projects and companies that share similar goals and values as me. These may be people I work with and they may also be people outside of my job. They may be companies that I’ve worked for or they may be companies that I simply respect and want to see succeed. I believe that aligning ourselves and supporting each other in this manner is how we now build our careers. It’s how we collectively work towards our potential.

#16. Confessions of a Job Seeker – Nov. 2012
This series is based on a design journal that I kept between 09/12 – 02/13. New? Start here.

Early on in the incubator, my co-founders and I talked through what the worst-case scenario would be if we didn’t raise funding in the amount of time we had allotted. This was an intentional exercise in fear. We were facing a significant amount of risk and navigating a lot of ambiguity. We understood that it would be critical for us to learn how to manage our fears.

The exercise helped us to get concrete about what could actually happen in the worst-case scenario. We agreed that we wouldn’t be exiled or shunned by our friends and family, but if things didn’t go so well we might have to move out of our apartments. I considered this potential scenario, but discarded it as a real possibility. I didn’t think I’d be willing to go there. That would just be taking things too far.

#17. Confessions of a Job Seeker – Nov. 2012
This series is based on a design journal that I kept between 09/12 – 02/13. New? Start here.

As the holidays approached, it quickly became clear that I would not find work until the New Year. Unfortunately, I’d reached the point where I was channeling all of my efforts just into finding ways to scrape by. Thanksgiving came and I didn’t go home. Anxiety was starting to take a toll on me. Something had to give. I finally made the decision to sublet my room and I packed up my stuff and left my home. As someone who is highly self-reliant, this was an incredibly difficult decision to make. I didn’t want to be a burden on my friends and family, but I had no choice but to ask for help.

Luckily, I have some wonderful friends who welcomed me into their homes. I distinctly remember a conversation that I had with one of them. She called me out and told me that’s what friends do for each other. She said that she expected me to ask her for help if I needed it and if things ever fell apart in her life, she would be coming to me. This was an extremely humbling moment. It taught me that being open to receiving is just as important as giving. It reminded me that relationships are built on trust and reciprocity. I can’t begin to express the gratitude I have for the people who showed up for me during this time. I absolutely could not have managed without them.

#18. Confessions of a Job Seeker – Dec. 2012
This series is based on a design journal that I kept between 09/12 – 02/13. New? Start here.

There’s that lingering pause and I cringe because I know what’s coming. “So, what do you do?” they ask. Depending on my attitude at the moment I either mumble some incoherent response about freelance consulting or I ask them back “What do you mean… like what do I do in life?” This doesn’t really make sense, so sometimes it throws them for a loop, but mostly it just draws out a long and painful response. The ‘so, what do you do?’ question is one of those social norms that no one particularly loves, but it exists for a reason. Mostly it’s a way for people to find commonalities with each other. Worst-case scenario, the person literally just wants to size you up based on your job.

At times I find myself guilty of asking people the same question. I try not to do it out of principle, but sometimes it just comes out because I’m genuinely curious about who someone is and what drives them. As we all know, jobs aren’t necessarily the best way to have that conversation. There’s got to be better a way, a different question. On occasion I’ve heard people ask, ‘what are you excited about?’ or ‘what’s the best thing that happened to you this week?’ I really don’t have a great solution though and would love to hear how other people handle these moments.

#19. Confessions of a Job Seeker – Dec. 2012
This series is based on a design journal that I kept between 09/12 – 02/13. New? Start here.

“Be kind for everyone you meet is fighting a hard battle.” – Maclaren

The night started out well. I showed up, smiled, and on the surface I even enjoyed myself. All in all I successfully navigated the holiday party. I was saying my goodbyes when it happened. A friend stopped me, gave me a hug and asked me how I was. He genuinely wanted to know and was checking in because he’d heard that things were tough. The tears welled up and I was done. I don’t know where it came from, except that there’s something about the holidays that can amplify the sentiment of feeling alone. That night I was surrounded by people I knew, but deep down I felt like I wasn’t seen.

For all I know though, the people around me were wrapped up in struggles of their own or they simply weren’t aware. I’m not sure what the lesson is here beyond the fact that I think it’s important that we remember to see each other. What my friend did for me that night was kind and thoughtful. He was willing to see me in my struggle. He helped me to understand that just because others might not necessarily get what I was going through, it didn’t mean that they didn’t care and I wasn’t alone.

#20. Confessions of a Job Seeker – Dec. 2012
This series is based on a design journal that I kept between 09/12 – 02/13. New? Start here.

I was serendipitously introduced to a 23-year-old girl who turned out to be one of the wiser folks I’ve met along this journey. A former colleague had passed on her LinkedIn profile and I reached out just because she seemed interesting. Turns out that both of our paths had taken us on quests to understand the pursuit of happiness. When we met, she shared some advice that has since stuck with me. She explained that when she was figuring out what to do after college she didn’t think about roles or companies, she thought about how she wanted to feel.

I’ve since asked myself that question on numerous occasions. The answer paints an interesting picture. It tells me what right feels like. When I came across this photograph, I was immediately drawn to it. What spoke to me was the way that the girl is surrounded by beauty and elevated above the clutter and distraction of a busy world. She is still and there is a clarity and softness to her, yet at the same time she emulates strength. Every day I aspire to that level of focus and the ability to stand strong and grounded, yet calm and flexible. To me this is what right feels like.

#21. Confessions of a Job Seeker – Dec. 2013
This series is based on a design journal that I kept between 09/12 – 02/13. New? Start here.

I was in mid-backbend when my yoga instructor hit me with some major wisdom. As he guided me into a high arch, I struggled to breathe in contortion while he announced to the rest of the class “you are not your body, you are not your mind, and you are not your job.”  I immediately understood. I had completely attached my identity to Joyo.

I was able to see the irony in this and almost laughed out loud. It had taken me losing what felt like everything, in order to understand that I am in fact, lacking nothing. The accumulation of events had slowly stripped me down and it was only there, in all of my loss that I could finally see what had been true all along. I am whole as is.

This realization was crucial and key to my ability to let go. It marked the beginning of a phase where I found myself to be more raw and alive then I had been in a long time. With this perspective in hand I discovered that there is both power and freedom in lacking nothing. It meant that I could let go of petty worries and false beliefs to instead focus on what really mattered. It meant that I could do less and as a result be more.

#22. Confessions of a Job Seeker – Dec. 2013
This series is based on a design journal that I kept between 09/12 – 02/13. New? Start here.

Up until this point I had held on to lingering hopes that I would find a way to continue with the company, but I was starting to understand why this wouldn’t be possible. At its core Joyo had been about living your truth, showing up as your best possible self, and working towards your potential. I had attached my identity to Joyo and had attempted to build the company in a way that did not reflect the values and vision that it stood for.

The only way I could truly embody Joyo would have to be by letting Joyo go. My advisor, coach and friend, likened this moment to the concept of Crucible Stories from Authentic Leadership. These are intense periods in life where like metal in fire, you are tested to your very limits. It can be deeply painful, but when you emerge you are forever changed. This perspective resonated and helped me come to terms with my decision. As raw and painful as it felt, I also knew that it was right.

#23. Confessions of a Job Seeker – Dec. 2013
This series is based on a design journal that I kept between 09/12 – 02/13. New? Start here.

While this experience taught me a lot about my friendships, it also made me acutely aware of the ways in which it had worn down some of my relationships. As the holidays approached I decided to try something different. Instead of buying gifts, I wrote gratitude letters to my family and to a handful of friends who had really shown up for me.

These letters were well received and my sense is that they were very much appreciated. Over the months that followed, I even received a few letters in return. This was unexpected and deeply moving. It’s easy to assume that our implicit gratitude or a passing remark is enough. I find that it’s less and less common, however, that we pause to be vulnerable and to explicitly share our gratitude and love for each other. It can be a simple act, but a very powerful one.

#24. Confessions of a Job Seeker – Jan. 2013
This series is based on a design journal that I kept between 09/12 – 02/13. New? Start here.

After two months of couch surfing, the time had finally come for me to go back to my apartment. When I left work that evening, however, I avoided going home at all costs. I went to the gym and then to my friend’s place where I had dinner with her and her husband. I wasn’t sure what the hesitancy was about, but eventually I headed back to the place I’d been staying, packed up my stuff and called a cab.

When the cab driver arrived, he helped me load two months of my life into the back of his trunk. Leaving one home for another, we drove in silence down to the Mission. When I finally walked into my apartment that night, it was 11:00 pm and the building was dark. I took a few steps in, stopped, slumped against the wall and broke down. I cried like I hadn’t in a very long time.

I immediately felt a massive weight lift – I hadn’t even realized I’d been carrying it around. It was pure relief. I felt safe. I was finally, finally home.