#1. Confessions of a Job Seeker – September 2012
This series is based on a design journal that I kept during 2012 – 2013

I started a company about careers and happiness called Joyo Inc. We didn’t make it and I became a job seeker myself. When I realized that I’d literally become my own user, I couldn’t help but see the irony in my situation. At first I wasn’t sure what to do about it, but then I realized that I had an important choice to make. I could see my situation as failure and admit defeat or I could see my circumstances as a gift and an opportunity to live my way to the answer. I chose the latter, and here I am.

#2. Confessions of a Job Seeker – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

On the morning of September 28^th, I was so bummed that I didn’t want to get out of bed. I didn’t see the point. This attitude contrasted sharply with the way that I normally jumped up in the morning to get after this dream that I cared so much about. I’d promised myself that I’d start my job search though, so I pulled my laptop into bed and half committed to taking action (rule #1 to being an entrepreneur). Between getting on Facebook and halfheartedly job searching on LinkedIn, I was not feeling awesome. I went back to what I had learned while working on Joyo: start by taking small steps. This worked. I was up and back at it, slowly, but surely.

#3. Confessions of a Job Seeker – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

My initial attempts at job search were fairly unpleasant, and the use of job boards proved to be especially uninspiring. What really struck me about the experience, however, is that job search makes people feel bad about themselves. While at first glance this might seem like an obvious truth, I think it’s an important one to acknowledge because people rarely speak of it.

This is a critical design challenge for any of the job search or career tools out there. It kind of amazes me how outdated some of the conventions of job search are and the extent to which we still continue to use them. Anyone who is involved in product development understands the importance of user experience (I would hope). Yet when it comes to job search it seems like we’ve completely missed the point.

#4. Confessions of a Job Seeker – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

Coming to terms with the fact that I’d completely burnt myself out while building a company focused on happiness, turned out to be a major wake up call. I understood that I needed to fundamentally change the way that I live, so I decided to do a life cleanse. This has entailed an ongoing and deliberate practice of deconstructing my lifestyle and building up a strong foundation. I’ve scaled back. I’ve slowed down. I’ve focused on developing habits related to nutrition, energy, exercise, and attention.

This has taken quite a bit of unlearning, personal honesty and effort.  What I’ve come to understand through this process is that you cannot be all that happy or effective if you’re not healthy and you can’t be very healthy if you’re not happy. The two are inextricably linked.

#5. Confessions of a Job Seeker – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

It occurred to me one day that this dream I was chasing, this place I was trying to get to, might not ever arrive. This might not be a phase. Could I really keep striving at the pace I’d been going for almost a decade? What if it did take an entire lifetime to finally get there? Was there even a ‘there’ to get to? How would I need to live on a daily basis to be ok with that? In many ways it has made me wonder if happiness as we traditionally define it is even the goal.

We’re all pursuing this elusive, one-dimensional definition of happiness when maybe what would serve us better is to focus on meaning. It does take work and it’s hard, but that’s kind of the point. Our lives are a creative process. Nobody wins by getting to the end first.

#6. Confessions of a Job Seeker – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

This was hard to put on paper, but it was important for me to acknowledge. It revealed the ways I was projecting my doubts and over time helped me to understand that I hadn’t failed at all. I had done what I set out to do. For a while, however, I avoided social events. I wasn’t ready to face up to the questions of ‘what do you do’ and ‘how’s the company?’

When I eventually did get out again, a friend from business school remarked “you did what all of us deep down wanted to do, but none of us actually had the balls to do.” Huh, that was definitely not what I had expected to hear. It’s funny how the stories we spin in our minds can become so distorted and at times even debilitating.

#7. Confessions of a Job Seeker – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

“Do I contradict myself?
Very well then, I contradict myself.
I am large. I contain multitudes.”
– Walt Whitman

As a designer gone MBA gone founder, I’m very comfortable wearing many different hats. Unfortunately, this doesn’t exactly make for an obvious job title. Over coffee one day, an acquaintance offered to help me with my job search, but left me with the question “So, what can you do?” Well, I said, I can do a lot of things. This didn’t give him a whole lot to work with. As I continued to explore opportunities, I started to ask myself the same question.

While in part this is very much a reflection of the generalist’s dilemma, I believe that it also taps into something much more fundamental. Asking people to search for jobs based on industry and function essentially requires them to tell a partial story of who they are and it limits the context of their value. For me this felt like I was being asked to show up as a subset of tasks rather than as a whole human being. The experience lacked dignity. It asked me to be less than who I am and what I’m truly capable of. Many of my peers advised me to just play the game and then expand my job function once I was inside the company. Out of principle though, I really struggled with this. I didn’t want to play the game and then bust out my true abilities after being selected in based on a partial and constructed story.

While I do believe that the underlying framework for job search is broken, I realized that what I faced first and foremost in this instance was a communication challenge. I decided to do a brainstorm of concrete ways that I can offer value and approached the exercise as if I were a business, rather than a prospective employee. I developed a list of my capabilities and then bucketed them back into a subset of more traditional functions. These categories then became the basis for my personal Capabilities & Expertise one-pager.

#8. Confessions of a Job Seeker – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

Sometimes this is how I feel. I’m learning how to not always battle the universe, but who ever knew that allowing things to be easy could be so hard?

#9. Confessions of a Job Seeker – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

One day while walking through the Mission, my friend veered a sharp right into a gritty convenience store. I followed her inside to find her buying lottery tickets. I’d never played before, but it made me laugh so I went along with it. We were both in the middle of big transitions and in dire need of lightening things up a bit.

With our lottery tickets and hope in hand, we proceeded to take ourselves out for a Vietnamese lunch special where we spent the next hour discussing in detail what we’d do when we hit the jackpot. We’d go to India, of course, and I would crash her friend’s wedding. Then we’d treat ourselves to a nice, relaxing yoga retreat. It was going to be amazing.

While sadly neither of us won the lottery that day, we had a blast and it taught me a valuable lesson: It is so important to leave a little room to dream. Job search and change in general can be heavy. It can mean operating from a place of exhaustion and fear. When we dream, however, and when we play, we’re able to see the world differently. It is precisely in these moments that we begin to create the space for possibility.

#10. Confessions of a Job Seeker – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

In a moment of job search despair, I went to my advisor and confessed to him that I was completely and utterly lost. He passed on some valuable advice and said “Stop trying to figure out where you belong. Be the solution to someone’s problem rather than the problem searching for a solution.” This simple shift in perspective completely changed my approach to meeting with people.

I now focus my conversations on understanding what keeps someone up at night, what inspires them, what milestones they want to hit, and in what ways I could potentially be of service. I take note of what I learn, and when there are ways to help, I try and do so. This subtle shift in my approach has enabled me to begin to build a number of authentic relationships with some really fantastic people. Focusing on what I can give has taken me in a direction that’s both rewarding and fun.

#11. Confessions of a Job Seeker – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

On a warm fall day, I made my way back to UC Berkeley to visit my professor and afterwards found my way to the bell tower. As I sat there eating fro-yo and watching students scurry by, it struck me just how far I’d come. How far we’d all come. Memories came rushing back and I recalled the dedication with which I’d made plans for my future career.

In the end, it was not the future I chose. My path led me in an unanticipated direction and that was fine. I had acted with intention, working towards a career that mattered to me. At the same time, I had lived with attention, allowing myself to explore a present that felt right and true to who I am. In that moment I kind of knew that everything would be ok. On a whim, I texted a few classmates to tell them how proud I was of them. I knew that we were all doing our best and that in the end the specifics of our goals didn’t really matter as long as we could say that we were proud of how we got there.

#12. Confessions of a Job Seeker – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

I used to think that being ‘stuck and lost’ meant not being able to figure out what you want or what you should do. I now know that it can also mean losing site of who you are, what you stand for and what you have to offer. For me, this was an unexpected and fairly painful part of the process. Working through it, however, led to one of the core learnings that I’ve gained from this experience:

When we ask ourselves what it is that we want to do, we’re also asking ourselves who it is we want to be and how it is that we want to live in the world.

Very few of the job search / career tools out there address these questions in a holistic manner. Doing so on your own can be an ambiguous process, but I think it’s an important one. When you can articulate how you want to show up as a person and what your criteria are for how you want to live, then you’re much better equipped to make decisions about what it is you should do.

#13. Confessions of a Job Seeker – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

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 – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

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 – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

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 – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

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 – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

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 – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

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 – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

“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 – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

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 – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

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 – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

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 – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

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 – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

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.

#25. Confessions of a Job Seeker – NEW? Start here
This series is based on a design journal that I kept during 2012 – 2013

I started this adventure with the intention of ‘helping people to live authentic and inspired lives, so they can reach their true potential.’ At the time, however, I didn’t fully understand what I was setting out to do. I now know that the journey is the gift and that to live a vibrant, passionate and heartfelt present is the goal. This may be one of the most rewarding things that life can offer, yet it is also one of the most difficult things to learn how to do. It requires that we accept the present as enough, which also means that we must accept ourselves as enough. This is easier said than done, of course.

I think what it comes down to is choosing to be all in without guarantee of any return. It’s asking how the experience of doing something can be worthwhile on it’s own, regardless of outcome. It’s doing what needs to be done so that you can show up as your best possible self. I ask myself these questions every single day and am still learning what it all means in practice. I hope that in some form my journey can serve others. That together we can learn how to live fully and boldly, while also being present for what is truly an incredible journey – if we allow it to be.

As I write the final post in this series, I am humbled and moved by the events of the past couple of years. I have been tested in ways that I couldn’t ever have imagined and have grown in leaps and bounds because of it. I am beyond grateful to the people who stood by me while I took the risks that I couldn’t not take. Their belief in me has helped me see that our ability to believe in ourselves is directly related to our capacity for love. It has reminded me that the truth is simple. The people we love are all that matter.