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

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 It kind of blows my mind how outdated some of the conventions of job search are and the extent to which we continue to use them.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 – Sept. 2012
This series is based on a design journal that I kept between 09/12 – 02/13. New? Start here.

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 – Sept. 2012
This series is based on a design journal that I kept between 09/12 – 02/13. New? Start here.

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

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

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

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

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

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

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

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 – 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.