Feb 3
A Different Type of Not Working, and Then Looking for Work
In June 2021, I left a job that I loved to take a break. A couple months later, I wrote about what I was doing “not working”, how it involved consciously resisting productive work and focusing on expanding in other ways. In this post, I want to describe what happened next.
After about 3 months of active not working, I loosened my constraints and started doing professional things again. I wasn’t ready to take a job, but I wanted to talk to people, engage with ideas, and explore conversational AI. In practice, that involved doing video chats with friends and acquaintances working this part of tech, trying out products, going to Voicelunch and other networking events, reading about companies, listening to podcasts, writing on my blog, and much more. A few highlights:
- Mentoring linguists considering jobs in tech, with LSA or through friends
- Doing research about conversational patterns with OpenDialog
- Chats with Rupal Patel in our Coast2Coast coffeehouse.
- Hanging out in conversation design Twitter
- Hosting a Voicelunch event
I loved this open-ended exploratory phase. I got to read lots of things, have lots of conversations, write about what I wanted to write about. Thinking that I might want to do consulting longer-term, I went through the process of formally forming an LLC (very creatively named Tyler Consulting LLC). But after a while, I discovered that I missed having coworkers and shared projects. I started to feel like I wanted to get a job and be part of a team again.
Pivoting to looking for work
This is a vulnerable part of the journey. It’s happening right now, and I don’t know what will happen! But after the luxury of months of not working, of time focused on my own growth, I have shifted to looking for ways to grow with others. What does this process look like so far?
The first thing I confronted was coming to grips with wanting a job. It was comforting for months to feel like I wasn’t invested in getting a job. I had this sense of openness and wild possibility! And I was excited for what a career break could give me. Making the shift to being ready for a job involves acknowledging that this phase may be coming to an end.
I started to tell family and friends about the shift, getting a feel for how it felt to be more open about my intentions. This gave me a chance to process my motivations and goals. It also started the process of putting out feelers for potential opportunities.
I started looking at job boards, especially Conversation Designer Jobs, Bot-Jobs, and LinkedIn, scanning to see what types of roles are being advertised, which companies are hiring, and how my skills and experience line up. I updated my LinkedIn profile and created an updated resume.
I also knew that many job ads ask for a portfolio. After crowdsourcing for suggestions, and referencing blog posts on the topic, I decided to build a portfolio page in Notion. I wanted my portfolio to show the results of my work, e.g. sample chatbot conversations, but also to show a diversity of skills and experiences. It was a fun process of defining key areas of expertise and collecting artifacts to demonstrate that expertise. If you want to see the result, it’s at josephctyler.com.
In addition to documenting the work I’ve done, I also wanted to gain new skills and experience. This included gaining experience with conversation design platforms. I have now made sample conversations in Botmock (since acquired by Walmart), Landbot, and Voiceflow, and explored features of others.
What have I learned during my time not working?
There was a part of me that was hoping that, by focusing so consciously on this period of not working, I would discover something unexpected about myself. A part of me was hoping for an epiphany. But I didn’t have an epiphany. What I got was time to myself. And clarity about the joy of sharing projects with others.
What am I looking for now?
Here’s my current answer. I’m interested in a role combining conversation design, analytics, and platform innovation. The idea is that you build conversational AI experiences, but in the process you track metrics, monitor usage, analyze data and learn about what works and what doesn’t. This builds a foundation of evidence-based insight into what makes for great conversation products. These insights then get fed back into the product and the platform. This could be in the form of product innovation, documentation and best practice guides, conversation templates, and more, all of which enable higher quality conversational AI. This vision captures a few things I love: conversation design, linguistics, research, writing, and analyzing data.
In closing…
Thank you for reading this far! If you have connected with any part of my story, I’d love to hear about it. And if you have ideas for jobs, companies, or people to look into, let me know! I know many people have left jobs during the Great Resignation, and probably many more are considering it. I hope that sharing my experience helps illuminate one person’s story giving it a try.
