10 Years of Teaching: What I’ve Learned as an Adult Educator and VC about Underemployment (& a Newsletter)

Jessica Lin
3 min readMay 5, 2019

I started teaching the GED to adults 10 years ago in Boston.

Over the years, I’ve had the privilege to work with adults preparing for the GED or college, volunteering with some of the most tireless organizations out there: teaching with X-Cel Education and serving as a board member, mentoring with YearUp, moving to New York and teaching with Opportunities for a Better Tomorrow, putting together workshops like Teacher’s Tech Tours for LaGuardia Community College, and currently teaching at the 1199 SEIU.

As I look back over the past 10 years…I want to feel hopeful and optimistic.

But…it is still hard. I generally feel like the opportunity gap has and continues to widen, more than ever. And the ability for adults to get good jobs — jobs that will help them save, get insurance, and provide for their families — is harder than ever.

Many of the students I have worked with are and remain underemployed, to this day. I have worked with so many brilliant, hard-working adults who remain in minimum wage jobs that are menial, manual, and require physical labor — jobs that don’t at all make use of their bright minds and true potential.

This is unfortunately corroborated by my perspectives of this space as a VC and investor, where we monitor the market from the industry side. Employers have been putting less emphasis on on-the-job skills training, and expecting employees to come on the job work-ready (though more recently there is now renewed focus on reskilling in the enterprise). I have met countless entrepreneurs in this space, tackling this learning and training space, but it is still early days — especially around content authoring and new forms and modalities of delivering training and coaching that I’m most excited about. There is still much to be done in skilling and reskilling, especially in tech-enabled, scalable ways.

Through these years, I’ve been collecting all of these stories as an adult educator and as a VC — stories from students, how they have gotten jobs, on the latest tools and platforms enabling jobs, and the most interesting tech solutions that show early promise in transforming skills training and underemployment. These stories need to go somewhere other than my head :) so I’m finally putting together a newsletter — Where the Good Jobs Are.

While there are many newsletters out there that cover the future of work — specifically statistics, research, but really, a lot of doom and gloom — I’d love Where the Good Jobs Are to feature stories of a different sort: stories of real people and their journeys to get better jobs, profiles of jobs and the latest tools and platforms, along with profiles of new technologies that may be working to help people get more skills and better jobs. And from there…let’s see.

Sign up below if you’d like to hear more. I’d love to connect if you are thinking specifically about underemployment.

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Jessica Lin

co-founder & VC @Work_Bench | GED educator | rethinking work