Match Quality and Why Career Exploration Needs to Happen Earlier

Alex Yang
8 min readJan 10, 2023
Vincent Van Gogh — Van Gogh Museum

In college, you have kids who come onto campus and already know what job they want. I never knew whether to find this impressive or annoying.

On the one hand it’s admirable that someone knows exactly what job they want at that age. On the other hand I’ve always wondered whether it’s too early to decide. There seems to be a natural tension between whether education/edtech should help students specialize or allow them to explore.

The Case For Not Specializing (At Least Early On)

In my sophomore fall, my social entrepreneurship professor assigned us a passage from Range by David Epstein. The beginning of the passage describes a young man’s seemingly endless career journey. One second he wants to draw and be an artist, the next second he wants to just sell art, and then somehow he’s back to drawing?

This was Vincent Van Gogh. In Range, Epstein offers the idea that this long journey to finding what one is good at has to do with match quality and the work of Ofer Malamud, a Northwestern economist. Match quality is a term used to describe the degree of fit between the work someone does and who they are.

Malamud found that those who specialized in their field later switched jobs less in their career (greater match quality), and that those who had greater curriculum breadth in a variety of topics seemed to have lower unemployment rates (better job security). There seems to be true, measurable value to exploring and taking a variety of courses. As Epstein summarizes, “Exploration is not just a whimsical luxury of education; it is a central benefit”.

Finding Match Quality

Beyond just reading the passage from Epstein and looking into Malamud’s research, I found that something in my personal life has convinced me about the importance of not specializing too early on.

Conversations with my sister (senior in high school) over the summer usually went something like this.

Sister: Ugh, I don’t know what I want to major in and do with my life

Me: Well, you must be interested in something. Don’t you like engineering?

Sister: Yeah, but I don’t know if I want to really go into that. I don’t know anything about engineering careers

Me: Uh, why don’t you google it?

Sister: Oh yeah. Well at least I know what I don’t want to do! Definitely not business.

Me: Do you know what kind of careers people do in business?

Sister: Nah, I just know I don’t want to do it.

Me: That doesn’t seem like a good reas-

Sister: I just know I wouldn’t like it.

I now realize that these conversations were essentially about match quality. I also realized that her process for finding match quality was extremely flawed.

Obviously no one has an infinite amount of time to explore every career, but I wanted to make sure that my sister was only eliminating careers for good reasons. I suggested programs like Curious Cardinals, where she could get paired with a college mentor and do a passion project, and even connected her with my friend in college who was majoring in something she was interested in. Doing this helped me realize that there’s a large market for helping teenagers and professionals find match quality.

From my perspective there are three current solutions for addressing the issue of match quality.

Apprenticeships / Virtual Internships

Companies: Multiverse, BuildWithin, Praxis, Forage, Acadium, Apprenti

Apprenticeships offer young adults and seasoned professionals the opportunity to get paid experience on the job. Virtual internships (like Forage) are often much shorter in length and unpaid. Apprenticeships / internships have great potential to help people find better match quality. I think what’s also great about this space is that there’s clear value for employers as well — the ability to source diverse talent and build a pipeline for junior roles.


Companies: Springboard, Acadium, Stepful, Prequel, Coder House, Generation Singapore (nonprofit)

Bootcamps are slightly different in that they’re more geared towards adults looking to make a career change and structured more as courses. Bootcamps can also have some elements of mentorship and projects, and can be either asynchronous or live learning.

I think there’s an interesting opportunity for companies to be very profession-specific. For example, Stepful focuses on preparing professionals to be medical assistants.

Passion Projects and Mentorship

Companies: Factor, Sora Schools, Curious Cardinals, Primer, Polygence, Riipen, BETA Camp, Kubrio

This is the bucket I’m most excited about and it’s targeted towards the youngest demographic. These companies provide high schoolers and teens the opportunity to learn about what they’re interested in through passion projects and 1:1 mentorship with young professionals or older students. Passion projects are great because they really allow the student to go in-depth on a topic, and not just make surface level judgements about it. Young adult mentors are also amazing because they remember what it’s like to be a high schooler and they can explain their path for finding what they’re passionate about and inspire younger students.

Why This Space Is Important

I understand that for many of the companies I listed, there are other incentives at play beyond finding match quality. For example, high schoolers might want to take on a passion or research project to boost their resume for college apps. Older workers might want to reskill into a tech job and enroll in a bootcamp. These are real, practical concerns.

But I wanted to bring up the idea of match quality and specialization because I’m convinced that learning about oneself is an incentive that isn’t emphasized enough, and is often lost amidst all the “boost your resume” or “get placed in a job” rhetoric.

However, one’s concern for match quality can start to diminish drastically as you get older and deeper into your professional career. If you’re still in high school and college, you’re young and you have time to figure it out. Compared to someone who may be older, you have way more flexibility to explore without having to worry about family or other responsibilities.

This is why I’m super interested in companies that focus on the K-12 demographic and try to help them explore. I personally feel like I wasted so much time on grades and mandatory classes in my K-12 years that I could’ve used to explore interests instead. I had so much more freedom as a high schooler and for the most part I used it poorly.

Further, if companies in the space can bring exploratory projects to the fore, I think we can cultivate a love for learning again in schools, where students can dive deep into areas that interest them and continue to learn about themselves. School is where fun goes to die for most kids.

We have to start the exploratory process early on so that kids not only gain more data points about what careers and topics they’re passionate about before becoming adults, but also find excitement in learning.

What It Will Take To Win In The K-12 Space

There are several key factors that I think will allow companies to win in this K-12 match quality / career exploration space:

  1. Strong Content and Messaging for Parents

It’s no secret that these companies will have to sell to parents, and that’s why you see every company in the space with extensive parent testimonials and FAQ sections. But an exceptional company will go beyond that — they’ll create engaging blog content for parents, host webinars and even in-person events and conferences to get parents involved and bought in. In many ways these companies will have to operate like a school.

2. Sourcing Extraordinary Mentors and Providing Value to Them

Mentors or instructors need to not only need to have expertise in their field, but also a passion for inspiring students and finding ways to guide students in the right direction. Further, I don’t believe that a company should rely purely on the generosity of mentors or paying them high wages (unsustainable economics over time), and instead should find ways to offer value to mentors. For example, companies can offer a Linkedin-esque platform exclusively for mentors, offering them opportunities to coffee chat, share job posting and opportunities, and connect with others in their field. Mentors often will help students out of their own kindness, but I think a strong business will offer mentors community and networking benefits as well.

3. A Student Community That Lasts Beyond College

The opportunity for students to produce a meaningful project that they can showcase and put on their resume is a good value proposition in itself. But I think a great business will not just let it end there in terms of the lifecycle of a customer.

I think companies in this space can take some inspiration from On Deck and the community that they’ve described in their long Series A memo.

For example, On Deck has a private social network (they describe it as “think: AngelList/LinkedIn meets ‘Quora’”) for On Deck Fellows. Companies in the match quality space could similarly have a private social network that students get access to after completing their passion project/program, and it could allow students to connect with each other and also get their questions answered. Now they can find other students around the globe who are excited about the same topics as them. Who knows what this could lead to in terms of collaborating on projects, and perhaps even starting companies. Naturally there are also opportunities to create job/internship boards that are exclusive to students who have completed the program, enhancing the value of the overall community.

Moreover, once you have students who are real “champions” of the program, there’s the opportunity to have these students contribute to great content (podcasts, articles, videos) that can serve as a tool for educating parents on the program (adderessing Point #1).

These are just a few ways to address student community, but I think a true winner in this space will be able to create a community that students are actively engaged with even after high school, creating a reputation and brand that will attract even more talented students. The winning company will get students to “come for the passion project/mentorship, and stay for the student community.”

Thank you for reading! If you’re working on something related to match quality, or would just like to chat about education or tech more broadly, I’d love to chat. You can email me at or DM me on Twitter!



Alex Yang

How I Decided Podcast | Articles about Culture and Decision Making