Rob Cobb

Leaving Flatiron

Updated Jan 27, 2020

This past Friday (1/24/2020) was my last day at Flatiron School. I worked there for just shy of two years, since starting as the first Software Engineering instructor in DC in February of 2018. I am going to miss it.

I had spent the last few weeks wrapping up all of my ongoing projects and passing responsibilities off to others on the team. My last day I spent saying goodbye to teammates. I wrote notes in slack and email to many of the people I had worked with, expressing gratitude for their impact on me, best wishes going forward, and sharing contact info in case they didn’t have it. It was really nice to be reminded of the amazing people on the team, and to feel love. It’s rare to get such a concentrated dose of gratitude and joy - even though leaving is bound to be bittersweet, expressing appreciation felt really good.

Things I loved (and still love) about Flatiron School

  • people who work there
  • students
  • mission
  • learning and growth
  • impactful work

Students, Mission, People

Flatiron school teaches people the skills they need to transform their career, and it helps actually get a new job (it’s no big secret that Career Services is Flatiron’s secret sauce). Because of this mission, Flatiron is able to bring together people who are deeply committed to helping others achieve all they can be. I’ve been fortunate to work especially closely with teachers and coaches across Flatiron, who are wholly magical. I learned so much from them about teaching, about software, and about working together.

Flatiron students are incredible. They have committed to an intimidating set of changes and challenges - (often) leaving their job, getting immersed in a new environment with new people, diving into brand new concepts and languages, in a field that is renowned for its complexity and beginner-unfriendliness. ‘Brave’ doesn’t begin to capture it. And yet - they show up! With humor and friendliness, dedication and compassion, students come to Flatiron and tackle every challenge. They overcome frustrating bugs, persist through confusing new concepts, build awesome new ideas, and with all that effort and grit, change their own life trajectories. I feel lucky to have met them. (Hiiiiiiiiiiii former students!!!)

This is a way that Flatiron is different from traditional education. As a K-12 or higher ed teacher, you usually don’t see your students reach their career goals. At Flatiron, I got to see students I taught move through their entire learning journey with us, from finding out about Flatiron at some event, applying, taking the program, graduating, to finding a job. It’s hard to match that reward and satisfaction.


I grew a lot at Flatiron. In two years:

  • I had three roles (Lead Instructor, Master Instructor, Learning Experience Designer)
  • I got to be there for the start of two campuses (DC and Atlanta)
  • Interviewed, onboarded and trained lots of instructors and coaches
  • Wrote a lot of internal documentation and process (mostly writing down what we did in our software engineering program, so that we could replicate it in new markets)
  • Built a new curriculum for our software engineering coaches
  • Helped write, maintain, and improve a ton of our Software Engineering curriculum
  • Helped revamp our software engineering assessments (and wrote a lot of rubrics)

Over my time at Flatiron, the school also grew from one campus to 12 (13?, depending on how you count), and from ~80 people mostly in New York City to 550, mostly remote or ‘distributed’ across our other cities. Like most rapid-growth organizations, lots of our processes were broken and fixed as we went.

My arc moved from teaching our Software Engineering program towards improving how that program works, and thinking about how we teach it at a consistently high quality to way more students. As I moved along that arc, I got to learn a ton about teammwork and collaboration.

Working on a team of teachers who also have experience as engineers meant resolving a lot of legitimate differences of opinion about what we should teach and how we should teach it. This was strikingly parallel to bridging communication gaps between different business units within our organization. When teachers wanted to cover Rails concepts in a different way, they usually needed to feel heard and to hear the context of each other’s perspectives. When education and admissions had a conflict about some process or handoff, they needed the same things. Providing the contextual information - constraints, goals, issues - was almost universally effective in getting to a collaboratively designed solution.

Relationships were also key to working effectively on a big team. Being open to connecting with people for coffee, being interested in getting to know people, and striving to support their objectives from my position meant that they would reach out if they had needs of our team. When things went wrong or there was tension between different objectives, we had the relationship to fall back on. On rereading this paragraph, it sounds obvious or trite, but I can’t stress enough how important it was to being effective, or how much I grew in my awareness and skill in this aspect of my work.

Why leave?

Flatiron has mostly figured out how to teach software and get people jobs. There’s always ways to improve (my Flatiron peeps know I had a long list of things that could still be better!) but, by and large, the program works. The next set of challenges are now in executing and managing at scale, and growing into teaching our newer disciplines (Data Science, Design, and Cybersecurity).

Those are really hard and interesting challenges!

Still, I’m really interested in focusing more of my time on a different set of problems. There’s a big difference between improving something that already exists and works and building something new to see if it can work. I want to try to do more building new things and innovating in teaching people to code, and I’m excited to do that on my own.

What’s next for me?

My vague big-picture, long term goals are something like ‘unlocking human potential and moving the world towards a vision of individual flourishing’. I’ve got a draft-blog-post-in-my-head that tries to reconcile my career decisions with the best advice on how to have the most impactful career, but for now I’m making a not-fully-theorized bet on a few projects that I think I can have a differential impact on.


  • Help build a community to connect code teachers across contexts
  • CS pedagogy corner - ways we ought to teach, from other things we know about how people learn + what is special about teaching CS
  • Write about the CS learning landscape
  • Helping early coders navigate the confusing and intimidating learn-to-code environment
  • Grinding out the rough patches in the learning journey
  • Create tools for explicit modeling of learning / career journeys
  • Create new structured pathways into coding for people of particular backgrounds

More to come on exactly what each of these mean - I’ll have a new site and a newsletter up by the end of the week!


There’s always more fundamentals to learn!

  • More computing fundamentals (probably Rust and some ML stuff, since those are exciting and new areas for me)
  • More teaching and learning fundamentals (particularly focused on how what we know about attention and memory and social construction of knowledge will impact online learning communities and online-first pedagogy)
  • Writing (how to have more output at a higher quality)
  • How to be productive and happy in this solo-work context!

How does it feel to leave a job (without another job lined up)?

I feel nervous! There’s no longer the security of a paycheck coming in. Beyond that, there’s many other aspects of work that have been part of my life - structure, accountability, socializing, people to lean on and learn from, shared vision and meaning-creation, externally defined objectives and goals, etc. I’ll have to replace those!

It’s sad to be leaving a team and work that I care so much about. I feel proud of what we’ve built, and secure that the team is on a healthy trajectory, but still bummed to leave it behind.

It’s exciting too. There’s a special feeling of ownership of my projects, and sense (maybe just a hope) that I can make them real, from scratch. I’m going to be spending some of my time reaching out to people I respect in the CS-teaching world, and I’m really excited to learn from them and spend time geeking out with old friends and new. It’s not goodbye forever for all the people I know at Flatiron, so I don’t have to worry about losing those friends.

Some details for those who are thinking about leaving their job

  • I have savings that ought to cover me for a year+ without missing rent
  • I have leads on some freelance and consulting opportunities that I hope will pan out and turn into ‘normal’ income
  • I’m lucky to be in a career where there are jobs, in case freelance / consulting / building my own things don’t work out
  • I’ve set a hard rule for myself that I’m not allowed to look for or apply to a job for 6 months, so I am not halfway in, halfway out on building my own stuff.

Call to action: let’s hang out!

I have lots of unstructured time now, so if you want to catch up, let’s chat!

I’m explicitly working on building community among people who teach coding, so if you have thoughts or opinions about how people learn CS, software engineering, or stuff like that, you’re especially invited to reach out!

(If you’re reading this, don’t be surprised if I reach out to you first 😉)

If you have part time code-teaching work (curriculum development, workshops, trainings, coaching, etc.), I’m also available for that.

Reach me @robcobbable on twitter, or email

Fun fact: Boomerang

This actually isn’t my first time leaving Flatiron! Way back in 2015, I worked as a teacher on a 4-month contract teaching Python, web development, and App Engine to recently graduated high schoolers in Seattle for Flatiron’s partnership with Google’s Computer Science Summer Institute. It was such a good time, I had to come back and do it again full-time 🤓.

For all my Flatiron peeps - Thanks. 💙

🤓😽 Rob Cobb
🐦 twitter