2018 Retrospective

Every year, I do a retrospective in which I review the past year. Up until this year, I’ve kept those retrospectives private, for many reasons:

  1. I’m a fairly private person (though this year I’ve tried to change that a bit).
  2. I’ve been afraid I didn’t measure up.
  3. I’ve been afraid that things I think might be helpful in my retrospective won’t apply to many other people who have different intersections of privilege.
  4. I don’t want to contribute to Compare & Despair™.

This year, though, I’m going to share my annual retrospective because I’ve found all the reasons for keeping it private to be lacking.

  1. As I said, I’m trying to be less private.
  2. Worrying about not measuring up, while not unfounded, isn’t a helpful fear; it doesn’t further my goals and may prevent me from sharing helpful information to others.
  3. Privilege is, by its nature, exclusionary, so if I keep what I’ve learned to myself, I end up reinforcing that exclusion.
  4. I don’t intend to just share my successes, so hopefully that will cut down on Compare & Despair.


Traditionally, AGILE software development retrospectives are structured around 3 questions:

  • What went well?
  • What went poorly?
  • What steps can be improved for next time?

I will be conforming to this format topic-wise.


What went well:

What went poorly:

  • I had hoped to be able to hire one or two full time employees for Thryv this year. We were not nearly able to.
  • Transit revenue was down by 6% this year. Given that every year before this it was growing at 25-50%, this is a big let down.
  • I’ve been spending money on advertising, with little effect.
  • Thryv lost a client, though through no fault of our own (they’re in the process of downsizing, and laid off most of their in-house workforce as well as us).
  • Of the 11 leads we pursued, only 2 have (so far) turned into actual work.
  • We lost money on a project, largely due to poor expectation setting on my part.

Looking forward:

  • Rather than looking to hire full timers, I’d like to hire one or two interns for the summer, and only look to hire FT if things go better than expected
  • I’d like to move into Asia with my transit apps.
  • I’d like to release more apps for bus systems.
  • I’d like to wind down the consulting part of the Thryv and focus only on products. To this end, I anticipate raising my rates, and pursuing fewer leads. However, I’d still like to add one or two more clients in the first couple of quarters to allow my products to increase in revenue.


What went well:

  • I made some huge changes to my up-market subway app for NYC. I added a bunch of features like:
    • it logs you into the transit wifi automatically,
    • crowdsources train locations for better predictions, (!)
    • gives realtime estimates from the MTA,
    • favorite stations,
    • made the map tappable,
    • added a ‘nearest station’ button,
    • I completely redesigned the station screen, and
    • it now allows you to navigate between two stations.
  • This was a huge amount of work, and brings the app to parity with successful competitors, and exceeds them in multiple areas.

What went poorly:

  • Despite being way better than ever before, and having more/better features than competitors, SUBWAY:NYC has been hemorrhaging users. Installs in 2018 are A THIRD of what they were in 2017, even with advertising on the Play Store to try and prop numbers up. This is devastating, both to my morale and my revenue.
  • The improvements to the app took months longer than I had hoped.
  • Making similar improvements on other apps are delayed indefinitely.

Looking forward:

  • I’d like to use the crowdsourcing features to build an AI that predicts, with higher accuracy than current methods, when trains will actually arrive at any given station.
  • I need to add navigation and some of the other Android features to iOS.
  • I’m hiring a PR firm to get more media coverage for it and hopefully drive downloads. By doing this, I’d like to make the app the first search result for “nyc subway” on both iOS and Android.


AskNot is a political app I made because progressives tend to be bad at framing their positions. Right now the app is very simple and just takes good frames and pushes them out to users for retweeting; this amplifies effective liberal messages.

What went well:

  • I published it! Getting it out there was really difficult emotionally because I’m afraid it will fail, either to get users or in its ultimate mission. I’m proud that I was able to make myself publish it in some form.

What went poorly:

  • AskNot was rejected by Apple for being too liberal.
  • A large part of AskNot is people management and so far that hasn’t been going well. AskNot needs people to comb through Twitter to find good frames, but it’s been hard to get even devoted people to do that regularly. I don’t know why and consider that a personal failing.

Looking forward:

  • Corporate censorship kind of makes me feel like others also think this could be important, and they fear it
  • I can still beta test it with up to 10,000 users on iOS.
  • I’d like to get better at the people management side of things so we can consistently amplify effective progressive frames.
  • I’m going to try to get more media coverage for the app.
  • I’d like to get the app published on the Apple App Store.


What went well:

  • I hired a social media manager! (Which may be how you found this article.)
  • As a result of her efforts, I started a new Instagram account for myself and my company which have more than 650 and 550 followers, respectively, since they started in October.
  • I spoke internationally twice, once at
  • I’ve been trying to write more. As of this post, I’ve written 10 blog posts this year on this site, and I wrote another 3 on Thryv’s website.
  • I’ve also started making videos… while I haven’t done many yet, I’m proud of the ones I’ve made, like my one on being an entrepreneur or another on how to start taking better pictures now.

What went poorly:

  • I applied to speak at about 8 or 9 conferences but only spoke at 2. Yikes.
  • I didn’t make nearly enough videos.
  • I didn’t do enough blogging.

Looking forward:

  • More videos. Probably based on my more successful blogs or teaching topics.
  • Many more conferences this year.
  • To that end, I’m going to be constructing a conference calendar with reminders to apply.


What went well:

  • I started running regularly.
  • I started lifting hand weights regularly.

What went poorly:

  • In 2017, I started doing HEMA. In 2018, I neglected it shamefully.
  • I also unwisely committed to helping coach the CCNY fencing team, and had to withdraw, which I’m ashamed of.
  • I wanted to lift weights every day, and so far have only been able to do so on the days I run.

Looking forward:

  • I’d like to maintain my current levels of exercise, maybe step it up one notch. I don’t want to push it though.
  • I’d like to do HEMA more often.

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