Welcome! It looks like you enjoy a good “about” page as much as I do.

Headway is a labor of love, born out of curiosity about (and frustration with) my own brain. It’s been quite the journey from concept to implementation. Lessons were learned, wars fought, governments overthrown, developers hired and fired, tears shed and bank accounts drained. But we made it to version 1, and there’s still plenty of time to paper over the messy parts before Guy Raz finally interviews me.

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Who is Dave Mongan?

I live in the San Francisco Bay Area, and I like to do outdoorsy stuff (particularly riding bikes) and hang out with my wife and daughter.

I have a bachelor’s degree in accounting from the University of Arizona, and most recently I was a product manager at Tesla.

If you thought you’d be reading about an Ivy League-educated wunderkind, then I’m sorry to disappoint you. But what I lack in pedigree, I make up for with grit and pizzazz.

Headway actually comes from my struggle with ADHD, as opposed to the self-optimizations of an overachiever. What some people find easy, such as organization and staying on task, I find difficult.  I’ve searched far and wide for ways to cope with my addiction to distraction. While Headway isn’t directly designed to combat ADHD, it’s part of a toolkit that helps me stay focused and moving forward.

For people without ADHD, it serves as great guardrails to what already comes easy, since much of this system was developed by people who work directly with high-achieving executives.

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Why build another app?

TL;DR I tried really hard not to, but ended up capitulating. Headway started as an experiment with Marshall Goldsmith’s nightly active-questions routine, outlined in his best-selling book Triggers. Each night, I'd call a few friends and family members and we’d run through six stock questions all starting with “Did I do my best to?”.

This was fun, but time-consuming, so I hired someone to do the calls instead. The third party, a lovely British expat named Joanna, lacked the social pressure of a friendship and was too expensive to make sense long-term.

Hell bent on finding a novel approach (and because I'm spending my own money), I moved to an SMS-based text-and-respond MVP with Twilio, Google Sheets, Zapier, et al. But the unit economics and UX weren’t great, and the latter required custom software to fix, so I moved toward an app instead.

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How’d you come up with Headway?

It’s a remix I pieced it together from years of reading, listening to interviews and TED Talks, along with personal experiments and trying other products. The core idea is that structure and feedback are incredibly helpful, provided they aren’t onerous.

This idea of “just enough structure” is a riff on BJ Fogg’s “tiny habits” concept, where setting a low completion threshold (e.g. a couple minutes each morning and evening) reduces the cognitive burden and helps you form a habit. Once you’ve formed a habit, the activity feels easier and you start adding things to it. For example, you start by flossing one tooth per night, and after a few weeks you’re flossing all your teeth regularly without much effort. Magic.

With that in mind, I knew the question sets (surveys, for lack of a better term) had to be as impactful as possible while still creating the desired feedback loop.

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What makes this so special?

The Morning Survey

Headway’s morning survey is all about priming your mindset for productivity using a few tricks. If you’ve ever played sports or competed in anything, you understand how important your mindset is to performance. Work should be no different, but we more often approach the work day in a reactive state. Thus, the morning survey employs the following concepts to help set your day up for success:

• Positive psychology - Focusing on both the things you appreciate about your life and yourself helps you feel optimistic about the day ahead.‍
• Prioritization - You only have so much energy, so attacking the most important item first is a springboard for success.‍
• Premortems - Created by decision-making researcher Gary Klein, premortems have you invert your approach by asking “what could go wrong?”. Some call it Stoicisim or negative visualization, but the idea is stunningly simple: much of what goes wrong is entirely avoidable. We can actually plan for traffic, meetings that run long, or normal disruptions.

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The Evening Survey

Headway’s evening survey uses active questions, created by author and executive coach Marshall Goldsmith (with Marshall’s permission, of course), and outlined in in his bestselling book Triggers. The process has you quantify your effort in key areas with the idea that consistent effort breeds results. Where passive questions, such as “Do I have clear goals?” might include some outside influence, active questions speak directly to your effort and start with “Did I do my best to…?”.

Marshall recommends six questions to start, which you score each night. These scores create a feedback loop that informs the following day. In Marshall’s research across 79 studies and more than 2,000 participants, 89% reported improvement in at least one item after just two weeks of daily use.

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Where does Headway go from here?

My humble-ish opinion is that the future of personal productivity will evolve from project and task tracking to a more holistic approach that focuses on psychology, energy level and approach. Thus far, personal productivity tools have evolved from paper lists to electronic lists with organizational and collaboration features. But we’re still largely stuck thinking about what and when, rather than how.

As we move to a more distributed WFH world, the psychological challenges move to the forefront for two reasons: our communication overhead increases and our work/home lives blur. I think there are many opportunities that will come from this shift.