I spent most of 2021 working on an app I believed I could grow into a company.

It was called Keep Posted and it used video messaging to give busy teams a way to stay in touch without overloading their calendars. The idea was simple, a lot of meeting time is spent going over one-way information, presentations, status reports, etc. If that content could be delivered in a different way that didn’t require everyone to be on a call at the same time, it would free up a lot of room in people’s days. Asynchronous video messaging would be the happy medium that allowed people to skip those “meetings that should have been an email” while still maintaining a personal human connection.

It seemed like a great idea, especially in the organizational Wild West brought on by the pandemic.

But it turns out, it wasn’t a great idea. Or at least, not an idea that I could get anyone really excited about after working on it for over a year.

It didn’t get traction, but I built a product that was technically interesting, stretched myself in a lot of new directions, and learned so much about the process of putting together a new idea. Some things worked. Many didn’t. I’m better for going through it.

There’s a lot I could say about the productivity space and why I now don’t think asynchronous video chat is going to revolutionize our workdays anytime soon. If you’re curious about that, please ask me. I can talk your ear off about it.

But as I look back over this past year, the bigger lessons I learned were about me, my relationship to work, and how I cope with doubt and insecurity.

The art of lying to myself—and believing it!

Building something brand new takes a lot of work, and building the thing itself is only a small percentage of what it takes to be successful. The product also needs to connect with the right people, and actually do the job of making their lives better. It’ll never be right on the first try, and it’s a constant grind of trying, learning, and revising ideas as you try to get them just right.

To stay motivated, I have to focus on the world that will exist once everything works out. I have to fully believe in that future so much that it’s worth the effort to get there.

The thing is, that world doesn’t exist yet. It might not ever exist.

That wonderful place where I’m changing the world is a fiction that I choose to believe exists because I need to believe it. And in that sense, I think being able to indulge in a little self-delusion is a useful skill. Sometimes I need to put on blinders and drink a lot of Kool-Aid to get to the point where I can figure out if something is actually viable.

Turns out, I’m pretty good at manufacturing excitement and enthusiasm, even if it’s for things that are objectively small and boring. I remember once early on in my career—at an HR tech startup—whipping myself into a near frenzy over the idea that a slightly better resume search engine would be utterly life changing for enterprise recruiters. (spoiler… it wasn’t.) I was pretty insufferable to be around for a few months.

Managing self-deception as a solo builder

When building a product all by myself, I found that the “reality distortion field” can run unchecked if I’m not careful. In past projects, there were always natural guardrails in place. Something that would bring me back down to earth when needed. Investors wanting a return on their investments, timelines from management or executives, or colleagues who didn’t buy into the hype as quickly and eagerly as I do. :)

When I’m working on a project all by myself, things can get weird.

• It’s easy to ignore and dismiss early signals that the idea isn’t landing. “I must not be explaining it right.” “It’s something you really need to use to understand, and it’s not fully built out yet.” Worst of all… “I don’t know what’s wrong with them, but other people just can’t seem to wrap their head around how much this would help them!”
• Because I’m the only customer at this Kool-Aid stand, the psychological stakes are higher. “What if I’m wrong here?” “Am I going to look like an idiot because everyone else could see why this wasn’t a good idea?” “What does that say about me?”
• When I’m already in a state of suspended disbelief, figuring out the difference between “refining the vision” and “hopelessly flailing” is damn near impossible.

Getting wrapped up in a dream of a better future is useful—even necessary—up to a point. But it's a fine line to walk, and this year I learned that I’m still pretty clumsy at it.

Dealing with bruises from the past

Right before the start of the pandemic, I left my previous job due to a pretty extreme case of burnout. There’s a version of my burnout-recovery that I enjoyed telling myself for a while. It went something like:

“I was a CEO of a VC-backed startup that was changing lives and helping people, but I had to step away after a series of events that would have wiped anyone out. After a brief break, I was recharged and ready to dig into building something else amazing. Going to work for another company doesn’t make sense. I’m too used to being at the source of decision making and I have a great mix of product, engineering, and executive experience that I can make something work from the ground up.”

In reality… I was a total wreck. I couldn’t admit just how bad the burnout was. I felt like a huge failure because of how things ended at my last job. I ran myself into the ground trying to achieve something I couldn’t, and at the end of it, all I could do was walk away from the company and a lot of people I cared about, feeling like a total loser. It was rough.

I also had zero confidence I’d be able to do any better in a new job somewhere else.

It took me a long time to realize what was going on in my head. Badly wanting to feel un-broken and in control put blinders on me that I’d only really understand months later.

There’s the rosy version, then there’s the real one

When I started working on Keep Posted, it was really easy to frame everything positively.

Let’s look at some of the thoughts that ran through my head:

“Being my own boss sounds awesome”—It’s true, but I also couldn’t bear the idea of making commitments with new people and then letting them down.

“I love getting to have a hand in everything”—Up to a point, this is also true. I do love being able to see and contribute to the entire picture of what makes a product work. Research, design, engineering, even marketing and sales are interesting challenges. But if I’m really honest, a lot of what was driving me to do all this stuff myself was being terrified of working with people again.

“Of course I need to bring other people in at some point, but I haven’t quite gotten the scaling signal I need to really commit to that”—In a lot of ways, I probably let the app linger in the “not quite working” stage for longer than it should because it gave me a safe cozy place to exist alone and lick my wounds.

I wasn’t being resilient, I was being scared.

To be fair to myself...

I’m beating myself up a lot here. It’s probably worth acknowledging a thing or two to balance it out.

First, the idea I was trying wasn’t a dumb one, especially in the context of the massive shift to remote work that the pandemic brought on. New ideas needed to be tried. Quite a few companies launched similar products during that time. It was a worthwhile thing to dive deep on. As far as I can tell, most of the other products I was tracking haven’t done a whole lot better.

Second, even though I didn’t have a clear sense of it in the moment, I really needed that time and space to step back and reorient. Basically, “Starting a new company” was the psychological cover I needed to give myself the space to heal.

Finally, 2020 and 2021 were pretty damn good years to hole up in a room by myself and be a hermit.

Clarifying what really matters to me

During the past year, I’ve gotten to sink my teeth into a lot of different parts of the product building process. I didn’t outsource anything, and when I ran into something I didn’t know how to do, I rolled up my sleeves and figured it out.

The many roles I stumbled through included:

• Design
• Programming (front-end, back-end, APIs, a web app, a Slack app)
• Ops (database admin, AWS config across multiple different services)
• Building and maintaining a roadmap
• Managing bugs/support/feature requests
• Communicating updates with users and managing a mailing list
• Marketing copy
• Running ads
• People research
• Quality assurance
• About a hundred other random things

It was a ton of work that I don’t regret doing at all. I learned so much through the process. But I also really don’t want to juggle that many different tasks ever again. It’s nice to feel capable, but never being able to sink deep into single part of it is a huge drag.

A good friend of mine once told me that being a startup founder is amazing because you get to do whatever work you want to do. He’d quickly follow that up with, “The only problem is, you also have to do everything else.” As a solo builder, that couldn’t be more true.

All of this taught me that I can do a lot of different things reasonably well, and that feels great. It was a good way of healing my crushed confidence. But, enjoying the challenge of getting my head around something new and difficult doesn’t mean I actually enjoy doing all of those things long-term. If I’m not careful, I can easily mistake my enjoyment of “cracking the learning curve” for a genuine enjoyment of the thing in general. I feel like—moving forward—being more picky about the rabbit holes I dive down would be a good skill to nurture.

Other discoveries, cheat codes, and hacks from a year of trying to build a something new

Here are a few other fun/useful/interesting things I picked up while working on Keep Posted.

People sometimes use things in unexpected ways: I was sure that I was so pigeonholed into the productivity space, that the only things of value I could build were there. Turns out, the most meaningful uses of Keep Posted were when people did completely off-brand stuff with it, like making a Christmas video message, or sending out updates to keep family members updated on a sick relative. Not sure what to do with that observation, but it seems important.

An easy customer research channel: Finding people to talk to about an early idea can be hard. Lunchclub worked amazingly well for generating a steady stream of conversations with people about ideas, challenges, etc... It would have been a horrible channel for more specific asks, but I got a ton of great early feedback about how people thought about communication and how it impacted their days from there. It may have been because everyone was stuck and home and starved for conversation. But it really worked well.

How to go from zero-to-one on marketing: Read this post by Andy Raskin. Then read this one. Then go listen to his podcast. He’s got a framework about storytelling that is easy to understand and put into use, with tons of accessible, powerful examples.

I still love Ruby on Rails: It’s not the shiny new darling it once was, but when you’re one person who needs to do front-end, back-end, and everything else in between, Rails is the biggest time saver. Not to mention the new stuff in Rails 6 & 7 is pretty damn exciting.

Accessibility is a really useful guardrail: Building with accessibility in mind from the start is more than just the right thing to do. It’s a force amplifier. The constraints that came with making accessibility-centered choices early on ended up saving me huge amounts of time down the road. Defaulting to simplicity is harder than it seems.

Botched deployments are the worst: It’s worth the annoying extra effort/money/whatever to get your deploy scripts rock-solid. Dev-ops is a hat that I want to put on as infrequently as possible.

Building solo for a team product is sort of insane: Building a team communication app as a solo developer is really hard, and kind of dumb. There’s no possibility of a true dogfooding experience, and the best I could do is imagine how other people would use something as I was building it. Building an amazing shared experience needs to be a shared experience itself.

It’s OK not to ride until the wheels fall off: Deciding to stop a project because it’s run its course feels a whole lot better than clinging to it until my body gives out.

Now that Keep Posted is on the shelf, it’s weird how much it doesn’t feel like a failure. Even though it didn’t meet any of the goals I had for it, I feel like I got what I needed out of it, which is a boost of confidence, some clarity about where my boundaries lie, and a reminder that I really, really love building stuff.