The Day I Installed My Third Monitor

The day I installed my third monitor I took a picture and sent it to my kids. Three screens, our logo on all of them. Their response: OMG!

Here is what led to it.

Nothing looked broken

Our work lives in more places than I can hold at once. Three of them are where the building actually happens: one holds everything we know, one holds everything we make, one is the website itself. That is before the shared drive, the boards, the inboxes.

For a few weeks my work had been crossing between those three without me knowing. Nothing looked broken. Everything I made was somewhere. Just not always where I thought it was. Lee, my co-founder, untangled it.

I thought another monitor would help me stay untangled and so I bought a third one. Now each workstream repo has its own screen and the hope is I can stop tripping over myself. That may not be very techy of me and it also only fixed the part I could put on a screen. Everything else is still everywhere: sticky notes, Slack messages, text threads. Oh and I multiplied the number of tabs I now have open, oh my.

The questions changed

Until about two years ago I knew enough about technology to get by, which mostly meant knowing who to ask. I spent my career in communications, and in the last month I have for the most part on my own built web pages, made sizzle reels and product videos, run analytics, written a little developer code, and learned a vocabulary I would have nodded along to a year ago without understanding a word of it.

In May, Lee walked me through saving my first file into the company's system. We skipped the command line entirely, on the grounds that I would never need it. I got as far as a password prompt I did not understand, then left it to go take a call with a nonprofit director. That was twelve weeks ago.

What I did not expect is what came with learning all of this. I notice arrangements now. When something is harder than it should be, I no longer assume the difficulty is mine. I look at how it is set up. And once I can see the better way, I cannot unsee it. The questions changed more than I did. It used to be, what does this word mean? Now it is, why is it built this way? I thought I was learning technology. I think what I was really learning was that I could have an opinion about it.

Seeing more does not make the list shorter. Usually it does the opposite. We are two people with no outside money, building as fast as we can, and there are dozens of things on our boards and most days I add more to them than I finish. Some days that feels like a hamster wheel. Then an email comes in from someone actually using what we made, and the same list feels like something turning instead. Those days are the best ones. I just do not get to pick when they come.

But there is a difference now between not knowing how something works and knowing I can figure it out. I did not realize how much that difference mattered until I started thinking about why it happened.

What I do not say out loud

I could not have done any of this alone. Lee is the reason, and not because he does the heavy-lift engineering work. Because he is there. When something breaks and I do not understand why, I ask him. When the question is a basic one, he does not make me feel like I have asked a silly question. It does not even have to be the right question.

Most weeks we spend hours on video calls working through details almost nobody else would sit still for, and he has a habit of saying it back to me. What I am hearing you say is, and then he says it. Half the time that is when I find out what I actually think. It is also where most of our best ideas have come from. Not his, not mine, but somewhere in the conversation between us.

For a long time I thought the useful thing about having Lee there was that when I did not know something, he probably did. I don't think that anymore. The useful thing is that I have somewhere for the unfinished question to go. I can start with the part I understand, or the thing that feels wrong, or a question that turns out not to be the question at all, and we can work from there.

That is the entire mechanism. Everything hard I have learned this year sits on top of the fact that there was someone to ask. I have come to think you can learn almost anything outside your own wheelhouse, as long as you have somewhere to think out loud.

Not everybody has a Lee

Most weeks I am talking with someone who runs a small nonprofit organization. One runs a foundation. One runs the fundraising for a library. One runs a national patient alliance largely by herself. I recognize something in all of them. They are doing jobs that would be spread across whole departments in a larger organization: strategy, fundraising, communications, operations, board management, technology, sometimes finance.

When something lands outside what they already know, there often isn't another office down the hall. There isn't a CTO to ask the technology question or a development strategist to think through the funder problem or a chief of staff to help turn six competing priorities into three. Sometimes there isn't even another person with enough context to understand why the question matters.

The distance between them and me was never ability. I have somewhere to ask. Not everybody does. And I have started wondering how much of what looks like a capability gap in small organizations is really an access gap instead.

The questions you never asked

Whether what they have now in BeMo is the same thing, I honestly do not know. It is software. It does not know them the way Lee knows me, and I will not pretend otherwise. But I have watched one nonprofit leader work out what her time was actually worth after years of giving it away, and another sit down and finish in an afternoon something that used to take her days.

At first I noticed the time saved. Now I think that may be the less interesting part.

Something else starts happening when there is always somewhere to ask. You start asking more, not because you have more problems but because asking gets cheaper. You can bring the half-formed question, the thing you are not sure is even a question yet. You can ask why something works the way it does. You can follow one thought into another without first deciding whether it is important enough to take somebody else's time.

And eventually the questions themselves start to change. How do I write this grant faster becomes, why are we pursuing this grant at all? Can you help me make this board report becomes, what does my board actually need to understand? How do I get through everything on this list becomes, which things on this list actually move the organization where we said we wanted to go?

Those are not really productivity questions anymore. They are the questions people with larger teams have other people around them to help ask. For a small organization, they are often the questions that get pushed aside because there is always something more immediate to do and nobody available to sit with the unfinished thought.

And then, every once in a while, the question becomes something else entirely: what is possible that I never thought to want?

Somewhere to think out loud

We are working this out in real time. Some of what I believe this week I will probably be embarrassed by within a year (Lee tells me that's a software thing). I still have three monitors. I still have too many tabs. Our boards still contain more things than two people can reasonably finish, and another screen has done nothing about the sticky notes on my desk.

But I keep going back to how long I spent not asking questions, and how much of that I mistook for not being smart enough to ask them. I don't think that was the problem anymore.

There was nowhere for the unfinished question to go.