I probably should have seen this coming. For the past two weeks I've been sleeping up to 10 hours a night because I'm having trouble getting up in the morning. My muscles have been aching, and I'm just not smiling as much as usual.

When I went to my cousin's home for Christmas dinner today, I spent most of the evening not talking, staring blankly off into the pile of mashed potatoes in front of me. I haven't seen some of my cousins, aunts, and uncles for over 6 months and I still didn't speak more than a sentence to most of them. I imagine I'm unpleasant to be around at the moment.

I feel like shit right now.

I recall when I started building this startup that it was easy to find treasure troves of great advice for what building a startup looks like (and doesn't look like), but I realized quickly that there wasn't much out there to help me understand what it feels like. Is what I'm feeling right now normal? Do most founders battle demons at some point in there journey? Does it tend to happen more often early on in the company's life or later?

It would make me quite the hypocrite if I complained about a lack of information about the personal side of being a founder without sharing my own experiences, so here goes:

What Founder Depression Feels Like

These feelings have been building up for about 2 weeks. Its been harder than normal to do things that aren't work, especially spending time with people that aren't my girlfriend (she's awesome, love her to death). Even my work has felt more difficult, but since I have an incessant need to be working I seem to get things done regardless of how I feel each day.

Right now everything feels slow, and I feel powerless to make things move faster. In startup-land, speed is everything and it feels like I'm treading water in molasses. Like I'm walking through a blizzard. Making things worse is the fact that all my (current and potential) customers and users are away right now, so any attempts to use to get some extra traction improve my mood would likely be in vain.

I'm playing the criticisms from some of the advisors at the startup space we're in in my head over and over, but its not a constructive exercise. It would be fine if I was learning from these criticisms, but its mostly quips about "you haven't figured out X yet!" or "you're not growing quickly enough!". I fucking know that already, thanks for point that out. Perhaps if you spent more that 15 minutes every 2 weeks getting to know what we're building you'd have something more helpful to add.

That's not a knock on those advisors as people or as strategic thinkers, they're trying to help out lots of companies and don't have much of a vested interest in us.

I think most of the bad feelings I have stem from my startup life and my struggle to be a better founder. The highs of startup life are very high, but the lows are downright awful.

So What Now?

Well here's what's not going to happen: I'm not going to quit, cut down my workload, or make excuses. I just don't have that in me, and I don't have a backup plan if things doing work out well with Steadfast. No matter how shitty I feel, I'll be in to work tomorrow bright and early.

Getting back on track is going to be tough, but there's a feeling stronger than this depression I know I can always tap into: anger. Its powerful if used in the right way, though very destructive if used indiscriminately. 

I think about the people who don't believe in us, who dismissed me, who think I'm wasting my time. How can thinking about that do anything but make my blood boil? I'm channeling the energy from that frustration into traction for our startup.

Think we're too small to care about? So was Google once upon a time. Think our vision is underwhelming? That speaks volumes about your imagination, not mine. Don't think we're talented enough? Fuck you.

I feel like shit today, but this won't last. Bet against our team, you're going to feel like an idiot for a long time. This is the mindset I always go to to push through these difficult times.

Manage xor Do

In short, managing is about focusing on this quarter, while doing is about focusing on right now.

The Humble Beginnings of Every Startup

As with the beginning of every startup, there are a whole lot of chiefs and not very many indians. Typically, each founder (usually about 2-4 founder per company) inherits a Chief [something] Officer role, which they then carry forward with them if the company is lucky enough to scale.

These executives are the supreme manager for whatever domain of the company they are responsible for, with the CEO being the manager of the managers and therefore of the whole company. Product is too buggy? Chew the ear off the CTO. Salespeople aren’t getting it done? Better have a serious chat with the CMO. Barely holding the company together while making progress on product? Actually that’s pretty much par for the course for the CEO.

Takeaway: in large organizations the success or failure of CXOs rests on the output of the people in the organization doing the actual work.

What happens when there are no people to do any of the work you are responsible for managing? I guess you could write reports chronicling the lack of progress and the reason(s) for it... presumably the fact that by definition there is nobody to do any actual work.

Of course early on in a startups life, all the work is done by the so-called CXOs. The CTO is doing all or most of the dev work, a CPO is responsible for designing product, and the CEO often does sales, customer support, fundraising, and any high priority work that’s nobody’s responsibility. Early on all the managers are the workers, so who is doing the managing?

Well what do we mean when we say manage? In this context, I mean effectively directing the actual work being done towards the larger objective of the organization and deciding what tradeoffs will be made and when.

So you have managers and you have workers, so what? Well, in my experience its very hard to manage and do at the same time. That’s not a problem in an organization with many people, because you have some people managing, and others doing. However early on at your startup, you have to do both.

The Struggle: Have I made any progress today?

Why is it so hard to manage and do at once? Sometimes I find myself at my computer for hours on end trying jumping back and forth between managing progress and making progress. At the end of the day I realize I haven't done much of either. Wasted days are not good for my mental health.

In my view, the root of the problem is that the focus of the managing and doing are opposite.

Management is about achieving a large, long-term objective. You have to constantly be aware of how each small project is progressing and how each project impacts the large, long term goal. As such a constant holistic view of a company is necessary at all times. Managing is about optimizing for the accomplishment of one large objective over weeks and months.

Doing work is the opposite. Work is about focusing intensely on one short-term problem at a time. You have to constantly ignore everything around you other than the one problem you're working on and achieving that short term goal. Doing work is about optimizing for the accomplishment of many small objectives over hours and days.

It takes time to shift your thinking from short-term to long-term and vice versa. When you're coding a feature, every time you reconsider some of the feature requirements, it takes an extra half hour just to catch up again to the code progress you've made so far.

In short, managing is about focusing on this quarter, while doing is about focusing on right now.

Dedicate Time for Both

So what do you do when you’re both the worker and the manager? I'm guessing the only way to be effective at both is to separate the two completely, and define when you’ll be doing each. For me, that means every Friday is dedicated to managing: planning my next week, evaluating my performance in the previous week, and tracking our startup’s progress against our long term goals. Every other day of the week, is for focusing on the work that I set out for myself the previous Friday. 

I imagine it will take some time getting used to this system. However, I can’t continue to be wasting time jumping back and forth from managing things to doing things and getting less done than I expect of myself.

I’ll update in a month and with some preliminary results :)

Are you afraid of being wrong? I am, and here's evidence:

• Blog posts started/written: 34

• Blog posts published: 2

That's 32 different ideas, theories and observations I've written and thought about that I never shared with anyone. The truth is that I'm worried about writing something that a more experienced or knowledgeable person may (correctly) say is false or even stupid. It feels shitty being wrong.

One of the reasons it is so important to build things quickly at a startup, is so that you can find out what part(s) of your product is/are bad. The faster you find out how you're wrong, the faster you can get to product/market fit (and build something people love).

You can be confident that when you do start a startup that your product theory will be wrong at the start (or at least very flawed). Being wrong for the sake of being wrong is a waste of time. However if you have a specific goal in mind and you are unsure how to get there, testing ideas you have and being wrong a lot is a great way to be right, fast.

A startup's mission is an exception: you probably have to be right about the raison d'etre from the get-go. But be wrong about what your product should look and feel like by testing many ideas.

My goal is to publish most of the 32 unpublished blog posts by the end of the year. I hope that by writing these posts I'll be better at coming up with new ideas, and starting conversations that may lead me to change my mind.

This could be a good change for myself and my work, but I could be wrong.

An Uninteresting Story

Last week I made a mistake. I had just run a series of mechanical turk HITs to collect 20,000 images for a project I was running at work. I looked at the images I collected from the mturk run and realized that they all had an extra number added to the name, which I had to get rid of.

I tried to make an automator application to rename the images. Unfortunately I missed a step when I wrote it. It was the step that chose where to deposit the images after they had been renamed. My desktop slowly started adding the jpegs to my desktop 50 at a time, until it promptly decided it was gettin’ real tired of my shit. I restarted my computer, but my desktop wouldn't load and I was screwed.

It took a couple of awesome folks at the startup I work at (thanks Amy and John!) to finally rid my desktop of the jpeg infection and allow my desktop to be clean happy and healthy once again. As I got back to work, I had this realization: computers are a lot like cranes.

Powerful and Empowering

Millennia ago, to build something big, you had to recruit thousands of people to push, pull and position building components into place. As an architect you were constrained by the limited ability of human strength to move and position building materials: its probably not possible to build a conventional skyscraper with marble slabs and human strength as the force to move them. Today, i’d guess it takes less than 10 people to lift and position a large building component onto the most obscenely tall and complex buildings that were unbuildable a century ago.

A computer is like a crane for the mind. Just as a crane allows you to quickly do the work of many muscles in one machine, a computer quickly does calculations and runs operations that would require the work of many brains. There are two key similarities between the cranes and computers:

1. Both are powerful, lifting heavy things
2. Both are empowering, allowing you to build new kinds of things

Limits

We may have reached or are approaching a limit in crane technology (there are only so many ways to lift heavy things into the sky). Personally, I can't tell much of a difference between the cranes of 1953 and the cranes of 2013, yet the differences between the appearance and functionality of computers in the last decade alone is enormous. Crane innovation is constrained by the laws of physics. I don't think computers are constrained the same way.

Computers, tablets and phones included, have changed from stationary grey boxes, to sleek, elegant, mobile machines that are orders of magnitude more powerful than the large grey boxes ever were. I'm sure more technical people could fill volumes explaining more of the differences between computing today vs years past. As far as I know, there is no reason to believe that innovation computing is going to slow down.

What does this mean for society going forward? I'm not sure, but with all the construction going on in our cities and on the web, it might be a good time for young people to learn how to operate a crane or a computer.

At Your Fingertips

Here's a good question: After about 25k in tuition (a bargain compared to some of my American friends), and 4 years of my life to do my undergrad, what do I have to show for it?

For starters, this is a bad time to ask this question. I probably should have asked this after first year and second year, (etc) because its a little late to make any changes. I guess I'll have to settle for retrospection.

I think there are three key elements to answering this question. From least important to most important they are:

1. Happiness
2. Development
3. Opportunities

1. Happiness

Happiness can't be measured in pints or consecutive hours spent awake on a saturday night. I measure it in terms of being able to remember how many things in the last year(s) you are proud of and can remember. Can't think of any? I doubt you'll be able to think of any in 10 years from now when your entire undergrad blurs into nothing but the routes you took to school and the seat you sat in during 2nd year biology. 

I think if you can remember 3 major accomplishments from the last year that you're proud of, you're on the right track. That could be a leading a campus club or earning a B+ in organic chem (*shudder*). These achievements should be independent of what others have accomplished or are capable of. Your achievements should be a reflection of how close you came to reaching your 'potential' (whatever that means). 

Also its good if you had an enjoyable time. I suppose thats relevant to happiness as well, I just don't think its the most important factor of happiness.

2. Development

At this point, how much more do you know and how much more can you do compared to when you started university n years ago? Would you pay (n)7k for it? While its great that you've memorized a comprehensive history of the Qiang Dynasty, and can tell me all the different ways we oppress everybody who isn't a white, heterosexual male, can you actually do something with you knowledge or skills acquired during that process? 

Generally speaking, I'm a proponent of 'the world doesn't owe you squat' worldview. So I think its important that while you blossom as a 'free thinking' individual in university, you should also learn how to do something that other people value, not just that you value (hint: people value knowing how to code a lot more than how to make a latte).

3. Opportunities

Unfortunately I only realized in my last semester or two, that I had immense opportunity at university. A bunch of really smart people were not only forced to make themselves available to me, but some even enjoyed talking with students. How awesome is that? On top of that, many people in the industry/profession you want to go into will make themselves available to get coffee if you send enough cold emails, just because you are a university student (its a great way to get a head-start on finding a summer job).

U of T, my alma mater, is a tough school. Its comprised of tens of thousands of the brightest and most hard working students from Toronto and across the globe. Everyone competes for spots on a bell curve, that has the same grade distribution of York U (insert York U joke here). I had the opportunity to develop myself through exchange ideas and spend time with lots of capable and intelligent students there, just like every university student (except York U students).

Parting Thoughts

I think theres a serious lack of self reflection among students in university. Big questions like "What skills have I developed", and "What do I even remember from the last 2 years" go unanswered. I went my entire university career without asking these questions, though I was lucky enough to come out alright. I think I could have done a lot better for myself if I had thought about this years ago, but hopefully some of you will have the opportunity to do so while you can still make changes.

University is expensive, and you don't get the 4 years you spent there back when you leave. Make sure its where you want to be right now, and that you are getting all you want out of it.