In mid 2007 Infinity Softworks was falling apart. The project we spent two years working on was ending with a big thud, I had already laid off most of the team and was about to let go of the remaining two. I was tired and worn out. A friend looked at me and said it was the first time in the eight years he had known me that I ran into a brick wall and stopped.

At that point in 2007 I was clearly depressed: depressed with my situation, depressed with the state of the company, depressed with my failure, nervous about fatherhood and the new pressures that brought on me. Brad Feld had a great post on depression last October.  As Brad said:

For some reason we’ve embraced failure as an entrepreneurial trait that is ok, but we still struggle with acknowledging and talking about depression. Entrepreneurs function with a wide range of stresses and emotions that often have overwhelming intensity. In many cases, we are afraid of admitting depression, and are often highly functional when we are depressed. But that doesn’t deny the fact that entrepreneurs get depressed. To deny this, is to deny reality, and that’s against my value system.

But by late 2007 a plan was in place and we kept it together by doing contract work. We survived to fight another day. I wasn’t blinded by the realities but I still believed in what we could do. We’ve battled for over five years now, learning a ton along the way.

Which leads me to the recent post in The Atlantic about optimism:

This questions turns out to matter a great deal if you are trying to figure out who grows after trauma and who gets swallowed up by it, a question that each movie [Life of Pi and Silver Lining’s Playbook] addresses and that psychologists have been grappling with for years. Think back to the last time you experienced a loss, setback, or hardship. Did you respond by venting, ruminating, and dwelling on the disappointment, or did you look for a faint flash of meaning through all of the darkness — a silver lining of some sort? How quickly did you bounce back — how resilient are you?

The roller coaster of start-up life never really fades away. Optimism, depression, it all turns on a dime. Keeping a positive outlook, though, that’s the key.

Charlie Kindel references this post awhile ago but wanted to make sure I recorded it for posterity. When most of us talk about business planning we think of it as a 20 to 40-page document that never again gets updated even though the business changes considerably. When Charlie talks about the plan, he is focused on a short, 1-2 page document that outlines the rules of engagement. He calls it the 5Ps and outlines them here:

• Purpose: Why do we exist? Why are we in business? Where do we want to be in the future? What will we deliver?
• Principles: What are the non-negotiable rules and key strategies? How will we act?
• Priorities: What’s the framework for tradeoffs?
• Plan: How are we going to stage and tackle solving the problems? What are the known dates & forcing functions on the calendar?
• People: Who’s accountable for every key part of the plan?

We’ve been doing a variation on this as we work on a new product. It’s a tiny team so people is not as important for us, but I’ve spent time outlining the purpose, principles and priorities all in notes shared across the team.

I highly recommend reading the entire thing. Great way to do planning.

In December I had one ball in the air. Juggling with a single ball is quite easy, after all, as long as I keep my eye on it. In January I added a second ball. Cash has been short here so I started talking to some friends about contract work. By February we added a third ball, a contract job. Now it’s the end of February and suddenly I’ve added two new balls but get to stop searching for contract work so dropped one. That’s a total of four balls now in the air. Things are getting much more complicated.

And then yesterday happens. I’m about to step into a team meeting to discuss timing and priorities when I get a call from a partner. Can you bring that test server back up again so we can finalize the requirements for a project we have been talking about for a few months? Sure! I say. These folks have been great partners and figured it would take an hour or so to get it running.

Ten hours later I got the server up.

The details aren’t important, just know it had to do with a version of Linux that apparently is no longer supported, although that really shouldn’t matter when recovering from a backup. What is important is that failure in the system can happen at any time, or as Murphy might have said, it is bound to happen when you least need it to.

It’s all fine. I’ve gotten better at not letting chaos annoy me. (Amazingly my ability to handle chaos improved once I had kids.) But it is inevitable.

I got my first job when I was 14. My job was to wash out golf carts a few days a week at the local college-sponsored course. In exchange, I received free green fees and a locker to store my clubs. I didn’t get paid in cash for that job — I was actually too young for that by state law, I believe — but to a 14 year old who probably would have spent most of the money playing golf anyway, it was a heck of a deal.

At the end of the summer my mom and stepdad moved us to Florida and the next summer I came back to Ohio to stay with my dad. That summer my dad talked to a friend of his who painted houses and got me on his crew. I worked hard that summer. It was grueling, physical labor with very long hours. I’m sure my dad got me the job partly to show me what life would be like if I didn’t go to college.

But that wasn’t the only thing I learned. I also learned a little about working with people, in particular managing them. My boss, a friend to this day, worked us from early until late every day but at the end of every day, he never failed to say thank you as we each left for home and dinner. It wasn’t a complex gesture, just a simple one, but it always made me feel wanted and respected.

I try to do the same thing to this day.