All work and no play makes Jack a dull boy

All work and no play makes Jack a dull boy.

All work and no play makes Jack a dull boy.

All work and no play makes Jack a dull boy.

Sure. But when you’re enjoying what you’re doing, is work actually work?

I remember back in the old days at Ask Jeeves I would work like crazy. OK, not as hard as I’m working now. But hard. I’d work 7 days a week. For fun. I even said I’d do my job for free (not that they should not pay me or anything). OK I was really underpaid. But I was young, and it was a startup. You’d think I would have learned. And I was learning.

A few years in, when I was in charge of product management for our little Ask Jeeves International subsidiary, I used to have competitions with my co-worker Chris Hanaoka (who went on to great things at Yahoo! and now Microsoft) to see who could stay up later into the night working.

He always won.

My brain shut down. It does that. I’m even better now at figuring out when it does that and going to bed. I have been very good at sticking to my bedtime since I made that decision a few weeks back. I think I still need more sleep though because I have been very cranky this last week or so. Like VERY cranky. Either that or I’m missing some micronutrient or have some hormone out of whack.

So last weekend was great and terrible at the same time. Most weekends, I train, then I work. The whole weekend. It’s the only time I get anything done.

This weekend, between the CrossFit Open and other training, and just hanging around Cape CrossFit, I spent maybe 6 hours at gym. Then I saw a friend I hadn’t seen in months, since pre-Skyrove. I kept meaning to call him, and see him, and I never got around to it. Only reason I made time now? He’s moving to Thailand for a while.

I kind of suck as a friend, lately, and I know it, and I’m not going to do anything about it.

Also, Sunday afternoon I went to hear Jeremy Loops perform at Kirstenbosch. Kirstenbosch is a gorgeous botanical garden I never go to, and it has a summer concert series I also never go to, mainly because I can’t stand crowds. They annoy me. But Jeremy is special.

And also, he’s very, VERY talented. It’s amazing, and I mean like almost heartbreakingly amazing, to see your friends’ dreams come true. Jeremy and Motheo had dreamed for years of playing at Kirstenbosch. I guess many Cape Town musicians do. Then they did. And they brought a ton of their friends along for guest performances. I sure as hell wasn’t going to miss that. Although, yes, I did kind of think about it, and actually there was some stuff I really wanted to get done on the weekend that didn’t get done as a result of the choices that I made.

It’s funny: we did also all go through this back at Jeeves. I wasn’t the only Skyrove employee working the weekend. You don’t do this out of obligation, you do this out of love. People used to criticise and say really, are you going to remember all the hours you put in working here? When you’re old, are you going to look back and remember the time you put in at work or the time you spent with your friends and family?

Actually, that is a strawman, and I hate strawmen arguments. They’re almost as bad as ad hominems. One of the things I didn’t do this weekend was review my brother’s resume. I did take 5 minutes to email him after he nagged me, and one of the things that I said was to focus on achievements. No one cares that you did this, that, that. They care that you saved X customers or upsold Y dollars or managed the team that was responsible for the following product releases. Whatever it is, it’s not the activity, it’s the achievement.

No, I don’t remember the hours I put in at Jeeves. I also don’t remember the hours we all went out to bars drinking. I remember election night. I remember the IPO party. I remember when Jeeves got hacked with an Elvis hairdo. I remember when Ask Iris got hacked. I remember when I learned WebTV’s proprietary scripting AND our ASP code in an afternoon because I had to (and no, I wasn’t a web developer). I remember when Gary deleted the colours table by accident.

I remember when I took Tony Chan into the server room on his first day, showed him how to compile a database, and as soon as I hit enter on the command line script, the power went out. I remember Ted Briscoe’s baseball bat, Jim Spencer wanting to turn the internet ‘up,’ Eric Stromberg tossing items out of his office without paying attention to who might be walking by, and Robin Keller raising his eyebrows in disbelief. I remember that party at the Metreon. Some of it. I remember that boat cruise with the sales team. Actually, I don’t really remember much of that. I remember late nights at Jupiter and Supenkuche with Tucker, and the day that the IS team all came into work with their hair dyed fluorescent colours.

I remember the time that I nearly started crying over my drink and said I hated my job when, in fact, all I hated was my boss.

I remember when we launched Ask Dudley for Dell, Ask Sam for Microsoft, Ask E*TRADE. I remember when we launched Ask Jeeves Japan, and my first trip overseas: to London. I still think a lot of what I like about South Africa is how much it resembles some parts of life in the UK.

I remember our first layoff. I remember our second layoff. I remember when they shut down AJI and I was the only one to keep my job, then when I had to quit because they wouldn’t let me transfer to Natick because Paul Gardi didn’t like DirectHit and I wanted to move to Boston. I remember when they shut down the text ads product (now known to the universe as Google Adwords) because a certain ad sales director claimed he could sell more text ads with humans.

Silly rabbit, Trix are for kids.

I remember when I found out Robbie Becker had died of a drug overdose, after he’d been clean for months.

I remember my friends. I remember my enemies. I remember the people I turned up my nose at. I remember the relationships. I remember a lot of stuff, good, bad, and ugly. I remember Not Beer. Most especially that. I still have a beer tool (Netra T1 mounting rail) …. Somewhere.

My point? I actually don’t remember what I accomplished. I remember more of that from later in my career when I was actually in charge of more stuff. But I’m in love with my job now the way I haven’t been since then, and I used to think that it was maybe just being young, and naïve.

I’m still young and naïve even if I try to pretend I’m not. Well, at least I’m naïve. No, I’m pretty young, too.

Would I have enjoyed that time of my life more if I hadn’t worked as much? Who the hell knows? You can never answer that. What I do know is that I’ve always been a selfish little thing in a way, where I do what makes me happy. Right now, working makes me happy even if that makes me a shit friend. It’s not that I don’t love my friends. It’s that right now, I have guilt about stuff I don’t get done at work. I hope this isn’t always the case, but it is right now, and my company is important to me.

It’s important because I care. Yes, I want to succeed and I want it and us to succeed. But also, I want us to do as well as we can. I want us to deliver for our customers. I want to be there for my staff. I want to deliver returns to the shareholders. I don’t care if these are one-way streets. There is a right way and a wrong way to do things. If I’m not doing things well, it’s not going to be for lack of trying. It’s going to be for lack of capability, or from over plain over-committing.

Let me be clear: I’m doing this for them, yes, but fundamentally I’m doing it for me. I’m doing it for me because right now, this is fun.

Also, I’m making new friends through this job. Some of my work relationships are crossing the line into friendships, and you can always try to keep things pretty professional but you won’t always, all the time. We’re human, right? You can tell who my friends are when they are the ones where the majority of communication happens over dinner, or some flavour of chat. Some relationships are deeper than the CRM.

One of the things that I remember most about that hazy feverish night in Denver was talking to J at the tip top of the Denver Broncos stadium. He was asking me how I draw the line, specifically when it came to relationships. You have to be super careful. You do. But you also can’t live your life in fear.

Well, it could be worse. I could be famous. That would be worse.

One more thing? I’m taking Saturday off. Cranky probably means over-worked.

• “You don’t even have to move and you will die.” – Deon
• “He really is brilliant.” – Kerry
• “And he’s different. You have to stand out.” – Kerry
• “This is probably the biggest show of my entire life.” – Jeremy
• “A more complicated formula is just a more complicated guess.” – Ellie
• “Only will have taken me 7 months.” – Ellie
• “My big thing is that there’s two things.” – Rudolph
• “Not every man can drill a hole.” – Bronwyn
• “One of the good things for us is that the service is so bad.” – Adam  
• “I’ve never seen it work that well.” – Doug
• “Bane isn’t a super hero. He’s a super villain.” “She’s right.” – Ellie & Bane
• “The only thing that I don’t like about it is that you seem to be slowly moving to Joburg.” – Jeff