The Eric Wroolie Blog

Overpass Experiences

How to Kill Someone’s Dreams

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The easiest way to kill someone’s dreams is to question them as if they should have an answer. Ask a lot of questions about hypothetical situations and watch the doubt fill their face. “What will you do if you get sick and can’t pay the bills?” “What is your plan b if it does not work?” “Are you absolutely certain you want to be doing this?”

Sometimes, finally getting yourself to do what you’ve always known deep down you should be doing is hard. Sometimes it feels like everyone is against you. You are trying to coax that higher version of yourself to take centre stage. And there are so many who are asking questions and shining a light on the doubt you have.

But, the truth is no one is certain of anything. I can’t tell you how many times I’ve had people question me about what I would do when I left a job. And, it really scared me. But, sometimes, those people end up losing their “secure” job anyway. No one really knows.

I think I experienced this most when I left the Army. I was so unsure of whether I was doing the right thing that I continued going strong until the last day. I elected to attend PLDC (Primary Leadership Development Course) and the promotions board to get my E5 sargeant stripes even when others I entered with were just waiting to leave. I still wasn’t sure.

I had all my friends and colleagues wanting me to give them my life plan. “What are you going to do for work?” “Are you going to college?” “If you go to college, what will you do afterwards?” And the most I said “I don’t know” the more I doubted whether I was doing the right thing.

And the Army recruiter was just as bad. I still get angry when I think about it sometimes. They just had to put doubt into my head. They just had to hint that maybe I was not doing the right thing and my fear took over. I very nearly stayed in.

On one of the many times I left a full-time contract to pursue Overpass full-time, I got the same treatment. It wasn’t so much that people doubted I could do it (but many did) as much as it was their constant questions about whether I had “thought everything through.”

But sometimes, you don’t need an entire plan. You don’t need to know how to get from A to Z. You just need to focus on A to B first.

And then you leap.

And it’s scary.

And if you can get used to uncertainty, the world is yours.

Are any Puzzle Pieces Missing?

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It was much easier when I just had a job. It was easier when my only goal was making enough money to pay the mortgage and raise the kids. But when I started to give into the things I really want, it got more complicated.

There is no map. There is no-one to follow who can give me the answers. I know I can find someone who has “made it” doing what I’m trying to do, but I don’t think that works. I get asked all the time from people how I got to where I am. I have ideas, but no single answer to give them.

Sometimes it feels like I’m putting together a puzzle. The pieces are all in front of me and I keep re-arranging them. The trouble is that I can’t be sure I even *have* all the pieces. If I don’t have all the pieces, then I’m just wasting my time.

But I have to trust the pieces are all here. That faith has served me pretty well up until now.

Software Development Skills like Currency – And the value is always falling

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I can remember a few years ago having an argument with a junior developer about how long he was taking on a simple task. At the time, I was a contractor working at one of the major investment banks (Very highly paid, I might add). I had given an overseas developer a task he spent more than a week on (with a daily “Where is this?” from me— and many more people chasing me from higher up). Eventually, the developer and I started up a screen share session and I completed the task in less than an hour while he watched me do it. This happened a lot but this case was extreme – one hour versus one week plus (he was still a “deer in the headlights” and paralysed with inaction). I asked him why I could figure it out quickly and he spent days hemming and hawing over it. I mean, he had enough time to try hundreds of possible solutions but spent the days Googling for the perfect solution. He said something very funny to me:

“Well, you have 12 years experience in IT. I only have 5 years.”

It was such a strange thing to hear. I didn’t know what to say. I wondered how many times he told himself this. I also started to see why people were coming to me when they were stuck expecting me to fix everything for them when they had all the same resources I did. I didn’t have anyone to go to so I figured out everything out on my own. But they all had me. In fact, I had been in many meetings with senior managers where it was explained that a project was held up because a junior developer was waiting for my time to help with an issue he couldn’t figure out.

I had 12 years experience, the junior developer had said back then. He only had 5. Let me tell you why this was so ridiculous.

At the time, we were working with C# (a programming language). I had been working with it for 2 years. I read a few books and did a lot of projects on my own. Before that, I was working on ASP with VB Script almost exclusively. This is all way before I started with apps. But the experience kept changing and was rarely transferrable. In fact, I worried that someone who was working with C# longer than I was would do better than me. Strangely, that’s never the case.

This is one of the big problems in IT. We quantify the wrong things.

I’m a big believer in experience. Experience is the reason I get paid what I do. But, despite what it may look like to outsiders, it’s very difficult to accumulate skill over a long period of time. Technology changes so much, that’s it’s very hard to keep up with it all.

I like to compare IT Skills with money. The more you learn, the more you earn. The problem is the currency keeps changing. You start to realise that the currency you’re earning starts to drop in value over time and you need to start earning a new currency (and learn new technologies) before you go broke. I’ve met many developers who just complain (“No one is looking for VB developers at the moment.”) but the good ones start on something new. They also, to a large extent, move into an area where they know as much as the guy who just comes into the field from university.

This is scary, believe me. When your livelihood is with VB and you decide to move into C# (way back when), you go from knowing how to do everything to knowing how to do very little. Some things are transferrable, but surprisingly little. I’ve been through this a lot. Most recently, it’s with apps. I go from being the guy who knows how to do almost anything to being on par with the guy just getting into IT.

This is why the guy comparing our years of experience was so comical to me. In a way, he had far more experience than I did. What I had was confidence and no one to turn to.

It’s the same reason I give little credence to recruiters who try to sell me on a developer with X years of experience. It’s the reason I am never impressed with a developer who says “I’ve been with this company for x years and blah blah blah”.

Someone once told me that if you redistribute all wealth so everyone had an even share, in 10 years the distribution would be back to where it is now. I’m not sure if that’s true, but it sounds like it could be. Those who know how to make money can do it again and again.

I believe the same is true with software development skills. Once you know how to learn a software language and are confident that you have what it takes to learn it, it does matter how the value of your software knowledge drops— because you know you can always move into the next skill.