On asking for things

I’ve had variants of this stuck in my drafts for a while now. It’s time I sat down and wrote down what’s been on my mind.

First of all, go read Salary Negotiation Tips from White Men in Tech (and part 2). It had been on my queue in Pocket for a while, and I hadn’t gotten around to reading it. However, after a friend tweeted about it yesterday, I went and read it. And it made me angry. Not at others, mind, but at myself, because it read like a litany of every single thing I’d done wrong professionally for the past almost two decades.

I’m pretty timid when it comes to asking for things. It doesn’t matter whether it’s stuff in my personal life, or my professional life. It’s been much too easy for me to trick myself into thinking that I don’t deserve what I might be considering asking for. The fear of rejection can hang there in the background too, warrented or not, goading you into not doing what you ought to. The very act of asking is a risk, and risk brings with it dangers. Those dangers may be real or figments, but they seem very real in your head. They can make you treat friendships and other personal relationships with kid gloves for fear of damaging them, even if the outcome of taking that risk would almost certainly be positive. In a professional setting, they can prevent advancement and career growth, and stop you from being adequately compensated.

I’m not going to talk about my personal life here though; just my professional one.

In retrospect, I’ve actually done surprisingly well in my career so far. I can claim few laurels though: much of my career advancement has been down to friends pushing me, giving me chances, and sheer dumb luck.

When I was in first two years of college, I fell into giving grinds. Initially, I didn’t ask for money for it; I literally had people forcing money into my hands. Which is ridiculous when you think about it, but up home in Sligo, unless you’re at a till, that’s always seemed to be the way people went about things: you refuse money for stuff, and eventually the person paying forces you to take what you’re due. It’s a fantastic way to inculcate the idea that earning a living, and accepting and expecting what you’re due is somehow not right; if you want to keep people poor, it’s a great way of going about it.

I got my start back when I was in college when taking a two-year sabbatical from my degree, as some friends of mine had decided to leave college and start a company. I went back to college after two years, and eventually moved on to other thing, but Pete and Dan persevered and built something great, and I’m so very proud of what they built! That was my first proper professional job, and it was all down to friends taking a chance on me.

After a while at a couple of other jobs which I don’t remember terribly fondly, I ended up at Blacknight. Now, the thing that I need to make clear before anything else is that I really like Blacknight, and have friends who work there. None of this is a criticism in the slightest of them. In fact, starting to work in Blacknight was one of those sheer dumb luck moments I mentioned earlier. However, spent ten years there, when I probably ought to have moved on to other things after about five. That was because I hit a ceiling as far as career progression went, spending years feeling like I wasn’t getting anything done. I never really felt at home in Carlow either, but that’s a story for another day.

I made several critical mistakes there on a personal level:

• I went into the job just wanting to get a job; I was essentially treating it as an escape from a less than ideal employment situation where I was dealing with a frustrating combination of too-regular trans-Atlantic flights and remote work with shitty internet connectivity. Hell is sitting on dial-up for extended periods attempting to synchronise StarTeam repo, wasting your whole day trying to get anything done because of that, and the funny kind of isolation that comes from a five/six hour time difference. It makes you forget your time is actually worth anything.

• I wasn’t assertive enough when it mattered. I didn’t make my case strongly enough for things that were costing the company serious time and money, and simultaneously sapping my morale.

• I worried too much about things I shouldn’t have. Some of the systems I put together were responsible for a significant chunk of the company’s income, and I let myself worry about that when it wasn’t really my responsibility.

• I let myself get pushed into a quasi-management position as a promotion that I was ill-equiped to deal with, which was ultimately to everybody’s detriment.

• I never really attempted to negotiate my salary upwards. When I started, I was essentially underpaid for my level of experience, but it was Carlow, so it was cheap anyway. That was forgivable when I started, but got less and less so as things went along. I was left in a position when I left where I was probably being paid less, adjusted for inflation, than when I began. Now, I could blame others for this, but ultimately I have to admit that it’s mostly my fault because I never really asked. I just went along with things, and that was a terrible, terible idea.

After years of pushing from friends of mine, I eventually ended up at Workday, which counts as another instance of sheer dumb luck, because I had a friend who worked there, and knew some people through the Irish tech scene who worked there. I was somewhat apprehensive about the interviews. I’d avoided moving up to Dublin for years, rejected recruitment attempts from a bunch of different companies, the most persistent being Google and DemonWare, IIRC, because the process terrified me.

One of the interesting things that happened in the interview process was when I was asked to submit my expected base salary. I was being hired as a Senior Software Developer, so I used Glassdoor to get an estimate of what I could expect to ask, added on a bit as a fudge against the average, and put that number down. That got me to over double my old gross salary, and I got that without anybody even blinking. No negotiation down.

Which is interesting, because I probably ended up selling myself a bit short, but I have absolutely no way of knowing.

Now, I’m very happy where I am. I even got to start working with one of my best friends again! But here are the takeaways:

• If you’re not happy in a position, you should absolutely move on. It’s not your responsibility to continue in a job that’s making you miserable, even if you like your co-workers. If you’re lucky, the company is big enough, and you can make an internal move, all the better, but you deserve better than being stuck doing something that drains the colour from your life.

• You probably underestimate your value. See that person who’s being promoted ahead of you, in spite of the fact that you’re as capable as them? The difference between you and them is that they’re not talking themselves down, and they’re not allowing themselves to be talked down. You’re better than you let yourself think you are.

• It’s a terrible idea to just let stuff happen to you. To this day, this might be my single biggest mistake: I let my career just happen to me. I’m trying to put an end to that for myself, and also make sure it doesn’t happen to anybody I care about. The funny thing is that I’d an opportunity to do something about all this a long time ago that probably would’ve ended up with me working in Workday much sooner, and would’ve ended up knowing the people I’m now friends with here much sooner.

Please, do not make the professional mistakes I did. If you skipped it, and it doesn’t matter who you are, go back and read Salary Negotiation Tips from White Men in Tech (and part 2). I sorely wish I’d read something like that a decade ago.

My plan going forward is to make up for that extra five years of unforced career stagnation by doing something about becoming a Principal Software Developer, which will mean going back to some of the things I did in college with people, and getting passed the raw panic I feel when I’m even remotely the centre of attention. It’ll also mean appreciating my value more. You should do the same.