Rise of the Úlluminati

I originally wrote this piece way back in April 2015, just after returning from speaking at Úll. It ended up not being published, but I figured since I’m preparing for my trip to Úll 2016, I would put it up here instead. And hey, first post on my blog in six years!

I wrote an article in 2014 for The Loop magazine about my experiences at the Úll conference in Ireland, and the mental state of the indie developer in general – or at least mine. You can read it here.

I’ll wait.

You didn’t read it, did you? Ok, fine, I won’t take that too personally. Well, it was about how at Úll (and at NSConf, and at WWDC), I was suffering badly from imposter syndrome – the feeling that I didn’t belong amongst the other attendees, that I was just not good enough to be there. As I wisely said then:

“I’m a successful developer, I make a living doing this, I’ve worked for Apple, and I’ve been around in the Apple world for a very long time. I have the respect of a lot of people in the industry, and call many of them friends. If I can still feel like a complete outsider when I’m walking around a conference of my peers, then I bet a lot of the other people there do as well.”

I had been considering writing a follow up already, as my experiences this year were quite different, and I wanted to document my progress. But what really got me is that one of the other attendees said in a quiet moment, that he’d read the first article last year and it had struck home with him, and I think it had helped. I’d had literally no unsolicited feedback about the original, so I didn’t think anybody actually cared or had even read it. Hearing that it had made even a small difference to just one person, I felt honour bound to write some more.

What a difference a year makes.

I’ve recently been trying to work on a bunch on social phobias I have, primarily a strong fear of public speaking, or really doing anything in public that draws attention to me. Three years ago, I’d agreed to speak at NSScotland, and I backed out with only a month to go, because I just couldn’t face it. But I finally agreed again the next year, and while I was still terrified at the prospect of standing up in front of a hundred people, I managed it. I spoke again at NSConf the next year to nearly three hundred, and the fear was a little bit less. I did another NSScotland after that, and was beginning to believe in myself. I’d also been on a number of podcasts, again trying to face up to the same kind of anxieties.

So, when the fine folks at Úll asked me if I’d like to talk this year, I didn’t hesitate. I was still very nervous on the day, and simultaneously under-prepared (not enough rehearsal by far) and over-prepared (slide deck polished obsessively over a period of about a month). If I’m honest, it kind of helped that both John Gruber and Jim Dalrymple had cancelled speaking at the eleventh hour, because I knew I wasn’t competing with them in terms of my talk, and they wouldn’t be sitting in the front row watching as I gave mine either.

Still, there were many other people that I really respect both speaking and sitting in the audience. However, despite this being the highest profile speaking gig I’ve had, I didn’t get paralysed by the sheer panic that had gripped me before. I didn’t want to let down the Úll organisers who had given me the stage, but I genuinely thought for once “I’ve got this”. I did a full rehearsal on stage in the morning to an audience of one – thanks Baz – and it went ok, and I was kind of, almost, looking forward to giving the talk.

There was a certain degree of uncertainty as to which day I was going to have to give it, but thanks to a cancelled flight out of Philadelphia – which I had nothing to do with – some of the speakers were delayed and I was back on for a slot on the first day.

It then turned out that not only was the talk being recorded for posterity, it was being live-streamed via Periscope, something I found out right before I was due to go on stage. I started to think that maybe I shouldn’t have included a few of those Apple anecdotes…

People said to me afterwards “you seem so confident speaking, I don’t know why you were so nervous”. Let me tell you, the key word in that sentence is “seem”. It’s really just a performance. For want of a better explanation, I play a character on stage that’s almost me, but is much more self assured and better at public speaking. Boy, can that person give a talk. So, I play that role. I don’t know if that’s normal, or if I have inadvertently revealed myself as a high-functioning sociopath, but that approach works for me, and not just when giving a talk. When in doubt, pretend to be the person you want to be, and the rest of you will catch up eventually.

One thing that I hadn’t quite realised is how powerful the feeling of euphoria is after getting off stage. The relief of having actually done it, combined with the (modest) adulation of the crowd makes for a pretty good high. I had a small insight into why performers actually like to perform in front of crowds, even if they are similarly introverted and anxious people at heart. Throw on the mask of a stage persona, go for it, and boom – lovely, lovely, dopamine!

But the point is, if you looked at me on stage and thought to yourself “I could never do that”, let me tell you that I thought exactly the same thing three years ago. The key is to gradually push yourself outside your comfort zone, and eventually you might find you can do more than you ever believed.

I thought that was me done for the conference, and that I could now relax, but no. I faced a far, far, greater challenge to my nerves the next day, but I’ll come back to that in a minute.

To get back to imposter syndrome, this year was different. Some of it might be down to gaining some confidence in my presenting skills, and having had a very good year in terms of PCalc sales and overall visibility. But I think being a speaker changed the dynamic completely, so it’s hard to compare like for like.

I did my talk early on the first day, so for the rest of the conference pretty much everybody in the building knew who I was. People came up to me and praised my talk. I seemed to have been accepted into the inner circle of speakers, and I made sure I sat with the popular kids at lunch and dinner. I was famous. I’d made it.

Yes, my problem had switched from imposter syndrome to the other extreme – being-an-asshole syndrome. Lots of people wanted to talk to me, and sometimes I kind of just wanted to hang out with my cool new friends and talk to them instead. And the worst part was they were people who I could tell shared the same social phobias as me, who were trying hard to mix, and I wasn’t always the best at inviting them into the group. I was doing exactly what I thought had been done to me in previous years.

I had a shared moment of clarity late one night with a fellow speaker that we were actually terrible terrible people and I tried to curb my isolationist behaviour after that and mix a bit more. But it was something of an insight into how quickly I could go to the dark side, with just the merest brush with celebrity.

But I was brought back down to Earth with a bump the next day. I’d been asked by Serenity Caldwell if I’d do a cameo in The Incomparable radio drama they were putting on in front of an audience as one of the special features at the conference. Just a couple of lines, she said. No problem, I said, I can do that – not entirely believing the words coming out of my mouth.

Now, at some point between me agreeing, and the actual rehearsal, I had possibly misheard a critical piece of information, and I was no longer just doing a cameo, I was actually now a supporting character with multiple pages of dialogue. And this would involve actually acting. And doing an accent. My rehearsal performance was not the best. Russell Crowe does better accents.

Now, the last time I can remember acting would be something like thirty years ago, and the last time I put on an accent was approximately never.

The irony of getting an actual Scottish person – who doesn’t have a strong Scottish accent at all – to play “Angus McInnes”, a rough adventurer with a thick Scottish accent amused me almost as much as it terrified me. At this point, I was so far outside of my comfort zone, I would need to go through customs and immigration to get back in.

Oh, and it’s all being recorded and the video is going up on YouTube and Vimeo later. Ok, universe, I get it – this is because of the whole believing-my-own- celebrity thing I did, right? Fine, let’s do this, I deserve it.

Something about the culture of Úll got me through it anyway. People there want you to succeed when you’re up on stage, nobody wants you to fail. Folk laughed at my line delivery, and I think with me. In my head it was basically a Scottish person trying to do an impression of a Canadian person doing an impression of a Scottish person. James Doohan would be spinning in his grave if his ashes weren’t already spinning around the planet. I did apologise at the end to any actual Scottish people who might have been listening. Please let me back in the country.

Thankfully, as I type this, the video has yet to appear, and I can always hope for some technical difficulties that will permanently prevent it from ever doing so. But despite my nerves, I did enjoy it, something I would never have thought possible. Angus McInnes will return.

Coming back from Úll was an interesting experience. It took me a day or two to decompress, and I needed extreme peace and quiet for a while. Having effectively spent five days in a sealed environment with a few hundred people, the oddest experience was walking outside and not recognising anybody and not being recognised either.

But I’m famous! No, no I’m really not. Oh.

Paul Campbell, one of the organisers of Úll, has talked about the mood crash they all experience afterwards, when it’s all over and there’s just the quiet left. I think I only got a small fraction of that as a speaker, but it still hit pretty hard.

The insecurity all returned pretty quickly. I watched a recording of my talk, and I could see every time I stumbled over a line. I thought that I’ve definitely run out of anecdotes now, and I could never do another talk – all I do is repeat myself. I was only at Apple for under four years, I’m making a big deal of it all, nobody wants to hear this stuff. And I saw a few negative comments online, by people who hadn’t even seen my talk, saying I was taking credit for stuff I didn’t do.

But, it represented some small progress. I expanded my personal comfort zone empire to encompass a few new territories. For a brief moment, I became one with my confident alter-ego, even if that guy can be a bit of a jerk at times.

And you too can be a bit of a jerk too, if you really try. No, wait, wrong message.

The point is, we’re all faking it to a certain extent. All you see is the surface, only what we allow others to see. Underneath, everybody is the same mess of emotions and insecurities that you are, and all just as complicated and conflicted as you are. Lots of people that you think of as extremely confident, who do things you think you could never do, share the same feelings you do. But we never talk about it, and you can’t see it. It’s certainly not just you.

But, to borrow a phrase from a more important cause, it gets better. Just by pushing yourself a little bit to do things you’re uncomfortable with, you’ll eventually get used to them. It might take years of practice, but you can do it. I never thought I could speak in public, and I’m now getting to the point where I might actually admit I’m not too bad at it. Maybe. On a good day.

And perhaps one day, you’ll be a world-famous-in-Killarney speaker at a conference yourself, and some nervous person will come up to speak to you. Try and remember then what it was like to be on the other side of that conversation.

As for me, I’m going to keep improving, slowly but steadily. Next time you hear me on some podcast, see me up on a stage, or hear me murder a Scottish accent, just remember that underneath it all, beneath whatever confidence you might see or hear, I’m still just as nervous as you are.

State (of Mind) Machine

Reprinted from issue 28 of The Loop magazine from March 2014, with thanks to Jim Dalrymple

It seems ironic, that despite our invention of near-instantaneous global communication, we are still not the best species on the planet at actually telling each other how we’re feeling. Probably not even in the top five. Instead, many of us actively hide it from those around us. We say what we think we should be feeling, because everybody else around us seems to be perfectly normal, and we don’t want to be seen as the crazy one.

I’ve just come back from two very interesting – and quite different – tech conferences over the last month and a half. NSConference in Leicester, UK, and Úll in Kilkenny, Ireland. I spoke at the first one, and barely slept at the second. I enjoyed them both immensely.

And yet…

Surrounded by some of the best and brightest people in the developer community, I had the nagging feeling that I shouldn’t really be there with them. I’ve had the same feeling at WWDC for years now. As I stood backstage at NSConference, about to give my talk to three hundred people, telling them the story of my professional life, I thought to myself, “I’m just not that important, will people even be interested?”. Right at the moment I walk onstage, it will turn out there had been some horrible misunderstanding about my presence there, and Tim Cook will appear from the wings and tear up my developer agreement in front of everyone.

Later in the conference, I was talking to one of the other speakers, and it turned out that they felt exactly the same way – if perhaps not that specific detail about Tim. That made me wonder how many of them had similar thoughts. Maybe all of them did at some point in their careers. Maybe a significant number of people at both conferences looked around at the other delegates, and thought “I shouldn’t really be here”.

This feeling is common enough to have a name, “Impostor Syndrome”. A highly scientific glance at Wikipedia suggests that “two out of five successful people consider themselves frauds”, but I suspect that number could be even higher in the developer community. We never talk about it, so we think it’s just us. And what if you haven’t had any real success yet? It seems like everybody else has. “Why are you even here?”, their faces seem to be saying.

Logically, I knew, after the twentieth person came up to congratulate me on my talk, that they couldn’t all be in the pay of some shadowy organisation that had the mandate to tell poor speakers that they were better than they actually were, for nefarious reasons unknown. Logically, I knew, my talk probably was pretty good. But even now, I just edited that last sentence from “very good” to “good” to “pretty good”. And then added the “probably” for good measure.

Part of this is an inability to take compliments well. They make me feel vaguely uneasy at best. After a lot of them, I start to not really hear them anymore, and just focus on the negative ones. It’s the same problem of ninety-nine five-star reviews, and the lone one-star review that gets under your skin. Or worse, people not saying anything at all. Of course I have searches set up for the mere mention of my name and my products, and I wonder occasionally if I should create an account on Secret to see what people really think about me. There’s probably nothing there, is the likely answer. Basically, both the presence and absence of comments about me makes me nervous. Even genuine success makes me somewhat anxious, because then you’re more visible and you have further to fall. But I still check the chart position and sales of my apps every morning, even though it often pains me to do so.

These kinds of anxieties are probably some of the things that make me a great developer, because I always want my apps to be better than they are now. And they also prevent me from typing the words “makes me a great developer” into this window without it sounding very wrong and self aggrandising indeed.

A dislike of such self-promotion also makes it quite difficult to write marketing copy. I find it much harder than writing the software in the first place, because you have to basically say “hey, this is really really awesome, you should totally buy this!” instead of “well, I think this is okay, but I could still really improve some parts of it…”, which sends something of a wrong message.

All this got me thinking about the state of mind of the software developer in general. Particularly those of us that work for a small company, maybe as the sole developer or designer. Our work is a direct extension of ourselves.

We want things to be perfect, we’re control freaks, we’re obsessive. We spend a day designing and redesigning a single comma, because it’s just not right yet. And when it’s absolutely perfect, we’ll still keep going a bit longer, because we know there’s a magical place beyond perfection we can get to if we try hard enough. Spoiler alert, there isn’t. And we hate finding out after we’ve shipped it that we’ve missed some blindingly obvious bug because we’ve spent a day looking at a single bloody comma…

If you create anything at all – be it stories, music, drawings, apps, people, or even whole conferences – it’s a part of you. If somebody criticises your work, it can hurt like they are criticising you personally. That’s completely normal. Indeed, I suspect people who don’t have any kind of emotional response to such things just don’t care about their creations, or are, in fact, complete sociopaths.

It seems clear that my own creative abilities are directly linked to my mood, and my mood is directly linked to the success or otherwise of my creative abilities. Now, imagine that instead of it just being an annoying one- star review, or a bitchy email from an entitled teenager, you’re getting sent piles of documents from lawyers, your whole company seems to be in danger, and it sounds like you could lose it all. That happened to me, starting almost exactly three years ago.

A so-called “non-practising entity” threatened, and eventually sued over an alleged patent infringement in PCalc. I’m not going to go into any of the details here, but you’ve probably heard of them. I didn’t write any code for about six months, and considered getting out of the whole business altogether. I know I wasn’t alone – at WWDC that year spirits were pretty low amongst some of the other affected developers. Beer was drunk. Suddenly, our nice world of writing the best apps we could, and hoping that people liked and bought them, had become much more complicated, and real, and unpleasant. In the end, after three years of stress and time that could have been spent writing code, that particular problem was resolved. Not to my satisfaction by any means, but it has gone away now. It was a long and dark road back, and I still blame those events for a lot of things, both personally and professionally.

As I write this, things are looking up. PCalc 4 just came out for the Mac and has been warmly received. I expected something of a backlash, because it was a paid upgrade, but so far there hasn’t been a single complaint. In the process of creating it over the last four months, I’ve learned a lot about writing modern Mac apps, and I can’t wait to add new features to both the Mac and iOS versions as they keep popping into my head. I realised recently that I’m actually enjoying writing code again, and it’s been a while since I could say that. Apple has been featuring PCalc on the front page of the Mac App Store for over three weeks now, and it has forty seven five-star reviews. And one four-star review, but we won’t dwell on that too much.

Anyway, the point I’m trying to make is, if you feel like any of this, you are not alone. In fact, you are probably in the majority. I’d wager that some of the best people in this business have similar thoughts. The links between creativity and certain personality types are well proven – to a certain extent, it’s why we’re so good at this.

I’m a successful developer, I make a living doing this, I’ve worked for Apple, and I’ve been around in the Apple world for a very long time. I have the respect of a lot of people in the industry, and call many of them friends. If I can still feel like a complete outsider when I’m walking around a conference of my peers, then I bet a lot of the other people there do as well.

Once you realise that many of the successful, confident people around you are just faking it, it makes things a little easier.

We’re all the crazy ones, here’s to us.