Starting A Conversation

21 August, 2014 06:00PM ยท 8 minute read

In the past few years I’ve been engaging with more people whose work I respect and admire from afar and it’s been an interesting experience. Prior to that people I admired I generally COULDN’T interact with except on very rare occasions when I was in the same room as they were, and given my tendancy toward social shyness I’d just hold back and say nothing. With Twitter and Skype in particular it’s easier than ever to get into a conversation with people you admire but otherwise could never speak to. I’m sure this has been written about before somewhere but what follows is my take on the reality of interacting with those you admire and starting a conversation.

Admiration isn’t a 2-Way Street

If you love what I do and I don’t know you or what you do, then how can you expect any admiration to be a two-way street. Be realistic. It’s usually just in one direction from you towards them. That said mutual admiration is a wonderful thing just don’t expect it out of the blocks: if ever. Be realistic.

They’re Different That What I Thought They’d Be

No kidding. You don’t say? Everyone acts and reacts differently based on who they’re talking to. If they’ve never spoken to you before then why would you expect them to talk to you like they have to other people that they’ve known for years. Is that obvious? Apparently not because I’ve heard that sentiment a lot. Any conversation you’ve had in your head with them (admit it, you have haven’t you?) isn’t going to play out that way in reality. Relationships take time to build and interacting back and forth on Twitter a few times or listening to them on a podcast has practically zero additive impact towards an actual relationship with that person. The image you build of that person in your mind is always going to be different to what that person is really like when you finally interact with them.

Zaphod just this guy…ya know

I don’t care who it is: your friend, the Prime Minister/President, the Queen, a stranger on the train/bus, we’re all just people. The problem with admiration is that human nature tends to elevate that person to a higher level of being, whereby they could be considered to be greater-than-human: so-called putting someone “up on a pedestal.” The sad truth is that when you talk to people they turn out to be, well, just ordinary people that did something you respect. When you’re caught up in the excitement of talking with someone you’ve admired from afar your excitement blinds you to that obvious truth.

The strangest thing that I’ve been dealing with in the last few months is the shift in people wanting to talk to me. For the first time really in my life, strangers have approached me and nervously struck up a conversation either on Twitter, on Skype or in person, and been gushing about being able to speak to me and that has been because of the popularity of Pragmatic. To me, this is extremely weird. Historically I’ve never really been anybody of any importance or interest (beyond my close family and friends). The attention feels awkward coming from strangers but it’s been an educational experience from the point of view that now I have my head around what I must have looked like when I previously sought a conversation with someone I admired. It’s flattering but it’s a bit creepy if you’re not careful about how you approach it.

If you are going to engage with someone you respect then try your best to talk to them like a person and keep any gushing to a minimum. Remember that Zaphod Beeblebrox is just this guy…ya know

You Can’t Always Invite Yourself

“If you don’t ask you’ll never know,” and “What’s the worst they can say? No?” are expressions I’ve heard time and again. Honestly don’t be angry, upset or annoyed if your attempts to strike up a conversation with someone don’t end the way you wanted them to. The people you admire have their own lives, their own stresses, probably including but not limited to their jobs, debts, spouses, children, in-laws and alligator swamps they need to contend with every, single, day. You are merely a tiny blip on a distant corner of their lifes radar. Remember that.

If someone respects what you do it’s always easier to strike up a conversation. Several of the guest-hosts that have appeared on Pragmatic did so because they listened to a few episodes and enjoyed the show. If not for that, they would never have agreed to talk to an otherwise complete stranger. Perhaps they would have agreed to chat given time and a lot of interaction back and forth. Perhaps not. There’s no point getting upset if they don’t respond or can’t respond. The best you can do is put yourself out there, be nice, be polite and courteous, oh yes, and be yourself. (hopefully there’s some alignment amongst those pre-requisites)

Ultimately though if you want to chat with them, you can’t always just invite yourself into their lives and expect to be welcomed. Send them an @mention on Twitter, an email or a message through their site feedback form (if they have any of those) but don’t expect a reply. Why shouldn’t you expect one? Imagine if someone like John Gruber typed a 140 character response on Twitter to each of his followers at 85wpm, 6 characters per word (23 words/tweet, 3.7 tweets/minute), 300k followers would take about 56 days, 7 hours, 21 minutes assuming no toilet breaks, no network delays and no fail whales. That’s not really a committment ANYONE can give. Ask yourself this question instead: Why should they respond?

What’s The Point?

People want to have their voices heard. The more voices there are in the crowd the harder it is to hear any one voice. Just because no-one is answering or responding to you today, or reading what you write today, or listening to your podcast today, doesn’t mean they won’t tomorrow. If you’re intent on being heard and you have something to say then stick with it. It took 4 years of blogging, 2 years of podcasting both of them on again and off again before any volume of people started listening to me. Even now my listenership/readership is relatively small compared to some in the tech-space-bubble-whatever-you-call-it and that’s perfectly okay.

The reason I’ve chosen to write this down (type this in? I guess) is I came across some people I admire (with small followings) on Twitter that expressed their anger and frustration with creating their own content and not being noticed. They wanted to be part of a conversation with others they respected on the internet but it wasn’t happening. That triggered my memory of how frustrated I used to feel years ago when no one was really listening to me. My recent interactions with people I’ve admired from afar got me thinking about what changed. I haven’t been annoyed or upset about it for years now - since well before Pragmatic and hence well before many people really paid attention to me. So what changed?

Do Good Work And You’ll Get Noticed?

This is where I lose people and we get the “privilege” accusation or maybe even an eye roll or ten. Why that happens is that I’ve lost track just how many times I’ve read and heard that sentiment. The problem is that the superficial interpretation of that sentiment is easily derided and the actual point is lost on a lot of people - myself included until the past year or two.

Of course if you’re not a narcissist perhaps it just doesn’t matter. I tend to think though that all people want is to be heard by somebody else and that alone does not qualify you as a narcissist1. How much energy you devote to starting a conversation with others is your own personal choice. All judgement aside, assuming you’ve made it this far, what’s the best approach?

If we assume that the people you want to notice your work have one minute each day to notice something new, and there are thousands of other people creating content just like yours, the moment when their eyes and your work align has to be some of your most impressive work or that moment will pass and you’ll be overlooked. The best approach is to simply keep at it and in time, eventually, people will notice. Maybe even the people you want to notice.

Perhaps then the expression should be: only put out your best work, tweets, blog posts, podcasts, software, graphical designs so that when your moment comes, the people you want to notice your work will see the best you have to offer. There’s still the possibility that the best you have to offer isn’t going to be good enough, but that’s really just a function of who you’re trying to impress. But once that moment happens, planets align, your work gets noticed, then the conversation can begin.


  1. Sorry Jordan. [return]