My coolest title right now is “Instigator of Awesome” at Awesome Ottawa. So what’s Awesome Ottawa? It’s a group of 10 trustees and a Dean of Awesome, and every month we give away $1000 to enable something awesome. So far, we’ve funded an art-flash-mob, a living-evolving installation, a 350-org climate change event.

When Levannia asked me to give this talk, I thought “how am I going to talk for an hour about starting Awesome Ottawa! It’s not a very interesting story”.

The reality is, that I decided to do it, pitched it to some people, blogged about it, about within two months we were giving out our first award.

See! Boring!

So instead what I’m going to do is talk to you about some things that I learned along the way, that have enabled me to do things like this. I don’t have it all figured out, and it’s not all easy – if you want to do something awesome, you’ll have to learn to fail, and be okay with that. Not everyone will like what you’re doing. Not everyone will like you, period. There’s times, and I’ve definitely had them, where I question why I keep going, why I keep doing what I do – but I persist. I’m going to try and explain why.

1. Give yourself permission.

There’s a great book by Tina Seelig, it’s called What I Wish I Knew When I Was 20 (Amazon). The main point that she makes in the book is that you have to give yourself permission – so succeed, to fail, to do anything of note. I’ve started three things now – Awesome Ottawa, CompSci Woman (a blog written by and for women in computer science), and WISE at uOttawa (that was really more of a resuscitation). Other people were really instrumental in every one of those things – I’ll get to that later – but first let me tell you why I started doing these things.

I worked in a crappy job. The person above me got fired, and my manager promoted this other guy, not me. I was pretty disappointed by this, and then this guy was not capable of this job. He was also kinda a drunk, and guess who picked up the pieces? Me. So I spent the summer proving to myself, and I hoped my manager, that I would be better for this position.

The following year, I had the weirdest “interview” with my manager. She was completely inappropriate, and I was so stunned by this, and so confident that my performance spoke for me being a better fit for this job that I never mentioned the guy’s drinking problem. You can guess what happened. I didn’t get it. Apparently the guy actually did a semi-decent job. I ended up in Shanghai (anther story).

And I decided that I didn’t need to wait around for someone to say, “OK Cate you can do this now”. I realized, that my manager at that company was never going to say that to me – she managed us remotely, and the people who I had actually worked with knew I would rock at it, which is what was important. So I knew that I was capable of it. In short – I gave myself permission to do something. And I did.

2. Say Yes. Then Learn to Say No.

A friend told me the other day about a survey that had found that the reason why most Canadians don’t volunteer is because no-one asked them to. But opportunities to do things are everywhere – sometimes explicit, sometimes implicit. Take advantage of them.

For me, the more I say yes to things, the more opportunities present themselves. The more I say yes, the more I get a reputation as someone who does things – so when I want to start something, I have people who have noticed me, and people who owe me favours. That’s a good position to be in!

Saying yes has taken me to a bunch of different places, taught me new skills (like presenting in French!) and meant that I have met so many cool people. But at some point, I reach capacity and have to start saying no. I’m moving tomorrow, so things are even more hectic that usual so this week, giving a talk to you guys means that I couldn’t go to a meeting to talk about what WISE achieved whilst I was president. There are tradeoffs, because I’m not superhuman and I can’t do everything.

In a job, you discuss your responsibilities with your manager and that determines your priorities. But as the President and CEO of Cate inc., for what I do outside of work or school, I have to make those calls. Evaluating tradeoffs and saying no is hard when you’re an opportunity junkie. Do I always make the right call? Almost certainly not. But I have to make one.

3. Ideas are cheap, Execution is expensive.

Who has an idea for a product, or web service, or piece of software?

As a programmer, I can tell you that there are lots of non-programmers out there who have some “genius idea” that they think a programmer should build, for “equity” – a stake in the eventual, hugely profitable company.

The reality is that the company is rarely profitable, if it even gets off the ground. And programmers have their own ideas, which if they want they could implement. This is why people – especially programmers – get angry about patents, because you can literally patent an idea and the person patenting it doesn’t actually need to know how to implement it. To a programmer, implementation is everything. Ideas are 10 a penny. What does this have to do with starting an organization (or anything)? It means that it doesn’t matter how amazing your idea is, it’s nothing until you actually implement it.

And if someone else gets there before you, the idea was good enough that someone actually did it – so be pleased! And either get on board with them, or come up with something else and move faster. It also means, that it can be hard to sell your idea until you start doing.

We were the first Awesome Foundation outside the US, but we weren’t the first period. The fact that we have a network of people to ask questions to and this model has been proven made it much easier to get going.

4. Fail

Think about how big your comfort zone is. What are you OK with doing? Introducing yourself to a stranger? Going to a foreign country by yourself? Standing up and talking in front of a bunch of people?

Chances are, there is a whole world outside your comfort zone. I really recommend going to explore that, but it can be scary. Stuff outside your comfort zone is stuff you don’t know – and as you go off discovering it there’s a good chance that things won’t go to plan. You’ll fail.

You know in Harry Potter, how the bogart turns into Prof. McGonnagall for Hermione and tells her she failed everything – that’s her biggest fear. It’s no wonder Harry always saves the day, he’s OK with failing, and that makes him more able to take risks. Hermione might seem more successful, there’s no doubt that she is academically, but that’s within her comfort zone. For her to be successful in other ways, she had to learn how to fail.

When we first started WISE, we tried an event and people were really enthused about it… but then no-one turned up. I was mortified, and really questioned what I was doing. We haven’t run that kind of event again, but we run different things that were successful. We’ve learned what our members want, and that’s what we put on for them. It was a setback, but it didn’t stop us from achieving a lot of other things.

In the summer, the Awesome Foundation didn’t get many submissions. Seriously, we’re giving away free money and people weren’t even filling out the application form! That was rough, because you get to this catch-22 – you don’t fund anything, and no-one hears about you. But now, our numbers are up.

There’s this great lecture by Randy Pausch. It’s an hour – go watch it. In it, he talks about how when you hit a wall, have a set back. He says that walls are there to keep out the people who don’t really want it. So when you fail, and I hope you do because I think that a life without failure is a life where you didn’t push yourself – you look at your failure, you evaluate what you can learn from it. And then you keep going.

5. Find Something You Believe In

Making something happen can be hard. That’s why not everyone does it. It takes longer than you imagine it will. Or it’s harder to get people on board with what you’re doing than you expected. You fail in some way.

In these moments of doubt, you need a story to tell yourself that reminds you why you’re doing it. When I moved to Canada, I knew no-one. And I’m in CompSci, so you can imagine how many women I met – not many. I’m sociable, so I met people, but I mostly met guys. Which is fine, but I would get homesick for my Edinburgh apartment and my roommates there, and girly movies and pizza. And so I really felt this lack of community, in terms of women in CompSci – because when there are only a few, it’s hard to meet them. So in times of doubt about what we were doing, and whether we could manage it, and when we didn’t have any funding, I told myself this story. That we needed this community here, and I knew that first-hand.

Now I run CompSci woman, and it’s a similar thing. We ask people to post for us, and it’s going pretty well but sometimes we don’t make the three posts a week that I would like us too. It’s discouraging, but the story I tell myself is that CompSci is changing the world, and we really need a more representative sample of humanity building our digital future. I tell myself that young women need role models, and that’s what we’re trying to do.

You don’t need to succeed right away. But you need a story for those moments of doubt.

6. Trying to get everyone to like you is a sign of mediocrity.

Colin Powell said, “trying to get everyone to like you is a sign of mediocrity”. Be likable – it’s important – but the reality is, if you want to stand out and do something extraordinary, there are people who will try and tear you down for it. People might not understand that ideas are cheap, and think that you “stole” theirs, because you got their first. If you do things, people might need to attack your success in order to excuse their own inaction – like “oh Cate, she just got lucky”.

I’m not going to lie – it sucks. Who’s had something bad said about them that they knew wasn’t true? Who was hurt by it?

I had this recently. I really thought that I left high-school a long time ago, but apparently I was wrong! I had someone I used to be friends with telling people (people I know!), basically that I was doing I terrible job with Awesome Ottawa. Of course it gets back to me, and of course I was upset by it. The way it all played out was interesting, because I tried to ignore it and just keep running around doing my thing, and in the face of my non-response, this woman managed to make a different story in which I played the villan.

It was difficult, but I did have the support of the board and it’s all worked out for the best now. But at the time? Horrible. And honestly, I could not comprehend why someone would behave like this, when they could have pinged me for a cup of coffee and got everything they wanted. I was talking to one of my mentors, and we talked about whether I could have done more. Of course I could – you can almost always do more to resolve situations, you can always try to reason with someone, no matter how determined they are to dislike you. But in the worst 2 week period of this, I went to New York to pitch to top IBM executives with my team. I interviewed at Google, and filed two patents (within IBM). I got on a plane, and went back to Europe. So the question is not, “could I have done more?” – it’s with these other priorities going on, should I have. I think I made the right call that time.

Haters will hate. I always take the time to consider if they have a reason for it, is there anything I can and should do to resolve it. But – if someone is determined to dislike you, they will find a reason to.  Anything you do can, will, be used against you. So at some point, you have to say – No. I’m doing what I’m doing, and I refuse to let you distract me.

Check out Leadership and Self-Deception and The Anatomy of Peace (both Amazon) for insight on managing interpersonal conflict.

7. Your Network is Everything.

I mentioned mentors earlier. Mentors are so important. Connect with people who have a little more experience than you in what you’re interested in, and benefit from their wisdom (and mistakes!). They’ll help you pick yourself up when you get knocked down.

There’s this idea of homophily – there was a study that found that if you hang out with people who are heavier, you’ll gain weight. I think, if you want to do something, you need a circle of people in your life who do things.

I’ve found Twitter to be a great way to connect with people like that – my friend Kelly, our new Dean of Awesome, and I connected on Twitter, but we became friends and work out together and hang out. She’s awesome. And she’s a great person to know, because she’s interesting and she does stuff, and she knows people. So when I’m having a crisis, she knows the story I tell myself and she has others to share with me. Recently, I got this nasty, anonymous comment on my blog. I was shocked by it and wrote a thoughtful response and doubted myself and what I’d written. Kelly called it right away. A couple of hours later, she was proven right. I really find that the more great, interesting, awesome people who do stuff are in my life, the more awesome I can do.

When you’re running something, you need other people to help you. With WISE, I had three really key people and we all have different strengths. Samera was amazing with bureaucracy. She can navigate piles of forms that would make me cry. Rachelle would take care of our communications. I basically live in fear of my inbox. Levannia is great at details, whereas every time I go anywhere and book my hotel and flight separately I’m double, triple checking dates anxious that I’ve messed it up in some way. They are all talented in areas that I am not. I might be more able to stand up in front of a room of people, or at networking, but that’s not enough and I couldn’t have done it without them.

I’m a programmer, and I love to code. This also means I’m practised in looking at a problem and decomposing it into manageable bits. But – this makes me bad at other things. I’m logical, and I don’t deal well will irrational behaviour. Aside from anything else, I find it inefficient. Philosophical arguments are another thing I’m terrible at. I got into a debate at one point with some guy, and he was talking about what the Ancient Greeks thought about something. And I was like, “they thought zero wasn’t a number!” So this guy goes off on one about how zero represents the absence of something and so in some sense doesn’t really exist. But as a programmer, the absence of something is a really important concept best expressed using a numeric datatype.

The point I’m getting at here – think about what you’re good at, and what as a result you’re not good at. The better you know yourself, the better you can pick a project that is a great fit for you – for example, one of the things that appeals to me about the Awesome Foundation is the lack of bureaucracy – and the better you can find a team whose strengths complement yours.

8. Give Up Control – Ask in order to Leverage

When you start something, you have this vision of what you want it to become. That’s great – and important – you need to have an idea of what you’re working towards. But at some point, you face a choice. You can build a tiny, solid steel, structure, completely controlled by you. Or you can give up some control and plant the seeds for an organization that will grow bigger than you could do alone, do different things you could never have imagined. There’s a risk that it will die. But – that’s another tradeoff you can make, because giving up control allows you to move on to other projects that excite you.

I stepped down from WISE and Levannia took over. I know that things are going to change as a result but I’m OK with that – I trust her to do a good job, I mentor her and encourage her. But ultimately, she’ll have her own vision – and that’s a good thing. I don’t want to stay in grad school forever, running the same thing!

With the Awesome Foundation, we have a very flat structure. As Instigator of Awesome I go around getting excited about things, and do a little more organization stuff but every trustee puts in $100 and every trustee gets a vote. I can say “I think we should do this”, but if I’m outvoted, I’m outvoted. My role here is not really a leader, more of a facilitator. There’s an important distinction.

If you want other people to help you, you’ll probably have to ask them! Asking for things is hard. Asking someone to join the board of the Awesome Foundation was terrifying for me at first – “hey! How about you give $100 every month to some crazy idea that may or may not work?” – I’ve got better at it with practise (and I don’t say that!). But you need to learn to ask for things, for starters you’ll need to ask for help.

Early this year I read this great book, Women Don’t Ask (Amazon). I highly recommend it. And I started asking for things, for instance the other day I asked for a t-shirt.

I know, random. But at Grace Hopper the Yahoo! people had these awesome t-shirts that said “I code like a girl and I’m PROUD of it”, and I wanted one really badly! It happens that I know a guy who works for Yahoo!, in fact before he moved I would take care of his cat. So I asked him if he could get me one of these t-shirts and he did.

When uOttawa asked me to create a programming curriculum for a workshop we run for high-school students, I thought it sounded like a cool idea. But – I’d already created a proprietary curriculum and wasn’t really interested to do another proprietary one. So I asked if we could open source it. They agreed to my terms, and now anyone can use the materials I’ve created.

I’m still afraid to ask. But I’m getting better at it. So try it.

And, pro-tip, start being more attuned to people’s implicit asks. When someone you think is awesome talks about this new project they are starting, introduce the topic of how you can help them before they have to. And then follow through.

Because – the real secret I’ve found in asking, is that it’s easier to ask when people want to help you because they’ve seen you paying it forward already. Or – even better – they are also attuned to implicit asks, and you don’t need to.

9. Share and Engage

Share what you are doing. It doesn’t matter if you’re still working things out – share. If you fail – share what you learned. When you succeed – share who and what helped you.

Document your path so others can follow. I use a related posts plug-in on my blog, so sometimes I write something and something I forgot I’d written pops up – past me giving advice to future me. Maybe I’m feeling discouraged, and I find a post I wrote another time I was discouraged and think about how I got through that. Maybe I read something that reminds me just how far I’ve come.

Even if you blog and no-one is reading, it can be useful. But most likely they will, and they you’ll have this new way of connecting with people and following their projects, successes, and failures, too.

Twitter is another good tool for connecting with people on the internet. 140 characters or less is way less intimidating than an email. Say hi! Chances are whoever you’re interested in will be happy to hear from you.

Check out my mentor Sacha’s blog – Living an Awesome Life – she has a lot of good posts on sharing and why it’s important.

10. Don’t Believe the Hype

There are so many people who come home from work at 5 and spend the evening watching TV, that if you do anything, people will start telling you how awesome you are.

Appreciate that, but take it as a thank-you. Every moment you spend believing it is a moment that someone else is overtaking you.

Someone tweeted something recently, and it was completely ridiculous. I won’t repeat the whole thing here for anonymity, but suffice to say the words “I’m so awesome” were used. I have no clue what this person does, but now I have zero interest in finding out. A couple of other people I know saw it and we laughed about it – her credibility was damaged by this gratuitously self-aggrandizing tweet.

The most impressive people don’t seem to need to talk about how gosh-darn impressive they are. They’re too busy getting on with things. Kelly and I were talking about this recently. At work, you need to document your achievements and put them forward to your manager for promotion. In the outside world, especially on the internet, if you’re awesome, people notice. Maybe not as fast as you’d like, but they do.

At my leaving party, this guy showed up and said that he’d wanted to meet me before I left. That was really cool, it totally made my day. That kind of moment is worth more than a million people agreeing when I say how awesome I am. I’m taking it as a thank-you, and encouragement to keep going. But I don’t believe that I did anything special, which is perhaps key to doing things at all. If you only believe that someone extraordinary can start something, you’ve set the bar way higher than it needs to be. Anyone can do it. Honestly. I did. You can too.

Someone said something really obnoxious to a friend of mine recently, and a group of us were talking about it and another girl nodded sagely and said, “low self-esteem”. I think she’s right. I could have stood up here and made the boring story last long enough, but I’m okay enough with how I’m doing to share the myriad ways in which I’ve failed. Because it’s more interesting, and because, I hope, more useful.

Apparently, Edison said about the invention of the lightbulb, “I have not failed 10,000 times. I have successfully found 10,000 ways that will not work”.

Every time we think we “fail” we can learn something important. These are just my 10, but don’t take my word for it – go and learn your own.