There’s only a week left in November so it’s a little late for doing a NaNoWriMo post but I figure better late than never…

For those of you who aren’t familiar with the awesomeness that is National Novel Writing Month, it’s exactly what it sounds like – people from across the US (and now abroad) get together and collectively write a novel. It’s a great experience and I highly recommend it. (So does Lifehacker!)

For those of you going through it now, here’s an email I wrote to a family friend (middle school student) looking for advice on her first NaNoWriMo. Might be just what you need to get across the finish line. Keep writing!

NaNoWriMo Poster

Hey Family-Friend’s-Name,

Thanks for reaching out! It’s great to hear that you are doing Nanowrimo. I tried and failed to do it in 2006 (got to 35,000 words) and tried again in 2009 and was able to do it successfully.

The hardest part for me wasn’t finding the time to write, it was coming up with enough words to actually get to 50,000.

1) Give your story a lot of twists and turns.

I’m not someone who likes to do a lot of description. I’m a dialog and action kind of writer so I really needed a lot of side plots to the keep things going.

A piece of advice I often hear about fiction writing is to make sure your main character is always has a goal in mind and keep throwing obstacles at him/her that they have to overcome. Don’t make it easy for your character to get what they want!

2) Write what you know

My first novel was a modern sci-fi thriller which I found interesting but there was too much I didn’t know to write a good book. For example – if you are a regular person, what’s a reasonably realistic way for you to get a bunch of weapons on the black market? I’ve never done this and would have to spend a lot of time researching it on the internet. I had a lot of questions like this in my first novel and this slowed me down. You gotta keep pumping out words!

My successful novel was a fantasy novel. This worked a lot better because I read a lot of fantasy growing up and you really do get to just make things up as you go a long since it’s your book and your world, things can work however you want (with regards to magic, dragons, trolls, etc)

If you read a lot of a certain type of book, it’ll be easier to write a book in that style. Also it’d probably be a bit easier to have a main character close to your age or younger, than to write about someone who is 50 or 60, since it’s harder to understand what kind of stuff they deal with / think about.

3) Go off on tangents.

This is similar to lesson number one, but more specific. I think I had a couple sections of the book that were totally random. Sometimes I got really into describing something – like the history of an ancient tribe of elves. Almost like a story within a story.

But you can get even more random. I think in one part of my novel some random character starts talking and all of a sudden its a list of stuff I have to for work or a journal entry about how I’m feeling about living in San Francisco. Totally random, doesn’t make any sense.

But again, it’s your book and you’re allowed to do that if you want.

4) Write consistently.

Its 1667 words a day. That’s a good amount, but not crazy. I wrote basically on my train to work, my lunch break and my train home, plus spent time at night and on weekends writing. You will have to spend a lot of time writing, ideally with a keyboard instead of by hand, to get this book done. It’s a lot easier of you just do 1667 a day and not have to play catchup. That’s really demoralizing. So write everyday!

I hope this wasn’t too long and was helpful. Let me know if you have any other questions.


Sometimes it takes very specific moments for people to realize their intense desire to change (I wrote about these ‘focal moments’ in another post). A friend that I have a strong affinity to (we think alike in many ways and treat our work and life with huge amounts of enthusiasm and a touch of masochism) sent me an email about three epiphanies he had over a recent evening. He clearly had a focal moment and I wanted to share a sanitized version of this email for you guys.

How dissatisfied are you really with your appearance? Or your career? Or your chances at starting a startup? These are the words of a man who has drawn the line and is going to do whatever it takes to make shit happen.

I was dancing shirtless to crazy techno at a party with some friends amid a huge crowd of half naked energetic people. Strobe Lights, Fake Smoke, Stage Dancers, Energy.

Looking around the crowd I noticed more beautiful girls than I’m accustomed to seeing in SF. Dancing shirtless (with arms flexed and stomach pulled in) right next to an attractive girl I was also aware of lots of guys with smaller stomachs and bigger arms. I could probably beat most of the guys there in a fist fight but from just looking at me I didn’t seem particularly special and potentially even below average. There and then I decided that I had enough. I was never going to be in that situation again. Starting that day I would start a consistent training program focused specifically on biceps mass gain, abs, and reducing fat.

I’m terrible at closing physical distance. It’s not that I’m never able to do it but it’s something that I’m so aware of and so bad at that it needs to be fixed ASAP. I would call it my #1 problem. My friend started grinding against her later in the night and it wasn’t a big deal while I danced close to her but not touching – I was afraid to do it and didn’t know how.

So both an amazing night but also a call for action. I’ve been thinking about many of these things for a long time but now I’m going to be laser focused on them. Athletics, Appearance, and Social Skills are only one side of the coin but I need to stop making excuses and work on them.

That night I went to sleep at 5 and that morning I got up at 8am to go to Muay Thai. Then I lifted weights. Then I climbed. Then Monday I went to Crossfit. I was scared of it like I always am for some reason but I went and I did it. Then Tuesday I sparred even though it scared me even more. And I’d love to say I kicked ass or really overcame most of my fear but I didn’t. But I did persist and I’m going to keep persisting and pushing. I don’t know if I really want these things as bad as the quote is describing – I don’t think I’m there yet. But I want to get there.

Whenever someone subscribes to The Art of Ass-Kicking (which you can do here!) I send them an email asking what I can blog about that would serve them. This post is inspired by email subscriber Simon Payne, who writes from the Czech Republic asking about self-coaching:

I’d love to know more about self coaching. I was training martial-arts under several teachers and masters yet it always came to me that I must be the ultimate coach to myself. I didn’t ever fully relied on anyone. And have some bad moments when I listened too much for advises of others. The point of having a couch is to have someone who is hard on you and reminds you and forces you to do the important stuff. And now, more than ever before, I need to train myself on my own. Not just in sports, but it’s much easier to create some routine in sports and then relate to it in other activities.

So my question would be: How can one be the best coach to himself?

… or at least make the inner coach better, without betrayal, not too soft and focused.

By the way, I’ve signed up myself for the 100push-ups challenge. You can see my progress here:

And here’s my response:

Hey Simon,

Thanks for the email. I’d be happy to try to answer your question – it’s a good one.

I think what you’re asking is really how you can stay motivated and make sure you do the things you know you need to do to succeed. I think there are four things involved in this:

  • Pursue activities that excite you and make you happy
  • Feed your mind with motivational stuff
  • Set up systems to support your efforts
  • Eliminate things that hold you back

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Got an email recently from a guy named Scott Balster. He had pinged me on Twitter earlier asking if he could pick my brain about something. [1] I agreed and here’s what he sent me:

I am building a concept called Employtown ( ) where basically the premise is to give job seekers a platform to build a digital billboard of themselves, promote their search among their networks, and receive bids from employers.

I have done some testing and with the signups I have received from the landing page and want to move forward. My hold up is that I have a limited technical background (have used Joomla and other open source programs). Basically, my options are:

  1. I can learn to program to build it myself in phases.

  2. I have a developer who can build it for 10-12K (the complete spec that I laid out)

  3. Or find a technical co-founder who wants to work on the project.

  4. Find a developer who can build it in stages and then test the features and user metrics to know when to adjust.

What are your thoughts in this situation?

I’m glad Scott emailed me. Personally, I don’t find the idea super compelling, but I’ve learned not to get too hung up about initial startup ideas, because they usually change. Plus he is a business cofounder and thus holds a special place in my heart. I spend a lot of time on HN and while the community is great, they tend to enjoy ragging on non-technical people who want to start companies. Though perhaps they just need to be approached the right way.

I want to help Scott – and I think his challenge is more than just how best to build the product, but in fact are three-fold:

1) Customer traction. You said you have some signups. How many? Are people lining out the door to get this? How do you know if this product is what people really want? [I shared with him a copy of The Entrepreneur’s Guide to Customer Development, which readers should really just go ahead and get it. Great read]. I know you didn’t ask for this and perhaps I’m not seeing the vision, but I don’t know if online billboards are going to resonate with hiring managers. Getting proof of customer desire (not just from jobseekers, but HR people) is key.

2) Technical ability. You don’t know how to build what you want to make right now and you’re exploring different ways to do it. This ties very closely to the first point, customer traction, because if you build something no one wants, everyone is frustrated and time is wasted. I would encourage you to outsource the barest MVP – saves money, time and easier to pivot. See a great post by Derek Sivers, founder of CDBaby called “How to hire a programmer to make your ideas happen“. After you build a prototype, use it to get feedback and interest in the product – then you’ll be in a better position to find a real technical cofounder, which I think is critical to building a successful tech startup.

3) Money. It seems like you have enough money to fund some development, but ultimately to really build this out, unless you have a bootstrapped model, you’ll need additional funding. Having traction and a strong technical cofounder will help a lot with garnering the bigger dollars you’ll need to truly build this out. (As will connections to angels and VCs.

There are few things worse that chasing an idea, spending a lot of time and money to build something, and then seeing it go nowhere. That’s why it’s so important to figure out if you’re building something people want – before you go out and kill yourself trying to make it happen. Once you know people want what you’re going to make, it becomes easier to find someone to build it and to raise money (or earn it through product sales) which will help you continue forward.

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