And it ought to be remembered that there is nothing more difficult to take in hand, more perilous to conduct, or more uncertain in its success, than to take the lead in the introduction of a new order of things. Because the innovator has for enemies all those who have done well under the old conditions, and lukewarm defenders in those who may do well under the new. This coolness arises partly from fear of the opponents, who have the laws on their side, and partly from the incredulity of men, who do not readily believe in new things until they have had a long experience of them.

Nicolo Machiavelli

The Prince – Ch 7 “Concerning New Principalities Which Are Acquired By One’s Own Arms And Ability”

On one hand, Machiavelli espoused an ammoral approach to obtaining power and counseled the ambitious Prince to be prepared  to commit heinous acts to rise in position that many of us would seek to distance ourselves from. (More nuance on that here)

On the other hand, we should not be afraid to learn what we can from a man who so intently studied influence and human nature.

The takeaway here: Innovating is hard and it’s because change may need to loss. Humans have a strong loss aversion and something new holds the chance for harm, either real or perceived, then we will do our best to resist and block it.

There have been always those who were willing to take risks to climb mountains, cross oceans and build new ventures. Explorers, entrepreneurs, and innovators are an uncommon but necessary part of our society. But never forget that making change happen will almost always be a steep uphill battle.


photo credit: alles-schlumpf

When people ask me what I write about, I usually say something like “I write about overcoming fear and making things happen.” The other day, I got a great follow up question: “So what are you afraid of?”

That sparked some thought for me. For all this talk about conquering fear, I haven’t written enough about my own insecurities, mostly exhorting to others. So in the name of open, honest blogging, here’s my Fear List:

  • horror movies
  • disappointing my parents
  • not living a life of significance
  • encountering a tough moral decision and not doing the right thing
  • flashing lights in my rear view mirror
  • not fully satisfying romantic partners in bed
  • hurting my knee again
  • not meeting someone special
  • getting trapped in an unhappy marriage
  • losing the trust/respect of my little sister
  • losing the trust/respect of my cofounders
  • Ridejoy failing/deadpooling
  • losing my memories (photos/videos/blog/journals)
  • not being understood
  • not taking full advantage of my youth
  • not living up to my full potential

Looking at that list, I realize I am generally doing the things I want to do in life, despite these fears, and that where I can, I am actively working to prevent these fears from coming to pass.

For instance, I am pursuing a really important idea with Ridejoy and I try to work hard (and smart) everyday. I make time to meet new people and I always wear my knee brace when I run. I backup my hard drive and I seek to communicate as clearly and compellingly as possible.

But these fears still exist, and it is worth acknowledging them.

So now it’s your turn. What are you afraid? Share your Fear List in the comments.

If you can’t see the video – click through to the post!

Nice little gymnastics montage pared with a great talk.

Get back and do it again indeed. That’s what I thought when I blew out my knee. My doctors tried to set expectations low but I had already decided my injury wasn’t going to hold me down. While you still draw breath, there are no excuses for not pushing ahead.

(hat tip to Gymnastics Coaching)

Full transcript below:

Life is tough, that’s a given. When you stand up, you’re gonna be shoved back down. When you’re down you’re gonna be stepped on. My advice to you doesn’t come with a lot of bells and whistles. It’s no secret, you’ll fall down, you’ll stumble, you’ll get pushed, you’ll land square on your face. But every time that happens, you get back on your feet. You get up just as fast as you can. No matter how many times you need to do this.

Continue reading

Or: How to regain confidence after you’ve lost it.

Dear Friend,

How’s it going? Alright? You don’t look alright to me.

You look like you’re going through rough times. Like you’ve had a couple setbacks and now you’re not so sure of yourself. Like maybe you’ve lost your way.

I don’t see that swagger in your walk any more. No wink and grin that says “Watch what I’m about to do.”

And of course, your results.

Your work is dull. Mediocre. You’re going through the motions – putting in the hours but not really giving it your best. You’re playing scared. You’re watching your back instead of charging ahead. You’ve lowered both the expectations you’ve set for yourself, and for how others will treat you.

You look like you’ve given up on yourself.

But guess what? Even if you’re giving up on you, I’m not.

I believe in you. I believe in what you’re capable of. I believe in what you’ve done, where you’re going and who you will grow to become.

I’ve been there man – been in the dumps because I screwed up. Everyone was counting on me and I blew it. It sucked. Hard. I know things have been hard for you. But you gotta shake that off. Don’t let the bastards get you down you know?

I know, easier said that done, right?

But there are tangible ways of getting there. Like winning some small victories.

Set some little goals for yourself. Maybe it’s going for a 10 minute walk. Or finishing two chapters of the book each week. Or it’s coding up one tiny shippable change to the codebase.

Earn little wins and start remembering what success feels like.

Take some time everyday to feed your mind.

From now on your mental diet is cutting out junk food. Like Fox News. Or any news for that matter. No more bad economy crap. No more  getting into flame wars with trolls on Reddit.

Instead read about how Airbnb almost hung up the towel again and again before becoming a $1B company. See  Heather Dorniden fall flat on her face in a championship 600m race only to come back and win. Or how Nelson Mandela spent 27 years in prison, many of them in solitary confinement before getting elected President of South Africa in their first ever multi-racial elections.

Or just order one of the many Chicken Soup for the Soul books off Amazon. Seriously! There’s a reason they’ve sold hundreds of millions of copies.

Our world is one of second chances, of comebacks and turn arounds. The more you fill yourself with the strength of others who have turned around, the sooner yours will be. Continue reading

Or: How I Transformed into a Douchebag of Epic Proportions

I recently read a great post by Jared Tame, author of Startups Opensourced on the process he uses to land meetings with almost anyone. It was great advice but he definitely got some heat for it – check out some of the comments on Hacker News:

  • This has to be one of the lamest things I have ever read on hacker news.
  • coincidentally, this is the same hack that celebrity stalkers use to get free restraining orders.
  • Good GOD this is a terrible system.

Here we have a guy who wrote a really valuable book where successful startup founders shared their hard-earned wisdom – and shares the actual technique he used (not just an idea he had) about how he was able to connect with these famous and busy people. This is really valuable stuff.

And while lots of people appreciated that, he got tons of hate for it – so much that he had to write a followup post. How is that fair?

It’s not. But guess what – it also won’t stop him from becoming successful. Consider this:

  • Every successful individual you can think of has a pack of people who just hate their guts.
  • Every successful company has people who think their products are worthless.
  • Every successful book / article has people who think the ideas are stupid and wrong.

Want to know my new motto?

Love the hate.

Embrace it. Realize that if you do something or say something and no cares – you’ve got a problem on your hands. The articles that were my most popular were also the ones that got the most hate:

What’s that line from Gandhi? “First they ignore you. Then they mock you. Then they fight you. Then you win.”

Mocking (aka hating) is a step up from ignoring. Having haters, more than having fans, lets you know you’re on the right track. Lots of things can generate positive feelings – few things inspire intense dislike. I would say the former are more likely to be mediocre and the latter are more likely to be great.

Of course the caveate here is that there’s a difference between critical feedback and hate. Critical feedback is something you can use to improve what you’re doing – make it better, more useful, more impactful, more sustainable. It’s important to always get feedback from the people who use/consume what you produce and from people who have a good/wise perspective on what you’re doing. Allow that feedback to inform your efforts. Ignore it at your own peril.

Hate is produced by people who aren’t trying to be helpful. Hate is done with a desire to tear down, to ridicule and mock for the purpose of destruction and marginalization.

Hate is when people post this on your “What Should I Write About” widget

(That’s my widget at some point last year, by the way)

Hmm – good question dude. The exact moment? I think it was sometime after dinner on March 12, 2009. I was over at your house and about to do your mom when I thought …

But in all seriousness, I don’t care that this guy was trolling me. I would laugh every time I saw this as the top suggestion. It meant I was saying something that struck a nerve. Now if all my feedback was stuff like this, I would reconsider what I was doing. You probably want to make sure your balance of positive to negative feedback is better than 50/50.

The fact is, I get tons of emails and comments from people who tell me they love what I’m writing about and really get motivated and learn stuff from reading my blog. It’s at least 70/30 if not better.

It’s the people who get value out of what you do. Those are the people you should care about if you do any creative work.

So remember – love the hate, because without enemies you are nothing, and continue to speak, write, build and work fearlessly towards the things you believe in.

I’ll close out with some wise words from Mr. Ralph Waldo Emerson from his fantastic essay Self Reliance.

Speak what you think now in hard words, and to-morrow speak what to-morrow thinks in hard words again, though it contradict every thing you said to-day. — ‘Ah, so you shall be sure to be misunderstood.’ — Is it so bad, then, to be misunderstood? Pythagoras was misunderstood, and Socrates, and Jesus, and Luther, and Copernicus, and Galileo, and Newton, and every pure and wise spirit that ever took flesh. To be great is to be misunderstood.