If you often find yourself rebelling against your own goals, your goals aren’t rebellious and edgy enough for you.

You’re trying to set goals like everyone else, but you’re not like everyone else, so stop trying to fit in. Start setting goals that you’re not allowed to set. Turn your rebelliousness into motivational fuel by setting goals that are edgy and rebellious to begin with. Otherwise you may find your goals way too boring and unmotivating, and you’ll eventually quit.

Do you give yourself enough latitude to explore rebellious or edgy goals?

Even though some of the stuff I did when I was younger was a bit crazy, I often found edgy goals easier to achieve because they were so much fun.

Here are some simple rebellious goals I achieved during the early 1990s:

• Steal every bottle of White-Out from the UC Berkeley student store in one day (many dozens of bottles).
• Steal a $40 ping pong paddle from a locked cabinet of a sporting goods store.
• Go out for a day of shoplifting with a friend till we filled the back of his pickup truck with stolen appliances. (We ended up filling much of the cab too, even having large boxes on our laps as we drove back.)
• Find a way to consistently steal items with sensors on them.
• Learn to count cards at BlackJack and play in the casinos in Vegas, including getting all of my meals comped.

I kept running into a conflict whereby someone would punish my edgy fun and try to set me straight, including four arrests. What gives?

Eventually I’d had enough punishment and tried to straighten myself out. But that didn’t work either. I felt like a shell of myself. Trying to make meaningful progress in life felt like pushing through molasses. Without sufficient edginess I couldn’t stay consistently motivated. There would have to be extreme time pressure and some kind of threat for me to get much done, and even then I couldn’t always motivate myself to push through.

If you’re the type of person who got into trouble when you were younger, always getting punished for this and that, why are you trying to play it straight today? If you struggle to achieve relatively straightforward goals, perhaps you’re not the kind of person who can play it straight and expect to succeed. Perhaps you’re too much of a rebel for that strategy to work.

The key breakthrough was when I asked a simple question:

What can I do that feels edgy, rebellious, and fun but isn’t illegal?

What might be against the rules? What might push some boundaries? What would have some element of risk?

I figured there must be some interesting goals I could pursue that would feel edgy but still be legal. I could still break some rules and have fun doing so.

Eventually this led me to achieve some goals that felt edgy but weren’t illegal, such as:

• Graduate from college in 1.5 years instead of 4 years
• Retain my freedom, and never be anyone’s employee again after graduating college
• Turn blogging into a viable business, starting at a time when most people didn’t know what blogging was, and those that did mostly thought of it as personal journaling with no viable business model

Knowing how to set edgy goals served me well, and to this day I still love projects and pursuits that feel edgy to me. If there’s no edge, then what’s the point of doing them?

Here are some more recent accomplishments from the past few years, all of which had an element of edginess to them:

• Create and launch an online club where members encourage each other to step up their ambition and their heart-alignment
• Do a 40-day water fast while making daily YouTube videos of the experience
• Create a highly original 60-day audio program in 60 days about a different way of relating to life, the universe, and everything.
• Do a six-in-seven (earn $100K+ in 7 days or less)
• Marry a delicious Canadian, and import her permanently 😉

If I try to set and achieve a “normal person” goal, the goal will suffocate me. And if you’re reading my blog right now, I seriously doubt that you’re a normal person either.

If a normal person would look at your goals and think they’re cool, that isn’t cool at all. A normal person should look at your goals and exclaim, “The horror! The horror!”

If no one thinks that your goals are too edgy or too rebellious or just plain weird, you’re playing the game of life without enough risk and fun.

Consider this standard: A good goal for you will torment a normal person.

Stop being so damned obedient all the time.

Where’s the fire?

If your current goals aren’t inspiring you, take the old goal list and burn it.

When you have a good goal, the goal ignites you like a match lighting a torch, and that torch keeps burning long enough to drive that goal across the finish line. If you keep feeling that you must push yourself with low motivation, your goal probably sucks. Throw out that goal – just give up – and set a goal that has more fire in it. Stop going for security, and go for character growth instead.

People think that risk is a bad thing that they should avoid. So they often set goals that they could easily achieve if they were motivated enough. And then ironically they can’t feel motivated enough.

Look at your goals and ask which ones you could easily achieve if you were 100% motivated to achieve them, all day every day, until you crossed the finish line. If you realize you could definitely achieve every goal by that standard – that the only thing stopping you is putting in the time and having enough motivation to keep taking consistent action – I suggest that’s a weak goal. It means there isn’t much character growth and edginess in the pursuit.

Instead, set goals that even if you were 100% motivated to achieve, you’re still not sure how you’re going to pull off that goal. In order to achieve the goal even with sky high motivation, you’re still going to have to stretch yourself, such as by developing new skills, new strategies, and new connections. You’re going to have to expand your previous limitations in order to achieve the goal.

The fire comes from knowing that even if you do your absolute best with daily perfect motivation, you may still fail. Success isn’t guaranteed. Just to have a shot at success, you have to do your best and then some.

Even if you don’t always succeed in achieving such goals, the experience of feeling ignited is so much more fun than trying to be normal.

As you work on an edgy goal, you grow as a person, and that growth is immensely rewarding. That’s the real treasure to be found. The goal is like a MacGuffin in a story – a plot device. The goal exists to help drive the story forward, but the story of how the goal is achieved is often a lot more interesting than the final achievement of the goal.

Perhaps it’s time to make a new list of goals for yourself. Bring the edginess back. Set goals that are against the rules. Set goals that people will tell you that you’re crazy to pursue. Set goals that no one else would care about but you. Set goals that look scary but also like they’d be a hell of a lot of fun. Set goals that you’re not sure you can achieve even if you had 100% consistent motivation to pursue them. Set goals that would torment a normal person.