Should you do the crazy thing?

If you’re entrepreneurial or creative, chances are that some of your dreams have felt a bit on the weird and wild side. If they stick around for a while there’s a good chance I think you should go for it. Here’s why:

1. If you don’t scratch the itch at some point it’s never going away (and remains a question mark or possibly a deathbed regret if you don’t try).
2. No matter what the dream ends up looking like in reality, it will always be a learning experience—new skills, new relationships, a new mindset, way of being and/or way of life.
3. It might only feel crazy because of who you’ve been talking to or how you’ve been taught to think about it. “Crazy” is pretty subjective at the end of the day.
4. There’s no free lunch: If you want big rewards, you need to take on big risks.
5. It’s fun! Many times the people who see their dreams and desires as crazy are the ones who could most use a breath of fresh air.
6. If you took away the fear and the judgments, you’d totally go for it. It logically follows that by not doing it, you’re living from fear and judgment. You can feel however you like but this is sad to me.
7. You’ll end up collaborating with people who are crazy in the same ways.
8. You can only deny your truth and your core drivers for so long—if you fight or dismiss them you will eventually feel alienated or existentially conflicted in some way.
9. It can be a big win-win. I’m all about service to the greater good (and there is definitely potential for doing what you want at the expense of other living things). But service should never mean making yourself smaller. Great service is to lead.

To be fair, I don’t know you and maybe you shouldn’t — because…

1. You feel entitled to comfort or success. See #4 above.
2. You don’t have the social or emotional support for a healthy or net positive experience. Big changes are exciting but stressful—the ability to take loving care of yourself is key. I’m not a fan of leaping so hard you break bones (I’ve done it). Note this is typically a temporary stop versus permanent. Uplevel your self-care and/or social support and revisit.
3. You’re escaping something painful or chasing joy. Your (real) dreams are an expression of joy, not a path to it. So face your fears and stop running, pointing fingers and giving your power away. It may sound harsh but if you can really get this it will be dramatically to your own benefit: You’re in the driver’s seat.
4. Similar to #3, the crazy thing is fun, sexy or interesting, but there’s not a lot of heart or substance. If it’s not growth-inducing, meaningful and connected to the big picture, the fiery flames fade and you get bored and go for the next thing. AKA, “shiny object syndrome.”

You can also calibrate based on what you know about your own patterns. Do you tend to play it safe? Go for it to develop more boldness. Are you doing “crazy” things often? Practice reflection or thoughtfulness.

I don’t know whether you “should” or you “shouldn’t.” I suggest that you scrap this framing because what I do know? There’s no right way.

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