The Math of Sharing Your Dreams

You have a dream to start a business, switch careers, or take a hobby seriously. You share it with someone you love and hear your own limiting beliefs parroted back to you: 

“But aren’t you too old for this?”
“But what about all the years you put into your career?”
“But you’ll never make money doing this!”
“But don’t you need to go to school first?”

There’s an eternal debate about sharing your dreams with others. Some say you should share them with as many people as possible for accountability and feedback. Others think you should keep them to yourself as long as possible so people don’t discourage you from chasing them. 

Anyone pursuing a challenging project knows there are days when you think it’s the best idea in the world and days when you believe it’s the worst. It’s not fun to hear “I don’t think this is going to work”, or even “hey, how’s your project coming along?” on a bad day from someone you don’t want to spill your guts to. Also, it can feel awkward to admit that you abandoned the idea that a month ago was your life’s mission.

I’ve been there many times and learned that the critical question isn’t when to share, but whom to share with. It’s easiest to share with people who are pursuing their own dreams and understand the ups and downs, fears, and uncertainty. It’s hardest to share with those I have to champion my ideas to, regardless of my emotional state, because I’m trying to assuage their fears and doubts.

Share your dream with people who will:

  • Give you an opinion that applies to your situation, and not just project their own fears, limiting beliefs, feelings of inadequacy, or regrets on you. “Fears” include concerns that your dreams will take precedence over any demands they may place on you (for time, money, emotional support, etc.). 

  • Be supportive and non-judgmental even if they disagree with your direction or methods. They should understand it’s your path to walk, grow from, and iterate on, not a fixed destination to reach.

  • See who you are and who you wish to be, not seek to preserve your past self.

You won’t always know for certain who will support you. If you get feedback that shakes your resolve or rubs you the wrong way, consider it in light of these three criteria: Is the feedback-giver projecting their issues on me? Do they understand it’s a journey, not a target to hit? Do they see me, or an old version of me? People’s feedback often reflects their issues, not yours, and the closer they are to you, the more risk-averse they tend to be for what they believe is your own good.

Finally, if someone “got to you”, don’t forget that the experimentation fiend—moi—is always happy to see more people on the dark side, so feel free to contact me anytime you need a pep talk.

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Weekly Share: Karl Ove Knausgård, What Makes Life Worth Living?

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Weekly Share: Seth Godin, When You Run Out of Good Ideas