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Weekly 3: How to do opportunity triage

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Idea Journal Weekly 3

October 3 · Issue #211 · View online

We combine 3 ideas to help you think differently and be more creative.


Summary: Having multiple opportunities (e.g., jobs, projects) is great, but how do you choose the best one? This issue offers a few frameworks to help you decide.
(~4 min read)

#1. Choose the experience you want to have
Author Josh Kaufman writes in his book The Personal MBA that many people have trouble figuring out what to do because they hesitate to make an actual decision: loss aversion prompts them to leave all of their options open, just in case.
But as Kaufman points out: “Without a decision … their brains can’t use Mental Simulation to figure out how to get from where they are now to where they think they want to be, so their minds thrash around unproductively.”
If you’re struggling to make a decision, Kaufman recommends asking yourself: “Out of the available options, which experience do I want to have?”
When you’re struggling to make a decision, it’s often because your brain is having a hard time figuring out which option is best. 
Kaufman writes that this can be an uncomfortable situation, “but what it really means is that it doesn’t really matter which one you choose.
And if that’s true, then you can just choose the option you find more interesting. 
Kaufman tells the story of using this approach when his wife Kelsey received an exciting job offer in New York City. They spent weeks torn between staying in Cincinnati and moving to New York. 
Where would they live? Could they afford it? What about Kaufman’s job?
Kaufman reflects on the lesson from this experience: 
“In the end, we realized there wasn’t a clear winner, so it didn’t really matter which one we chose. Living in New York was an experience we both wanted to have, so we decided to move. Almost immediately, we felt a sense of clarity and relief.”
#2. Update your ranking system
The number 7 isn’t always lucky.
Athlete and author Kyle Maynard says in an interview that the big shift in his approach to evaluating opportunities came after listening to a successful CEO describe his company’s hiring philosophy. 
“When his company grew and he ran out of time to interview people himself, he had his employees rate new candidates on a 1-10 scale. The only stipulation was they couldn’t choose 7.”
For Maynard, hearing this made him realize how many invitations he’d received that he would rate 7. If he thought a coffee date, meeting, or speech invitation was a 7, then there was a good chance he felt obligated to do it.
Which is why removing the 7 ranking is so useful.
As Maynard puts it: “if I have to decide between a 6 or an 8, it’s a lot easier to quickly determine whether or not I should even consider it.”
#3. Don't be afraid to switch strategies
Author and entrepreneur Derek Sivers writes on his blog that life is like any journey: “You need to change directions a few times to get where you want to go.”
For Sivers, when you’re early in your career, the best strategy is to say yes to everything. The more things you try, and the more people you meet the better – each one could lead to a lucky break.
He recalls in a separate interview how this strategy led to success in his own life while he was a student at Berklee College of Music: 
“I’m in this band where the bass player, one day in rehearsal, says: ‘Hey man, my agent just offered me this gig—it’s like $75 to play at a pig show in Vermont.’ 
He rolls his eyes and says, ‘I’m not gonna do it, do you want the gig?’ 
I’m like ‘a paying gig?! Oh, my god! Yes!’ So I took the gig to go up to Burlington, Vermont.
And, I think it was a $58 round-trip bus ticket. I get to this pig show, I strap my acoustic guitar on, and I walk around a pig show playing music. 
I did that for about 3 hours, and took the bus home, and the next day, the booking agent called me up and said: ‘Hey, yeah, so you did a really good job at the pig show.’
So many opportunities, and 10 years of stage experience, came from that one piddly little pig show.”
Sivers explains that once you find something that’s especially rewarding, it’s important to focus all your energy on that one thing. “Don’t be leisurely. Strike while it’s hot. Be a freak. Give it everything you’ve got.”
If instead what you settled on turns out to be a dead end, then switch back to your strategy of trying everything. 
Eventually, your focus on something will pay off: “Because you’re successful, you’ll be overwhelmed with opportunities and offers. You’ll want to do them all.”
Now it’s time to switch strategies again.
Quote of the week
“Do you ever feel that there are too many opportunities to pursue?
Abundance has a downside.
Having too many opportunities—starting this company, funding that project, pursuing yet another partnership—can leave you distracted and stretched thin. And it can take the focus off your most important goals and activities.
As my dear friend Joe Polish says, the problem with many successful entrepreneurs isn’t “What should I do?”
Instead, it’s “What should I NOT do?”
What you say “No” to can be just as defining and useful as what you say “Yes” to.”
- Entrepreneur and futurist Peter Diamandis on his blog
Idea Journal
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