Spell out the real worst case of reaching out next to the best case. The risk-to-reward ratio is skewed strongly toward reaching out.
The idea
Fear exists to keep us from getting eaten by a sabre-toothed tiger or kicked out of the tribe. Today the odds of either are close to nil, yet the fear fires anyway over a two-line email. Fear-setting makes you look at the true costs and benefits of the thing you're dreading. Spelled out, the risk-to-reward ratio for reaching out is skewed very strongly in your favor. Seneca had it: "We suffer more often in imagination than in reality."
How to do it
Name the message or ask you've been putting off.
Ask what the worst case really is.
Ask what the best case is.
For each fear, find a fix:
- Worried you won't seem genuine? Be genuine. If you have an ask, be upfront about it. - Don't know what to say? Showing you care is already a good start. - Think they dislike you? You're probably wrong. We underestimate how much people like us.
Ask the regret question: at the end of your life, will you regret the times someone didn't reciprocate, or the times you didn't invest in a relationship when you had the chance?
Example
Try it on a check-in with a past client. Worst case: she replies that she's not interested, or doesn't reply at all. Neither sounds so bad. Best case: a new contract, or a rekindled friendship. Those sound pretty great. Ryan Holiday compares courage to a cold shower: you suffer more in anticipation than in the water, and the longer you stand there, the worse it gets.
Watch out for
Doing nothing feels safe because nobody ridicules you for it. You just don't gain anything either.
Rejection Math: A yes is worth maybe 100 times the small ego hit of a no, so the math almost never justifies staying silent.
Attachment, Aversion, Catastrophizing: Outreach fear comes from tying the outcome to your worth, avoiding to stay safe, and imagining the worst rejection ever.
Most People Won't: Fear keeps most people from reaching out at all, so simply doing it puts you ahead. Their fear is your competitive advantage.
The Liking Gap: People like us more than we think and enjoy compliments and outreach far more than we predict, so say the kind thing.