Asking for Help Is a Skill, and I Was Terrible at It
For most of my life I’d rather have spent three days figuring something out than thirty seconds asking someone who already knew. I told myself it was independence. It was pride wearing independence as a disguise, and it cost me more time, money, and opportunities than any other habit I’ve had.
What the refusal costs
The obvious cost is time. The three days versus the thirty seconds. Over a career that adds up to months spent reinventing things other people had already solved.
The less obvious cost is relationships. People like being asked. It tells them you respect what they know, and it gives them a role in your story. Every time I refused to ask, I was declining a connection that would’ve cost me nothing and often come back tenfold. The men who helped me most in my working life became friends precisely because I’d finally let them help.
Why we don’t
Fear of looking incompetent, mostly. And it’s backwards. People who ask good questions are read as confident, because they’re clearly comfortable with not knowing. People who never ask are read as either arrogant or lost, and often both. Nobody respected me more for the three days. They just wondered why it took so long.
How to ask well
Do the first bit yourself. “I’ve tried X and Y and I’m stuck at Z” is a question people love answering. “How do I do this?” with no work shown is a request to do your job, and it gets the reception it deserves.
Be specific. One clear question beats a vague request for guidance. The specific question takes them two minutes; the vague one takes twenty and they’ll avoid you next time.
Make it easy to say no. “If you’ve got five minutes this week” gives them a way out, and people who have a way out say yes more often.
Report back. Tell them what happened. This is the step almost everyone skips, and it’s the one that turns a favour into a relationship. People who hear how their help landed will help again, gladly.
Ask early
The worst time to ask for help is when the thing’s already on fire. The best is when you first feel the uncertainty. “I’m about to do X for the first time; is there anything you’d warn me about?” has saved me from more mistakes than any amount of after-the-fact rescue.
What changed when I started
Projects went faster. I learned things I’d never have found alone. And something I didn’t expect: people started asking me, because the asking had opened a channel in both directions. The independent man had been lonely in a way he hadn’t noticed. The one who asked had colleagues.
Today
Pick the thing you’re stuck on. Do the first bit. Write the specific question. Send it to the person who already knows. Then tell them how it went.
Launch list
Be there on day one.
One email when the book opens on Kickstarter. Nothing else. Already reading the book? Your Cheat Sheet is at wisdomdeck.com/free.
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The book itself — 40 laws in ten parts, 320 pages, each ending with The Work — is funded first on Kickstarter.