On How to Know When I’m Ready

The Weekly 4: one question, one answer, one insight, and one resource to help you on the path to business ownership.

Most people who dream about business ownership aren’t stuck because of lack of ambition or lack of ideas. They’re stuck because they’re waiting for a feeling that never comes.

They want the fear to go away first. They want to feel confident first. They want to feel certain first.

But when you’re standing on the edge of something meaningful, those feelings rarely show up on their own.

This week’s topic digs into why that happens and what to do instead: “How do I know when I’m ready?”

One Question
What is one action you have been putting off because you felt you were not ready, and what would it look like to simply begin?

One Answer
Someone recently asked me, “How do I know when I’m ready to start or buy a business?”

So I shared a personal story. Years ago, I signed up for a twelve-hour Navy Seal training event. I felt completely unprepared, even the night before. But a few hours into the event, in the middle of the hard part, I realized I was more capable than I thought. The fear didn’t go away. I just proved to myself that I could handle the next step by doing it.

Business ownership works the same way. Most people try to answer “Should I do this?” before they have done any of the work that would give them the clarity they need.

A better approach is to start small and focus on the How questions:

  • How would I find the right business?
  • How would I finance it?
  • How would I protect the downside?

Instead of worrying about whether you are ready, working on the How questions helps you become ready.
I talked about this on my most recent video, including a simple challenge you can start today: How Do I Know If I’m Ready… to be an Owner?

One Insight
“You do not have to see the whole staircase. Just take the first step.”
– Dr. Martin Luther King, Jr.

One Resource
If you feel like you are waiting to feel ready, Tim Ferriss’ Fear Setting exercise is one of the best tools I know for creating clarity through action. It helps you define what you are actually afraid of, break it into specific risks, and see the steps that would make those risks manageable. Readiness grows when uncertainty shrinks, and this exercise is a simple way to start. You can watch his short TED Talk and walk through the framework here.

That’s it for this week. Send me a reply email if you’ve got a question you’d like me to consider for a future Weekly 4.

Cheers, 

What’s on Your Mind? 

I write this newsletter with you in mind… the best questions come straight from readers. If you’re wondering about something related to business ownership, please join in the conversation. Send your questions, thoughts, or comments my way and I’ll do my best to answer it in a future issue or video. 

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