The Fear of Starting Over Is Just Two Empty Boxes
Sahil Bloom says mapping what you know about today, and what you lack about tomorrow, shows you exactly what to test next.

Curiosity Chronicle · How to Reinvent Your Life In 30 DaysIn 2020, Sahil Bloom reached this point in his own journey. He knew he needed a change and was committed to it, but felt paralyzed by fear. He described it as "standing on the edge of a canyon," looking at the life he wanted on the other side, with nothing but empty space in between.
Being analytical, he decided to take that fear apart. He concluded it came from two gaps. The first is an information gap: you have almost perfect information about your current life and almost none about the future one. The second is an evidence gap: you have proof you can pay your bills and meet your responsibilities today, and no proof you can do it in a reinvented life.
His fix is a paper exercise. Draw a simple two by two grid. Label the top half current life and the bottom half future life. Label the left column information and the right column evidence. Fill in the top with the basics of today, what your days look like, how you make money, and how you handle bills and responsibilities.
Then look at the bottom. You will be able to fill in almost nothing, and Bloom says that emptiness is the fear. On a second sheet, list small actions that would fill those two empty boxes. His examples include having ten informal learning chats with people doing work that interests you, going to an industry event in person or online, contacting ten prospective customers about a new business idea, building a landing page for a new advisory service, or doing free upfront work for one ideal customer and sending it as a cold outreach.
Those tests are entirely within your control and cost little besides your time. Each one adds a bit of information about what the future life looks like, or a bit of proof that you can live it, and that is what shrinks the fear.
Start with the grid and reach out to one person for a learning conversation.
Questions people ask
What if I do not know what future life I want yet?
Start with curiosity, not commitment. Bloom suggests ten informal chats to explore what the reinvented life might look like, plus attending an event in the space that excites you. You are collecting information first, not picking a final destination.
How do I ask someone for a learning conversation without being awkward?
Bloom does not give a script, so this next part is my suggestion as the writer, not his advice. You could keep it short and specific, explain you want to learn how they started, and make clear you are not asking for a job.
Should I start with an information action or an evidence action?
Pick one action that creates information and one that creates evidence. Information is learning how the new world works, while evidence is showing you can do it, like contacting prospective customers or building a simple landing page. My advice as the writer, not Bloom's point, is that doing one of each keeps you from only researching and never testing.