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Questions to Ask Before Starting a Business

The biggest tragedy for any founder isn't failure. It's becoming trapped inside a business that makes you miserable.

If you can build any business you want, why build one you don't like?

Ideally you wouldn't, but it happens surprisingly often. I've interviewed hundreds of successful founders, and many of them can't wait to quit so they can start over and "do it right this time."

It doesn't have to be this way.


Businesses grant wishes.

Some of us want to be rich. Some want recognition, status, and glory. Others want more time, creative freedom, or the ability to work from anywhere on any schedule. It's not hard to see how a business could provide these things.

But what about more exotic wishes — can a business help with those?

What if you want to hang out with your heroes? Or have a guarantee that you'll easily meet new friends in any city you travel to? Or regularly dine at the newest and most exclusive restaurants? Or have tons of people sharing your writing and ideas? Or get fit and stay that way without relapsing?

I know people whose businesses have enabled them to do each of these things. In fact, I'm a prime example. I'm literally forced to talk to smart, interesting people every week, because I started an interview-based podcast. I'm guaranteed to meet friendly locals in any city in the world, because I started a global meetup program for indie hackers.

Starting a business is like waking up a magical genie who can eventually grant you any wish. No matter what you want in life, your business can help you get it.

But you have to know what you want first.


Put more thought into your wishes.

Before you come up with an idea, before you find a partner, before you do anything, take the time to examine who you are. This should be your first step as a founder.

I've found the easiest way to do this is to ask and answer questions about myself. You can do the same. I've typed up some example questions to get you started:

Sure, it's a lot of questions. But any business you start might last for years or even a lifetime, so it's crazy not to spend an hour or two upfront thinking about the kind of person you've proven to be.

Proven is the important word. Don't guess about who you are. Looking at actual past experiences will help you glean the truth. Getting these answers wrong is a form of self-sabotage.

Later on when you're coming up with a business idea, you'll be better equipped to evaluate whether it will grant your wishes (and tweak it accordingly) if you have accurate answers to these questions.


A Working Example

Before I started Indie Hackers, I knew I wanted something…

Having a list like this made it easy for me to toss my bad ideas and focus on the right one. In fact, this list helped me come up with the right idea in the first place.

We instinctively fear that constraints will limit our choices. But more often than not, they simply serve as prompts to boost our creativity.

Your business can help you accomplish anything you want in life, so remember to aim high. But more importantly, just taking the time to aim at all can work wonders.