Don’t Start A Project Unless You Answer These 5 Questions

Don’t Start A Project Unless You Answer These 5 Questions

A lot of us entrepreneurs have a tendency to chase bright and shiny objects. Enthusiasm can fade on a project and rather than look into why we’re losing interest, we’ll chase something new and exciting. Quitting what isn’t working is an important skill to master. But what if you had a set of questions to guide you before you even started a project in the first place?

It almost always takes longer than you expect to gain traction with an idea. I’ve rarely seen people take something from concept to breathing life into it in the time they thought it would. And in cases where they underestimated on time, they end up with a rushed product that feels clunky, not thought out and sloppy.

It’s like following a recipe for an eight-hour slow-cooked roast, but realizing you only gave yourself two hours to do it. Things that are delicious take time. People will notice the quality difference.

I’m going to put a big fat asterisk here and say this is not an excuse to hide behind perfectionism. The spit and polish that takes a project from 80% to 100% are almost always done for your own ego. No one else cares about the nitty-gritty. Unless you’re clearly articulating and showing how that attention to detail means it makes that persons life easier.

I recently met with an entrepreneur and we started discussing some of his marketing. He used to send out a weekly newsletter, but it was taking him an entire day each week to put it together. At the time of doing it, he wasn’t super clear about what he wanted from the newsletter so it was impossible to measure its effectiveness.

A lot of marketing is like slow cooking, it can take a damn long time to create something that people want to consume and sink their teeth into.

Before you consider taking on a new project, throw your phone on airplane mode, grab a blank piece of paper or notebook and answer the following questions:

  1. What is the goal of this project?
  2. Why am I doing it? What do I hope to get out of it?
  3. What is the worst thing that might happen if I fail?
  4. What steps can I take to reduce the risk and mitigate failure?
  5. Is it worth it?

If you’re struggling to get a big project off the ground, you may need to lighten up and try something smaller. If your newsletter takes you an entire day, what could you do in an hour that still provides immense value?

In the case of the entrepreneur I talked to, if the goal is to bring in more leads, what can you provide that serves to inspire, educate and spark the curiosity of those that hear from you?

He quickly realized that he could still put something together once a week that not only inspired potential clients, but it gave him an excuse to consume architecture, design and things that he was passionate about.

It turned something that felt like “work,” into something fun and he was excited to do.

As Albert Einstein said, “Any fool can make things bigger, more complex, and more violent. It takes a touch of genius — and a lot of courage to move in the opposite direction.”

By starting with the things you value most, then working backwards to ask whether a given decision, routine, or strategy performs more harm than good, you’re given an opportunity to take a proactive approach to prune projects that are unnecessary.

What is one thing you could simplify or remove from your business that would improve it?



Chris is a lover of simplicity. As the owner of Simplify Your Why, he helps people create a simpler, less frustrating way to perform at their best and enjoy life. When he’s not coaching, you can catch him walking his plump little pug Chugs or going on an adventure with his partner Lindsey (which often means devouring delicious food, binging on The Office, or convincing Lindsey to buy a tiny home).

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