The Most Important Question You Can Ask Yourself

When I started full-time freelancing in 2012, fresh out of college, I barely earned enough to support myself for the first six months — while living with my mother.

Then, around the eighth month, it dawned on me that I made a huge mistake; I started my full-time freelancing career based on the what (to make money), and freelancing was how I made some money. But the difference between surviving and thriving as a freelancer was determining why I wanted to freelance in the first place.

Ultimately, the key to any successful venture — whether it’s starting a business, developing a hobby, or honing a skill — is to start with why, a phrase I’m borrowing from one of my favorite books (“Start With Why” by Simon Sinek).

Once I discovered my “why” — freelancing was best suited for a work-life balance that allowed me to work from wherever, travel the world, and leverage currency exchanges to maintain my lifestyle expectations — my freelance career skyrocketed, both in terms of income, as well as the type of clientele I attracted.

In 2018, when I started running operations for the company BlockGroup, I asked myself the same question: Why?

• I want more stable income.
• I want to work for a company that allows for remote work.
• I want to improve my productivity and time management skills, so I can make more time for life.

So, I have a question for you: Why do you want to be more productive and time-efficient?

Without a definitive “why” in place, you’ll be hard-pressed to stay consistent and disciplined with constantly honing your time management and productivity habits. And, without these habits, you can’t fully develop the skills (e.g. Deep Work) necessary to flourish in our digital, distraction-heavy world.

The 5 Whys

Turns out, the question “Why?” isn’t just the greatest impetus for starting and sticking with a business, developing a hobby, or honing a skill. It’s also the basis of a technique developed by Sakichi Toyoda, who founded Toyota Industries Company (the company from which Toyota Motor Corporation developed).

Toyoda’s technique, known as the 5 Whys, is commonly used in problem-solving; when a problem arises, ask “why” five times to identify the root of the problem. Then, find a solution to prevent the problem from recurring.

For example:

Problem — I can’t concentrate for long periods of time.

1. Why? — I’m constantly interrupted at work.
2. Why? — My phone is always in front of me.
3. Why? — I’m addicted to my phone.
4. Why? — Social media.
5. Why? — Social media is the first thing I turn to when I’m bored.

Solution: Turn off notifications on your phone, delete social media apps from your phone, put your phone away while you’re at work, and only use it when you’re on a timed break.

The 5 Whys technique can (and should) be used when you assess your time management and productivity habits. And, really, it should be used at every juncture of a problem.

For example:

Problem: My company prefers weekly meetings, which end up wasting everyone’s time.

1. Why? — Meetings keep people accountable to their projects and tasks.
2. Why? — They require people to “check in” on their progress.
3. Why? — When you’re in front of your peers, you’re pressured to say something meaningful.
4. Why? — You don’t want to look like you’re not contributing to the company.
5. Why? — You don’t want to get fired or become expendable.

Solution: Use a project and task management software (e.g. Monday.com) to keep people accountable and track their progress in real-time, while minimizing the need or desire for weekly meetings.

Article Recap

1. Answering the question “why” before you start something new (or continue with something you’ve already been doing) will increase the likelihood and extent of your success with it.
2. The 5 Whys is a commonly used technique in problem-solving, in which you (a) ask “why” five times to identify the root of the problem, and then (b) find a solution to prevent this problem from recurring.

There’s more where that came from at Hack My Time.