Answer by Cristina Hartmann:
Unfortunately, deep thinking isn't very common in our society. People look at television pundits for their social and economic ideas. Conventional wisdom rules, despite the fact that unconventional people shouldn't follow such wisdom.
Why? Well, we're just too busy to think. Many of us are running from one place to another, trying to make our lives work. There's data overload, but a drought of original thought.
So, what's an aspiring thinker to do? Here's a few suggestions:
Stop. Think. A lot of people pass through life, too busy with the daily doings of life. Focusing too much on the relatively minor details hampers your thinking. Just take a few moments every day (or one day per week) and just think.
If you don't allow yourself time to think, then you end up substituting conventional wisdom for true thinking. There's a reason why busy people don't write deep philosophical texts, or even think broadly. They just don't have the time. Thinking isn't something that you can do properly when you're focusing your mind on something else.
2. Question Assumptions
Shortcuts are fun. Shortcuts are easy. That's fine for walking to work, but not for thinking. Intellectual shortcuts mean that you're not thinking about the brass tacks. You're not thinking about the foundation of your ideas and theories. It's intellectual laziness, pure and simple.
Think about why you and other people think a certain way. Consider what factors contribute to conventional wisdom. Do these factors apply to your case? For example, it's conventional wisdom to buy a house when you have money. But does it really suit your life? What if you're the nomad type and you want the freedom to pack up your bags and go at a drop of a hat? A house purchase is a great idea if you're planning to stay somewhere for years.
Analyze the brass tacks yourself. Don't rely on others to think for you.
3. Break it Down
Henry Ford had it right when he automated his factories. Tasks are easier when they are broken down to smaller pieces. This process applies to thinking as well. Thinking about an issue or problem in discrete chunks makes you a more thorough and meticulous thinker.
Yet, that begs the question. How do you break down your problem into smaller pieces? That takes some serious intellectual horsepower. Here's where my next point comes in -- find patterns.
4. Find Patterns
Pattern recognition requires high-level abstract thinking. It's truly seeing forests, not obsessing over individual trees. There's no one direct route to pattern recognition expertise, so I won't even try to list them.
There are, however, some universal themes and rules -- especially in writing and fiction. If you gather enough knowledge and insights, you may be able to recognize these themes when they arise. Over time, you'll develop an instinct for pattern recognition. This is an art, not a science. For anyone to achieve pattern recognition skills, one must explore.
5. Explore Different Subjects and Interests
It's great to become an expert at something. Specialization is crucial in today's economy, but it doesn't do much for independent thinking. Break free of your usual books and television shows. Try some new subjects and ideas.
As you become more knowledgable about a variety of subjects, you get better at pattern recognition. You get more creative. Maybe that theme you read in a literary novel can apply to economics. Your intellect is a muscle, you need to exercise it in different ways for it to fully develop.
6. Ask "What if...?"
As others have said, learn about different viewpoints on a subject. That will help you think about possible angles. No problem has only one angle. It's your job to find all possible distinctions that you may make.
The best way to test the boundaries of your ideas and issues is to ask what if? This will allow you to understand distinctions. Great thinkers can address ambiguities because they understand that details matter. Details can affect outcomes. it's just a matter of figuring out which details are important. That's why it's important to ask "what if..?"
7. Rinse and Repeat -- Practice Makes Progress
Thinking is like any other skill. Practice leads to improvement. Once you practice something often enough, it'll become a habit. You'll think critically and logically about everything -- including your grocery shopping list. (Not sure if that's a good thing.)
Opportunities for concerted practice are hard to come by these days. Purely intellectual conversations are relegated to college students, hipsters and academics. Fortunately for you, there are some great places to practice. Quora for one. You should write every answer -- even frivolous ones -- seriously. Think about pattern recognition and alternative arguments. Also, surround yourself with intellectually curious people. Their conversations will get your brain spinning.