I’ve been known to monologue about the importance of knowing oneself. It’s a topic that, if presented on a Venn Diagram, would be a massive circle overlapping all others. If you don’t know yourself, how can you know what goals to work toward, or what you’re willing to do to reach those goals?

The oft-unasked inverse of that question is, “What wouldn’t you do to reach your goals?” What lines are you unwilling to cross? What personal changes are you unwilling to make in order to fulfill your hopes and dreams?

Knowing what you will do is only half the picture. It defines the ground floor, but you don’t know where the ceiling is. You can’t have a complete, stable structure without a surface upon which to hang the chandelier.

Put a different way, what aspects of your morality are more important to you than the goals you’ve set for yourself? Which would you trade for the other? If you’re dying to be the top dog in your field, would you kill a stranger to make it happen? How about a friend? Family member? Or taking it in another direction, would you commit corporate espionage if no one you know is directly harmed by the fallout and you’re unlikely to be caught? Certain to never be caught?

I wrestle with these kinds of questions, not because they’re likely to be situations I’ll face (I doubt I’ll ever have to choose between killing a guy or not, with my entrepreneurial ambitions hanging in the balance), but because the answers tell me something about myself, and help me make decisions in the real world that would otherwise seem quite murky and difficult.

Knowing that I would much rather succeed moderately and adhere to my standards than succeed wildly knowing that I had broken my ethical code (something I’d have to live with for the rest of my life) allows me to make better decisions when, say, I’m trying to decide between expansion opportunities. Which one better aligns with my sense of morality? ‘Difficult questions’ become far simpler when you’re able to eliminate options based on what you know will make you happy and what you know will lower your quality of life.

Of course, everyone has different moral standards and priorities, so this isn’t something that can be easily taught. The only way to know which paths are ideal for you to take is to better know yourself, and to do that, you have to ask yourself questions. A great many of them, if you want to know yourself intimately.

I like to ask myself one tough question per day, and really ponder it until I come up with a confident, comfortable answer. They don’t have to be complex questions: even something as simple as, “Your house is on fire, and you can only grab two things (pets and people don’t count) as you run out the door, what do you take with you?” works well. And the actual answers (rather than the ones you feel you’re expected to give) might surprise you.

The more you know yourself, the better your decisions and lifestyle will be. Take the time to ask yourself difficult questions and answer them honestly. Otherwise you’ll never be able to hang that chandelier.

Update: February 19, 2017

Yes. This is still something I think and talk about a lot. And learning about myself in this way has been one of the better investments I’ve made. There have been a lot of choices I’ve had to make over the course of the last few years that would have been very difficult, had I not already known what I won’t do to get ahead.