The Real Questions You Should Ask Yourself When You’re Wondering What You’re Doing With Your Life


In zen a koan is an impossible question given to students to short-circuit the logical part of the mind and bring on enlightenment.

While they have yet to bring on enlightenment, there are two koan-like questions that have opened the doors to significantly higher levels of happiness and fulfillment in my life. These two “career koans,” as I call them, have helped me to not only recognize difficult truths in my life but also to act on those insights. They’ve had a major influence on how I live my life for the better.

Like a koan, these questions aren’t intended to have one clear answer. This may feel frustrating at first but I hope you will stick with them. If you do, I think you will find (as I did) that they can serve as a powerful rudder, steering you toward amazing places. The answers I arrived at from my own contemplation were not easy nor did they come quickly —often my first reaction was to try and ignore them. But by persistently returning to the question on the good days and the bad days, by continuing to explore them from different angles, the answers gradually began to solidify in my mind.

The eventual conclusions I arrived at have been the catalyst for some of the biggest and hardest decisions I’ve made in my life: the type I’d truly consider life-changing. In one instance I walked away from a comfortable job with a six figure salary. In another I dissolved a year-long business partnership. Now I am traveling the world. In all three instances these questions helped me see what is much easier to see now with the benefit of hindsight: the right thing to do for me.

I’d recommend coming back to each question for a few minutes daily, weekly or monthly over the course of a year (and if you find them useful, the rest of your life). This will give you a chance to approach them from different perspectives and in a variety of moods and circumstances.

The aim is not to come up with one clear answer (although you might) —but to help you step out of the entanglements of your current situation (fear, comfort, convenience, security, etc…) and see things from what can be a very enlightening point of view: the long term.


1) What would you do if you had an endless supply of money?

2) Imagine you are lying on your deathbed after having lived a long life. If your life continued on the same path it’s currently on, what would you regret?

Below I’ll share my own experience with these two questions in the hopes it might persuade you to give this practice a serious shot. But don’t substitute my conclusions for your own. The value is in contemplating the question for yourself. My answers may not be yours.


The answer I reluctantly came to was that I had no clue what I’d do with piles and piles of cash. It took me over 6 months to truly admit this to myself. Because I knew that if I did, I had a serious problem to confront: I was spending a significant portion of my life-force and 40 to 60 of the best hours of my week (and maybe my life?) in exchange for something that if I had more of, I didn’t know what to do with. This wasn’t just a surface crack —it ran all the way down to the foundation.

I had two things going in my favor while considering this question. I don’t think either are essential but they definitely gave me an advantage.

1) I had spent the last 5 years building up a stash of “fuck you money.” 1 In The Black Swan, Nassim Taleb defines “fuck you money” as “the amount of money you need to have before you can say ‘F#$k You’ to your superior before you hang up the phone.”

In gentler words: it’s the amount of money you need to do what you want or conversely to not do what you don’t want. By 2014 I didn’t have enough money to never work again but I definitely had enough to buy myself a few years to try and figure things out.

2) I have a loving and supportive family. If anything catastrophic were to happen I am fortunate to have a very strong safety net to fall back on emotionally and financially. I am overwhelmingly grateful for this and knowing this has been a big comfort at times but again I don’t think it’s a requirement.

Money is a seductive measure for progress. But progress towards what? Without knowing what money is for or how much would be “enough” working for money seemed more like a steady march towards my grave than progress towards anything meaningful, albeit probably a grave on a nice plot of land with a respectable funeral service.

As a result, beyond securing what was essential for living, I began to see my time was best invested actively working on the question of what I’d do if money were no object. The default strategy I had been blindly operating out of up until then —trading more of my life for more money— was now seriously suspect.

I don’t want to make it sound like this all came as a clear epiphany and once I realized it I immediately gave everyone at work the bird and quit my job —I didn’t. I also don’t want to make it sound like my job sucked —it didn’t. I did engaging work with great people and was compensated well for my contributions. Rather as I chewed on these questions things gradually began to come into focus and as a result I began taking focused action.

I started reading more. I began journaling. I joined groups and went to events that interested me. I partied less on the weekends. I started waking up at 5:00 AM to give myself 3 hours before work to pursue my own interests. I learned to live on less and funneled what I wasn’t spending into a savings account because rather paradoxically, money was no longer meaningless to me: it could buy my time.

Eventually I realized my time and energy —my life— was worth more than six figures. I still didn’t know what I’d do if money were no object but I was ready to find out. Money, at least for the moment, was no longer an object for me. But fear still was.


Considering death is a powerful tool that all major contemplative practices I’ve come across use. The great stoics all used it, the Buddha used it, hell even Steve Jobs used it. I have found no better way to slice through the thick, tall reeds of fear and uncertainty than by reminding myself that no matter what I do, I’m going to die anyway.

But there’s a particularly powerful and pungent flavor I find in thinking about it from the perspective of my future deathbed. It’s the bitter taste of regret. It’s a taste I find hard if not impossible to ignore. Luckily I don’t have to ignore it —I can still do something about it.

And from the perspective of my deathbed everything has already played out. Dying me is free of all the fear and uncertainty that present me might be experiencing about a situation. It gives me a detached, long term perspective that helps me see the present moment clearly. It allows me to transcend my fear and realize that dying me only really cares about one thing: was I true to myself?

Wishing they had the courage to live a life true to themselves is the most common regret of the dying, reports Bronnie Ware, an Australian nurse who worked for years with the dying 3. In her book The Top Five Regrets of the Dying she writes:

When people realize that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honored even a half of their dreams and had to die knowing that it was due to choices they had made, or not made. Health brings a freedom very few realize, until they no longer have it.

Constantly reminding myself that I’m only renting a room on this planet reminds that the matters of my heart are urgently important. As I stay with the question I begin to see that much of what feels safe is actually incredibly risky. I also begin to see that the results of my actions are rarely as important as the action itself. What is now uncertain will one day be history —what kind of story do I want to tell? Any decision made out of fear now is a surefire recipe for regret later. This hasn’t vanquished my fears, but it has given me the courage to act in spite of them.

There is one more realization I’ve come to as I continue to contemplate these two questions in my life: I must live my answer. And every day I’m given is another precious opportunity to bellow out at the top of my lungs my answer: THIS is who I am! Thought Catalog Logo Mark

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