Most of you will probably know the popular college drinking game ‘Would you rather…?’ where you have to choose between two (usually horrifying) dilemmas.

Apart from being an entertaining drinking game, I’ve discovered it to be a rather useful life tool to create ultimatums for yourself, especially when it comes to the difficult yet important issues in our lives.

For example, how do we balance our money/job needs with our desire to be more minimalist?

The best way to answer this question is by asking a different set of questions…

three better questions

When we think about work, it’s all about choices. A lot of people neglect asking themselves important questions regularly. They just blindly go with the flow from school > university > job > retirement and forget to stop and check if they’re even going where they would like to go

Now, here is where most people ask obvious questions like, “Are you passionate about your work?” or, “Where do you see yourself in 5 years’ time?” and so on, but those aren’t the kind of questions I’m interested in. I prefer something more challenging.

Most of us are so lucky to live in a day and age when it is possible for us to do anything we want. We have more freedom of choice than any other generation in history. Most of us are no longer hindered by the information and communication obstacles that stopped our predecessors from learning and doing what they wanted to do, when they wanted to. So it’s time for some new and better questions that make the most of the opportunities we have.

Money or Time?

Would you rather:

• work 8 hours a day and have extra cash
• work 8 hours a week and have only what you need

How you answer this question is important because it decides what kind of job you want to do. Some jobs simply cannot be done in less than a full day’s shift (such as working in retail or service)—you’re paid by a company to help customers out for that many hours a day. This kind of job can be done by anyone, and it shows on your paycheck.

On the other hand, there are jobs that are highly paid per hour because of the high value you deliver. What kind of job would you want?

Which one you prefer usually depends on which you value more—having cash in the bank, or having free time.

BUT you can have both money and time! It all comes down to how much money you need to sustain your lifestyle. In my case, I don’t have a costly life overhead, so I don’t need to work more than a few hours a week, and then I use the rest of my free time to do what I want—read, spend time with my loved ones, etc. So now I’m left with enough money, and plenty of time.

Connection or Freedom?

Would you rather do a job that requires:

• your presence
• what you create

There are advantages and disadvantages to both sides, and they’re not always mutually exclusive, but which one you choose largely depends on the kind of person you are. Jobs that require your presence usually involve being interacting with customers and usually some sort of trained skill. Some people find these jobs quite fulfilling too, because they’re able to connect with new and different people.

The flip side is that you have to show up to wherever the customers are, which, if you like your freedom, can be a pain in the ass. Jobs in service sector are examples of these. On the other hand, jobs that only require what you can create, provide more possibility of freedom. You can create something of value, and send it to the customer from wherever you are.

Now or Never?

Would you rather:

• do great things when you’re retired
• do them now (even on a shoestring)

This one is a trick question. A lot of people think that they have to choose between the things that truly matter, and the things they think they have to do right now, like getting a well-paid steady job, buy a nice car/house, start a family etc. But they forget that they don’t have to wait until they’re retired to do what they’ve always wanted to. Or until they’re rich. You can live a millionaire’s lifestyle from right now.

There’s no guarantee you’ll be rich, or even alive, when you’re ready to retire. The only guarantee you have is the present moment, make the most of it!

As for myself, I tutor English for a few sessions per week. My fees are quite high per hour, so even if I have to show up for work, it’s worth it. I’m also working on moving towards freelance translation so that I would be able to work from anywhere in the world… and/or from the comfort of my bed. I’ll see how that goes.

EDIT February 2016: A few years after I wrote this post, I started freelance translations in my spare time, and now I run my own investment business which gives me a comfortable passive income. I’m living my dream from five years ago.

In any case, it’s important to keep asking status-quo-challenging questions because you may discover a new path in life. Some of the best ideas and revolutions in history came from people asking the right questions at the right time.