11 Questions To Ask Yourself When You Don’t Know What Comes Next


There is quite possibly nothing worse in life than feeling directionless. It trumps failures, heartbreaks, and setbacks for misery value because it begs the unfortunate question of “Where the hell am I supposed to go from here?” Courtesy of someone who’s fallen into the trap of feeling directionless more than once or twice, here are a few questions you can ask yourself that are slightly more helpful than listening to “What Now” by Rihanna for the four hundredth time on repeat.

1. What’s going right?

In the words of Robin Williams, “What’s right is what’s left if you do everything else wrong.” It sounds ridiculous but it’s true. Whatever you have left when everything else hits the fan – that’s the good stuff. That’s the durable stuff. That’s the stuff that’s going to be the foundation of the new, more resilient life that you’re building for yourself. Don’t let it go unacknowledged.

2. When do you feel the most attractive?

I’m not talking about which slinky shirt gets you the most attention at the bar. I’m talking about what makes your eyes light up with the specific sort of fire that only you have. I’m talking about the times when you feel most comfortable in your own skin, when you are proudest to be voicing your thoughts and when you are certain that your most vivacious qualities are beaming straight out of your skin. Because those are the times when you are the absolute most attractive and the absolute most yourself. Wherever you are going next, you’re going to want to bring more of that person with you.

3. Which pain is growing you and which pain is holding you back?

An old psychology professor of mine used to say that there is growing pain and then there is just pain-pain. Growing pain happens during times of bold change, when we are actively working towards creating a brighter future for ourselves. Pain-pain diminishes us – it holds us back and makes us smaller, meeker versions of the people we could otherwise be. The sooner we realize the difference between these two pains, the sooner we can cut the dead weight loss. Pain is inevitable. What we make out of it is optional.

4. What do you do when you procrastinate?

When you’re procrastinating you’re almost always pursuing something that brings you natural energy. Pay attention to what you’re doing while you’re putting off other things – which TV shows are you watching? Why do you like those shows? Which articles are you reading– what appeals to you about that train of thought? We can learn a lot about ourselves by examining what we do when we’re under no obligation to do it. Our natural talents often lie hidden somewhere within these mindless habits.

5. What is worth failing at?

Here’s the deal – you’re going to fail anything you do for long enough, whether you love it or not. But you’re only going to succeed at the things that you’re willing to try for, over and over again, without regard for how many times you fall short. If you hate what you do, this is going to be a very exhausting process. If you love what you do it’s going to be invigorating. Because each time you’ll get better. And each time you will find yourself that much closer to achieving what you’ve wanted all along.

6. What does your fantasy life look like?

I used to think we all had the same fantasy life. I was like “Duh, I’d win the lottery, build a waterpark in my backyard, have my friends over 24/7 and go travelling every second week. That’s a no-brainer.” Then I asked the question to a friend and got the answer “I would live in a cabin in the woods all by myself.” Which quite frankly sounds like hell to me.

The idea of having a life without limits isn’t important because of it’s practical value – I’m not planning to win the lottery and my friend isn’t planning to build an isolated cabin in the woods (that I know of). But it tells us a bit about what may be missing in our lives. I’m craving human connection and external stimulation. My friend needs more exposure to nature and a little bit of time to reflect. When we think about the lives we wish we had, it gives us indicators as to what is missing in our lives currently. And when we’re not sure where to go next, moving in the direction of what we’re missing is never a bad place to start.

7. What would make you disappointed at the end of your life?

If you never had kids, would you wish that you had on your deathbed? How about if you never travelled? If you never went to school? If you never worked a particular job or made amends with a particular person? The best thing about analyzing our future regrets is that we still have so much time for them to become goals instead. And setting goals is the natural first step of getting our futures back on course.

8. What are you a part of that is bigger than yourself?

In North American culture, we’re taught that all the causes and solutions to our problems lie within us. If you’re not happy it’s because you’re not trying hard enough and if you want to be happier you just have to try harder. This is largely a pile of bullshit. So much of what we’re lacking in our lives comes from external sources. And a major source of fulfillment can be gleaned from investing in the success of something that is larger than any of us as individuals. When you’re lacking direction, take advantage of the fact that so many organizations, groups and causes already have an established direction – and they’re looking for people just like you to jump in and help that cause move along. Being a part of something bigger has the power to absolutely transform you as an individual – it just works a little bit backwards that way.

9. What do you still have in common with your childhood self?

Few of our ambitions or inclinations stand the test of time – but those that do are really worth listening to. Thinking back to yourself at age ten or twelve – which traits did you exhibit at that point in your life that you still possess now? Conversely, what would your childhood self think about the current life you’re living? Pay attention to the ten year old inside of you – he or she is smarter than you think.

10. What are you doing now that is going to pay off later?

Knowing that you’re working toward something takes of heat off the BE HAPPY RIGHT NOW pressure that is constantly being applied to us. Figuring out what we’re working towards and what is going to pay off in the future gives us a little bit of extra motivation each day – and reminds us that there is a light at the end of the tunnel, even if we can’t see it yet.

11. What do you want to see happen?

It is actually insane how hard this question can be to answer. When we’re lost, when we’re floundering, when we’re out in the middle of the ocean without a single life raft in sight, it’s easy to forget that we want to find the shore at all. But once we fix our sights on that coastline, it becomes the simplest thing in the world to swim towards. The beautiful thing about not knowing what comes next is that you get to decide what comes next. And then it’s all up to you to make it happen.