Finding your path part 2: 7 questions to help you on your way

I’ve spent a lot of time trying to figure out how to create a life worth living. This included learning to love myself, meditation, therapy, and a lot of time and money wasted on personal development and coaches.

My most recent step has been learning to find meaningful direction with my career path. For most of my professional life, I’ve been modestly successful, but also sort of miserable.

2019 has been very, very different. As it turns out, finding your path is one of the ultimate life hacks for happiness and productivity. There’s still plenty of frustration – as a student and an intern, a huge amount of my time is dedicated to pedantic busy work. And since I’m still consulting and training to be a meditation teacher, my spare time and energy is truly scarce. Despite the demands, I’ve found myself waking up happy, playful, and with tons of energy and space.

This is the second article in a three part series. In the first article we covered the subtle signs of being successful, but off the path. In this article, we’ll discuss different questions to help you find find your path. In the third article, we’ll discuss how to summon the courage needed to take the first steps.


I’m not sure that I believe that people have purposes, per se. What I do believe is that if we find something good enough, and dedicate ourselves to it, that we can create amazing lives for ourselves. What does this mean when it comes to finding your path? It means that you can take some of the pressure off of yourself. Instead of getting it exactly right, I suspect that all you need to do is come close enough.

Right now, it’s trendy to try to turn passions into jobs. In fact, it’s so trendy that I’ve met people who feel guilty for having a normal job, and not one that they’re disgustingly in love with.

As we’ve discussed, I think that turning your passion into a career is misguided, unnecessary, and at times, destructive. A far better move is to find something that you like well enough, and move forward from there.


Finding your path is an art, not a science. The following 7 questions helped me find my path, and I hope that a few of them help you too.

1) Do you secretly know what you want to do? In many cases, we know exactly what we want to do, but we hide it from ourselves because we’re afraid. If you’re in this position, for now, just work to own your dreams. We’ll talk about bringing them to life in the next article.

2) Did you used to know what you wanted to do? I know that sounds like a strange question, but it was a valuable one for me. As a teen I knew I wanted to be a psychologist. I was (and still am) amazed that some people understand the mind so well that they can help it heal. But then I got distracted. I quit my psych major in college because my peers were too crazy, then I traveled, then I got involved with international development, and then got sucked into the business world. For a decade or so, I lost myself.  

As you find yourself searching it’s worth pausing every now and then to ask, “What did my teenage self want to do?” She may have been more on the mark than you ever imagined.

3) Is there space in your life for new possibilities and ideas to emerge? Trying to find the right path can be a deceptively difficult project. If you don’t dedicate time to reflection and experimentation, you may never succeed. Most of us stay pretty busy these days, and when we aren’t busy, we fill the space with distraction.

If you want to get clarity about yourself, one of the best moves is to spend time doing less. I wrote about my experience doing less last year. Not only did it lead to the happiest part of 2018, it also helped me get clear on what it is I want to do when I grow up.

4) What are some weird paths that you could fall in love with? It’s tempting to try to get your life to fit neatly within the lines. For some, it’s totally possible. Others, like me, need to go way outside the lines in order to find something that feels meaningful and worth doing.

Are there seemingly disparate skill sets that you can combine to create something unique? Or can you wrestle with something and get it to serve you? I know this sounds a bit abstract, so I’ll explain how it played out in my career.

I love writing, psychology, speaking, business, working for myself, and serving the least fortunate. If my work didn’t include most of those attributes, I would feel like I was leaving valuable parts of myself behind.

So my plan is to open a high-end mental health spa that includes psychology, meditation, and cutting-edge interventions. Then I’ll use the profits to fund a mental health center for those who can’t afford services. Along the way, I’ll continue to blog and give the occasional speech. Does this fit neatly inside the lines? Not at all. Will it work? I’m not sure. Does it feel right? Absolutely.

5) What do the people in your life think you should do? Sometimes, other people have good insight into what might make you happy. My dad was the first to point out that I would likely be unhappy if I were a full time executive (a path I seriously considered). My guy friends from college and high school encouraged me to become a therapist. In both instances, people close to me had a clearer idea of what might make me happy than I did. Asking people for suggestions can prove fruitful.

But this is not a fool proof strategy and can potentially cloud your vision. The trick is to ask for other people’s opinions, but not take them too seriously. When someone makes a recommendation, spend a bit of time considering it and trying it on for size, but don’t take it as gospel.

6) What do fortune tellers and personality tests suggest you do? Don’t get me wrong. I don’t believe in fortune tellers or personality assessments (and yes, that includes the MBTI, Strengths Finder, Enneagram, and whatever other silly assessment is currently en vogue). I mean, it would be lovely if figuring ourselves out were as simple as taking a multiple choice test, but of course, little in life is truly so simple.

That said, you can use career and personality inventories as well as fortune tellers to get the creative juices flowing. Maybe you’ve only been thinking about white-collar jobs when a fortune teller (or whatever) suggests that you’re destined to work as a police officer. Suddenly, you start imagining yourself as a cop. While that isn’t quite right, it opens a whole new realm of possibilities including: firefighter, barber, construction manager, bike mechanic, etc. Doing this can shine light in unsearched corners of possibility.

7) Have you actually tried your dreams on for size? Big decisions often feel like an all or nothing proposition. We either stay in our dead end jobs, or we burn it all to the ground to become a tortured writer.

While this approach can work, it’s needlessly reckless. Instead, try your dreams out before you commit to them. If you want to be a writer, force yourself to write for an hour or two every evening to see what it’s like. If you want to start some sort of business, work on it during the nights and weekends until it’s generating enough income to support you before you quit your job. If you’re thinking of becoming a hospital chaplain (which I was) take a few days off to shadow one and see if you like it.

Note: It’s possible that your job is taking up so much space in your life that you can’t dream while you’re still in it. In that case, consider building an off ramp. Spend time saving money and then quit, or get a job that doesn’t demand as much of you. Yes, this requires making sacrifices and can take a lot of time. But doing this will give you the platform you need to really dream and pursue something that is a better fit.


It took me several years and about a dozen false starts to find my path (seriously). I think the important part is finding work that is an honest reflection of how you want to live and what you value. That includes working at Burger King or some other place that you’re apathetic about in order to support the rest of your life. I hope that the strategies above help you find the next few steps on your path. They’ve been invaluable to me.

PS: One thing to keep in mind while you’re searching

There are literally billions of people out there who don’t have the luxury of considering how they want to spend their time. Any job that helps avoid hunger and exposure to the elements feels like a gift from God. I think this is worth considering for two reasons. First, it gives some perspective to our own struggles. Yes, the problem of existential and professional unrest is a problem, but it’s an amazing one. Second, I think it offers a bit of insight into finding a path that you’ll love. My experience is that we all tend to be a bit happier when we use at least a small part of our lives, to improve those of others.

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