Oh, the everlasting millennial black hole of “what should I do with my life?” How many hours have I spent pondering this question? How many books have I read, podcasts have I listened to, and people have I questioned? I stopped counting. And while I do believe this is a life-long question that we will continue to ask ourselves as we grow and evolve, I believe we can find answers along the way if we try hard enough.
Here are my top five questions that actually provided clarity and helped guide me towards a more fulfilling life:
1. How do you spend your free time?
To start, ask yourself what activities you spend your free time on. Not what you like to do, but what you actually do.
It’s easy to think of hobbies “the ideal you” aspires to adopt, whether it’s creative projects, intellectual endeavors, or sports. But reflect on what you actually choose to do, because often our intentions to pursue an interest don’t translate into consistent action.
Sure, I like playing the piano. But how often do I actually play it? Not that much.
If you work nine-to-five, look at weeknight evenings and weekends. Be honest and acknowledge what you actually do in your downtime.
If you’re in school or have a more irregular schedule, look at those periods in between where you just occupy yourself to bridge time. If this means you spend hours delving into the depths of Instagram and YouTube — which accounts do you stalk? Which topics do you nerd out on?
Sometimes it’s obvious, but often it’s not.
If I think of all the free time I’ve had in the past five years, I probably spent the most significant chunk on research — drifting off in the world wide web, books, and podcasts on topics that occupied my mind. I never realized how much of my time I actually spent on consuming self-help resources until I did this exercise. When someone would ask me what I liked to do for fun, I would often give a mediocre answer such as “working out, meeting friends, the usual”. But I actually spent much more time doing things other than those.
If you truly think you have no discernible interests, try things out. Give yourself a month of dipping your toes into new activities and see what sticks.
2. What activities allow you to be in “flow”?
Once you have that list of activities, approach it from a different lens: When are you in flow?
Psychologist, Mihaly Csikszentmihalzi defines this mental state in his book Flow as “performing an activity you are entirely immersed in — full involvement, energized focus and enjoyment in the pure process of the activity”.
This will help you in two ways: First, it will eliminate passive activities, such as watching Netflix. We all spend plenty of time doing those things, but they do not result in a state of flow — they let us zone out, not zone in.
The perfect example for being in flow is the freestyle rock climber who is so in the moment with every movement he makes it requires him to be 100% present. The kind of activities that make you forget to eat and poop, as Mark Manson would say. No one wants a job in which you just wait for time to pass.
But what this also does is it filters out activities that you do for the sake of the result: for some that may be working out, for most that will include daily chores such as cooking, cleaning, running errands, and so on. Those are all tasks which let your mind wander, and from which you will therefore never get full satisfaction, as Mihaly would argue.
What remains should be a shortlist of things you spend a lot of time being fully absorbed in.
And then, you start looking for patterns.
It’s not about the specific task, but about the nature of it.
Depending on the extent to which you enjoyed previous jobs, you may want to include activities from previous roles that felt enjoyable and “in flow” on your list.
My list looked something like this: Workouts and Yoga. Reading non-fiction. Researching various (mostly personal growth-related) topics on the internet. Attending workshops. Creating art and designing things. And lastly, any type of writing — whether it was assignments I was required to do for work or school, journaling, or writing short poems in my free time.
The common pattern? Curiosity combined with a quest for insight and beauty. I would not stop until I felt my questions had been answered, my designs were aesthetically pleasing, or the sentences I had written flowed and communicated ideas in a logically consistent, clear, and creative way.
3. What lifestyle do you aspire to live?
To be realistic, not everyone will pursue a passion if they do not think it has the earnings potential they seek.
Some do, and I admire the advice of “love what you do and you will not work a day in your life”.
Or, similarly, “pursue your passion and money will follow”.
But that requires an extent of optimism and confidence (some might even say naivety) not everyone has, and that is okay.
And while I personally do believe one can earn a living off of any passion one fully dedicates themselves to, I’m also realistic enough to realize that there is a range: What I mean is that yes, you can earn a living from everything, but (a) the amount of work you need to put into something to be able to do that can differ a lot from one thing to another and (b) there’s a lot of subjectivity in how one defines “a living”.
If you’re fine with living in a van in the woods, yes, you can make a living thrifting fun vintage pieces and selling them for a markup through your Instagram account. But if you want your own apartment in a bigger city and the ability to splurge on the occasional meal out, you’ll need a better return on your time.
When you think about how much income you will need to afford your desired lifestyle, think about where you want to live, what kind of apartment (alone vs. roommates), whether you want kids, and what your level of spending on daily lifestyle expenses such as fitness, dining, and shopping would be.
In my consulting career, I’ve come across many people who are in it for the money. I recall a manager telling me that he had considered other careers in earlier stages of his life, but after all, realized he wanted the lifestyle consulting allowed him to have more than a potentially more fulfilling profession in his day-to-day. And that’s perfectly fine, there’s zero judgment, everyone knows best what will make them happy.
If you are fine with sucking up to your finance job so you can afford your expensive golfing hobby, there is absolutely nothing wrong about it — as long as you are aware of the trade-offs you are making and fully accept them.
The answer to this question may change with time, so it’s important to revisit it. I initially loved the idea of a career that would leave me well off, allowing me to splurge on luxuries without thinking about it too much.
But at some point, I realized I did not need as much money as I thought I did. And that opened up a whole set of new potential professions for me.
Yet, I still did have certain expectations: For example, while I loved working out and doing yoga, the likely income from being a trainer or full-time yoga teacher did not feel like it would be enough.
4. Who do you envy?
To maintain the big picture and find confirmation in your early ideas, ask yourself who you are jealous of.
Negative emotions can be extremely powerful in admitting to ourselves what we have difficulties acknowledging. It broadens your sight and makes you think outside the ‘shoulds’ that you may have been primed into by your environment.
I always envied two types of people.
Solopreneurs that authentically pursued a genuine interest and grew a business out of it — be it hobby cook-turned-plant food guru Ella Woodward of Deliciously Ella, cocktail waitress-turned-health coach Melissa Wood Tepperberg of MelissaWoodHealth, or options trader-turned-photographer Brandon Stanton of Humans of New York.
I was especially intrigued if that person had ditched a prestigious career to do so, as Stanton did, or, similarly, lawyer-turned-writer Gretchen Rubin.
And obviously, I always envied non-fiction writers.
Rubin. Susan Cain. James Clear. Glennon Doyle.
“What a life”, I would think. “How lucky are those people to just write for a living.” It’s so interesting to observe the kind of tricks our own minds will play on us. Instead of urging me to start writing, my mind would rather take me to a place of self-pity about how far I was personally from being a writer, or it would take me to sheer reverence of the success and life these people had built for themselves.
When you think of a few individuals you find inspirational, research their careers: What’s their story? How did they get there? Determine what exactly it is about that person and their path that makes you envy them.
Personally, I realized I was jealous of the autonomy in their work and the flexibility they had in designing their days. And the fact that they were creating from a place of true passion for the topic. That they were following their curiosity for a living, that they were helping other people by providing structure and insight around complex topics.
I thought those were all things I could never have, being on a corporate career track. And to be honest, I hated it. Until I started to realize that I, too, could have all those things if I truly wanted to.
5. What do you want your day-to-day to look like in 20 years?
This last question can be incredibly insightful: Picture yourself at that age at which you think you’re grown up and have your life together (i.e. realistically never, but for the sake of this exercise mine was the mid-40s).
What would your ideal day look like, if you had complete freedom to design it from scratch? Disregard all norms or work environments you’re familiar with.
And I’m not saying that you should know today what your life in two decades should look like. But thinking about what you’d want it to look like now can be a helpful exercise: It will help you set your direction and formulate a vision that can provide you with further insight into what you should and maybe shouldn’t pursue.
Take the following things into consideration:
- How much do you want to interact with other people vs. work independently?
- Do you want to spend time in the same place or travel a lot (or a little)?
- Do you prefer having a boss or not reporting to anyone?
- How many hours you are willing to work each day?
- Do you need a consistent daily routine or like each day to look different?
If you have difficulties answering any of these questions, I recommend taking a personality quiz. Myer Briggs MBTI really opened my eyes to why I needed so much alone time and helped me understand and honor my introversion and need for solo work. It also provides insight into the kinds of work environments in which the different personality types thrive.
Past jobs can also be useful in this exercise. Go for the process of elimination. What was part of your day-to-day that you disliked in previous jobs? What drained you, versus what gave you energy?
Once you know what you’re trying to avoid, you can dig deeper into what remains. Research careers that seem fitting and find out what “a day in the life” actually looks like.
At some point in my career, I thought about working towards a role in Venture Capital, given my business background, my ease around numbers, and my curiosity for other people’s stories. But once I looked into what a Venture Capital analyst does all day, I realized all the networking and cold-calling wasn’t for me — I was craving more solitude.
Similarly, I played with the idea of working for a sustainable direct-to-consumer brand for a while, but knew going to the same office every day with limited control over my schedule would eventually antagonize me.
Writing on the other hand would provide me with the independence, flexibility, and solitude I was looking for while allowing me to help people, share knowledge and experiences, and express myself creatively.
Yes, I may be far away from being a full-time writer. But after years of drifting in my career, I finally feel like I have direction. More on the process of getting there another time!
