“Ask the right questions and the answers will reveal themselves.” —Oprah
What should I do with my life? That’s a really scary question.
When I started out in my career, I thought I needed a mentor to tell me exactly what to do, when to do it, and how to do it.
I prayed for this fairy godmother to drop down out of Silicon Valley and into my inbox with a complete roadmap for my life.
As it turns out, fairy godmothers don’t exist, and no mentor—no matter how brilliant—can deliver a complete roadmap to anyone’s life.
In the words of Steve Jobs, you can’t connect the dots looking forward, you can only connect them looking backward, so you have to trust that the dots will somehow connect in your future.
Advising you to just trust that the dots will connect later isn’t exactly helpful, though. It certainly won’t help sort out your career path or relieve any anxiety.
I do know something that will help, though: Asking yourself the right questions.
“Questions can be like a lever you use to pry open the stuck lid on a paint can.” —Fran Peavy
Whenever I feel overwhelmed or when I don’t know the answer to something, before I bother someone smarter than me for the answer, I open a blank doc and start typing out questions. Then I try to answer them. I just type—no editing, no filtering—only me scribbling my thoughts on the page.
And you know what I’ve discovered since doing this?
I can answer nearly all of my questions and feel confident about my answers without ever pinging my imaginary fairy godmother. This includes finding the answer to the old favorite, “What do I want to do with my life?”
Knowing what to ask can be difficult, so I’m here to share some thought-provoking questions to jumpstart the process for you.
These nine questions will help you discover who you really are, what you truly want out of life, and how to get it someday.
And trust me, this is the closest thing you’ll get to a complete career roadmap. You’re welcome.
Look at where you are now
When attempting to answer the question, “What do I want to do with my life?” the best place to start is with the past.
Examining the road you’ve traveled to get to where you are today can sometimes illuminate a path forward, particularly when you begin analyzing the ups and downs and the major catalysts of your life so far.
What led me to where I am today?
This question will tell you:
What you care about and why you care about it (Your purpose, story)
What you’re good at and should explore further (Your skills)
What you enjoy doing (Your interests)
There’s a lot to unpack in this question, even if you’re still a young adult. So start by making lists of the milestones, relationships, people, jobs, and experiences that brought you to where you are today.
Consider the classes you’ve taken. Which did you excel at? Which were a struggle?
What extracurricular activities are/were you involved in? Did you enjoy some more than others?
What part-time jobs have you had? What did you love/hate about each of them?
What major events in your life have happened that shaped who you are today?
Who were the most influential people in your life, and how did they impact where you are now?
Consider all of the above when answering this question, then try to connect the dots. Note patterns, industries, themes, and clues that could inform your next step in life.
Ask yourself: What do I want to keep doing? Do differently? Learn from? What industries or careers pop up that may have been hiding in plain sight?
Take time to reflect on what you’ve done so far, and develop a healthy self-awareness of your strengths and weaknesses. Use your past experiences to make thoughtful choices about your future.
What have I always thought I’d do for work? Why?
This question will tell you:
Why you’re doing what you’re doing
If you should be doing what you’re doing
People often ask little kids, “What do you want to be when you grow up?”
Though the answer to this question will likely change as you get older (and you’ve given up your dream of being an astronaut or firefighter), you may find that other people’s expectations still interfere with figuring out what you want to do with your life.
What expectations do you have for yourself? What expectations do others—parents, friends, teachers, etc.—have of you?
Write them down and note why you (and others) have these expectations. Where did they come from?
For example, maybe your dad wants you to be a doctor because he thinks it’s a secure, well-paying job, and he wants you to have a steady income to support yourself.
If this is the case, perhaps you’ve spent years planning on becoming a surgeon someday. But now, as it’s time to start applying for med school, you are paralyzed by the whole idea. This may indicate that the dream of being a doctor wasn’t your own, but one given to you by your parent.
A lot of us, if not all of us, have this little “should” monster in our heads.
“I should go to law school.”
“I should live close to my parents.”
“I should study business.”
“I should say yes to every invite from friends.”
“I should become a doctor.”
The dangerous thing is we never really explore why we think we should do these things. Not investigating why you’re doing something is a surefire way to wake up one day in your 40s, miserable, thinking: “I am not enjoying this life. WTF.”
If you routinely find yourself waging war against this little “should” voice, I recommend checking out a few of these resources. You’ll find tips for talking back to this voice when you catch yourself thinking, “I don’t know what to do with my life!”
Key Takeaway Why do you do what you do? Our motivations matter. Make career choices for the right reasons (so silence the “shoulds” and ignore the haters).
Find your purpose
Want to know the secret to a happy life? It’s all about finding a higher purpose—something bigger than yourself that activates your personal values and gives you a deep sense of meaning.
Make a big list of everything you want in life, including material items. Brain dump everything, even your most distant dreams and desires.
Do you see yourself living in a big house with a large family of your own? Or maybe your ideal life is in a bustling city, with your own one-bedroom apartment. Or maybe you’d rather live on an artist’s commune, or become a digital nomad.
Do you want to be able to afford high-tech gadgets and exotic getaways? Or are you happier spending more time at home, growing your own food in a garden and enjoying quiet evenings with friends?
Answering these kinds of questions can help you set an end goal. From there, it’s a manner of figuring out how much money you need (and what kind of job will provide you with that salary/time) to achieve your dreams.
Key Takeaway Understanding your dreams and goals will help you make better, more educated decisions when it comes to your career and life. Be honest with yourself and revisit this question over the years, as priorities can (and likely will) change.
What can I see myself doing every day?
This question will tell you:
What careers you should consider
How to enjoy getting what you want
There’s a path—a journey—to getting what you want. It’s not an overnight type of journey either. This path spans your entire life, so you best love whatever it is you have to do to get all the things you want in life.
The path you choose is how you get what you want (i.e. your career/job).
Regardless of the avenue—no matter how glamorous—there will definitely be struggles and steps you’d rather avoid, but you have to do them to get to the pot of gold at the end of the rainbow.
So a better question might be: What pain can I tolerate in my life? What am I willing to struggle for?
Do you want to take a lower-paying job with fewer hours, so you have time for family and friends?
Do you want to work longer hours for the first few years of your career journey, to earn more money faster?
Ultimately, the question you must answer is this: How do you want to spend your time in this life?
Key Takeaway Create a vision of your ideal life. Think carefully about what brings you joy, what keeps you happy and calm, and what makes you thrive. Also, think about what things you don’t want in life, so you know what to avoid.
What are you good at and find interesting?
This question will tell you:
Your skills (you have or want to learn)
The passions that drive you
A list of careers you should test out
I declared business as my major immediately upon entering college. I thought any other degree would be useless in today’s professional landscape.
The thing was, I couldn’t pass my business classes. Macroeconomics still gives me nightmares to this day!
Then I noticed something. I was killing my English classes, scoring 100s left and right on papers.
Because those As felt so good, and because I seriously loved “Sex and the City” at the time, I began exploring the thought of becoming a writer.
The thing was that it just seemed too damn impractical—totally unrealistic.
How would I ever make money as a writer when the news industry was crumbling before my eyes? (This was years ago before content marketing was a thing.)
Plus, I wanted to earn a good wage—something writers aren’t exactly known for.
It took failing macroeconomics—multiple times—to realize I just wasn’t cut out for numbers, and finally, I applied to the journalism program at my school.
Today, I’m a full-time, well-paid (on-my-way-to-rich) writer.
I am where I am today because I tied my skills with my interests, and voila, out popped a phenomenal career that I enjoy waking up for each day. It also helped that I trusted that the dots would connect in the future.
If you have trouble figuring out what you’re good at, ask others who know you—teachers, advisors, friends, etc. They may be able to shine a light on some of the strengths you’re currently taking for granted.
If you’re really stuck, here are a few more questions to consider.
What are your top talents and skills?
What kind of tasks excite you and keep you engaged?
What is your favorite pastime or hobby? What do you do when you have no more work to do?
What topics of conversation are always interesting to you? What do you find yourself talking about passionately with others?
What are your strongest beliefs and convictions in life?
What have previous employers or teachers praised you for?
What would your friends and family say are your greatest strengths?
In the jobs you’ve held, what tasks have been the most satisfying and enjoyable?
Key Takeaway Take time to get to know you. Figure out what your passions and skills are, so you can then make sure you centralize these aspects of yourself front and center as you decide what to do with your life.
Identify your tribe
A huge part of the enjoyment you get out of life depends on the people you surround yourself with. Your colleagues, friends, and family (or chosen family) play a huge role in both the direction of your life and the satisfaction you feel.
But you don’t have to leave your social circle up to fate. As you’re planning what to do with your life, you can design a path for yourself that will introduce you to your tribe—the people who bring you the greatest fulfillment and enjoyment, and get the same back fro you.
Here are a few more resources on this subject:
Who are your favorite types of people?
This question will tell you:
The type of people you’ll work best with
The type of people you shouldn’t work with
Think about all the people you’ve had to work with so far—teachers, peers, toxic bosses. Who drove you the craziest?
No need to write names. Instead, detail what about these folks irritated you so much.
Maybe they were bossy and always telling you how to do your job. Or maybe they slacked off and never held their own in the group.
Now do the same for the people who you have enjoyed the most—colleagues you’ve adored, close friends you trust, and family members who have been there for you.
What characteristics define these people? Are they honest, loyal, funny, weird, kind, or brilliant? Rank these characteristics based on how important they are to you.
Every career has a characteristic “people environment.” These different environments have been divided into six groups, in what is known as the “Holland Code.” Having a good understanding of the groups and how they’re different can guide you toward choosing jobs and a career path that will connect you with like-minded people you enjoy working with.
Understanding which people environment you prefer can help you choose a fulfilling career.
This infographic showcases the six general people environments.
According to the theory, each of us has three preferred people environments from the six above.
While you can take a test to find your precise three, Richard Bolles of “What Color is Your Parachute?” recommends a faster route.
Pretend you’re at a party where people with the same interests are gathered in the same corner of the room, and that’s true for all six corners.
Each corner is composed of people who fit into one of the six categories above: C, R, I, E, S, A.
Which corner of the room are you instinctively drawn to? This is the group you’d most enjoy being with for the longest period of time. Write the letter for that group.
After 15 minutes, everyone in the corner you chose leaves for another party, except you. Of the remaining groups, which corner/group are you most drawn to as the group you’d most enjoy being with for the longest period of time? Write the letter for that group.
After another 15 minutes, this group leaves too, except you. Of the corners that remain, which would you most enjoy being with for the longest time? Write the letter for that group.
The three letters you chose are your “Holland Code,” which tells you your preferred types of co-workers. When thinking about what you want to do with your life in terms of a career, think about jobs that are likely to attract these types of people.
For example, if your Holland Code includes Realistic, Enterprising, and Social groups, you might consider a job in the nonprofit sector. If you are looking for Investigative, Conventional groups, you might want a job in the sciences.
Key Takeaway The people you surround yourself with will shape the life you lead. Asking this question allows you to know what kinds of friends and colleagues you should seek to build a happy life.
What do you value? In what order?
This question will tell you:
Where you should work (the type of work culture you’ll thrive in)
When you start making career decisions, deciding what’s most important is a must.
Maybe you’ve dreamed of working at a startup. Let’s say you get a job offer and the salary is lower than what you were hoping for. But the entrepreneur in you is hungry for the responsibility and autonomy you’d gain in this role. Do you value experience over money?
Or you could be deciding between two jobs. One is the perfect fit—exactly what you’ve been looking for, but will likely be long hours. The other is slightly different/less ideal, but offers a great deal of flexibility and work/life balance. What do you value most?
One day I got a call from the HR department at Vogue magazine, and they offered me a promotion. So it was an opportunity not only for a better job, more money, and the top fashion magazine in the world.
So I had this fork-in-the-road moment. I was like, ‘Either I’m going to do this and take this promotion and have the steady paycheck, have the health benefits.’ People understand what you do when you say you work in magazine. Or I’m going to quit and do this weird coaching thing, which I have no idea what the hell I’m doing. I have never started a business. I had no money. I’m in debt. But God this feels right in my bones. So I turned down that promotion, and I quit my full-time job and I went back to what I was doing in college, which was bartending and waiting tables.
The point is: Not only must you recognize what you believe in, but also, in what order you believe it, so when it comes time to make the hard decisions, you can make them and feel confident about them even when the overwhelming majority is trying to convince you that you’re a flaming idiot.
Once you sort out your values, you’ll know the type of work culture you’ll thrive in someday.
Key Takeaway If you’re like most people, you’ll spend a significant portion of your life at work. When you enjoy the working environment you’re in, it becomes much easier to find fulfillment.
Imagine your future
Dust off your crystal ball—now that you’ve considered where you’ve been and what you want out of life, it’s time to look to the future.
These final questions are designed to help you not only envision the life you want for yourself, but also build a strategy to get there.
What do I want to do before I die?
This question will tell you:
What you want to achieve in life (big picture)
How you can start ticking things off your bucket list
What would make you say at the end of your life, “I went all in”?
List absolutely everything you want to accomplish before you die. It doesn’t matter why. There could be 100 items on the list. The number is irrelevant—just brain dump.
Once you’ve spent a decent amount of time brainstorming and developing a solid bucket list, divide it up into four categories:
Things I can do immediately (Examples: Master your chocolate chip cookie recipe, spend more time with your mom)
Things I need new skills to accomplish (Examples: Get your SCUBA diving certificate, learn to play the harp)
Things that I need time for (Examples: Win a major award, start a book club)
Things I need money for (Examples: Backpack through Asia, get a dog)
First, go through the skills category and list the skills you’ll need to accomplish each bullet point. Then lay out the action plan to acquire each skill you need.
Next, pick something on your immediate list to tick off straight away so you gain some momentum and motivation to keep going.
Finally, which items on the third list would you feel the worst about not accomplishing at the end of your life? Answer that, and you have your priorities.
Key Takeaway The sooner you get started on your bucket list, the sooner you can start ticking things off. Take care of the big-picture stuff, and you’ll one day look back on the life you led and smile.
Where do I derive my inspiration?
This question will tell you:
Who you can look to for guidance and mentorship
What you want to show others about yourself
If you’ve done a lot of the exercises in this article and you’re still finding yourself thinking, “What do I do with my life?” then it may be time to look at some people you find inspiring.
Make a list of people whom you look up to. These can be people you know—parents, friends, colleagues, etc.—or they can be people you’ve never met, like social justice advocates, celebrities, or politicians.
For each person you come up with, list out the attributes, behaviors, and events that have made them so inspirational to you.
Finally, do a little research into the people on your list. If it’s someone you know, simply ask them if you can pick their brain about their journey. If it’s someone you don’t know, head over to Wikipedia or pick up a biography. Learn about what they went through to get where they are, what they wish they could do differently, and what choices they made to find success.
While your journey in life will be completely unique, hearing from people who have done what you want to do can guide you as you carve your own path.
For more guidance on finding and getting the most out of a good mentor, check out these articles:
Key Takeaway Finding people who have lived a life similar to the one you want for yourself can give you a roadmap for your future. You may also want to consider getting a mentor to make this experience more personalized.
Bring it all together to create a roadmap
Remember at the beginning of this article, when I said no one was going to come along and hand you a roadmap for life?
Now you know what really matters to you in life, what stands in your way of getting what you want, and what areas you need to focus on to make it all happen.
Take some time away from your answers to let them settle—you may find as you ruminate on it over the next few days, you want to add some new reflections to flesh out and refine your answers.
When it’s been a few days, come back to it and try turning your thoughts into an actionable plan. Start with the big tasks you want to achieve, and break those up into smaller steps.
For example, maybe you’ve decided that you really want a career that allows you to enjoy the great outdoors. You might create steps like this to achieve that goal:
Research average salary for national park workers
Look into survival training course at community college
Visit local nature reserve and interview an employee there
Plan a month-long camping trip to see how I like it
Once you have these achievable steps planned out, you’ll be well on your way to answering that devious question, “What do I want to do with my life?”
Trust that the dots will connect
“I saw my life branching out before me like the green fig tree in the story. From the tip of every branch, like a fat purple fig, a wonderful future beckoned and winked. One fig was a husband and a happy home and children, and another fig was a famous poet and another fig was a brilliant professor, and another fig was Ee Gee, the amazing editor, and another fig was Europe and Africa and South America, and another fig was Constantin and Socrates and Attila and a pack of other lovers with queer names and offbeat professions, and another fig was an Olympic lady crew champion, and beyond and above these figs were many more figs I couldn’t quite make out. I saw myself sitting in the crotch of this fig tree, starving to death, just because I couldn’t make up my mind which of the figs I would choose. I wanted each and every one of them, but choosing one meant losing all the rest, and, as I sat there, unable to decide, the figs began to wrinkle and go black, and, one by one, they plopped to the ground at my feet.” — Sylvia Plath