What Should I Do with My Life? These 8 Questions Will Tell You.

Lauren Holliday
12 min readOct 25, 2018


“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 godfather to drop down out of Silicon Valley and into my inbox with a complete roadmap for my life.

As it turns out, fairy godfathers 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 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 I 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 godfather.

Knowing what questions to ask can be difficult, and opening a blank Word doc can feel overwhelming, so I’m here to share some thought-provoking questions to jumpstart the process for you.

Keep reading for a long list of questions to answer. They should 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.


Photo by Fab Lentz on Unsplash

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)

Brainstorm 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?

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?

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

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.

It’s important to know his underlying reason in case you don’t want to be a doctor and need to tell your father this someday.

I like this question because 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 study business.”

“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 sure-fire way to wake up one day in your 40s, miserable, thinking: “I absolutely hate what I do. WTF.”

Finding your purpose

Photo by Austin Chan on Unsplash

What do I want?

This question will tell you:

  • How much money you need to make (Salary)
  • Where do you want to live?
  • What do you want your home or apartment to look like?
  • What things and experiences do you think will make you happy?

List everything you want in life, including material items. Brain dump everything, even your most distant dreams and desires.

What do I want to do every day?

This question will tell you:

  • What careers you should consider
  • How to enjoy getting what you want

This question plays a massive role in our overall happiness, but it’s often overlooked, if it’s even considered at all. It can also be a bit vague.

Here’s what I mean by it.

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 to walk is the process by which you get what you want, i.e. your career/job.

Regardless of the path you choose — no matter how glamorous — there will definitely be struggles and to-dos that you just don’t want to do, but that you have to do, in order to get to the pot of gold at the end of the rainbow.

So a better question might be: What pain do I want in my life? What am I willing to struggle for?

Do you want to have time for family and friends?

Do you want to work a lot or a little?

How do you want to spend your time?

Do you imagine yourself in an office or working from a coffee shop?

If you don’t answer this question, you’ll default to the easiest and most obvious path to get what you want.

For instance, if making a lot of money is important to you, you may study medicine and become a doctor. Later in life though, you might have a mid-life crisis, when you realize that you hate the life of a doctor.

What are you good at and find interesting?

This question will tell you:

  • Your skills (You have or want to learn)
  • Your passions
  • A list of careers you should test out (Freelance projects, internships, jobs you should try to see if you like)

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 seven years ago before content marketing was a thing.)

Plus, I wanted to be rich. Writers aren’t rich.

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.

If you’re stuck, here are a few more questions to consider.

  • What are you ridiculously good at? What are your talents?
  • When was the last time you massively over delivered on something? What was it, and why did you work so damn hard?
  • When was the last time you were in a state of flow (in the zone) and totally lost track of time? What were you doing?
  • What topics do you find yourself continuously arguing or defending with others? What beliefs does your stance represent?
  • Out of all your current work roles, what would you gladly do for free?
  • What do your friends always tell you you’d be good at, that you should do for a living (i.e. “he’d make a great…)? If you don’t remember, then go ask them.
  • What careers do you find yourself dreaming of? What jobs do others have that you wish were yours? Why?
  • What do you hate doing? This will help you weed things out.

Identifying your tribe

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, 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.

Every career has a characteristic “people-environment.” Tell me what careers interest you, and based on a theory, I can tell you, in general terms, what people-environment it will offer.


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.

Ask yourself:

  • 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.

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?

There’s no right or wrong answer, though saying “yes” to one thing might mean saying “no” to another. Life and business coach Marie Forleo shares a major turning point in her life when she chose to follow her passion over financial and career security:

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.

If you’d like an example of values, read mine.

Once you sort yours out, you’ll know the type of work culture you’ll thrive in someday.

Imagining your future

What do I want to do before I die?

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 three categories:

  • Things I need skills for
  • Things I can do immediately
  • Things that I need time for

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.

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

Growing up is overwhelming, to say the very least.

While I hate the idea of being 30 soon, I absolutely despise the idea of being 18 again.

I don’t miss the figuring yourself out part at all because it’s really freakin’ hard and scary.

I mean, what if you make the wrong decision?! Are you screwed?


You WILL try things you don’t like and work with people you can’t stand, but as long as you learn from it, you’re moving forward. And that’s all life is about — getting one percent better every day.

Also, don’t forget to trust… Trust in something — your gut, destiny, life, karma, whatever. Like Jobs, this approach has never let me down, and it has made all the difference in my career.

It will make all the difference in yours too… if you let it.

Originally published at www.thevectorimpact.com on October 25, 2018.



Lauren Holliday

Outsource your job search to a woman who lands jobs like it’s her job. https://contra.com/lauren_holliday