6 questions to eliminate self-doubt and illuminate purpose

The post-college world presents a dizzying array of career options — so how, exactly, do you pick the best path?

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6 questions to eliminate self doubt - Caroline BeatonWhen Caroline Beaton graduated from Colorado College in 2013, she wanted to pursue a career in psychology. She landed a job as a university research assistant, but she soon discovered working in research was not what she hoped for: It was dense, tedious, and involved a long-term investment of time as findings often aren’t revealed for years. Caroline decided to take her passion for psychology out of the lab and into the public. She’s now a freelance writer covering thought-provoking topics tailored for her generation, such as decision-making and willpower, creativity, motivation and more.

Halfway through the tenure of my first post-college job, I asked, “What am I doing with my life?”

My inquiry seemed benign, at first. After all, I was only six months out of school. I was just poking around, seeing what was out there. But the question persisted: on the bus to work, twiddling my thumbs at my computer, trudging through the rain, half-heartedly making friends, thrashing between career options.

When we’re directionless, we doubt ourselves. We see a situation that’s not working and feel like we’re not working. We inadvertently flush our confidence and, in turn, lose our conviction that we can dictate our lives — that we matter. So we often avoid the questions that make us feel this way.

Yet feeling pointless and lost also often precedes purpose.

When I started asking questions, I began to see my circumstance as a changeable environmental condition, not as a personal failing. Asking questions gave me autonomy. It was my first step toward becoming a freelance writer with a personal brand.

Questions, particularly the ones below, have aided me since. They continue to direct me toward my evolving purpose.

1. What do I definitely not want to do with my life?

“What do I want to do with my life?” is often a non-starter; it’s too hard to decide, especially in the beginning of your career. Instead, write down and cross off avenues that don’t appeal to you either through experience or observation. It can be satisfying — and effective — to shut doors. This purpose-driven process of elimination helps you spot what remains on the list and reminds you of what matters.

2. What do I value?

Research shows that we suffer from too many options in our life. With so many opportunities to make money online, move anywhere, or work in hundreds of different industries, making choices can feel like a dizzying burden to recent graduates — and it can be crippling when coupled with fear of missing out on any particular option.

But conflicting options can also activate your values. What do you find yourself wanting to spend time on? What do you feel like you never have enough time for? These questions can help you find out what matters most to you, thereby measurably and symbolically ranking your priorities and solidifying your values.


When we’re directionless, we doubt ourselves. We watch a situation that’s not working and feel like we’re not working.

— Caroline Beaton


3. What are my landmarks?

Savvy hikers use prominent landmarks — mountains or a well-defined trail — to avoid getting lost in the wilderness. Similarly, setting your own landmarks by asking questions such as “What do I love? What am I good at? And what does the world need?” (from Jeff Goins’ “The Art of Work”) can serve as your purpose landmarks.

Your responses to these questions may shift over time, but if your answers have nothing to do with your current activities, it may be time for a change.

4. Who makes me jealous?

When I was studying abroad in college, my friend exclaimed, “Caroline, I’m going to become a yoga master when we go home. I’ll get trained and then I’ll teach, and it’ll be amazing.” For the rest of the day, I felt inexplicably mad at her. You can’t just decide to become a yoga teacher, I thought. Deplorably, I wanted her to fail. When I later reflected on my reaction, I realized I wanted to be a yoga teacher. My jealousy illuminated my desire. I got certified and started teaching six months later.

Jealousy exposes what we care about. Don’t repress it; make it productive.

5. Can I commit?

Though we tend to assume they’re lifelong, passions change more than we anticipate because we change more than we anticipate. A better way to find purpose is to pursue not what’s exciting right now but what’s meaningful long-term.

Imagine each path you’re considering 20 or 30 years down the road. What does your career look like when the excitement has worn off, years after the honeymoon phase? What profession would you care about through sickness, sadness, and old age? It’s a tough question to answer off the cuff, but one worth mulling over.

6. What can I do that’s irreplaceable?

In “Deep Work,” University of Georgetown professor Cal Newport argues that focused, intellectually rigorous work is increasingly valuable in today’s economy and is an instigator of personal fulfillment. Contemplate what you’re uniquely equipped to do: Identify your skillset that can deepen with pointed training and time.

Final thoughts

If you’re like me, your answers to these questions will change as you change. But asking the questions is more important than the answers anyway. This inquiry is the foundation of self-awareness and the impetus to act with confidence.