How to tell if a career is right for you when you’re feeling self-doubt

self-doubt

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A funny thing happens sometimes when I’m coaching someone new.

Most of my clients come to me feeling stuck and utterly confused about what to do next in their career. They’ll say things like, “I have NO idea what I’m passionate about” or “I’m completely directionless.”

But then, after a few calls, some of them will reveal a secret dream they’ve had for years or a recurring idea that they keep dismissing.

This admission is usually prefaced by something like, “I know this sounds crazy, but…” or followed-up with, “…but I know that’s not realistic.”

I’ve heard a lawyer admit to her secret passion for interior design, a government consultant share his fascination with social entrepreneurship, and an HR manager confess that she’d almost gone back to school for therapy 3 separate times.

Whether or not they’ve ever admitted it to anyone before (including themselves), on some level they’ve known what they wanted all along.

EXCAVATING BURIED DREAMS

Remember when we were kids? It was so easy to say that you wanted an incredible life doing exciting, important, creative things.

But as we all got older, the limitations and obligations and “shoulds” started piling up. We started getting weird looks and discouraging feedback when we admitted that we wanted something risky or outside the norm. We had to get respectable degrees and stable 9-to-5s to pay the rent.

And the secret dreams got buried under self-doubt and judgments and responsibilities.

Sometimes these secret dreams are constantly in the back of your mind, nagging at you to pay attention. And other times, these ideas get so suppressed that you “forget” all about them for months or years at a time.

But either way, they tend to make whatever else you’re doing feel bland, like you’re settling.

How can you tell if you’ve got a secret dream that you’ve been dismissing? Here are 4 questions for you to reflect on to determine if, underneath the doubt and second-guessing, you actually do have a pretty good idea of what kind of career you want.

QUESTION 1: WHAT WOULD YOU DO FOR A LIVING IF NO ONE EVER KNEW WHAT YOUR CAREER WAS?

One common dream killer that sparks all kinds of self-doubt and second-guessing is worrying about other people’s reactions to your career choice.

For example, my client Maddie has been on a path toward becoming a nurse practitioner and eventually a physician. Her family and friends are all so proud of her big ambitions.

It was clear from the way she talked about this, though, that her heart wasn’t with the traditional medical world. When she got on the topic of natural and holistic health, however, her entire demeanor brightened.

I finally asked her, “If you weren’t worried about prestige or anyone’s opinions about your career, what would you do?” Almost instantly she answered, “I’d become a naturopathic physician.”

That was the first time she’d admitted out-loud what she really wanted.

The same is true for my client Emily. When she was a kid, she loved the idea of being a personal assistant to a change-maker or important businessperson. It sounded like such a fun job, and it perfectly suited her personality and natural skills.

But as she got older, she felt family and societal pressure to become something “better” than a personal assistant. She felt like there was a stigma on being a “behind-the-scenes” person, and she assumed she should be the one wanting to change lives and make her mark on the world. So she pushed the idea aside and went back to grad school for public health, even though she never really felt inspired by it

Truthfully though, she still really wants to be a personal assistant. She’s just as attracted to it as she was as a kid, and through coaching, she’s now realizing that the only thing stopping her is fear of judgment from other people.

Emily told me on a recent call, “I wish I’d given myself permission to pursue being a personal assistant years ago before I invested so much money and time in something that never felt right. But I’m glad to finally now be on a path that’s right for me!”

QUESTION 2: IF YOU COULD GO BACK TO SCHOOL FOR ANYTHING, WHAT WOULD IT BE?

Imagine if someone handed you a blank check and said, “Use this to go study whatever you’d like for as long as you’d like.”

I don’t know about you, but I’d feel the same way I did when I was 4 years old and woke my parents up at 2am to open Christmas presents because I was too excited to sleep.

I have all kinds of things I’d want to study, but if I had to choose, I’d probably go back to school and study psychology on a deeper level. Which just confirms that I’m in the right career field now since, as a coach, I’m already in one segment of the broader psychology world.

If you’re not as nerdy as me, though, then the idea of school might inherently turn you off. So you could change the question to something like:

“If I could take a sabbatical and explore anything I wanted, what would I learn about?”

Or maybe, “If I could be in an apprentice-type role and learn from someone I admire, who would that be?”

The point of this question isn’t to make you feel like you need to go back to school. (I have lots more thoughts about whether or not you should go back to grad school, and in most cases, it’s not necessary.) It’s more meant to reignite your sense of curiosity, fascination, and interest.

QUESTION 3: WHAT KINDS OF ACTIVITIES PUT YOU IN A TIME WARP?

Have you ever had one of those experiences where you’re doing something — reading, drawing, researching something, laughing with friends, playing with your dog — and when you eventually check the time, you’re shocked that somehow hours have passed?

Or maybe it’s the opposite. Maybe you’re in a creative flow and you easily, effortlessly bust out two hours worth of work in 15 minutes.

Those kinds of activities that put you in a time warp are incredibly important. Whenever time starts to feel weird and fluid like that, take note of what you’re doing because those are the things that are core to who you are and what comes most naturally to you.

For my client Aimee, that’s creative writing. She can sit down at 2pm on a Saturday to do an hour of writing, and she won’t snap out of her flow state until her stomach starts grumbling because it’s 7pm and she hasn’t eaten since noon.

Aimee actually has no intention of making a career out of creative writing (unless, of course, her plays and stories end up making it big-time) because she’s a Thriver who doesn’t want to put pressure on her passion to provide for her financially. But she does want to find a career that evokes the same kind of creative flow state that she feels when she’s writing.

QUESTION 4: IF YOU INHERITED ENOUGH MONEY TO TAKE CARE OF YOUR BASIC LIVING EXPENSES FOR THE REST OF YOUR LIFE, WHAT WOULD YOU DO WITH YOUR TIME?

I’m sure you’ve been asked a version of this question before, or at least considered what you’d do if money were somehow taken care of, but I want you to reflect on this more deeply than you have in the past.

If your quick answer to this question is something vague like “not work” or “travel” or “spend time with friends and family,” ask yourself some follow-up questions to get more specific:

How would you spend your non-working days? What would a typical day look like for you?

Where would you travel? Where would you explore? Why?

What kinds of plan would you make with friends/family?

What would you want to learn more about? Why?

What would you create?

Who would you want to help or impact?

ARE YOU SHUTTING DOWN YOUR DREAMS PREMATURELY?

Your answers to these questions may point directly to a particular career path (or might open up a few clear options), but more than likely it’s not going to be that linear. So you’ll have to get creative about how you could possibly incorporate some of your fascinations and secret dreams into a career.

Or, for all of my Thrivers out there (like my client Aimee), consider how your career could best support you in spending as much of your non-working time as possible doing these things that light you up.

For those of you who came up blank trying to answer these 4 questions, don’t fret! That’s totally normal. These questions were intended to help you determine if you DO have a clear direction that you’ve been muddying up with self-doubt and second-guessing.

But it’s just as common to simply have no idea what you want right now. It doesn’t mean you’re broken or a lost cause — all it means is that you’re at a slightly earlier stage of the “figuring out this passion & career thing” process that requires revealing your deeper values and giving yourself permission to more seriously explore the things that fascinate you.

(Side note: If you want WAY more guidance about this, you’ll definitely want to get on the VIP list for our Passion Plan Virtual Experience program. That’s our month-long virtual course where we lead you step-by-step through figuring out your passion, and it’s re-opening for enrollment next month.)

Bottom line: One of the most common things that makes people feel lost and discouraged is shutting down their dreams before giving them space to fully form and become real possibilities. So use these 4 questions to give your ideas room to breathe.

Leave a comment below to share your answers to one or more of these questions! There’s real power in sharing your secret dreams with other people — speaking them out loud automatically makes them feel more real.

IF YOU LIKED THIS, THEN YOU’LL ALSO LOVE …

How to transform knowing what you DON’T want into knowing what you DO want

How to get over your fear of failure

What to do when you feel like you’re behind in life

How I narrowed my options and finally figured out what I wanted to do when I “grew up”

Much Love,

Kristen (& Rachel)


FREE E-BOOKS … HAVE YOU DOWNLOADED YOURS YET?

This month marks our second annual Summer Freedom Series — one month of surprise bonuses meant to inspire, uplift, and make you feel free.

Last week we announced that we’ll be releasing a new (and FREE) e-book every week for four weeks (on Thursdays in August).

If you missed last Thursday’s post, you can read the announcement and download the first e-book in the series here.

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This one is for you if you’re going through a period of doubt, confusion, or existential crisis and need someone to sit you down and help you figure out what to do next.

You’re DEFINITELY not going to want to miss our announcement of the second e-book in the series … the whole book is the answer to the #1 question we constantly get asked. 

So, we’ll see you this coming Thursday, August 17th with e-book #2! 🙂

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9 Comments // ADD COMMENT

9 comments

  • Gillian

    I’ve mentioned this previously on related blog posts and the PPSC forum.

    I want to work in the entertainment industry. I’ve made some steps toward doing so by taking classes but what continues to stop me from moving forward is lack of experience. If I could quit my current job that I hate, I might be able to intern or something but it’s not financially possible which leaves me stuck.

    Recently, I also had a setback from a person I trust. I have uncles who work in the industry and he is pushing me to apply for jobs within the finance sphere but at a major studio. I cannot work in finance or billing any longer. It is not where I want to be and I already feel like I can’t get out of this position. He used to be one of my biggest supporters and now I’m struggling even more (well, I’m also dealing with some mental health issues).

    I love posts like these but because I’m a realist, I somehow feel worse because I’m trying so hard and never get anywhere.

    • Kristen Walker

      Hey Gillian! I first want to say that it’s so awesome that you’re clear on what you want. Honestly, having that certainty is half the battle! The main reason I wrote this post was to hopefully help some people get to the level of clarity that you already have about what you want. So it’s important to give yourself credit for figuring that out!

      Now, I totally understand that making it happen is a whole different challenge. I’m really sorry that you’re feeling discouraged by your uncle’s feedback. While I’m sure his intention was only to be helpful, it still stings to feel misunderstood in the face of those kinds of suggestions. To your point of not having enough experience, I’m sure you’ve heard us talk about this before, but it bears repeating — it’s not important that you’re 100% qualified for a job. The relevant classes you’ve taken combined with your natural talents/soft skills could very well be enough to at least get you in the door to an entertainment job. I talk a lot more about this in this blog post, and you’ll want to listen to the audio we included at the bottom of that post, too! You could be a lot closer to your dream than you believe you are.

  • NARLENE

    Every time I read one of the questions, one thing comes to mind. Saving the ocean’s wildlife. I’ve always loved dolphins, but my passion has grown to all forms of ocean life from large creatures to the smallest. I would love to study marine life. Tag sharks or orcas, study walruses or sea lions. I am most alive and centered when I am at the ocean or on a beach. I live two hours away from the ocean, but my gosh I feel wonderful there.

    • Kristen Walker

      How amazing, Narlene! It’s incredible that you’re so clear on what brings you the most joy and passion. To me, it sounds like being near the ocean and doing your part to save the ocean’s wildlife is a huge priority that deserves as much of your time/energy as you can give it. We need as many people as possible working to save our environment, especially ocean wildlife, so your passion is very much needed right now! Thanks for sharing. 🙂

  • Michelle

    For as long as I could remember, I loved to create things: whether it was writing, painting, sewing or folding paper. If I didn’t have to work for a living, I would do those things all day and never get bored. Sadly I can’t figure out how to make this a reality.

    • Kristen Walker

      Love your creative spirit, Michelle! Sounds to me like it’s really important for your career to support your creative work by making sure you have the stability and time to devote to creating things. But I also do think it’s possible for you to bring your creativity into the workplace in a fulfilling way. I’m curious — what’s your definition of creativity? What would it mean to you to feel creative at work? Just some questions to hopefully spark some outside-the-box ideas! 🙂

  • Charlie

    When I look at these questions, all I can think is that I don’t want to do anything. I know I’m exhausted after years of searching for my place in the career world and being chronically sleep deprived (small child). I’d love a blog on how to get at your passions through the tired (both physical and existential) fog.

  • Jen

    Hey, I got a mixed bag for some of these questions.

    First of all, does browsing the internet count as a time warp? That stuff passes me by in seconds. Maybe it matters what im browsing, which is usually interior design, and Egyptology, Norse mythology and sometimes building cars…
    My other time warp would be playing computer/ video games. – trust me,ive tried the creation of these, shuffling vertices is no fun, but creating the levels were (interior design in a fantasy area? yes please!).

    when it comes to if money was taken care of, id be exploring the ancient ruins of past cultures. I would visit Egypt, Cambodia, Mexico, anywhere where a giant monument built hundreds or thousands of years ago can be. I love the mystery that even today we don’t 100% know what they were thinking, and i like exploring the ideas as well as the places. But at the same time, I kinda wanna rescue a bunch of dogs and find them nice homes.

    If i had free time or a sabbatical to fully explore a subject, it would probably be mythologies of ancient cultures, but at the same time, I feel like maybe thats just how I feel right now, and I don’t need a whole year to do it, that sounds intimidating, maybe just causally research like i have been. Maybe i want a mix of interior design, mythology and video games? What on earth would that look like?