Illustration of man choosing a career.

Career Coaching Questions:

How to Choose a Career

There is a reason that people are lining up out the door to get involved in career coaching services. Choosing a career is an exceptionally momentous and stressful decision. With the possible exception of choosing a life partner, it’s one of the biggest decisions any of us will ever make. It’s anxiety-provoking — even paralyzing — to choose a career out of many options, and commit your life to it. I know that for me personally, I had this experience before I decided to go back to school for counseling.

This anxiety is completely valid and normal, but it’s also worth listening to: This decision is actually a big deal. It is overwhelming to sort through all of your different options and settle on THE ONE career that you’re going to devote potentially the next forty years of your life to. This is especially true if you have lots of talents, abilities and opportunities, and could plausibly have a very successful professional development trajectory in many different areas. Which to choose! 

Some people cope with this existential anxiety by not making a conscious choice at all. They just do the easy-ish thing. While it may not be the best career path, they’ve settled the immediate angst and feel better in the short term. Others choose to lean in to the anxiety, stay in the ring of indecision and unknowing long enough to spluenk the depths of their personalities, values, and life goals. Like a miner walking out of a cave clutching a huge, raw gem, they now have something valuable to work with — self awareness, clarity, and direction — that they can continue to hone over many years of their successful professional arc.

Even if you have sorted through the “what should I do with my life” existential questions, with or without the help of a good Denver career coach or helpful online career counselor, there comes a new round of paralysis when it’s time to commit, and understandably. When you choose a career path, you’re making a huge investment in time and energy, particularly if — as many professional occupations do — your career goals involve acquiring education and specialized training to be successful in a certain field. 

You’re also taking a big risk. Like, what if you put all this time and energy (and often money) into attaining this professional role only to find out that you don’t love your chosen career path after all? A troubling possibility to consider!

I hope that my giving a voice to what you’ve probably been grappling with lately if you’re choosing a career didn’t stress you out further. While no one can tell you what career is right for you, I can give you some guidance on how to make a big decision based on the life you want to create for yourself.

Choosing a Career? First, Know Yourself.

Here’s some good news: If you’ve been entertaining how to make your passion your career in your mind, feeling pulled between them, unable to weigh out the pros and cons and settle on the “best” possible choice, you can stop doing that right now. 

The first step in how to find your purpose in life, before letting any possibilities through the door, is getting in touch with who you are, what you value, and what makes you happy. This step should not be rushed — taking a few months for some in-depth personal reflection is completely reasonable before making a decision of this size. 

If spending that much time building self-awareness sounds like overkill, keep in mind that you probably have a lot to untangle (most of us do!). Well-intended people may have pushed their own hopes and dreams onto you, and over time, you may have gotten them mixed up with your own. It’s important to sort through these ideas about what you “should” be or do before making any decisions, so you can be sure that whatever you choose is your own heart’s desire, not someone else’s. 

Career Counselors Help You Choose a Career

What is a career counselor? A career counselor is someone who can guide you through this process of choosing a career, giving you personality assessments and asking questions to shed light on what you care about the most in life, what you’re good at, and what you enjoy. 

Do you like collaborating with a team, or do you prefer owning every step of a project? Do you place a higher value on creative expression, financial success, or service to others? What are some activities that leave you feeling competent, satisfied, and like you’re performing at your best? 

Even if your answers point to something that probably wouldn’t be a realistic career choice, you can drill down further into what it is about these activities that’s so rewarding for you. Maybe you love improv comedy because it forces you to take risks and think on your feet. You might love cooking because it creates opportunities to experiment. Or because you find joy in sharing something you’ve made with others. Or because you’re simply passionate about food. 

When you understand why you find certain things engaging and others not so much, you can begin to look for those qualities elsewhere. 

Next, start to think about which settings you thrive, how you “win” at work, and also which jobs turned into toxic workplace experiences. The thought of sitting at a desk for eight hours a day might make you feel stir crazy, or it might not. Being on the road for a week every month sounds exciting to some people, and like a nightmare to others. Maybe you’re thrilled by the idea of constantly meeting new people, or maybe that sounds exhausting. Clarity about these basic personal truths will come in handy when you’re choosing a path. 

Working with a good career counselor can help you know yourself better, in order to wisely and with self-awareness, choose a career most likely to bring you authentic happiness, personal growth, healthy relationships, and “whole life” success in the long run.

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Choose a Career By… Giving Yourself Permission to Imagine and Play

Once you’ve taken some time for self-reflection, and hopefully emerged with new insights about your values, your personality, and what brings you joy, you can begin toying with some possible career paths

At this stage, keep your mind open, letting in every possibility that sparks your interest and feels even remotely viable. You could apply to medical school and become a cardiologist. You could start selling paintings and bartending on the weekends. You could move to Alaska and become a ranger in Denali National Park. The point of this exercise is not to be realistic. It’s to get your mind unstuck and remind yourself how many options you truly have.

Once you’ve generated a long list of ideas, you’ll probably be able to rule out the majority of them right away. Most careers will feel too impractical, or too incompatible with your other life goals. But hopefully there are a few possibilities that you don’t want to cross off the list. These are ideas to explore more deeply, considering how they may compliment (or clash with) the things you’ve learned about yourself so far. 

A Denver career coach or online career counselor can help you identify all the career options that match your hopes and goals, explore the industries of each, and help you think through the qualities that would make a good (and satisfied) dentist, or teacher, or museum curator. Most importantly, your career coach can help you think through whether or not these qualities match up with your personality, your values, or your interests. 

If you’re not sure how well a career would fit you, how could you learn more? Is there someone you could ask about the day-to-day reality of their job? The more information you can gather at this stage, the better. Your career counselor can help you figure out where to find the information you need in order to make informed career decisions. By learning everything you can, you have a more realistic basis for choosing a career.

All careers have pros and cons. Some might not seem like a good fit for you at first blush, but when you learn more about the day to day opportunities, you might find them more attractive. Others might seem exciting, but then start to feel like a bad match when examined up close. However, by thoughtfully exploring your different options before you jump in and formally choose a career, you can find a number of possibilities that may have potential for you.

Choose a Career by Researching Career Paths

It’s one thing to say you’d like to do a certain job, and another thing entirely to get yourself to the place where you’re prepared to do it. 

When choosing a career, evaluate the entire career path, not just the end goal. If you’re interested in holding a certain job, check out the LinkedIn pages of people who have it, and trace their route back. What jobs did they hold along the way? For how many years? What would that be like for you? 

Some careers will require you to go back to school or to learn new skills before you can work a day in the field. If this applies to a career you’re considering, start looking into what you would need to do. Are there programs in your area? Could you take classes online? Would you need to take out loans, or could you get funding? 

If a career feels intriguing to you, but the barrier to entry is just too high, that’s ok. Moving across the country for a graduate program, or going into debt, or working a full-time job while studying at night, are all major sacrifices, and not everyone can make them. Furthermore, there are plenty of masters degrees that are not wise investments for you or for anyone, given the cost and the probability of finding a job in that field. There’s more than one career that would light you up; cultivating grit and perseverance is half the battle.

But, if you hesitate to invest time and money into a given career because you’re not sure whether, after all that investment, you’ll like the work, keep looking for more information. Reach out to people who work in that field, ask if you can shadow them, read and watch as much as you can about what the job is like. 

There’s no guarantee that you won’t complete some onerous graduate program, get hired, and then realize your first day on the job that you can’t stand it. But not setting yourself up for success by actively working toward your dream career (because you’re scared to commit) would be a mistake too. Personal share: I was nervous that I wouldn’t like being a counselor before I went to counseling school. The best that you can do is learn as much as possible about yourself and the job before you start down the path.

Find a career coach who can help you develop genuine understanding for everything that will be involved in creating a successful long term career path. They can help you anticipate the hurdles, figure out the nuts and bolts of resume writing and interviewing well, and how to take small, low-risk steps that keep you moving forward.

Even better, a really good holistic career counselor who’s also a therapist can help you deal — mentally and emotionally — if you need to try something out, learn about yourself, grow as a person, and wind up going in a different direction. Even though this might sound hard, it’s a good thing, and can be part of the process of choosing a career.

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Create a Flexible Career Path Plan

How to stay motivated: Having a career plan for how you’ll get from point A to point B is smart. But you also need to be prepared to deviate from the plan, because you will. And that’s ok — it’s growth. Professional growth and career development are just as important as choosing a career, in the long run.

Ask someone who loves their job to tell you about their career path. You may be surprised by how many plot twists the story contains. They may have spent a decade in a job they hated before they finally felt miserable enough to start chasing their dream. They may have always planned to do one thing, but fell in love with some other thing along the way. They may have held on for dear life in a dying career with no future, only to find real satisfaction and fulfillment once they finally let go.

In all of these examples, the person ended up choosing a career they loved because they were willing, at some point, to check in with how they were feeling, honor their personalities and their values and their desires, and make a career change. Somewhere along your path, you’ll probably have to do that, no matter how much planning you do at the outset. 

There’s only so much information you can gather and research you can do. Much more will become apparent once you’re actually doing the work. Working with a good career coach can also help you create a realistic, flexible career path plan (and learn how to mentally and emotionally cope with the twists and turns along the way.) As long as you remain flexible and responsive to whatever comes up, you’ll be able to make course corrections as you go, and you’ll never be stuck.

How to Choose a Career

Just as there’s no “one” person who you must find and marry in order to have a life full of love, there’s no one career path that you have to walk down in order to break free from what’s holding you back and choose a career that’s rewarding and meaningful. You’re allowed to try something out, hate it, change course, and experiment with something else — and you probably will. 

Whether you’re just starting out or you’re starting over, choosing a career path can be an overwhelming decision. But it can also be one of those times in life when you’re fully alive, looking at all the possibilities in front of you and unapologetically pursuing the ones that speak to who truly you are. 

Why not have some fun with that?

I hope that this discussion helped provide you with some basic clarity and direction around how to choose a career, and the growth process involved in creating confidence about your career path. You deserve to have a career that you love, and the word needs your gifts!

Wishing you all the best,

Dr. Lisa Marie Bobby

Meet a Few of Our Expert Career Coaches

Colorado Coach and Counselor

Ronni M.


Illuminate Your Possibilities

Meet Ronni: a career counselor, life coach, and individual counselor with a caring personality and a flare for adventure. Whether you want to embark on a new career path, work on personal growth goals, or pursue greater life satisfaction, she’s here to support and motivate you to create positive change.

Susan H. M.A., LPCC

Susan H.


Empathetic, Insightful & Growth-Oriented

Susan specializes in helping clients reach their goals and achieve a sense of purpose and fulfillment. She has a warm, honest, and collaborative style. Whether you’re seeking support in your career, or want to be a better version of yourself, Susan will walk alongside you and support you as you create positive change.

The therapists and career counselors of Growing Self have specialized education and training and years of experience in helping people achieve their personal and professional goals. We use only evidence based strategies that have been proven by research to help you get clarity and direction, have better relationships, feel happier, and design your ideal life.

This website is devoted to your wellbeing, and offers loads of free information and actionable advice that you can start using today to create positive change in your life. Browse around to meet our experts, get free advice on our blog, listen to a podcast, or take our “How Healthy is Your Relationship” quiz. Or, if the time is right, you can schedule a free consultation with any of us to talk about your situation — and, most importantly — your hopes for your future.