Career Coaching Questions:
What Should I Do With My Life?
Many years ago, the end of summer was a hard time for me. I was not in a career that felt meaningful, and I struggled with the question, “What should I do with my life?”
At the time, I didn’t have the answer. Back-to-school season, for whatever reason, was the worst: The aisles with their crisp, virgin notebooks and rows of un-chewed pencils seemed to look at me disapprovingly as I slouched past, prepared to waste another year of my life in a career that I did not love.
The coming of fall made me feel tired, depressed, and a little guilty that I wasn’t doing more with my life.
But one fall morning over twenty years ago now, something different happened. I woke up early because the Adventure Husband had turned on the TV. Loud. As I walked into the living room prepared to tell him how annoying and inconsiderate he was being (this was before we figured out it was time for marriage counseling), I saw an airplane on the screen plowing into a tall glassy building, high above New York City.
I didn’t know it yet, but I had just watched my cousin Jimmy get killed. He would have been sitting at his desk on the 104th floor of One World Trade Center, probably booting up his computer and sipping coffee, right up until the moment that a plane piloted by zealots crashed through his window.
That day changed me in many ways. But in the midst of my shock and grief and trauma and fear, one message stood out to me clearly: “Your time here is short and could end at any moment. Stop screwing around and do something more important with your life.”
The most important and meaningful thing I could imagine doing was being of service to other people. Connecting with that core value was the spark that sent me to graduate school to embark on the career path of becoming a counselor. That drive motivated me through many years of working for a Master’s Degree and then a PhD as I evolved into “Dr. Lisa,” and the founder of Growing Self. It is still the reason I sit here now, on this August day, writing this love letter to you.
What to Do With My Life?
I don’t want you to have to go through tragedy or trauma to get connected with your inner values — the lighthouse that will guide you toward your best possible life. But I DO want you to feel satisfied with your life and your career. You deserve to be happy. Your life is too short and too precious to waste one more day in a career that is meaningless, frustrating, joyless, or boring.
Working people spend more time at their jobs than doing any other single thing. Your job gets more of your time and attention than your marriage, your kids, your friends or your personal interests. Wouldn’t it be amazing if your passion, your meaning and your reason for being were all linked to your career?
When you’re in a career that suits your personality, showcases your natural talents, ties into your interests and your passions, and creates meaning and value for you, you stop having “a job.” You have a career, and it’s woven into the fabric of a happy, satisfying life.
Finding Your Purpose in Life
If you’ve read this far, you’re probably in the same spot I was. You’re wondering: “What is my purpose?”
That question likely has you feeling paralyzed, and understandably so. In America, we face a lot of pressure from parents, teachers, and others to choose our career paths early. Did you truly know who you were when you were eighteen years old? Neither did I — that’s why I was a biology major in college.
But the truth is, very few people finish high school or even college actually knowing which career is right for them. Some respond the way I did, moving ahead without a clear road map, until they find themselves working jobs they don’t like, wondering how they got there. Some of us take our best guess, and sometimes we guess wrong.
As a licensed therapist and certified career coach, I meet plenty of people who’ve already dedicated a decade or more to their careers, only to find themselves asking the same questions: What should I do? What is the purpose of my life?
These are big, difficult questions. Confronting them means getting honest about how limited our time is, and what value we’d like to add to the world while we’re here. The search for these answers is understandably intimidating, but the alternative to the search is to flounder aimlessly or to spend years or even decades working toward goals that feel empty to us.
In a painful way, I got lucky. Jimmy’s death forced me to address the question I’d been avoiding. The good news is, you don’t have to wait for a catalyst, like losing someone dear to you. You can begin making intentional, clear-eyed choices about your life’s work now, based on who you really are and what you really value.
You may be able to navigate this process alone. But in many instances, you may benefit from working with a good career coach or counselor. If so, it’s critical when choosing a career coach to find someone with the proper training and experience. Anyone you hire should understand the goal isn’t merely to pick a job that pays the bills. It’s to help you find a vocation as big and varied as you are, that can grow as you grow, infusing your life with meaning and purpose.
Here’s some more good news: The first step is easier than it seems.
What Should I Do With My Life? Step 1: Learn as Much as You Can.
The first step in deciding what to do with your life is learning as much as you can about yourself, and about the possible paths available to you.
What’s your personality like? Are you outspoken or reserved, structured or spontaneous? Does spending lots of time with others invigorate you, or leave you feeling depleted? Understanding your personality is important. No matter how interesting the job, if it’s out of step with who you fundamentally are, you’ll always feel like you’re swimming against the current. If you’re working with a career coach, they’ll likely ask you to complete some personality assessments, to find a good match and avoid a bad one.
Spend some time thinking about activities you enjoy and that you excel at. Maybe you’re a talented guitarist, a dedicated gardener, or a master-level chess player. Don’t just identify these activities, think about what it is about them that you really like. Your hobbies and interests are probably not solid career choices in and of themselves, but they can point the way toward possible careers that share some of the same basic qualities, like creativity, nurturing, or strategic planning. By identifying these qualities and seeking them out, you have a much better shot at finding work you love.
At the heart of choosing a career is getting in touch with what you value and which potential career paths will give you opportunities to live out those values. Keep in mind, any value you hold can be matched up with a wide variety of careers. If you value adventure, you may want to build a career as a photojournalist, or a skydiving instructor, or a whitewater rafting guide. If you value helping others, you may want to become a teacher, a physical therapist, or a social worker. Getting clear about your values before making any big career decisions will guide you toward work that feels meaningful and reflects what you care about the most.
Many people make the mistake of not thinking about other goals they have for their lives, and how their career choices will help those goals, or stymie them. Having a large family is a beautiful goal, but how will it match up with a career that demands 60-hour work weeks? It’s possible to have both, but can you have both in the way that you really want? And if not, which goal is more important to you? Some careers may keep you on the road for weeks at a time, making it difficult to maintain a relationship, unless you’ve got an incredibly understanding and flexible partner. Is that a sacrifice you’re willing to make? Thinking through these tradeoffs can be stressful, but it’s better to do it early, rather than realizing a decade into the future that you’ve built a career that’s incompatible with your other goals for life.
Finally, spend time learning as much as you can about a wide variety of possible careers. Brainstorm a long list of jobs that appeal to you, and begin researching those career paths, considering how they match up with your personality, your values, your talents, what you enjoy, and your other goals for life. If you’re having trouble generating ideas, a career coach can help get you started.
Don’t just consider these careers from a distance, but really dive deep into the day-to-day reality of what these jobs are like. Do some research online, and reach out to professionals who work in the field for informational interviews. Talking with someone who’s actually doing the work can give you a better feel for what the job would be like than reading about it ever can. As long as they can find the time, most people are happy to talk about their career paths with interested newcomers.
Why Holistic Career Coaching Matters
Whenever you’re making a big decision, it’s important to have as much information as possible. You wouldn’t marry someone just because you had a good time together on a handful of dates (hopefully!). You’d most likely spend years getting to know them, considering what kind of life you’d have together, how well your goals for the future align, and how your personalities complement or clash with one another.
Choosing a career is no different. It’s impossible to make an informed choice without digging deep into who you are, what you care about, and what you want, and then learning as much as possible about potential careers to evaluate how well they line up.
Unfortunately, a lot of career coaching is narrowly focused on landing a particular job, and doesn’t go far beyond some interview prep, some resume writing, and some networking advice. While “job attainment” skills are valuable, choosing a career is about so much more than getting a job.
What if you’ve set your sights on a particular career, but deep down, you’ve chosen it to please your parents, or to emulate a successful friend? You probably won’t even realize this yourself, and a job coach whose approach doesn’t go deep enough certainly won’t. If you don’t understand why you’re choosing what you’re choosing, you’re unlikely to land in a career that feels meaningful and satisfying over the long haul. (For more on this subject, check out the “Quarter Life Crisis” episode of the Love, Happiness and Success Podcast.)
Holistic career coaching will not only help you win at work, it takes the whole person into consideration, helping you understand the “why” behind your career goals so that you can design a career that’s a reflection of you. When the work that you do and your purpose in life are one and the same, work won’t feel like work at all, but like a natural extension of who you are.
What Should I Do With My Life? Step 2: Give Yourself Permission to Experiment
To extend the dating metaphor a little further: You’ve probably had the experience of meeting someone you like, feeling the sparks fly, and beginning to daydream about a long and happy life together, only to notice a month or two later that they have some qualities (Dishonesty? Anger management issues?) that would make them a terrible long-term partner for you.
Hopefully, this was a relationship you walked away from, although it probably wasn’t easy. Giving up on a dream, whether it’s a promising new relationship or a long-held career goal, can bring up feelings of disappointment, failure, and even heartbreak. But the alternative is much worse: Spending decades of your life in a situation that leaves you unhappy or unsatisfied.
Whether you’re choosing who you’ll spend your life with or what you’ll do for a living, you have to be willing to try something out and to pivot or change course if it’s not working. A career coach can help you narrow down your options and get some clarity about what kind of career is most likely to be a good fit for you. But at some point, you’ll need to experiment and accept that you can’t make a perfect choice until you have more information — the kind that comes from actually doing it.
I had this experience when I decided to go back to school at age 27 to pursue a degree in counseling. I remember thinking, as I was filling out the enrollment paperwork and signing my name on the dotted line for student loans, “Wow, I really hope I like being a counselor.” It was a leap of faith, and one that felt like an enormous risk at the time. In order to feel comfortable taking this step, I had to give myself permission to try it out, and trust that I would be able to reassess and go in a different direction if it didn’t feel right once I got in there.
When you’re just starting out, internships and entry-level jobs are a good way to explore potential careers before you fully commit. You can take eight months to a year and really scope out the job, then check in with how it’s going for you. Do you like the work? Are you good at it? Do your coworkers seem happy?
If your “experiment” goes well, you can continue exploring that career. If not, that’s ok too. Most career tracks split off into a number of different paths branching out from the starting point, and won’t pin you into a single destination. Becoming a counselor is one of the more structured paths, but even that offers quite a few options. After earning my graduate degree, I could have gone to work in a community health center, a hospital, or a school. After I finished my doctorate, I could have taught at a university or started consulting with community organizations or companies.
Eventually, I decided to open my own practice focused on positive, growth-oriented coaching and therapy. It eventually grew into the group private practice it is today, but that didn’t happen overnight, and it wasn’t even the original plan. I just took a first step. It wound up being the right choice for me, but I didn’t have all of that figured out on day one. You don’t have to either.
Finding Your Purpose Later in Your Career
As a career counselor, I meet many clients who don’t have the freedom to wing it. The younger ones, usually in their mid-20s, often have scary amounts of college loan debt. Others have dedicated years to their careers only to find themselves, in their 30s and 40s, feeling depressed at the thought of going to work.
When we’re unhappy with our work, it can be hard to know exactly what the problem is without a little outside perspective. Toxic workplaces are a common culprit; when people encounter an abusive boss, bullying colleagues, or work environments where their contributions aren’t recognized or valued, they often blame themselves, believing that if they could just toughen up and try harder, then they’d succeed.
But it’s impossible to do your best work in a workplace that’s disempowering and emotionally draining. These clients don’t need a career change, they need a change of environment. When I meet a client who’s in a toxic workplace, I help them think through ways to improve the situation, whether that means switching teams, learning new strategies to deal with difficult people, or leaving their jobs.
In other cases, clients are unhappy at work because they’ve bumped up against an internal obstacle that they need to overcome. These are growth opportunities, and the need for growth often shows up as frustration about not moving ahead, or confusion about why things keep playing out in the same ways (arguments with coworkers, missed deadlines) again and again.
Our internal challenges follow us wherever we go, so it would be a mistake for these clients to switch career paths rather than seeing these problems as the opportunities for professional development that they are. A career coach or counselor can help you to identify any skills you need to develop, like emotional intelligence, organization, or communication, so that you can not only continue to advance but so that you can feel satisfied and happy with your work again.
Emotional intelligence is an especially valuable skill, as it impacts not only your success and satisfaction at work, but in virtually every area of your life.
But many clients really are in careers that are just the wrong fit for them. By the time they call me, most of them are depressed. They feel trapped, and don’t know how to get unstuck. This can happen for so many reasons. I studied biology in college because I was good at it, and because nerding out about science remains the best way for me to connect with my dad. Thank goodness I realized I had no interest in medicine before applying to med school.
Many people have these realizations much later, and confronting them requires a fair amount of courage. By the time we’re approaching mid-career, we often have major financial responsibilities, like children, a mortgage, car payments, or all three. Making a big career change isn’t as simple as trying out a new field through an internship, or applying for an entry-level job.
If you’ve invested years of hard work into a career that’s wrong for you, a career counselor can help you make peace with that, explore your options, and figure out how to get from where you are now to a place that feels meaningful, satisfying, and rewarding. Your years of experience don’t have to go to waste — they’ve no doubt helped you build valuable skills that can be channeled in another direction.
Finding Your Purpose: Personal Growth is Professional Growth
Over time, our relationship to work grows more complex. I find that many people in the middle of their careers still enjoy the work they did when they started. Computer coders love to write code. Writers love to write. Corporate executives love making deals. It’s the other stuff that becomes difficult.
I met a web developer who couldn’t keep a job for longer than a year, because everywhere he went, he failed to get along with his co-workers. After working with him for a while, I discovered he experienced some pretty profound emotional neglect as a child. That caused him to feel distrustful of others, and unable to recognize unspoken social cues.
A brewer I worked with had a history of sexual assault. She loved making beer in solitude, but being around tipsy customers made her seethe with rage she couldn’t understand.
Work is not an island, and our personal traumas are bound to rear their heads in our careers sooner or later. In that way, professional challenges can be warning signals that we have some internal wounds that need healing, so we can feel more emotionally balanced in our lives overall.
Emotional intelligence impacts how effectively we can tune into our own needs, manage our feelings, and respond to those of others. By working with clients to raise their emotional intelligence and regulate their inner states, I not only help them professionally, I help them personally as well.
Finding a Career Coach
When choosing a career coach or counselor, it’s important to work with someone whose approach dives deep enough to get to the real root of any problems coming up in the workplace, as they often begin long before we start down our career paths.
Here’s an exercise. Type the name of your city and “career coach” into Google. Take the first ten hits, then look up the credentials for each one.
You most likely won’t find much. Many worked as middle managers in company HR departments. Others were counselors at a local high school. Most have never taken courses on coaching from an accredited university. Almost none have degrees in psychotherapy. Recently I met a “career coach” whose most recent job was managing a nail salon.
When you tell an inexperienced, untrained, unlicensed coach, “I need a new career,” that coach will probably believe you. In the best-case scenario, let’s assume you’re right. Without training, the coach will have no method — beyond their own guesswork and intuition — to guide you toward fulfilling work.
And if you’re wrong? You might throw away a career that you love over a problem you can fix. You might let a stressful job ruin your relationship, or spoil other important parts of your life. If you carry buried emotional pain or interpersonal challenges you need some help working through, these problems will remain unrecognized and unaddressed. They will show up in your second career, just as they did your first until you get the help you truly need.
Wondering what a career coach costs, what a career coach does, or about the difference between a career coaching and counseling? We have answers to your career coaching questions.
The Many Paths to Finding Your Life’s Purpose
During my freshman year of college, I briefly considered becoming a writer. That seemed really impractical, however, so I chose biology instead. From there I wandered through years of fashion design, waitressing and graduate school. Finally, I became a counselor and started helping others decide what to do with their lives, work that has fulfilled me now for nearly 20 years.
The funny thing is that between patient reports and stories for this website, I write almost every day. In those painful months after 9/11, I had no idea that following my desire to maybe someday become a therapist would eventually lead me back to writing, my first love.
I see this dynamic repeat itself over and over. People who stay in careers they loathe find that their lives feel small and restricted. Those of us lucky enough to do what we love find that our careers expand our lives, and give us unexpected opportunities to become the best version of ourselves.
There’s no “one” answer to what you should do with your life, but many paths that will offer you chances to reach your fullest potential in multiple ways. The key is getting clear about what you value, what you enjoy, and what work feels like the best use of your precious time, and letting that be your guide.
I hope that me sharing my story, and a few tips to nudge you in the direction of clarity around that “what should I do with my life” question has been helpful to you today. Of course, doing the work of figuring yourself out and finding your calling requires more than reading an article on a blog. It’s an experiential process that requires you to dig pretty deep. If you’d like to do this soul-searching with a phenomenal career counselor / therapist, you’re invited to work with us. Just schedule a free consultation meeting with one of our holistic career coaches, and we’ll get to work.
Wishing you all the best,
Dr. Lisa Marie Bobby is the founder and clinical director of Growing Self. She is a licensed psychologist, a licensed marriage and family therapist, and a board-certified coach, as well as the author of “Exaholics: Breaking Your Addiction to Your Ex Love,” and the host of The Love, Happiness & Success Podcast.
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