• Alyssa Barton

Directionally Challenged

Updated: Apr 23, 2019



What do you do when you find yourself all grown up but lost in Adultville without a concrete idea what you want to "do" or where to take your career from here? Whether you're in school, between jobs, or considering a job or career path change, a lot of adults I've spoken to aren't sure which direction to take moving forward.

There seems to me to be three camps amongst the directionally challenged:

  1. Comfortable: they’re not necessarily doing what they want yet they find enough satisfaction with their current job or career path to stick with it. This can be because it’s easy, familiar, or maybe just because it pays the bills.

  2. Afraid: they are perpetually dissatisfied and often complain about their job. Due to whatever excuse (and I’ve heard oh so many!) they won’t (they think they “can’t,” but it’s almost always “won’t”) make a change, and

  3. Restless: those convinced that the grass is greener elsewhere and who actively search for their “dream job” - maybe job-hopping or else just soul searching, trying to figure out a way to the greenest pasture.

I have a hard time relating to type 2, the fearful – and yet I’ve been there! It once took me three years to leave a job that was grinding me down and making me unhappy. Having found my courage to move on, I now know the best way to handle people in that situation is with compassion and repeated encouragement to move on! The most effective encouragement for a miserable employee is to provide them with tools and resources that will empower them to move on – like books, articles, podcasts, or even access to workshops or classes.

In regard to the “Comfortable” versus the “Restless,” I’ve been thinking a lot lately about which is better: to find satisfaction with your current life situation and, like the Buddha, just chill? Or to be hungry, to struggle and stubbornly seek a job that aligns with your values and reflects your passion, not knowing when or even if you’ll ever reach your dream job? I fall into category 3 – the Restless.

How Did I Get Here!?!


As a teenager there was no question about how my career path would start off. I knew I would go to college. I view this expectation of tertiary education as a forward-looking-with-blinders kind of mentality that both carriage horses and struggling middle-class bootstrappers share.

In the intro to Rich Dad Poor Dad, Sharon Lechter talks about Robert Kiyosaki’s perspective on the modern day education system and how it fails to teach children how to think like the rich. “ “Today, the most dangerous advice you can give a child is ‘Go to school, get good grades and look for a safe secure job,’” he likes to say. “That is old advice, and it’s bad advice...because if you want your child to have a financially secure future, they can’t play by the old set of rules.”…Robert was describing not only the difference between an employee and an employer, but also the difference between controlling your own destiny and giving that control to someone else.”

Unfortunately I didn’t read Rich Dad Poor Dad until I was in my 30’s, so college was a decision predetermined for me at my birth by my parents. My parents only wanted the best for me and my sister. They wanted us to achieve more than they did. But I doubt they were thinking in terms of “how and where can our daughters learn the skills needed to create and run their own businesses?” or “how can we best equip our daughters to reach financial freedom?” Instead, I think they were thinking: “how can we help our daughters get the best credentials for a resume so they’ll be more hireable, and able to land a good paying, secure job?”

College doesn’t seem like a choice.

Because college is considered a credential rather than a vehicle for learning new skills, the decision whether to attend college isn’t always debated – or even really discussed. This means attending college is not a strategic decision. This is unfortunate because robotic enrollment in college relies on the unspoken assumption that the experience will be valuable and help you achieve your life goals. How can you make these assumptions without first determining what your life goals are? At a minimum, you should understand what types of skills and tools you can learn at college that will benefit you in the business world, generally.

Would you make an investment decision to buy $50,000 to $100,000 worth of stocks, before carefully assessing the costs and benefits of the decision, the strength of the underlying company you’re investing in based on a review of its business and financial documents, and the return you’ll get on the investment? Probably not – yet that’s what many kids do when they – or their parents - decide to go to college without coming up with a strategy for the skills they will learn and connections they will make while there, based on the outcome they want.

When I was a teenager, some questions I wish I’d talked through with my parents before making a decision of whether and where to attend college and what degree to pursue, include:

  • What kind of lifestyle do you want to live as an adult? Do you want to own a house, do you want to live with a spouse, do you want to live in city, suburb, or rural area? Do you want a car? Children? What about two houses, or three houses, or a mansion, or a boat? To help think about these questions, I wish I’d been educated about how much it costs to live different kinds of lifestyles! Once armed with the answers, you can start mapping out a course to get to your dream lifestyle.

  • What types of work or settings do you thrive in? Do you like working under a deadline in school, or do you perform better with no pressure? Do you like getting up really early or are you a nightowl? What type of people do you like to be around? Do you like to work on a team or by yourself? What are your favorite classes, and why? What has been your favorite assignment? What things have you accomplished in the last 10 years that you’re really proud of, that make you feel really good about yourself? The information from answers to these questions can help you map out a course to your dream job.

  • Who are your role models? I also wish I’d educated myself to have some specific, wealthy role models of good character. Role models help you create dreams and goals of your own. Who are your role models? Why? What do they do that you respect? How did they get to where they are today? What can you do to emulate that person? What types of information and knowledge can you learn so that you can become more like that person?

  • What skills and marketable experiences can college provide? And, what other activities, settings or resources are accessible that might provide these same skills or experiences?

For me, these foundational, strategic lifestyle questions were back-burnered. Fortunately, I’m asking these questions and finding the answers now, at 34.

Decisions based on enjoyment instead of strategy.

Towards the end of my high school career I landed a full scholarship to UMBC (the University of Maryland, Baltimore County). Because I was not so good in the lifestyle planning department at that time, it seemed like the best choice because it was conveniently located 30 minutes away from my then boyfriend – far preferable to more prestigious universities that accepted me out of state.

When I was in college, I was only thinking one step at a time instead of five steps ahead. I loved college. I love research, reading, learning like a sponge, and writing. An English degree with a writing minor was a perfect fit – again, not because of any strategic planning about what I wanted to “be” when I grew up, but because it was fun.

I came into undergrad as a sophomore with about 30 college credits earned from AP courses in highschool. Because I had a full scholarship and a head start I had the opportunity to dabble in a variety of courses outside of my major. I took Philosophy, Anthropology, Economics, German, Political Science... I even double-majored in psych before dropping the second major 2 courses shy of completion my senior year because I didn't find it academically challenging. I also didn't have a great impression of my psych-majoring classmates: for whatever reason they seemed to be predominantly on athletic scholarships and prone to sleeping in class if they showed up. (I've always been judgy.)

Anyways point being: there was no clear purpose or direction to my choice of coursework other than satisfying the requirements for my BA and my curiosity.

When I finally addressed the question “what do you want to do when you graduate”? in my junior year of undergrad, I realized that while I had learned a lot of facts and academic information in college, I hadn’t learned about sensible modern day applications for that knowledge. I didn’t learn how my training might translate into marketable job skills. When people asked me “what do you want to do?” my response was inevitably “I don’t know.” This was primarily because I didn’t know what my options were, but also because I never asked myself: what do I love? What makes me tick? What brings me joy and feels like fun instead of work?

¯\_(ツ)_/¯

Graduate School.

I decided to go to law school for several reasons. As with college, I definitely felt I needed to get a graduate degree in the face of pressure from my family. But I took it a step farther and thought more about my future this time around. I had the expectation that a law degree is a lucrative asset and is easily transferable into a successful career. I thought I would enjoy being an attorney because I really enjoy researching and writing, as well as arguing. Another selling point was because a law degree would give me 3 more years to figure my shit out!

Law school was a logical and deliberate decision, to the extent that choosing a path that will almost certainly lead to an increased number of options in terms of the variety, quantity, and quality of jobs available to you is logical. But to the extent that my choice wasn’t motivated by a desire for a more career specific outcome, or for acquiring specific, necessary tools, it was also arguably short-sighted. But, perhaps as a result of my general directional cluelessness, when the law school acceptance letters started coming in I still couldn’t answer the question: "do you actually want to be a lawyer, and if so, what kind?"

I graduated law school in 2009 and took the first job offered to me. The market was down, attorneys were struggling, and a friend offered me a great opportunity to work for him practicing insurance law. A great opportunity - but not a strategic decision.

I left in 2012 to take a cushier job (less responsibility) with a larger firm practicing HOA and condominium law – essentially foreclosures. Again, not a very strategic decision because it wasn’t based on a self-assessment of the type of law I might want to practice. Instead, the decision was based off of: where can I branch out into new areas of the law based on my prior experience, make more money, and have both mentors and office support staff? While I enjoyed my job in the sense that I liked my co-workers, the work environment, and didn’t feel stressed out by the caseload, I felt empty and dissatisfied because the work wasn’t challenging and I wasn’t passionate about it.

Then: I got laid off. In 2013, a year after joining my last law firm, I was blessed with the opportunity to question my values and career choices when I was laid off and given a decent severance package. The foreclosure market had dried up and we’d recently relocated to a newer, nicer downtown Miami office space. Cuts were made and several employees were let go. Given the freedom of time and money to really think about my life and assess who I was and how I wanted to live, I can’t explain what happened other than using the cliché: the lightbulb went off!!

I realized that I wanted to practice environmental law, or work in environmental policy. Throughout my life, I’ve had strong environmental values instilled in me by my parents and other adults. I reuse or recycle all that I can. My mom used to take my friends and I on beach and stream cleanups when we were kids – we loved it! In fact, in law school I took several environmental law classes, which were some of my favorite courses. I always signed petitions or wrote my own unique letters in response to calls to action to protect the environment or endangered species; I volunteered on and off with Sierra Club and participated in lots of their meetings and events as I got older.

There’s something about contributing that gives me pleasure. There’s something about cleaning something up that was dirty that makes me feel like I’ve done a good thing. I want to help make the world a better place – not just for me, but for everyone, and for future generations. I want to stop pollution, protect forests and wild lands, and prevent species from going extinct. Taking a walk in the woods, or spending a weekend camping in Big Cypress National Preserve or the Everglades, calms and soothes me, its good for my soul.

They say that when one door closes, another opens. It is so true! Getting laid off was the opportunity that made it possible for me to discover and pursue my dream job as an environmental advocate.

So how’d I get lost again???

I spent two years struggling to break into the field of environmental advocacy in Miami. I attended workshops and classes; I volunteered; I landed a fellowship with National Parks Conservation Association; I worked pro-bono on several environmental law cases; I networked. Finally I even opened my own law firm – but that’s another story for another time! I ended up taking a contract position with a consulting company where I could work flexible hours, while continuing to pursue an environmental law job on the side – but my efforts were all to no avail. The jobs that become available in South Florida paid too little for me to support myself, and require more years of environmental litigation practice than I have. Ultimately, I re-evaluated my values and needs and decided to move to a new city that more closely matches those values and is more likely to meet those needs. In moving to Seattle, I’ll have to start from scratch again, so to speak.

As a 32 year old attorney I'm open-minded, enthusiastic, and excited to take my next steps in life and in my career… but boy did I hit a wall!! So hard that it was a factor motivating me to move to the opposite end of the country. When you try for three years or so to reach a goal and cannot, it makes you question your choices. So, I'm still not sure of what exactly I want to "do."

To be clear, I've had a successful seven years as an attorney in Miami. I'm confident about who I am and how I'd like to live my life. Also, I can hustle!! But I'm still just a little fuzzy as to whether I should hold out for the dream job in Seattle or settle for an alternative, because lately I’ve been feeling like a hamster running in a wheel, going nowhere.


There is a line of thinking espoused by my father that you should take whatever job you can get, work hard and do a good job, and that ultimately you will find some happiness in it. The Comfortable worker bee, happy to maintain the status quo because the alternative is frighteningly uncertain. Perhaps the idea behind this mentality is that you should make the most of the life that you’re given, be grateful for what you have and don’t risk losing a steady job due to a vague selfish desire for something better.

Those of us who are hungry for more, the fulfillment seekers, don’t see the desire for passion in our lives as selfish. The Restless mentality, frequently seen in the 20 and 30 somethings I know, is based on the idea that individuals should search until they find the "right job,” a job that brings us full satisfaction – we just haven’t found it yet. But we still feel we have some kind of moral obligation to do more with our careers, to reach our full potential as human beings by maximizing our meaningful work output and thus our contribution to society. <Insert picture of Tony Robbins pointing meaningfully at a tearful audience>.

I’m sure there’s a lot that can be read into my generalizations about Baby Boomers vs. Millenials.

Anyhoo I've tried both methods – finding joy in jobs that weren’t a good fit, and pursuing a “dream” job - and I'm still not sure which is the right way to go.

It seems to me that my own personal search for the dream job has lead to a (small) amount of job hopping, a lot of juggling, and has perhaps delayed the speed at which I'll reach the same income bracket as my "same-job-since-lawschool" and "focused-career-climber" peers. I also suspect that the fulfillment-seeking mentality could result in poor quality of work and transience in the workplace when it comes to quickly bored millenials, whether they are following their values or simply hoping to get rich quick with little investment. And then the tantalizing conundrum: after searching for fulfillment, how will we know when we get there? And if we do recognize that we've hit job-gold but we have no patience or staying power built up, will we ultimately get bored with the career of our dreams, too? Or even worse – lack the focus, drive, or skills to excel at it?

On the other hand, do the modern day dilemmas of lack of sufficient retirement benefits in the face of increasing healthcare and costs of living + skyrocketing student debt + loss of jobs to automation and technology + shrinking and disappearance of the social security net for millennials, etc. etc. etc.., actually reward job hoppers who recognize and act on opportunities to earn more? And in this framing, aren’t baby-boomers kind of, well, responsible for the distracted job-hopping behavior they now complain of in millenials since they sort of, well, created the environment we all now must survive in? Moreover, narrow expertise in one field can mean vulnerability to changes in the marketplace due to low transferability of niche skills. Getting too comfortable at your job could be a warning sign that you're about to get downsized. The times when folks worked for 50 years for the same company with a steadily increasing salary and ever expanding retirement account may be over, threatened by the modern, volatile marketplace and lightning speed of technological change. What worked for my dad may simply not work anymore.

Whatever the answer may be, I continue to seek it!

I’m clearly in the Restless camp for now. I’ve just moved to a new city and am actively and open-mindedly job-seeking. I don't advocate job-hopping aimlessly or frequently, but I do think it's important to "go while the getting's good" in circumstances where you are incapable of advancement or justifiably unhappy to the point it effects your health. I also think that dreams are worth fighting for.

As I search job postings on Craigslist, Monster, Indeed, Careerbuilder, and scope out all of the different environmental non-profits websites each week for new opportunities, with all my heart I hope that if one day I find myself at my dream job I recognize it, appreciate it, and hold on to it for as long as I can!!!

#Moving #soulsearching #lifegoals #followyourdreams #findyourdreamjob #dreamjobhunter #neversettle #dreamsareworthfightingfor #nevergiveup #believeinyourself #dreambig #dreams #lifesaboutthejourney #passion

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©2019 by Alyssa Barton