Crossing the Career Chasm

Crossing the Career Chasm

Chasm, poetically speaking, is used to describe a deep gap or divide. During these times, I believe we all are crossing an emotional chasm of our own. Unfortunately, countless would-be interns are watching summer opportunities vanish in front of their eyes. Thus, I’m inspired to pen a letter to our aspiring leaders of tomorrow who may feel like their world is at a standstill today. 

The chasm I’m describing represents your career. Your journey will likely be a gruesome one filled with heartache, joy, and ample self-discovery. Hopefully, you'll eventually find yourself doing things in your career that you are both highly passionate about and skilled in. If you were to take that first job out of college, or that internship this summer, where on the scatterplot below do you think it'd place you? What do you think it takes to make it to the upper right hand of the Career Chasm Index?


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“There’s beauty in the struggle” - J Cole


If you haven’t noticed, there isn’t a huge concentration of points at the far upper right of our Career Chasm Index. I believe it's because a lot of people [solely] see their career as a series of promotions and advancements. I recommend you begin to think of your career as a marriage between skill and passion. 

Skill is something that is really hard to evaluate objectively, even in sports careers, because “great” is always relative. "Great" compared to what and who? When you’re just starting your career, your Skill level will likely be “under 10” [in reference to our Career Index] or next to nothing really. Spend time understanding the measurable components used to evaluate one’s performance in your prospective role. For example, if you are an aspiring lawyer or doctor then you’ll need to know [specifically] how a doctor’s or lawyer’s performance is evaluated. For surgeons, is it the quality and/or quantity of surgeries? If so, how is a “quality” surgery defined? During my early career as a recruiter, my skill set was evaluated a myriad of ways:

  1. The number of cold calls I made per day.
  2. The "quality" of my calls. I had to further define “quality” as a measurable component because it was too vague. After some experience, I broke quality down further to:  
  • My understanding of the prospective candidate’s needs;
  • My ability to counter objections, and;
  • My ability to draw valuable information from the call.

3. The number of prospective meetings I was able to book per week.

4. The number of deals (candidate placements) I was able to close per month.

5. The dollar (gross margin) amount in revenue I “booked” per year.

Whether you are taught explicitly or implicitly, you need to break down “great” into very measurable and identifiable components. In the list I shared above, I can define what each and every component is and how to measure them; this took many years of recognizing patterns, making mistakes, and learning from others. Nonetheless, this is your north star. Spend time understanding what makes a great [fill in the career blank] and you’ll get an objective understanding of what the bar is. Caution: your understanding will likely move through these three phases:

  1. Early in your career: I don’t know what great looks like.
  2. Middle of your career: I know what great looks like and while I’m not great yet, I know where the gap in my skill set is and how I can work towards it.
  3. Mid to late in your career: I’ve closed the gap and I’m great. 

 Understanding the metrics that will be used to evaluate one’s performance in your prospective career will allow you to move upwards in the Career Chasm Index because you’ll have an appropriate north star. While Skill is extremely important, let’s talk about the role Passion plays. 


“If you’re not careful, your success will take you places your character can’t keep you”.


If you’re not careful, you’ll end up spending a lot of time on the upper left hand of the Index where you’ll be highly skilled, yet very miserable. Don’t worry, you’re not alone...I bet you can recall vivid conversations with friends and old peers who’ve embarked on career journeys in service of social acceptance and job security. While you’ll likely end up on the far left of the Index at some point of your career [really, you’re not alone] the point is to avoid spending a hefty amount of time there. As you progress in your career you’ll come to crossroads and junction points that will challenge you. I faced a similar inflection point ahead of becoming a finance recruiter.

 During college, I started to build a career interest in finance; I was lucky enough to get some strong internships under my belt. After a few summer internships, I realized that while I enjoyed finance as a conversational stimulant, I wasn’t a fan of the daily demands of spreadsheets and financial models. I landed on becoming a headhunter in the finance industry because it afforded me a tailored combination of my passion and skill. While I was passionate about finance, my skill set was better suited for some form of sales. Outside of those finance internships, I frequently gravitated towards sales and marketing internships. There was something exciting about the constant networking, public speaking, and selling I experienced. Moreover, I was heavily invested in the success of my peers. I facilitated career workshops, reviewed resumes, hosted speaker events, and offered plenty of internship and interview consultation. So you can see where I was able to connect the dots that led me to recruiting.

I enjoyed life as a recruiter in the finance space. I was pretty passionate, and I was getting pretty good. I spent a lot of time on the far right center of the Career Chasm Index where I was highly passionate and becoming increasingly skilled. As I continued to progress, something started to happen; I started to fall out of love with the work...These are the really tough, heart-wrenching moments you’ll face. In an article I wrote some time ago called, “Open Letter to my Generation”, I talked about the ability to have tough conversations with one's self. I entered a state of deep reflection and asked myself a myriad of questions, like:

  • What is it about the work am I not enjoying? Is it just simply what I’m experiencing at the moment?
  • What specifically am I not enjoying about the day-to-day? Or do I enjoy the day-to-day, but am not being challenged?
  • Or maybe I love what I do, but I don’t love where I’m doing it, or the team I’m doing with?
  • Perhaps I'm falling out of love with sales or recruiting in general? What initially attracted me to sales in the first place? How has that changed?

It was extremely tough, and answers did not come overnight. I was moving “up” in Skill, but I regressed in Passion; I was slowly moving towards the upper left hand of the Index.

After some deep reflection, I was able to [specifically] pick apart the many things I liked and didn’t like. I wasn't entirely unhappy, but there was something missing. While I enjoyed connecting people with opportunities, I was less keen on the transactional nature of third-party agencies. I wanted more visibility into my clients' organizational structure, goals, and needs. The scope of my role, and ultimately the nature of the agency model, did not afford me the visibility I yearned. I also grew less and less interested in the world of finance; I wanted to diversify. I was able to lean on the shoulders of mentors who helped me “map” my career path. If I wanted to pivot, in which I did, I had to build an understanding of where my Skills translated elsewhere. 

  • What do other agencies in this space do? Are there different business models?
  • Are there opportunities to do more of a hybrid role? Do I go "in-house" as a recruiter?
  • Where do my skills translate outside of this industry? Perhaps, I should consider another function altogether? Business development? Marketing?
  • Are there other industries and/or roles that are related yet different that I’d enjoy? Where would they potentially take me?

Again, this took very deep reflection and a ton of very real conversations. A few “chess moves” later, I was able to translate my Skill into areas of interest I was passionate about. Today, I work at the inter-section of recruiting and consulting and I couldn't be happier. I figured, if I wanted to get to “D”, I needed to figure out how to get to “B” and then “C” first. I wasn't aware of this at the time, but I was crossing my career chasm. 

More than likely, you won’t be doing “cool work” in the beginning of your career; you won’t be focused on “building strategy” and “leading people”. Understand that the work you’re doing today is foundation building for tomorrow; the slow yet steady progress to understanding what “great” looks like. After some time, and tons of questions, I was able to pinpoint very specifically what I liked and didn’t like. More importantly, I realized it was less about my day-to-day and more of a misalignment with the long-term vision I had for myself.

Having looked at [literally] hundreds of thousands of resumes in my career thus far, I can tell you a lot about someone’s career journey. I come across folks who are junior [and even sometimes senior] in their careers who often inflate their resumes with jargon and buzzwords that clearly indicate that they do not know what “great looks like” nor are they interested in investing the time and energy into learning how to get there; they’re unfortunately playing the game they were taught [the resume game]. I’m not saying that you can’t spend time figuring it out; you’ll have setbacks and missteps. But ultimately, your goal is to spend time connecting your career experiences together so that they resemble a woven and calculated story; not a basket of unrelated experiences and jobs -- you don’t want to just “end up” somewhere in your career. Your environment, whether it be shifts in industry, technology, or your personality, will move you by force across the Career Chasm Index

Parting Thoughts

While the release of my debut book, Intern Talk, has been impacted by COVID-19, I look forward to providing a consistent stream of content and resources until its release. In the meantime, I’m offering free resume consultation to college juniors and seniors looking to cross their career chasm. Please reach out to me directly at [email protected] with your resume. Feel free to keep up with content at interntalk.co. and share this with any peers or friends that are seeking resume consultation.

Anthony Louis is a career advisor and Talent Partner at Beacon Talent helping high-growth startups build and retain teams.  

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