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Eight lessons I’ve learned in my career (so far)

Writer's picture: Jason HeckendornJason Heckendorn

Throughout my young career – from undergraduate to now – I’ve learned a lot. No more than you or anyone else, really, but a lot nonetheless. In understanding my failures and celebrating my successes, I’ve collected eight pieces of knowledge – thematic lessons that have helped pave a roadmap to success. Each is distinct and has enabled me to overcome adversity, develop my skills, or further pursue my passions, yet many of the ideas overlap and have been most effectively utilized in harmony. Several may seem to be obvious or cliche, but their meaning and value are still vital.

The purpose of this particular blog post is to share these career learnings with my friends, colleagues, and whoever else might care for them. (I also think there is substantial value in self-reflection and analysis, especially through the use of journaling as a creative outlet.) Of course, there are bountiful other sage pieces of advice I would love to give to anyone requesting an information interview (e.g. learn technical skills, constantly ask questions, be proactive and take initiative, etc.), but let’s focus on the eight below for now.

And please note, reader: I tend to embrace simplicity and write somewhat freely and unstructured in blog form. I’ve attached each message with a personal experience to more effectively illustrate their impact on my career, but each can apply to your own situation in innumerable ways. These are also relatively bite-sized lessons; if you’re interested in learning more on any of the following, I am happy to discuss further or direct you to other resources. If you’re reading this, I hope that you can find some benefit in your own unique way, even if it’s just one nugget or sentence. Happy reading!


1. NOTHING IS GIVEN

This is a pretty straightforward lesson, and it was one that humbled me in the harshest way possible. During my senior year of college, I expected a post-graduate, full-time job opportunity to fall into my lap. I had the grades, internship and job experience, on-campus leadership experience, etc. – everything a prospective employer would seek in an entry-level employee. Yet when the end of the academic year rolled around, nothing. No job offers. Despite an impressive resume, employers didn’t seek me out. Quite frankly, that’s not how supply and demand works for a graduating senior; high-quality roles are in low supply, and the demand is high from hungrier, more persistent students. YOU have to go and WIN your job. I didn’t have the “Mamba Mentality” in my job search, so I hobbled into the real world without anything in place.

After graduation, however, I was still 100% committed to working in the sports industry. Despite the lack of opportunities available at the time, I followed that dream. Nothing was going to stop me at this point. Over the next nine months, I supported myself on two part-time sports jobs – with adidas (retail) and STATS LLC (remote sports analytics tagging). I swallowed my pride and did work that was arguably “beneath me” because I had to sacrifice and work as hard as possible to achieve my goals. Ultimately, my hard work and devotion paid off: I earned my dream job at U.S. Soccer. But it wasn’t without effort, sacrifice, and a serious grind. In short: “the only thing that works when things don’t work is hard work.”

2. FAIL FORWARD FAST

With the Navy SEALs, our nation’s elite Special Forces, there is no present time to dwell on a mistake. Any lack of focus on the mission at hand can be catastrophic. Instead, our operators are taught to fail forward – to use a mistake as a learning opportunity for the next rep or mission. Once the mission at hand is over? Reset. Recognize the mistake and understand how it happened and how it can be corrected – but then quickly move on with that new knowledge at hand.

Failure is one of the most effectively learning mechanisms; humans are innately good at correcting behaviors. In fact, many organizations understand this and are adopting the “fail forward” approach in the workplace. Spotify, for example, publicly lists employee failures in its work spaces. This practice doesn’t serve as a punishment but rather as a notice to everyone that 1) everyone fails, it’s natural, 2) don’t make THAT mistake again, and 3) our culture is committed to failing forwards. If you fail, understand your fail point, reset, and move on.

In my young career, I’ve only failed twice. Just kidding – I probably fail at least twice per day! If it wasn’t for all of my many, many failures, I wouldn’t be prepared for future mistakes, and I certainly wouldn’t know how to pivot or recalibrate afterwards. One instance in particular: when I was working at U.S. Soccer, I prematurely sent an email to a prospective youth soccer club, alerting them that they were admitted to our program. The problem: they weren’t accepted to the program. As you can imagine, cleaning up the major communication error was a massive headache. However, I learned how to better communicate to validate information, and the organization developed better protocols to ensure more effective, accurate communications. Ultimately, it’s all about having a fail forward mentality and rapidly adapting to the environment, learning, and trying again. As Thomas Edison once stated, “I have not failed. I’ve just 10,000 ways that won’t work.”​

3. CULTIVATE A RELATIONSHIP

I remember hearing about how vital networking was in college. In the business school in particular, if you weren’t building your network at an exponential rate, you were somehow falling behind.After every professional interaction, I was quick to send a LinkedIn request and follow up with a “let’s stay in touch” email. My goal was to build as many industry connections as possible. While this practice absolutely has value and can lead to fruition at some point in a career (I’ve undoubtedly reconnected with one-off connections from networking events and the like), it’s a flawed approach. Rather than focus on quantity, always, always focus on quality. Find the people with whom you want to cultivate a true relationship.

At the MIT Sloan Sports Analytics Conference in 2013, I created a list of ten people I was determined to meet. Just ten – out of almost 3,000 attendees. Of course, I wanted to meet dozens of other industry experts, but only a few really struck me as someone who could do one of the following: support me as a mentor, provide insight for my undergraduate thesis, or build a genuine, lasting professional relationship. This approach allowed me to really cultivate those connections and make the relationships more meaningful for BOTH parties.

At this point in my career, I maybe have twenty or so people that I have developed valuable, trusting, communicative relationships with; as a matter of fact, each received a holiday card this past season. Several have been invaluable mentors, leaders, and friends, and one directly referred me for my current job. Rather than focusing on quantity and spreading yourself thin, take the time, effort, and resources to develop QUALITY relationships.

4. BEST FOOT FORWARD

Only a few months into my career, I was at my first major event with U.S. Soccer – the Development Academy Summer Showcase and Playoffs in Indianapolis, Indiana. In my first professional role dealing with a plethora of important and influential soccer figures, it was evident that I was bit raw. So raw that, at the hotel, I took the elevator downstairs in basketball shorts, a tank top, and no shoes – only to immediately see my two direct supervisors and one of our organization directors. Representing the crest of U.S. Soccer, I was dressed like I was about to go on a spring break trip. I can laugh about it four years later, but the look on the director’s face was one of shock and disapproval, to say the least…

The reason for that anecdote is that, in the professional world, you’re always on display and have the opportunity to make a good (or bad!) impression. In this instance, having only been hired three months earlier, I was still making an impression with my managers and peers, and this interaction didn’t necessarily inspire confidence in the decision to hire me.

Whether you’re in the workplace, at a company event, or even on social media, your best foot must always the lead the way – especially when you are representing a major organization with a reputation at stake (e.g. U.S. Soccer, Naval Special Warfare…both qualify here). Remember: always consider your environment and be cognizant of your appearance, words, and actions as they can have immeasurable consequences in your career.

5. IMPOSSIBLE IS NOTHING

I heard these three words a decade ago through an adidas soccer marketing campaign. Several internationally acclaimed soccer players narrated short advertisements, explaining how they overcame adversity and matured into superstars. Being a soccer player, I was mesmerized by the clips; I watched them all. One in particular stood out – it was narrated by my idol, David Beckham. He explained how, after a controversial play in the 1998 World Cup, he was virtually banished from his native England. Death threats were commonplace; effigies were hung in the streets. Three agonizing years later, he scored the game-tying goal in a crucial match on a patented free kick, bringing England to its feet. It was the perfect fairy-tale ending. Beckham’s story inspired me throughout even the hardest times.

This is, without a doubt, my favorite of these eight learning lessons. It’s tattooed on my chest in honor of my late mother, and despite its impact in my personal life, it has considerably influenced my career decisions. As previously mentioned, landing my first post-graduate job wasn’t exactly the most pleasant process, taking a total of about nine months after graduation. Despite this adversity, neither my confidence nor my purpose ever wavered. With those words on my chest and in my mind, I knew that my experience/education, dedication, and passion would enable me to find a job that truly aligned with my ambitions. Sure enough, on the way home from a Las Vegas trip, I received three phone calls and job offers: one from Nike, one from STATS LLC, and one from U.S. Soccer. The rest is history.

My advice: let these words resonate with you in every arduous life or career moment. Have the mental fortitude and relentless belief to push through barriers and create your own destiny. Get fired? Startup failed? Didn’t get a big promotion? Understand your fail points, learn, and keep striving toward your goals with even more zeal than before (see: fail forward fast). We’re all going to fail and fall short at times; it’s about overcoming those obstacles to achieve your greatest successes.

6. FOLLOW YOUR PASSION

Listen, I get it. This one is really played out: passion is such a trite word in today’s landscape. But I have three distinct thoughts on the subject: 1) you must first find what inspires you, 2) pursuing your discovered passion takes sacrifice, and 3) your passion will change as you evolve.

I went to school pursuing the most generic business degree possible: management. Like most freshman, I had no idea of what my post-graduate career consisted. Eventually, in 2012, I realized that sports analytics was a thing (a burgeoning industry, at that), and BOOM – I was hooked. Without any hesitation, I knew that it was the perfect fit for me. Since then, for the past seven years, every single career-related decision has mirrored the goal of being a leader in the sports analytics and human performance space. However, there have been many sacrifices to align my passion with my goal: three unpaid college internships; a lack of a full-time job or real income for almost a year after graduation (see above); and long hours and an unexceptional salary once I did have a job. Additionally, while my passion is still in the same ballpark as it initially was, it has certainly evolved as my career and life experiences have unfolded. I wanted to use data and analytics to influence soccer decision-making (tactics, load management, etc.), and now I support the tactical space with Navy SEALs. What gives? Well, I’ve developed and learned; I’m using that same knowledge in a different, tangential landscape, yet my end state has not really changed. I’m still applying sports science and human performance principles in my analytical work, yet the environment and end users are slightly different.

Discovering your passion – your purpose, really – is a process, one that requires time, patience, maybe a dash of luck, and a zealous commitment to what makes you happy. In many cases, applying the idea of “impossible is nothing” is required to make your passion a reality. Want to align your career with your interests but don’t have the required skills? Go to school, talk to industry experts, or maybe create a new position: just make it happen. Sometimes the biggest leaps of faith bear the greatest rewards.


7. FIND YOUR BALANCE

Back at U.S. Soccer, I generally worked 50-60 hours a week (note: I am well aware that many of you work more than this!). Add in an hour commute in each direction, and there was minimal time for much else during the work week. The pattern was: wake up, go to work, get home, eat, go to the gym, get ready for bed. Not much room for extracurricular activities here. For me and many others, this schedule was unsustainable and led to exhaustion, burnout, and an overall dip in happiness. Fast forward two years, and I work a government-mandated maximum of 40 hours per week. I’m generally home by 4:30pm and have time to cook, read, watch TV, and play with my dog. I have the flexibility to pursue things that I care about outside of my career.

Everyone’s environments and priorities are different. For me, while my career is extremely important, having a strong work/life balance is more even more valuable. I would rather trade in that early promotion or several thousand dollars in exchange for the opportunity to live my life – the one outside of work – as freely as I’d like. Going home without the burden of work on my shoulders is one of the most relieving feelings I can fathom. However, everyone is programmed uniquely and has different priorities; some of you may want those late hours and the extra work in exchange for career advancement, money, or other incentives. And that’s perfectly okay. We all get the same 168 hours per week, and it’s up to YOU to find YOUR balance, whatever that may be.

My last thought on this matter: finding a harmonious balance is both external (time) and internal (mindset). It takes time and effort to find and maintain that balance, but having the self-discipline and awareness to mentally “turn off” work during your personal time is paramount to a healthy lifestyle. In fact, doing so is directly correlated with reduced stress, more focus/energy, and a happier you. As the saying goes, “balance is not a destination, but a constant journey.”

8. BE UNAPOLOGETICALLY YOU

For those of you that don’t know me well, I love to make others laugh and inject enthusiasm into a situation. When my friends and I participate in trivia, I often joke that I’m merely there for comedic relief. I even took a two month stand-up comedy course to really hone the craft of comedy and cross off a bucket list item. With that said, humor and fun don’t just belong outside of work; I am a firm believer that they belong in the workplace as well.

A few years ago, I remember sharing some fun banter with a few colleagues (all the while working our asses off). We all sat in close quarters, so it was these little things – the witty jokes, personal stores, etc. – throughout the day that helped us maintain our sanity and give us another reason to continue the constant, head-down grind. At one point, a colleague interjects with a line similar to this: “it doesn’t sound like you’re working. Stop joking and get back to work.” We were all shocked; despite our incredible work outputs, we were criticized for sharing a human moment. At this point, I knew that there was a clear cultural misalignment and that one of us didn’t belong (update: I’m no longer there).

Many employers understand the massive shift in today’s workplace climate: employees care about culture and a sense of belonging. These core principles dictate how we perceive our job satisfaction and how likely we are to stay with an organization. Many companies are embracing these ideas and separating themselves as the places to work. Come work here; it’s rewarding, empowering, AND fun. If the organization actually delivers on those ideals (and that’s usually a BIG if), then they are doing something right and will attract the best talent.

If you’re anything like me, don’t be afraid to express yourself in your career. Be fun, quirky, and whatever else it is that makes you you. If your current environment shames or discourages this, look for a job elsewhere – somewhere that appreciates unique personalities (or, if you’re happy, don’t. That works too!). When your career represents 40+ hours of your every week, you can’t afford to be someone else. To close with a quote from the great Oscar Wilde: “Be yourself; everyone else is already taken.”

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