How To Change Careers When You've Only Just Begun

One of the most harrowing aspects of the college experience is figuring out what in the world you want to "major" in before getting any real introduction into the subject matters you have and, more importantly, don't know you have interest in. When I was in school, I declared myself as a Meteorology major, then transferred schools and went undeclared, then decided on Economics and Nutrition and Fitness, then dropped the latter, and settled (the keyword being "settled") with Economics.

This indecision is common for many students, but we're all led to believe once we receive our degrees, the exploration needs to narrow to the subject area printed on our diplomas. So, when you get your first job and realize just six months later you want to take your career a completely different direction, what do you do?

You don't want to go back to school and throw your money into a system that may or may not expose your passions, and if you want a real change, you would have to go back to stage one (i.e. undergrad) because graduate school programs demand too many prerequisites you didn't attain in your previous degree program.

So, I guess that's it. You're fate has been carved in stone and you'll have to spend the next 40 years of your life working in an industry that stimulates nothing more than your desire for the weekend. Sorry, not sorry.

FALSE! You can change your path, and I am going to share my story about how I did that very thing. When you take ownership of your future, your imagination will run wild and you will find unexpected ways to live out your dreams. This is my story (which is always developing).



When it comes to résumé construction, these are the first items I would expect a potential employer to scan in the first stage of the job applicant review process. These are the generic tried and true credentials that are meant to lead me down a narrow career path of analytical work with some flexibility of chosen industry.

So then, how is it that I can say, as of mid-June 2016, I officially accepted a job offer as a Writer and Communications Associate? How is it that I can say I will be working in education? How is it that I can say I will be developing web content, conducting interviews for a bi-weekly e-magazine, and taking the lead in social media strategy and communications?

One word: DESIRE.

So here I am worried about what three or four years would have done to me, when there are people who have swam so far down into the depths of the “get a degree, get a job, retire at 65” ocean, they had to self-assess in complete darkness.

I knew for a fact if I could manage to garner enough interest in the uniqueness of my life path along with promoting my recently published writing portfolio (i.e. Your Pen Paul), I would accelerate to the top of the applicant pool upon my first face-to-face or phone interaction. Given the spoiler alert in the intro, I was obviously able to accomplish this task and more (i.e. I got the job), but the question is how?

If I solely look at the moment I submitted my résumé, cover letter, and writing sample, it took a little over nine weeks before I was accepting my new position, which is already a really long time pursuing a single job opportunity. However, the reality is I have unknowingly been working on this job application since January, so nine weeks is a small fraction of the time I spent.

The moment I made the decision to go for broke, buy a domain name, and develop Your Pen Paul, I announced to the world, “I will not be constrained by the external perception of my academic degree.” Now, to be clear, I had landed my job as an Analyst last July and was provided a wooing salary along with transparency on what my next three to four years in the position would look like. It was, and still is, a very attractive proposition if you have a passion for auto insurance (and I worked with people that truly do, which was great to see).

After my first six months on the job, I recognized a) I do not have said passion and b) I don’t even have a passion for the general analytical work I was conducting. Although this was an unfortunate realization, I’m happy to have noticed this truth sooner rather than later. The more years I put into this work, the more difficult it was going to be to make any significant career transition.

This is certainly not to say it can’t be done. Plenty of people out there have made drastic career moves after working in their industries for decades.

So here I am worried about what three or four years would have done to me, when there are people who have swam so far down into the depths of the “get a degree, get a job, retire at 65” ocean, they had to self-assess in complete darkness.

These folks had the chutzpa to create a flashlight from nothing, illuminate the world around them, and swim back to the surface to discover the myriad options life was still presenting them. These are the people, along with those who shared their stories, whom I’m thankful for. If it wasn’t for their courage, I would have happily thrown on my swimsuit and began the same descent.

There is nobody but yourself that can tell you what your passion is, but I guarantee if you’re willing to explore the unknown and take a wholesome look at each spark that flashes in your mind, you’ll discover the flame you want to fan.

Instead, I have used the opportunities life has presented me in a “Yes Man” fashion in order to fail fast and grow continuously without being constrained by the credentials on my resume (I can always develop new credentials), the numbers on my paycheck (educating myself on finance frees me from this burden), or the perception of others (this is and never will be their life).

Eliminating these three heavy hitters from my decision making process has created, at this stage in my life, the most freedom I could possibly ask for. Although I certainly enjoy traveling, I’m not a nomad. I still have a need to be deeply engaged and present in work that I believe will reshape the world we live in, and I don’t believe I can accomplish this goal with an all-out wanderlust mentality.

While great for self-discovery, which we all need at multiple stages of our lives, I’d rather spend the majority of my time discovering solutions to problems within an inspiring community of thought leaders than contemplate how small the world is while staring up into the Northern Lights (which I fully plan on doing at some point).

Of course, the key operator here is “majority.” I will certainly find time to do incredible travel things, but they will fall under the title of “vacation” rather than “lifestyle.”

Ok, now that I have gone about as far away from the meat of this article as possible, let me stop this digression and get back to the question at hand. How did I go from working as an Analyst for a private corporation to working as a Writer and Communications Associate with an inspiring non-profit?

The strategies I invoked for each of these three components are what I believe increased my chances tenfold for an actual interview.

Step one was discovering my passion. This is the very purpose of my Monthly Challenges, which were developed more concretely through the creation of Your Pen Paul. Although I have never written about it, developing this website was the first few challenges I took (playing around with WordPress and then Square Space, researching about blog creation, and researching about social media strategy).

There is nobody but yourself that can tell you what your passion is, but I guarantee if you’re willing to explore the unknown and take a wholesome look at each spark that flashes in your mind, you’ll discover the flame you want to fan.

Step two was pursuing my passion with full steam ahead. While working the not so usual 37.5 hours per week (apparently some odd request from the past that happened to pass with upper management), I took on a second job (building my website) that had me waking up at 4:00, sometimes 3:00, in the morning, working diligently before and after my paid job, and putting visible and invisible strains on personal relationships.

Thank goodness for the strength of my fiancée, Morgan, because without her support and belief in what I was pursuing, things could have gone wrong very quickly.

Step three was Launch Day. On April 4th, Your Pen Paul was up and running with around eight articles ready for the world to read. I took the day off from my paid job in order to revel in what I had accomplished. I felt a little self-high-five was more than appropriate, but I knew full and well this was just the tip of the iceberg.

Step four was dipping my toes in the job search pool not realizing I would find myself in the deep-end, discovering a few immediate opportunities that were playing with my heart strings.

Step five was editing my resume, drafting intentional cover letters, and deciding what I should use for my writing sample. The strategies I invoked for each of these three components are what I believe increased my chances tenfold for an actual interview.

First, the credentials you saw at the beginning were not going get me any recognition, so rather than placing my current job as an Analyst as the first bullet under my “Work Experience,” I led off with my website. This immediately expressed my priorities of being a Writer first and Analyst second (regardless of which one was bringing home a paycheck).



Second, I took the dreaded cover letter, which is all too tempting to template and just change a few things around for each job application I submit, and personalized the bejesus out of it. Given that I was applying for a writing position, this acted as a writing sample in it of itself, and I needed to concentrate on expressing my unique personality and passion in every sentence.

Finally, my writing sample. I was stuck between using this or this as the way to express my writing style. The first option directly shows my interest in self-discovery and why I think it is important to be a learner for life. The second option shows my ability to create a light-hearted analogy when expressing a valued belief on how important community is to anyone’s overall development as a human being.

Ultimately, I decided to go with the second option. I believed it was the riskier choice, but I thought it was a more entertaining piece and would fall far outside the norm of other writing samples given by other applicants.

The final, key feature in submitting all three of these “documents” was the way I submitted the information. Rather than submitting my cover letter as a document, I used it in the body of my email. I also integrated my writing sample into the cover letter by simply hyperlinking to my website because it was the optimal reading environment. The only true attachment was my résumé. Another important point was my intention to hyperlink to my website, in one way or another, in all three components.


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Each of these documents stood alone as individual pieces of information, but at the same time emphasized my writing ability. This was absolutely necessary to provide any semblance of the fact that I truly had writing credentials.

Step six was interview numero uno. Shortly after submitting my application, I was contacted by one of the staff members to set up a phone or Skype interview within the next two weeks. This was it, I was in.

The first decision was easy; I requested a Skype interview. If you’re ever given this option, always opt for face to face communication. Heck, even if they only offer a phone conversation, don’t hesitate to request a video call. Express the more intimate connectedness you value in a face to face conversation and the worst the interviewer can say is “no,” and you’ll proceed with the phone interview without any bad marks against you.

The second decision always puts me in a pickle. If I interview on the front end of the two weeks, I will set the bar for future applicants, and if I set it high enough, the organization will continue to fall back on my name. On the other hand, if I choose to wait until the last day or so of the two-week period, I will be the grand finale—filling the void of that “perfect” candidate and immediately receiving feedback on the next stages of the interview process.

I decided to go with interviewing early. Personally, if I waited the two weeks, I would have over-prepared for the interview and sounded scripted in my responses. Setting up the interview immediately allowed me to keep my responses genuine, and more importantly, if the answers didn’t come easy, it would be proof that the job wasn’t right for me.

Long story short, the interview went fantastically (lasted about 45 minutes). I immediately made a personal connection with both interviewers, and rather than feeling like I was participating in a standard Q&A, I was able to hold an actual conversation. Once the interview was finished, I wrote a handwritten letter to each of my interviewers thanking them for the opportunity and personally connecting to something they said in the interview.

Ironically enough, the agony I avoided by scheduling the interview immediately still managed to rear its ugly head, since I had to wait those two weeks before finding out if I would move on to those nondescript “next steps.” And, as I would come to find out, waiting was going to play a significant role in the process.

While hammering away at my keyboard, working on what had become mundane tasks in the mundane auto insurance world, I anxiously waited for my iPhone to light up with a new email from my point of contact.

Step seven was taking on a writing assignment (x3). There were three tasks I needed to complete over the course of two days and each component was something I had absolutely no experience in.

The first task was to create a book synopsis that avoided reading like a summary and connected to the readership for the organization’s e-magazine. I also needed to construct two Tweets that would bring the social media audience to the newest issue of the e-magazine.

The second task involved clicking through an organization's website, writing a short paragraph about their mission and objectives, and identifying tools the e-magazine audience would find useful in developing their work.

The third and final task had me sifting through choppy notes from an interview that was conducted, filling in the gaps in conversation as needed, and creating a publishable version of the interview that would integrate the language used by the organization, while maintaining the personality and voice of the speaker.

Yes, this was pretty daunting. I was going to quickly discover how my writing adapted to new writing styles. After putting in a total of six hours, which was right in line with the organization’s expectations, I submitted my assignment and was back playing the waiting game.

Step eight was an unintended step, but caused enough of an emotional impact that I would be remiss not to mention it (it even prompted me to write about things here). Once I submitted my work, my point of contact let me know the team would be unlikely to reach back out to me until after their trip to Denver, so it would be around 10 to 11 days before finding out about “next steps.”

Time passed slowly, but the distress started to come into play when day 10 came around. While hammering away at my keyboard, working on what had become mundane tasks in the mundane auto insurance world, I anxiously waited for my iPhone to light up with a new email from my point of contact.

Then day 11 came around and the minutes ticked slower and slower. Once again, I didn’t hear anything. Then came days 12 and 13, one of which I reached out via email, but still heard nothing. Finally, on day 14, I decided to reach out via telephone with the expectation that the organization had moved on, but I wanted hear my fate firsthand.

To my absolute surprise, my point of contact let me know the organization was still very interested in my candidacy and apologized for the lack of communication (which had been great up to this point). She promised I would hear from them the following Tuesday, which I believe I actually heard from them on Monday.

Step nine was interview numero dos and an in-person interview to boot. I went ahead and used a vacation day from my current job in order to get a little extra sleep and avoid the anxiety of being at work, while thinking about slipping out for an interview for another job.

I was scheduled for two hours of interviews, which consisted of meeting the Director, then the Communications and Design Lead (who I spoke with on Skype), and then the Chief of Staff (also my point of contact and who I spoke with on Skype) and Operations Associate (who had just started five weeks prior). The most significant thing that occurred in all of these sessions was that the Director came back into the room during my final interview. To me, this was an immediate indication that I caught her attention and made a great first impression.

The two-hour interview ended up going 30 minutes over, which was also a sign of the depth of my interactions and want of the staff to continue speaking with me. I was reeling with excitement after leaving the building. Not only did I feel like I answered a majority of the questions well, each member of the team was a joy to speak with and I could see myself fitting in with the office culture.

Later that day, I wrote to all four members of the team, reflecting on our conversations and asking various follow up questions. These questions served two purposes. One, it showed that I valued each team member’s opinion and perspective, regardless of their experience or job title. Two, I was genuinely hungry for more information, and I wanted to express my interest in digging deeper into the issues the organization works with.

Step 10 was the onset of some frustration, but in hindsight, the organization was taking to heart the “hire slow” mentality. And I certainly can’t argue against that given the fact they were considering a candidate with a degree in Economics and someone who is currently working as an analyst at a private corporation. This wasn’t exactly the candidate profile they envisioned when looking for a new hire.

The day after my interview (literally at 5:10 in the afternoon), I received an email requesting to set-up an immediate phone call with all the people I interviewed with the day before in order to ask some follow-up questions. I wasn’t sure if my follow-up emails from the day before accidentally raised some red flags, so my mind was racing all different directions. At 5:30 I was back at it.

Fielding some of the most difficult questions I had received up to this point, I was solely relying on my intuition and self-assessment in order to provide as much clarity as possible. After a little over 30 minutes, the conversation concluded by the Director speaking with me personally and asking about my salary expectations. Ding, ding, ding! That had to be a good sign, right?!

Step 11 was one last follow-up that reiterated the job responsibilities, the expected work hours, and needing another dose of reassurance that I understood what I would be getting myself into. At this point, I was all out of ways to explain my understanding and desire to work in this role and with this team, so I kept my response very brief, and hoped for the best.

Your capacity to succeed is far greater than the challenges you will face along the way.

Step 12 was another waiting period followed up with an informal job offer. I had once again been told I would be contacted “early in the week,” which for me can equate to any time before 12:00pm on Wednesday. Well, 12:00pm Wednesday came and went, and I had yet to hear anything. The next day, Morgan and I had to drive 14 hours to Saint Louis, so my mind was able to focus on the road rather than the silence about my job prospect.

After finishing a round of golf Friday morning, I was on my way home and my phone began to ring. I knew the number by now, and I had no idea what to expect. I allowed it to ring a few times as I collected my thoughts, then answered the phone.

The Communications and Design Lead, who I would be working under, was on the other end. After exchanging salutations, she formally, yet informally, offered me the position at a salary that was lower than I expected. She also wasn’t able to provide me with information on the benefits package, so I let her know that I would need that information in order to make a sound decision. She completely understood and said a formalized letter would be sent to me on Monday.

I had a reserved excitement. The job was mine for the taking, but the official acceptance was still pending.

Step glorious-lucky-number-13 was the official offer letter and counteroffer. The benefits package was solid, particularly for a nonprofit that has only been around since 2009, so I focused on the salary negotiation and a small request about the 403(b) match. You know you’re in the non-profit sector when you’re talking about 403(b)’s and not 401(k)’s.

I had never drafted a counteroffer before, so I had to do some research before submitting my requests. Once again, I had to wait a bit before hearing whether or not my requests would be honored, but in the end, it was all worth it. One piece of advice I read about making counteroffers is that silence can be a good thing. When you don't receive an immediate response, the company/organization, might be looking for room in the budget to increase their offer.



On June 15th, 2016, two full months from the time I had my first interview, I officially accepted the Writer and Communications Associate position for Education Reimagined, an initiative of Convergence. Unashamedly, I turned in my letter of resignation at my current job about five hours later.

On July 5th, just three months after launching Your Pen Paul, I will officially be making money as a writer. The euphoria of this moment is too much to take in all at once, but just as Your Pen Paul was a stepping stone to something bigger, I will view this new job in a similar frame of reference. I will be diving head first into the most inspiring work I have ever had the opportunity to indulge in, and my eyes are about to be opened up to a world of possibilities for the future of American education.

If there is one thing I would like to leave you with, it is this. Never, absolutely never, allow anyone, including yourself, to place restrictions on your future. When you want something so bad that you spend every waking second wanting to pursue that idea, interest, or passion, you will find yourself exactly where you’re meant to be. Your capacity to succeed is far greater than the challenges you will face along the way. As long as you can build up the courage to move forward during your greatest failures with the same conviction you had when starting your journey, you will only end up in one place and one place only: the finish line.


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