Why I’m Sharing My Open & Vulnerable Upworthy Cover Letter

Why Am I Doing This?

Few, nay, no-one thought this was a good idea, and that includes myself as more time goes by, but if I know anything it’s the importance of story-telling and being self-aware about the experiences you go through in life and how they shape you.

Everyone who’s been on social media the last few years has come across this Silicon Valley hindsight gem:

In case you don’t know the story, that’s Whatsapp co-founder, Brian Acton, who just some five years later sold Whatsapp to Facebook for a whopping $19 Billion dollars— yes, billion with a b. It’s one of those stories that comes along every few years to remind people that everything happens for a reason and to remember to never take any one loss too harshly, because it may be the one that precedes your biggest victory ever.

It’s no secret if you’ve known me or read my writing work over the past year that I’ve been going through a rough period in my life. After being laid off early last year, I looked for work every day for some 8 months coming up with nothing. Frustrated, scared, angry and without confidence I finally decided to just do things for myself again.

Writing, photography, teaching, a podcast, consulting, joining the board of a non-profit — all these things to help keep me motivated, keep me moving forward and not wallowing. Yet, if I’m honest with myself, after giving up on looking for opportunities outside of my own endeavors, I came across a job posting that I thought was a perfect fit & came at a perfect time in my life when writing was starting to pick up traction with multiple clients/employers like BorrowLenses, Chimera, Fstoppers, Petapixel, + more.

The job was at feelgood, viral content powerhouse: Upworthy.

I even wrote about applying to it on my Facebook, something I rarely do anymore out of fear for building something up for nothing. Yet, there was something about this job that made it stand out as it was the first position I applied to in some 9 months.

The cover letter process for Upworthy jobs is to write it as if you were writing an article for Upworthy themselves aka hit them in the feelz.. hard. So with that in mind, I decided to do what anyone does with their cover letter:

Tell my story.

So here it is below:


The Incredible story of a family man who lost a job, battled with depression, and found self-awareness to build a career on his terms becoming the newest Managing Editor at Upworthy

If I was honest with myself, I wouldn’t have ever pursued the things I did for 10 years at 75–85% merely because doubt had disabled me from ever hitting 110%, throwing myself entirely into a big, dream goal. Growing up as the youngest child of three in a Puerto Rican family, respecting your elders was a deeply engrained value. Coupled with great supportive parents and a retired Army Capt. for a father, it’s easy to peg me as the eager-to-please type.

After struggling in school early on in life through high school, I went onto college as many in our generation did with the promise of a great career, stable work and overall happiness. Yet, after graduating with honors and going onto grad school for my MBA to ‘round out’ my resume, I graduated in 2008 — the worst year in 21st century history to have a business degree looking for work in NYC. A harsh reality set in that I always knew but thought I prepared for; nothing is owed to you in this life…ever.

Having my photography hobby turn into a career helped for a few years, but then the pressures of needing to justify my six years of schooling and two degrees kept leaving me to let off the throttle, pivot and interview at places like Bank of America, Corp., Hess Corp., Wall Street, and Morgan Stanley. These few years were the second time in my life I struggled with depression. Becoming more self-aware around this time let me understand that as a high-functioning person idle time was my arch-nemesis. Previously while in grad school full-time at night I worked at a high-end studio full-time during the day and even after weekend shifts I drove to the city to shoot at nightclubs to make my $30k salary stretch as much as I could.

Then There Was a Girl

Fast-forward through my twenties, finally working remotely for a NYC company, I met a girl at 28 who did the one thing I said no one could ever make me do; make me move to the suburbs. It wasn’t simply stating how much square footage you get for your money, but instead introducing me to her two beautiful kids, Lyric & Riley, whom I quickly grew to love as my own. After two years of the long-distance thing, we decided to move in together and I became an ex-Philadelphian living in the suburbs of Maryland. This was around the time that life reminded me that nothing is owed to any of us in this life.

After almost four years of working for said NYC company, going public was a rougher transition than anyone had thought, effectively calling for layoffs. As a 1099 employee in the new post-recession gig economy that many our age found ourselves, I was in the first round. No one cared that I just wiped out my savings between paying taxes and putting the large deposit down on the new place for our family to live. It was a dark reality I once knew well, back again to haunt me but this time with a small family in the picture, no longer just myself. These new pressures forced me into yet another box.

The pressure to provide and maintain my previous salary meant another full-time corporate job. At first I tried to stay working from home to help with the kids, then I settled for a 30–60 minute commute, then opened myself to a $20k pay cut, and finally opened my search to NYC, Philadelphia, DC and beyond, vowing to simply make it work only coming home on the weekends — nothing. As some eight months passed by, with some interview processes lasting two to three months with multiple phone screenings and in-person interviews, I grew angry, depressed, and with little confidence to speak of. I started working overnight construction jobs for money doing demolition, laying floors, cutting and laying tile and anything else that was needed and provided a paycheck. Mind you, even with a very handy father growing up, I never once worked with large power tools, did backbreaking work over long shifts, so every job was a learning experience — and that part I cherished. A far cry from the Technical Producer who ran six-figure digital campaigns for blue chip clients like Best Buy, McDonald’s, Virgin Mobile, & others.

What a difference a few hard months make.

Self-Awareness Here We Go

Out of money, time, and hope I came to a vivid realization. In an attempt to please everyone around me, I had put my own creative endeavors on the back-burner to do what was expected of me. Yet, that was seemingly no longer working, so I made the decision to go back to what I knew; my art. Once I sat my family down and asked for one month to concentrate on my work, a funny thing started to happen.

I started writing heartfelt, open long-form content again to help support my photography work, garnered the position of Staff Writer at one of the Internet’s largest photo websites, became a paid contributor for many other big sites, started a podcast called The Angry Millennial where I interviewed all the biggest names in the creative industry I admired and respected dearly for years about their fears, regrets, turning points & most meaningful moments, and best of all — I was happy. I wasn’t making the money I made before, but I was more present with my kids and girlfriend, more motivated and inspired than ever and for the first time in my life, could finally say I was giving something 110% effort towards a big, lofty dream goal.

You Can Already See It, Right?

You see, becoming the Managing Editor for Upworthy would be the best possible end to this story, which would really be a beautiful new beginning. For years I had been trying my hardest to please everyone else, but it wasn’t until my lowest of lows that I realized just like Chase Jarvis said during our interview, I needed to learn to put on my own oxygen mask first before helping others.


Let me join your team to make my dream come true of doing just that. Helping others.


If reading my cover letter mirrors your own struggles in any way, or if it reminds you of someone you love + care about, please SHARE + hit the heart below in an effort to remind everyone that all they can do is keep going and keep taking swings.