Disclaimer: This will be the longest post I will ever write

I have spent most of my life actually knowing what I wanted to do when I “grew up,” which is more than I can say for about 90% of the world’s population.  I felt almost guilty at times for being so sure about what I wanted to do, when most of my friends sat in contemplation upon graduating from college.   Many would resign themselves to the fact that they would have no choice but to go back home and attempt to begin a new life with mom and dad and this thing called a bachelor’s degree.

It was 2001 and jobs were scarce.  We all thought we could rule the world.  Well at least that’s what our professors lead us to believe.  Man they couldn’t have been farther from the truth.  I had always held a job since age 15, so I thought that I would have no problem.  You name it, I had done it.  I had been a nanny, picker and packer for a medical supplier, telemarketer, administrative assistant/receptionist, HR recruiting assistant, retail sales associate for a major sports retailer.

I knew that I had a ton of transferable skills, accompanied now by a degree in social work so I was definitely going to get a job.  With my bachelor’s degree in hand, I ventured out into the world with the utmost confidence, however, all of our professors neglected to mention that we were in a recession and the rules had been changed.  There were very few jobs available especially for new graduates.  Lesson # 1 You can never be guaranteed anything in life other than death and taxes, unless you don’t pay taxes and you are a vampire. Interviews were reserved for those with master’s degrees and extensive experience.   I realized after a couple of months that without that master’s degree, I was pretty much dead in the water.   At this point after shooting off over 250 resumes in 4 months and realizing that going back to school was not an option, I settled on a different career direction, snowboarding.

I was offered a position running a non-profit snowboard program in Boston but declined as it had no health benefits, inconsistent hours and was only temporary.  It was at this time a friend of mine, who worked for the Department of Social Services in Western Massachusetts mentioned that there was a group of schools in the area that wanted to start an outdoor recreation program. My thinking at the time was, sweet I can start a skateboard and snowboard program for troubled youth and I will get paid to do it.  Who wouldn’t want to do that?  I drafted up a proposal and sent it to the school and the next thing I know I am the proud director of a snowboard and skateboard program making 25K per year, emergency medical insurance only with a $3000 deductible no dental and no vision, no negotiation necessary.  AWESOME!

Wait?  Not awesome! What was I thinking?  Had I any idea how much money I needed to pay Uncle Sam, Sallie Mae, and the US Department of Education?  Not to mention my car, my rent, and you can forget about fun because that didn’t exist on this salary.  Here was my Lesson #2 ALWAYS negotiate, ALWAYS! The worst they can say is no.

After struggling for 6 months working 14 hour days and taking on entirely too much, I realized that I needed to part ways with my “dream job” and find something that was going to pay the bills.  I took a year-long temporary position at a private woman’s college in the Boston area, meaning I was forced to move back in with my parents.  At 23 years old I felt like a failure as I swore up and down that I would never go back home.  Lesson #3 Accept help when it’s offered, don’t be a dumbass, Take it!

During this time my father lost his job and at 57 years old and found himself asking the existential questions we all ask ourselves.  What is my purpose?  What am I good for?  I watched his struggle firsthand and lived it with him.  Lesson #4 Even at 57 you can still not know what to do with your life. In my attempts to help my dad, I found myself reading every book I could get my hands on and researching every job search strategy and tactic that existed on the internet.

I spent the next 5 years researching career trends and planning my next move.  I needed to go back to school but I needed a plan.  I was a nanny for a family in the Boston area making a decent amount of money, traveling all over the place with my 7 weeks paid vacation per year and enjoying no stress, but this job was not going to last forever and I knew it.  In the summer of 2005 I left my job for greener pastures in Burlington, Vermont with no job lined up.   My plan was get a job at the University of Vermont and have them pay for me to go back to school to get my degree in Career Counseling and Professional Development.  Everyone I told thought I was crazy for leaving my “cush” job for no job but I knew in my heart it was the right move for me.  

I took a part time job as the director of an after school program to get me through until I would land that job at UVM.  I had been applying to the university for the last couple of years and had no luck.  Actually it was 22 applications to be exact.  I applied to everything from administrative and admissions positions to coordination and advising positions.  I knew I could be successful in any of those positions with my wide variety of skill sets, but to UVM it may have appeared as if I were lacking focus. Lesson #5 If you are applying to the same company over and over, don’t apply for just anything otherwise you look desperate. Make sure you have focus.

I was a persistent little lady but with 22 applications and no movement, I knew that I needed to make a change to my tactics.  I decided to take a new approach by hand walking my resume into the office.  After a brief introduction, I found myself shaking the hands with the hiring manger.  After the interview process I sent them a book related to some of the initiatives they happened to be working on.  You are probably thinking, she totally got the job.  Well you are wrong but what I did get upon my asking for any feedback on my interview, was a great reference, if I should apply to any other position at the school.  That is what lead me to the job that paid for my graduate education.  Lesson # 6 Think outside the box and send a small token like a book along with your thank you note. Oh and yes a hand written thank you note is highly unusual now-a-days but is a ticket to a final interview or even an offer. Lesson #7 If you don’t get the job contact them and ask if there was anything you can improve on for next time.  The only thing it will hurt is your pride for a second until you realize that the next time will be an improvement.

Don’t worry this dissertation is almost over.

During the time I spent working at the business school at UVM I networked with many alumni.  I knew that these connections would help me later on down the road when I would need connections in the business world for my future career as a career professional.  Lesson # 8 Stay connected!  Network your pants off!  You never know who is going to give you your next job.

I stayed true to my path and continued to pursue opportunities in the career counseling field but kept finding the proverbial door being slammed in my face.  It was at this point where I thought maybe I am not meant to be a career counselor.  I knew that I was great at building relationships, writing and had a passion for the action sports industry.  My networking skills proved to be the ticket as a contact of mine had a PR position open at his company, so I jumped ship and found myself working for one of the top youth and action sports marketing agencies in the biz.  I spent my days working with endemic media outlets, talented athletes and consulting for some of the most recognizable brands in the space.

However, only nine months in I knew something was wrong.  I wasn’t leaving work every day with a sense of self-fulfillment.  I was stressed out and working 12 hour days all the while feeling empty.  I knew that this was the opportunity of a lifetime and that I should be grateful to travel, party and shmooze with people.  No sooner did I realize this when a former colleague of mine mentioned that a position was coming up at a small private Vermont university for an assistant director position within their Career Development Center and she was going to put in a good word for me.  Three weeks later I found myself accepting the position and facing my boss for my resignation.  Lesson #9 It is natural to feel bad when giving your resignation.  But remember that there is always another person chomping at the bit for your job.  Your boss will forgive you, eventually.  Oh and you may want to check out their resignation policy before you actually resign. Sorry that was kind of two in one.

In the end my gut told me where I needed to be.  No apologies needed.  Lesson # 10 Be patient and your time will come.  Listen to your gut except when you are wearing drunk goggles.

Although I have traded my hoodies and jeans for professional attire in the workplace, I am much happier for it.  I truly love my job but still have a passion for action sports industry trends.  I have coached many people in action sports over the years with career exploration, strategy, negotiation and personal branding and I hope to bring some of that knowledge to you with a touch of humor for good measure. – Ciao