Some Thoughts About Old Jobs and My New Life


Travaasa Hana

This is a personal post versus a travel related one, but this is a blog after all and I want to share with you all a little more about what makes me tick. If you’d prefer to read about exciting travel experiences, please check out My Five Favorite Adventure Travel Experiences in New Zealand.

I got my first job when I was 15 ½, which at the time was the youngest anyone could legally work in Virginia and my parents made sure I had applications in the day after my half birthday. But rather than resent that, I appreciate it. Being brought up to believe that hard work and perseverance is the only way to a happy life was a valuable lesson and one which I bought into completely – still do. I guess it’s the New England puritan spirit in me.

Since that tender age in high school I’ve had a lot of jobs, but never for a day have I been out of work, until a few weeks ago. It’s been a strange shift and not one that I like particularly, but it has enabled me to contemplate some of the jobs I’ve had over the years and how they have shaped me into the person I am today. Here’s a brief run down of every job I’ve ever held, as best as I can remember.

  • Rally’s (Fast food chain now known as Checker’s)
  • Walden Books
  • McDonald’s
  • Ben and Jerry’s
  • Williamsburg Winery
  • College tour guide
  • Telemarketer
  • Tour guide at a Virginia plantation house
  • Employee at college language lab
  • Barnes and Noble
  • Liquor Barn (yes, it’s what it sounds like)

Then in my professional life

  • Two higher education trade associations
  • Two recreational boating trade associations

I think that’s a lot of jobs, and not once was I fired from one, until recently, a fact that gave me immense pride. I can say a lot of things about my parents but if nothing else they instilled in me a Puritanesque work ethic and a deep desire to put one’s nose to the grindstone in order to make life better for oneself. I believe that, always have, and now more than ever it’s vital that I keep to that philosophy. But I’ve changed, which is not all that strange and I find myself drawing upon some key lessons I learned from old jobs.

King Family Vineyards

Retail – I worked retail for so many years and the lessons learned have really helped define me as a person. A good retail employee is all about creating an experience for their customer, although many retail employees don’t seem to realize this. A customer can stomp your toes and call you the worst names in the book and all you can do is put on a smile and say, “I’m sorry you feel that way.” It teaches you the ability to be extroverted without being too showy and at its core there is a desire to help other people. It’s sounds silly, but it’s true and it’s frankly a recurring theme throughout all of my various jobs. For whatever reason, my personality is programmed to want to help others, not always in the most apparent way, but it’s there nonetheless. Retail also instilled in me an OCD level of attention to detail and to this day I cannot go into a bookstore without making sure all the stacks are nice and straight.

Tour Guide – If retail was the primer for customer satisfaction and extroversion, then being a tour guide was the master class. There is nothing quite so daunting than the expectation that you have to know everything there is to know about a particular subject area. If you think you can skate by, you can’t. There are certain people who only like to try to trip up tour guides it seems and they were almost always on my tours. That’s when I adopted the philosophy “If you say it with confidence it becomes true,” which went on to help me in my career as a lobbyist. But just like my retail experience, being a tour guide taught me a lot about people and more specifically how to read them. Again, this would help me in later years, but there’s nothing quite like being subjected to scrutiny by hundreds of people to make you perfect the art of social interaction.

Nonprofit work – It was unusually hard to explain my occupation to people. I was a lobbyist, but I worked for a variety of non-profit trade associations, so not what one typically thinks of when sleazy, smoke filled rooms in Washington, DC enter the imagination. (Although I was once in such a room and it was super fun) It was also a career I never, ever wanted to be in. I have two degrees in international relations; foreign cultures and travel have ALWAYS been my passion. But I moved to DC without a job or a place to live and so I took the first job I got, which was in the government relations shop of a large trade association. Everything snowballed from there. I found that, like every job I’ve done, I was good at it and I applied for and got promotions, new jobs until I found myself twelve years later in a job I hated and had absolutely no interest in. On the plus side though I feel like I did a lot of good work that will help millions of people and in order to do all this I absolutely drew upon skill sets learned in my years of retail and tour guiding. (And definitely Liquor Barning)

So what does all this mean and why am I ranting about past jobs? Well, because I believe that everything I’ve done since I was 15 ½ and flipping burgers at Rally’s has prepared me for my next professional step. I’m in the process of becoming an entrepreneur and it’s both frightening and exciting. Will I work for someone else again? You bet and I’m in the process of pursuing an amazing opportunity, but it’s an opportunity that will still afford me an incredible amount of freedom; the likes of which I’ve never experienced. But every job in my life has not only defined me as a person, it’s shaped my future. I will absolutely depend on my extroversion and empathy in my new career, just as I will my attention to detail and strong work ethic. I would never have guessed that I’d ever be in the position I find myself now, but for all the immediate problems I seem to have at the moment, I know that the future rewards, mostly non-pecuniary, will be well worth this short term sacrifice.

Are you at a place in your life you never expected? How did you get there?

By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer.

18 thoughts on “Some Thoughts About Old Jobs and My New Life”

  1. Just extrapolating based on your list here – did you go to W&M? I did, and I worked at Busch Gardens as a cashier, the college bookstore as a barista, and later at the American History Museum in DC in retail. Now I’m a teacher. I guess I enjoy interacting with people in my jobs, especially now my Korean students. I never expected to be working in South Korea and preparing to travel the world for a year but here I am. I have no idea where why life is headed and it’s a little scary but mostly exciting! I wish you luck in your next endeavor.

  2. It’s amazing how much you can learn from even the most mundane jobs and how they can help you later in life. I’ve changed careers a few times and am now a full time travel blogger – never expected it and I’m sure I made more per hour selling popcorn at the movie theater which I did when I was 16, but I love it and also believe it’s a short term sacrifice.

  3. I think everything we do shapes our future – and when we can actively take steps to do so we are all the better for it. Good luck Matt – I can’t wait to see what you get up to!

  4. Matt- I think any kind of professional struggle is ultimately beneficial, because it allows us to re-focus, re-prioritize and take a leap onto the next step. You can leap and take a big chance because there’s really no other option! I know the future has amazing things in store for you, and I for one can’t wait to hear all about them! :)

  5. Matt – what a great post! I think most will agree when I say that we’re all cheering you on! Six months ago I embarked on my own entrepreneurial venture. It has been both frightening and extremely gratifying. There are no guarantees, but it really is true that if you don’t try, you’ll never know what could have been. And now, more than ever, I think it’s incredibly important for people to find satisfaction in their job. Best of luck to you!

  6. I really liked this post Matt. Like you, for the first time ever, I’m not working at the moment. It’s been two weeks and I’m at a loss why anyone would choose to be unemployed (dole bludger is a common career path in Australia). What do they do all day?

    I’ve never considered the collective experiences of all my jobs before so you’ve given me something to think about.

    Good luck with your entrepreneurial pursuits.

  7. Good luck, Matt. You can do it.

    Leaving the corporate world to start my own business was the most rewarding change I’ve ever made. You’ll get more satisfaction from the smallest entrepreneurial win than from your biggest success working for the man.

  8. I started working at 15 1/2 too – I am extremely independent and I needed to assert it at quite a young age. This post has made me reflect on my career path and what is says about me and what I have learned from it. I went from many years as an executive assistant to a project manager to a program manager – it would appear that I like to take care of things and people (and that I am Type-A and like to be “in-charge” of things!). Considering the path I took to get through all these places, I pinch myself everyday because I am far luckier than a lot of people in terms of my job, my life, my ability to travel and enjoy life. Despite being an introvert I will always want to take things and people (and then need downtime for me to resupply alone) and I think that is a good thing!

    1. Well said and thank you so much for sharing. I too am lucky and believe me, i realize that. But I also think that we make our own luck to a certain degree, so don’t sell your own talents short!

  9. Hi Matt, thx for sharing your story. When I stll lived in Holland, i lost my job 8 x times in 3 yrs. There was alway something: reorganizing, 911, bankruptcy, last in first out. However, i always managed to find a new job. It was terribly frustrating and I had no clue why this would all happen. Until I moved to South Africa where I became an entrepreneur and needed all the skills and endurance I’d been taught in the years before. You will feel the freedom to explore and be curious and get involved in all kinds of projects that your heart wants to follow. You will thrive!!

  10. Jo (the blond travels)

    I like the fact that u’re emracing all the experiences and not slacking off ur former bosses etc. it’s a good attitude!
    I also worked for retail and didn’t like it very much but on the other hand it gave me a lot of experience and customer service knowledge.

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