How to get out of your crap job (Tony DaSilva’s climb from the bottom)


The shit jobs, the awkward conversations, the insecure moments, the poverty, the kerosene heaters, the studying, the writing, the graduating, and the growing up: all fucking worth it. I exited out of skating’s back door years ago, but somehow managed to find my way back through the front.

—Tony DaSilva

This is Tony DaSilva.

how to get out of your crappy job

Age 19 – backside smith in Thrasher / photo: sean cronan

In his early twenties, he was a professional skateboarder. The picture above is from Thrasher, the world’s most respected skate magazines with millions of readers. Back then, it was endless partying, sponsors, and getting paid to do what he loved.

But with a long-standing injury, he decided to quit skateboarding. He moved back into his mom’s house and found himself without a degree, zero employable skills, and no idea of where he wanted to go in life.

He worked at a gas station and lived in a crappy studio apartment with no heat in the ghetto of New Haven. As he wrote in his article Is There Life After Skateboarding?

Many of us that step out of the skate industry after making a living at it are left over as society’s bottom feeders. We don’t have anything to offer. We don’t have a degree. We don’t write with proper grammar. We speak our own language. We don’t want to talk about the Phish show you went to last weekend on spring break. Fuck you and fuck that.

But I was now alone in that world, on my own. I had to put on the face and force myself into the room I didn’t want to be a part of. I had no choice. I was quiet, insecure, and felt completely fraud when even speaking to someone outside of skating.

While Tony started at the bottom, he began to climb. Now, he works for Emerica (a global skateboarding brand) as a Digital Marketing Manager.

So how did he climb from minimum wage to a new career he loves?

I emailed Tony and asked him to share more of his story. If you are working a shit job and looking for a way out, this interview is going to shake you up.

After you left your skateboarding career, what was your lowest point? 

I’d say my lowest point came when I was working as a gas station cashier and it was robbed the night before my morning shift. I saw myself again for the first time and how far I had fallen in life. One of the biggest reasons for how low my life had gotten I think came from just not been present for so long. I let time pass me by for too long.

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It was always easy to say I’d go back to school or work on my resume later. But this was one of those times I realized I let things get to far and forced myself to move forward in life.

I knew I was smart and talented, but that doesn’t mean anything if you don’t put any motivation or energy behind it.

At the time, I didn’t know what to do, but just living in that new mentality put me in a place to figure it out slowly.

You built your skills and now work for Emerica, a global brand. How did you decide on digital marketing?

When I went back to college I wanted to write, which led me to major in journalism. I am also a gamer, so I worked on becoming a games writer. While doing so, I saw the benefits of using social media, especially Twitter, to gain a network of like-minded people and look for work. This was very early on in the social landscape and nowhere near as accepted of a marketing tool as it has become.

Seeing the opportunities that came my way from this new technology sparked me to keep at it. I saw it only growing and the potential was endless.

Did you try other career directions? How did you know this was a good path to try?

I knew I had to get back to school, not just as a means to learn and get a degree, but also for the structure that it would create for me in my life. The direction my life had before going to college wasn’t a life of my own making. It was a lack of pursuing anything.

So, after signing up for classes, I knew I wanted to write, maybe be a reporter, and create awesome stories. So, I majored in journalism.

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But when I was embedded in these classes in college, I saw a lot of what they were teaching to be an old school way of seeing things. They didn’t really grasp how important online journalism was becoming and how the rules of journalism were being bent and molded to a different style of reading. The internet does not have a lot of patience (most of the time). It’s not the same as sitting down with the Sunday paper.

It’s a mix of people wanting immediate gratification through the portals they’re clicking. I had and have a lot of respect for the old school ways of newspapers, but I was drawn more to the full scope of writing, from the actual writing phase to self-marketing through social media.

If you aren’t ready to help promote and be a part of the story after it’s printed or posted, then you’re missing a big piece of the discussion and interaction. Starting out on this road lead me deeper into the digital space.

Before I knew it, I was part tech nerd, part writer. They go hand in hand at this day in age, in my opinion.

How did you take that first step and start building skills? Did you buy books? Get an internship? How did you get your first start?

Like I previously mentioned, I was a pretty avid gamer in college and made some great connections in those couple of years through writing. I learned everything I could about the games industry and would go to events where I could meet some of the people I was talking to on social media.

This was huge.

Having this skill set and printed work on my resume landed me an internship at MTV Games (publisher of the Rock Band franchise). My passion for games and background in writing and social, helped get me to that point.

I learned a lot at MTV. I was a small fish in a big pond. I attended weekly meetings, had deadlines, had to be organized, and most importantly, accountable. These were things that I thought I was decent at previously but realized quickly I had a long way to go.

I have no experience. I don’t know what career I’d like. I have no skills. What advice would you have for me?  

Me. Me. Me. Me. All of that was who I was and it made me scared to death. It’s one of the reasons I did nothing for so long in my life when I was younger. The idea of starting a path with no confidence or skill set terrified me. Hell, it’s what landed me at a gas station register and stacking bags of cement at a construction distributor. Nothing wrong with those jobs, but I knew I wanted much more.

I would ask yourself: what have you always been drawn to in life? What’s the one thing you seem to have always enjoyed doing? What do you have a passion for?

There’s always something if you look hard enough. For me, it was writing. I always kept a half-ass journal or would write to myself when things got really hard. It was a means to vent or express my feelings when I didn’t have a lot of people to talk to. I took that thought and built upon it, through college, and after, and it’s brought me to some special places.

Sure, I’m not a writer for the New York Times and do more with my writing these days for PR and marketing, but it’s what lead me to the place I felt comfortable living within. Now I write on my own terms and when I feel the urge, which is a freedom I enjoy having within a passion that means a lot to me.

What advice would you give to your younger self who doesn’t think that a normal career will make them happy? Are you happy now?

I use to tell myself that. I’m different. I don’t want to be part of the system. Blah, blah, blah… But the thing is, you don’t really have to be. If you stick to the things that make you happy and stick up for yourself along the way, you’ll find yourself in a career almost by accident. That’s what happened to me.

I realized I had a career and that, yes, I liked what I was doing and wanted to learn more about it. Sure, you’ll get some bad bosses and you’ll be stressed out sometimes, but it’s nothing compared to how stressful living in a place where you’re lost and don’t know how you’re going to pay your rent next month.

Having a career gives you more freedom than you think. It lends choices to you that you will not have if you stay stagnant. Happiness is something I think about a lot. I think I’m happy, sure.

Like everyone else, I have good days and bad days, but the bad days are nothing compared the feeling I lived with for so long before I decided to not wait for life to help me anymore. I just woke up I guess and was sick of feeling like shit.

Anything you wish I asked?

I think you had some great questions, just hope I didn’t rant for too long.

Where can readers connect with you? 

Twitter: @T_DaSilva

Instagram: @tonydasilva


Go from broke to a career you love with these resources: 

[Incredible interview with Michael Edmondson] The ultimate guide to finding a career as a English major]

35 awesome jobs for English Majors

5 more jobs for English Majors that you never knew existed 

The 18-week practical career roadmap to finding a career with your humanities degree (eBook)

How to market your humanities MA or PhD to employers

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