robwoolford.com

Just seen this on High Fidelity (film with John Cusack).

If you haven’t seen that film, basically John Cusack makes “Top 5…”s pretty much all the way through the film. Most centrally, his “Top 5 break ups”, but other things like “Top 5 funeral songs” creep in to the film too.

One that got me thinking was his “Top 5 dream jobs” which he all managed to fit in as a sort of career.

So, in a High Fidelity style-y… “Top 5 Dream Jobs”.

Sports Journalist (2008-2018)

After deciding to settle in Sunderland at the age of 21, I start writing freelance, but am recruited by either The Guardian, The Times or a well paid website to cover international leagues outside of England. This would see me doing a lot of travelling and attending faraway matches on special occasions – random derbies in Argentina, relegation battles in Eastern Europe and lots of stops in Brazil. Tim Vickery does something similar on the BBC’s website, and I absolutely love it.

After five or more years of doing this, I move to The New York Times (or some New York based website/publication) to help with their ‘Soccer’ coverage, including reporting of America, The Premiership and yet more random domestic leagues. This isn’t particularly well paid, but it bases me in the Big Apple and sees me free to cover as much global football as possible.

Oh, and ummm, this also doubles up as commentary too. On a minor scale though.

Radio Station DJ, New York (2018-2025)

Now that I’m based in New York, I decide to pursue my love of hip hop and apply to various hip hop radio stations. I don’t become the next Funkmaster Flex or Tim Westwood. Instead, I score a stupidly late show on Hot 97 (or similar) where commercial hip hop isn’t a must, and I’m free to play the best hip hop available – both past and present. The show is only on a couple of times a week, and I don’t gain huge notoriety, but I earn a small fortune DJing all over NYC and the surrounding area, whilst still reporting on the football in a part-time position.

It’s not that inconceivable. Colin Murray did something similar with BBC Radio 1, then to sports reporting and sports talk shows.

Travel Writer, Worldwide (2025-2030)

After a successful period on the radio, and having enjoyed travel so much in my earlier days as a journalist, I decide to travel again. By this point I will have been stationary in New York for nearly 10 years, and I’ll be late 30s.

At this point I write a well received travel website. You know, because I’m such a good writer by this point (haha). But I also branch off to a more travel-related job in the media. It’s 20 years in the future, so it’s hard to know what exactly that would be, but I envisage something along the lines of a video-blog or a video-podcast about different cities around the world. A dedicated team would visit all the corners of to bring all these cities and wonders of the world to the public. But, they would also be guides, so we would compile places to stay, how to travel, interviews with locals and all that garbage… I don’t know the details… but it would be a hit on the net and make us all a small fortune.

The best part though is that the team would all hit the road together and we’d stop in each location for a week. We’d work, of course, but in our spare time we’d get to follow our personal interests in these places. 5 years, (52 weeks x 5) spending a week in a new place. Shit, that’s 200+ cities or countries I’d get to visit… a definite dream come true!

Bar owner/manager, Various places (2030-2035)

Having travelled for so long, I fall in love with a number of cities and places.

I would be 50 years old by this point, and at that age there’s only so much you can do whilst you travel, so I decide to open a bar in some quiet corner of the world. South Africa? Australia? Brazil? Argentina? … who knows. Somewhere nice, with a lot of sun to keep the Mrs happy, and somewhere nice for the hypothetical children to spend their teens.

The bar is a success, and I’m able to open a couple more in some other lovely destinations.

And therein lies a family business. Hoorah! A chain of low key bars/pubs in exotic locations. Holiday homes for all of the family, but a nice stress-free way to retire I think!

York City Chairman, York (2035 onwards)

After galavanting across the world, writing almost non-stop for the previous 30 years… I decide it is time to get back involved with my first love – football. I’ve never been any good at playing, and by this time I’m too old, so I look to get involved on the executive side.

York City are a club who’ve never really been successful. They’re currently outside the top 92 clubs in the country, but the city deserves a club that matches its beauty.

The club are still nowhere special when I miraculously manage to buy them, but as this is my dream, I somehow manage to set up a structure at the club that sees them progress and work their way up the leagues towards the top few tiers. Premiership is nice in the dream, but I’d be happy with any of the top few tiers.

With ‘chairman’ being such a loose role, I can still run the aforementioned worldwide bars, amongst other things… but relocating back to York is something I’ve always expected to do in later life.

Anyway, the club’s stadium expands under my reign, as does the fan base, and the club are a consistent, respected part of the football league for as long as I’m alive.

So… New York Times, Hot 97, worldwide travel, bars and York City Chairman. Hey, it’s my dream, why the hell not?!?

What are yours?