Working in the arts means I’m kind of used to long periods of being wildly overworked followed by weeks or months of downtime with no pay in between projects.

My favorite variation of this was cruise ships, because by the time I walked off my ship, I always knew the date I’d be returning to the next ship. This made it really easy to budget and to not freak out over making no money. I might do some overhire work or substitute teach while I was home, but it was more because I was bored than that I absolutely had to.

What I liked a lot less was freelance work when I would finish a gig and wonder “is this it? Was that the end of my career? Am I going to have to go work at Starbuck to get by?”

Sidenote: Not knocking Starbucks. They actually pay ok and offer health insurance, so they’re fairly awesome. But I hate early mornings, and people who haven’t had their coffee yet are monsters.

So I’d finally get some time off and be able to hang out with friends and live a life and I’d be so freaked out about if I’m ever gonna work again that I would overthink a lot of expenses and spend barely anything.

Now – I know this is a personal finance blog, so we should be all about the spending less. And there are tons of low cost and free things you can do and they’re fantastic and you should use the heck out of them.

I’m talking about when you become a weird hermit who never leaves the house because you’re already paying for internet, so why not just scroll Facebook and watch Netflix every. single. day.

Am I the only one that does that?

Maybe.

However, another side effect of this arts life on the road is that the days can really be long. And when they are, pretty much the only thing I’m blowing money on is food.

So this time, going into this period of change, I’ve started trying to front load some fun. At least, that’s what I’m calling it.

First, I checked out discounts and anything I already had “lying around” that I really wasn’t using or paying attention to, to take some stock of the possible fun options.

I realized I had an unused Groupon for a massage that never happened, so I booked it for a few weeks into the unemployement, right before it was going to expire.

I used a black Friday discount code over at Raise to pick up a discounted Starbucks gift card that’s good for $100, so I can get out of the house and blog from a new location once in a while with no guilt – especially since I learned last time that the change in location can be really good for my focus.

I cleaned out my wallet and found that I have 2 lattes left on a 5 latte Dunkin Donuts gift card from lastChristmas.

I have $50 to Outback Steakhouse that I got as a gift at the end of last year that I’d forgotten about.  And who has tine to actually go find an Outback Steakhouse on tour? One never appeared right in front of me. However, I know there’s one near my parents in Jersey.

I even realized I have enough points for a free flight on a card I’d like to cancel before April, so I have some tentative ideas in the works to meet up with BFF who lives in Vegas somewhere for a long weekend and I’ve been scouring sites like Living Social for a cheap hotel deal somewhere.

I’m supposed to pickup a friend from the airport in NYC and drive her home to Vermont so we can spend some time together and I’m trying to  look into stuff we can do and get it all purchased now.

I’ve also been lucky over the last year and a half to have an opportunity to offer a lot of friends comp tickets, and a lot of them offered to do the same, but I couldn’t take them up on it. I finally squeezed in a trip to the Met. Another friend was able to get me cheap tickets to the Papermill Playhouse. Another offered seats to see the filming of a show, and there’s a tiny, tiny chance I might actually get to go to Sesame Street.

The main point, is to spend the money now – to front load the fun – while I still have regular steady paychecks coming in to easily budget it around.

True story – I’m really cheap when I don’t have steady income. Like – when you guys see my expenses at the end of the month, there’s no note about how much I agonized over spending that money, even though, as folks who just see my financial situation, you know I don’t have to.

I mean – the agonizing over it for years is part of why I don’t have to – but, if I start to think of some of my bigger money regrets, it’s that I don’t spend a little more to make memories or spend more time with friends and family when I have opportunity to do so.

So if anyone sees a good deal on anything fun to do in NJ over the winter, drop me a line.

And keep your fingers crossed for me that I pick up enough freelance work to stop worrying about money – and that I don’t worry about money so much, I pick up too much work and miss out on the reason I’m going home in the first place, which is more family time.

Does anyone else get Scrooge-like cheap during times of transition?