To Job or Not To Job

That is the question.

To anyone who is keeping up with my writing at this early stage, forgive my relative lack of posts lately. I have been awfully sick the past couple of weeks! Starting with a stomach bug (just in time to ruin a date! *sigh*) then right as that was tapering off, I caught a cold. I am just beginning to feel human again.

I have also been spending a lot of time applying for new jobs. Last I reported here, I had got a job with the US Postal Service. But it turns out that they stop calling you into work once you knock over a mailbox. I was luckily able to find another job quickly, and so I’ve been working at a local furniture store for the past year. It’s a good job, I love the owner, but I find I’m not putting nearly as much money in savings as I would like. So currently I’m looking for something that might pay better.

This search has led my thinking in this direction: do I go ahead and do what I want or do I double down and find another job? 

Let me ‘splain.

THE GO-AHEAD-AND-FREELANCE OPTION

I will need to freelance in one way or another if I want to travel full time. Blog income will be a long time coming, so I need to figure out some way to earn money on the road. One such way that appeals to me very much is teaching English to children in China through VIP Kids. It seems relatively easy to get hired, it earns real money, and it sounds fun! Tutoring spots are generally in the early morning due to the time difference, giving me plenty of time to work on my blog. And I’d be at HOME, eating real food at meals and not just what I can grab to eat at my desk. I’d be able to work in my slippers and sit in the sunshine all day.

While I am at home, I can combine online tutoring with more housesitting, which I already do a fair amount of. I can promote myself on the Next Door app and join Rover.com for more clients. With time, I can build up tutoring clients and dogsits and possibly earn more than I am making now. The idea of not having a boss and being more in control of what I make feels very freeing to me. And since I have moved in with my mother, I can afford to try this option.

And once I travel, I can take VIP Kids with me, adjusting my hours to my needs. I couldn’t continue with Rover.com, but I can housesit anywhere in the world with services like Trusted Housesitters, saving me on accommodation costs. This route makes me feel closer to my goals of full-time travel, gets me away from corporate America and feels like the change I have needed for years.

CONS

The biggest problem I see with this approach is that I don’t foresee being able to put much money in my travel savings this way. It will take some time to build up tutoring and dogsitting clientele and at first, I may not make much at all. And while I may be able to (in time) replace my current income, I will have to pay taxes and insurance (or in 2018, lack-of-insurance penalties) out of what I earn. And my savings account hasn’t budged in months. I seem to be hemorrhaging money lately–car repair, rental agency fees, photography fees, my part of the family beach house. The good news is that because I paid for professional photos, my house rented sight-unseen in less than 24 hours after it was listed. The tenants moved in right away, and I should start seeing some rental income in the next few months.

And I have more big expenses to come–the car needs brakes and A/C, I desperately need to update my phone while I have an income, and I don’t actually have a proper laptop. I currently have a storage-heavy desktop and a Chromebook, and even if I sell both, I’ll need to shell out quite a bit more for a good-quality replacement. I expect I’ll do that during the back-to-school sales in late summer.

Maybe it’s fear, but I want to see that savings account get much, much bigger before I quit any job. I feel I’ll have a greater chance of lifetime success if I put in the work now, in order to let my online pursuits have a chance to grow.

NOSE-TO-THE-GRINDSTONE APPROACH

This is the option I have been pursuing–keep my job and continue to search for a better-paying one if I can get it. The goal is to build up my savings and afford the repairs and purchases I need to make my future a possibility (which for me, includes my car.)

It kinda sucks. I hate working in a windowless back office. I don’t like having bosses. An 8-6 workday is exhausting. I don’t have time for rest or exercise. And the whole thing makes me feel farther from my goals. I’ll be pursuing another job that I don’t intend to keep for very long, which feels dishonest. But I’ve got to make more money!

But is that the siren song of something foolish? Is money a false security that I don’t really need? Can I just go and “follow my heart”, “jump and the universe will catch you” or any other Pinterest-worthy platitude? Do I follow what my heart really needs or what my mind says is wise?

CONCLUSION(ISH)

I don’t know. Since my whole life has changed in the last few years, I don’t seem to know much of anything anymore. But in my life-long habit of putting off what I really need in order to be “smart”, I will probably stick with a real job until my savings is in better shape. After all, this is a conscious career shift, not a college-age gap year or an irresponsible post-divorce freakout. I’m not ruling such things out as positive life experiences, and maybe I’m missing out on something divine by not jumping until I’ve created a net.

I do think I’ll add in more local house- and dogsitting via Rover and Next Door, at least I can do that part of my freelance plan. And eventually, I will transition to something that looks more like it so that I can travel with it. I can do this, it just takes time.