I’m a big fan of the mentality that you are where you need to be and mistakes help make you who you are.

That doesn’t necessarily make them suck any less.

The funny thing is though, my two biggest money mistakes both turned into things I didn’t regret.

Money Mistake #1 

Move to one of the most expensive cities in America without a job or a plan.

Right after I graduated, I was in a little bit of a tail spin due to a bad breakup and decided to move to San Francisco with my best friend… because I’d never seen the Pacific Ocean and she had a job offer out there.

Her job was pretty good, so we wound up in an expensive apartment and I wound up paying rent of $1,250 a month, which wasn’t even fully half.

I had about $7,000 in a savings account and a small balance on my credit card when I loaded up my car to drive from Virginia to California.

I spent the first 3 weeks completely panicking that I’d made the worst job ever while I scrambled my butt off applying for jobs and trying to find work.

One day, I was sadly wandering around Fisherman’s Wharf alter being told by The Rainforest Cafe there that I wasn’t qualified to work at it (always an exciting thing to hear when you just finished up grad school with 3 Master’s degrees) when I noticed a few cruise ships docked there.

I went home and applied to every line I could find. By the end of the week I had a job.

By the end of the year, I’d spent about 3 months total in San Francisco.

Total cost – $15,000

Theoretically, I could’ve wound up working for a cruise line from anywhere in the world, but I don’t know if the stars would’ve aligned to have me wander past several and remember that cruise ships have theaters the same way it all wound up going down.

So $15,000 for an apartment I barely lived in was nuts.

But $15,000 to make around $175,000 over 5 years and see a ton of the world while building up my resume skills like a boss?

…not the worst thing that’s ever happened to me.

Money Mistake #2 

Going to grad school in another country on a whim.

3 years into that cruise ship stint, I was a little burnt out on that life and decided I wanted to go back to school.

I looked up several programs in America and found a few fully funded PhD programs. I applied to them and was promptly rejected by them all.

Several months later, I was chatting with the Tour Guide on one of the ships and mentioned I was thinking about going back to get another Master’s degree first now, since all of my original ones were in areas of religion and I was more interested in studying theater. I thought a theater M.A. might help more, but I’d missed all the deadlines for the U.S., so I’d have to wait another year.

He was British and informed me that not only are there no deadlines in the UK, but an M.A. program is only a year there.

Within a week I’d found a school and applied and within 2 weeks I had been accepted and decided I was moving to England.

I had about $9,000 in savings, but needed about $30,000 total for tuition and living expenses. I planned to apply for a private loan, but when I finally mentioned my mad plan to my parents, because I needed to borrow $20,000 from anyone to have in my bank account for at least a month to get the visa in May and I was hoping they’d lend me the $20,000 for a month without interest and then I could sort out the private loans closer to leaving for England in September, they said I should talk to my grandmother.

I wound up borrowing the $20,000 from her and paying her back without any interest, which was definitely a huge blessing. Towards the end of my time in England, I actually came up a little short and took out a $3,000 loan from Sallie Mae. So… $30,000+ later, I had spent a year living in England and had a Theatre and Performance Studies M.A.

And all of the decisions that created that debt were made on a whim in a week.

None the less, studying in England broadened my horizons more than 18 years of education in the United States did. Advanced studies there are designed to actually make you think rather than just jump through hoops, which is how my first grad school experience felt.

I often think about going back there for a doctorate, but it’s difficult to find international funding and without it, the 3 year PhD program with living expenses would probably run me about $100,000… which is definitely not a decision I’m going to make on a whim this time.

That’s the main thing I learned from both mistakes – it can be great to take some giant risks, but if you actually take a little time to plan for them, they’ll cost you a lot less. I could’ve moved to San Francisco with my best friend and not lived with her, instead living somewhere that better suited my budget needs. I could’ve gone to school in England a year later after researching funding and scholarship options.

A little planning can go a long way.

Have any of your biggest money mistakes actually paid off for you?