In 2009, I was 27 years old and a year into my first full-time job with benefits. I was working as an executive assistant at a think tank in Washington, DC, and had ended up in this job after spending the past five years telemarketing, temping, going to grad school to get a MFA in theater, coming out of grad school no longer wanting to work in the theater, and asking a professor whom I trusted how I could get a job that paid at least $50,000 a year.
“With your skills, you’d make a great executive assistant,” he told me—so I went to one more temp agency, told them I wanted a temp-to-perm executive assistant job that paid at least $50K, aced the typing tests, and got myself hired.
(It helped that all of this happened before we were fully into the swing of the Great Recession. Timing really is everything.)
Making $50K a year felt like an enormous amount of money compared to telemarketing and temping wages. I had no undergrad or grad school debt—made it through both on scholarships and stipends—so once I paid off the $5,000 my parents loaned me to cover the cost of the semester I spent teaching Shakespeare at the University of Hyderabad, I bought myself enough clothes that I could go two full weeks without having to repeat an outfit and then began focusing on saving as much money as possible.
I was already hugely interested in personal finance and knew the path I was supposed to be following: get out of debt, build an emergency fund, start saving for retirement. In 2009, I was debt-free and managed to save $10,000, which felt like a huge accomplishment and also like it was barely a drop in the bucket. How would I ever save enough to retire, let alone retire early like all those books in the library claimed I could?
I mean, I didn’t want to be an executive assistant forever.
I ended up working as an executive assistant for four years. After that, I quit my job to move to Los Angeles and try to make it as an indie musician. I wasn’t completely terrible at the musician thing—I was playing gigs and geek conventions nearly every week—but by the end of that year I had spent all my savings and was $14,000 in credit card debt, so I began Mechanical Turking to bring in a little extra cash.
Amazon Mechanical Turk, if you’re not familiar, is a site where you can sign up to do short, repetitive tasks (taking surveys, identifying objects, confirming whether a review is positive or negative) for pennies. Back then there were a handful of Mechanical Turk clients offering better-paying gigs, including the content writing company CrowdSource, which has since rebranded as OneSpace. I started Turking for CrowdSource in late 2012, got invited to join up as a freelance writer and editor, and quickly became the site’s fourth-highest earner (though I would assume that record no longer stands).
I also finished recording an album—like, a professionally recorded and engineered album, funded by Kickstarter money, credit cards, and my Roth IRA. (Pulling the cash out of that Roth is one of the biggest money mistakes I made in the past decade, let me tell you.) When I met with the sound engineer to go over the final mixes, he said “You know, you’re a good musician. But you’re a great writer. Have you ever thought about—”
“Yeah,” I told him. “I’ve thought about it.”
From there it was pitching and writing and pitching and writing; spending five years at The Billfold and getting my byline everywhere from The Penny Hoarder to Popular Science; publishing two novels; becoming a regular contributor at Lifehacker and Bankrate and Haven Life and Vox.
This year, I grossed over six figures as a freelancer. I don’t have the final numbers yet because I’m expecting a few more checks before December 31, but my 2019 earnings currently include $119,831.57 in freelancing income and $204.30 in publishing royalties. I also more than doubled my net worth this year—from $84,700.47 to $174,809.19—after moving to a low cost-of-living area and pursuing what you might call an aggressive saving and investing strategy. The FIRE calculators suggest that if I keep this up, I could retire in 2025.
I don’t know what your finances were like ten years ago, but it’s worth taking some time to think about where you’ve been, how much you’ve earned, how much debt you’ve paid off, and so on. Remind yourself of your biggest accomplishments; ask yourself about your biggest regrets. Be honest about any advantages that may have helped you along the way; when I ended up $14K in credit card debt, for example, my parents essentially sat me down and said “We are going to give you an interest-free loan and you are going to pay us back.”
What’s interesting about doing this kind of reflection (at least in my case) is realizing that my core financial values and interests—frugality, financial independence, making and publishing my own creative projects—haven’t really changed since 2009. The biggest difference, over the past ten years, is that I both worked and lucked my way into a career in which I could grow my income exponentially. I know well enough to treat my current earnings rate as temporary, which is one of the reasons why I don’t really trust those FIRE calculators (even though they are a lot of fun to play with). 2019 may have been a six-figure year, but in 2012 my total income was $23,878.
How have your finances changed, over the past ten years? Have your financial values changed as well, or do you feel like your values have stayed consistent and you’re simply living on more/less money than you were a decade ago? If you were to tell a story like the one I just told you, what would it include—and how might it shape what you hope to do with your finances in the next decade?