Far better than you could have ever dreamed

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I have a memory of working out on the elliptical at the Gold’s Gym less than a block from my apartment in Virginia Square, right outside DC. There was a row of TVs facing us, with at least a few always playing network news.

I studied journalism in college because I loved reading the news. It took me a long time and many awkward conversations with strangers to realize most people didn’t have heavy policy debates with their families around the dinner table. I spent my youth playing Freecell while my Drudge Report pages loaded.

I never wanted to be a reporter though. Feigning objectivity offended me on principle, and feigning anything has never been my strong suit.

At my school paper I exclusively wrote columns about my political opinions.

Writing was the only thing I was good at and journalism was the only degree I could stand getting that would qualify me for an office job without going to grad school.

My dream was to be an opinion writer, a columnist. But with my socioeconomic background, and considering the economic opportunities in Alabama at the time, getting a full-time office job with benefits doing something I didn’t hate felt like it would be a huge win and was anything but assured.

I was so dense, and had so few friends in my department, that it wasn’t until senior year that I overheard my classmates talk about scrambling to get things published. that I realized I needed to have a writing portfolio to get jobs. In Birmingham, Alabama, where I graduated from Samford in 2008, the school paper didn’t even publish to the web. So I literally cut my columns out of the school newspapers I’d saved and pasted them into a kind of “I’m a writer” scrapbook and took that with me to interviews.

The economy generally wasn’t amazing in 2008, publishing especially. Birmingham was home to Southern Progres, and their slew of magazines like Southern Living, Cooking Light, etc. were shedding jobs. I was competing with writers who with decades of high-profile, local experience for a shrinking number of writing jobs.

After a stressful four months of newly married joblessness, I finally nabbed a role writing search engine optimized descriptions of deer urine, magazine displays, (and my personal favorite), new urbanist real estate developments. I asked my recruiter for $30,000 for a starting salary and he laughed and said he’d get me $40,000. This put me in Birmingham’s median area household income. My parents paid for school, so I was debt free, had no expensive health problems, and no kids. If my husband had earned what I did, we’d have actually been rich. I’d achieved the hard dream, if not the ultimate one.

By year two or three, I had the role pretty much down. I still wanted to write columns, and couldn’t really see an appealing career path. Thinking about moving up to management, I liked the idea of earning more money, buying a bigger house, wearing expensive suits, and girlbossing. But that would require me to have a much more intimate relationship with people and numbers, and I’m not good with either.

To give myself a way to write columns, even if no one would pay me, I asked my best guy friend at work to help me launch a Wordpress on my current political obsession.

Together, we gave birth to the anarcho-capitalism blog. I really thought there would be more search interest for “anarcho-capitalism.” So, being the good (or at least passable) SEO expert, I included it in the domain. I wrote that at home and in my downtime at work.

As with my school paper, there was no real plan. I hoped to somehow change the world with my brilliant analysis. But had no idea how that might happen.

Then I got hired by Reason and joined the Koch Associate Program (KAP) on their insistence. The job was in DC, and by the time my class went around the room stating our career goals I’d formed a plan.

Full-time columnist still wasn’t likely to happen. The media landscaped had changed permanently. There were fewer of those jobs and they went nearly exclusively to Ivy Leaguers, advanced degree holders, Washington insiders, and people who’d been doing it before the economy tanked.

But I was young, thin, blonde, and reasonably well-spoken. I told the class I wanted to be a libertarian pundit. I was going to be one of those talking heads I’d seen on the news at Gold’s Gym. Once people saw my face and heard what I had to say, I thought, they’d start reading my writing. Ann Coulter, but more the era when she was mostly mad about TSA and less the anti-immigrant version.

I recently thought back to what happened instead. I accomplished a lot of what I’d dreamed on the elliptical at Gold’s. I went on TV a few times. I got my political opinions published in some major outlets. I got people to read my column, even if it was still just a blog and no one paid me to write it. I even got paid to write, edit, and publish my own and others’ political writing.

It was the second time I’d dreamed bigger than my circumstances would suggest, went hard after it, and found some degree of success. In the process, I discovered it was draining to constantly fight about politics online. I’d start drinking at work and fire off tweets that nearly got me fired. And the pay was atrocious. As it turns out, it’s really hard to get paid for punditry if you’re not mainly preaching to some choir. And I found that intolerably boring.

Eventually, I accepted the ceiling to my current path and found a nice tech job that paid me pretty well and didn’t demand too much of me. I continued to write my blog for free on the side. I saved up some money and found myself financially in the black for the first time since my divorce. But the question nagged at me. What’s next? Is this it? What am I doing with my life?

After five years in DC, three in politics full-time and two working my tech job, I moved to SF. This time, I dreamt of marrying the man I was moving there to be with. Maybe I’d be a happy semi-housewife, working my tech job remotely and organizing for YIMBY in my spare time. Maybe I’d get a high-paying tech job. Dude and I broke up. But some of that happened. I wrote influential columns about housing policy and worked at three different startups, making more money than I ever had. And a few things that I didn’t expect happened. I became somewhat of an organizer in the Bay Area sex-positive scene. I started writing about sex work and doing sex work again, this time online.

As I start to think about next steps, I think back to what I envisioned before making major moves in the past. I think about which parts of my vision I was able to realize, and which parts I didn’t foresee.

I think about the role scarcity played in all of my decision-making. How I wanted to be a columnist but didn’t really try because of the economy. How I kept trading on my youth and beauty in DC because I didn’t think I was smart enough to lead with my intellect. How I didn’t think I could afford to live in SF without a partner to help me pay rent. Scarcity literally makes us worse at thinking.

Last night I was thinking about risk-aversion, as one does. I think the human brain tends to overestimate risk and underestimate reward because it’s evolutionarily advantageous. I know for me, I’ve noticed a tendency for risk-aversion that I’ve actively tried to correct for. And the results have been almost uniformly positive.

Of course that’s not true for everyone. I imagined a tuner for risk aversion, and the ability to turn a knob like it was volume up and down to maximize utility. Some people need to turn that sucker way down.

Then another thought occurred to me. What if the scale isn’t 1-10? What if it’s 1-1000? What if I wouldn’t benefit from turning the knob a few notches, but many, many notches? More notches than I know exist. What if I’m still a million times more risk averse than would be optimal for me right now?

Risk aversion ultimately comes down to likely worst-case scenarios. I’m extremely practiced at playing out worst-case scenarios in my head and trying to evaluate their likelihood. But like best-case scenarios, we’re all very limited in our ability to imagine possible outcomes.

In most cases where I played out the likely outcomes and took what felt like a big risk, it’s played out much differently than I imagined in many key ways. It’s been harder than I imagined, mostly in ways I didn’t expect. But, if I could snap my fingers and trade my life now for any of my previous dreams as I’d imagined them, I wouldn’t even consider doing it. Overall, every big risk has always brought me to a place that turned out to be far better than I could have ever imagined.

There are many more things I dream of doing. Hard things. Risky things.

And I find myself finally in a place where the likely worst-case scenarios seem pretty manageable. I’ve taken my immense privilege and natural risk-aversion and begun turning it into the beginnings of a workable safety net. A net that won’t just keep me from falling all the way down, but can serve as a platform for getting up and starting to walk back up to wherever I want to go next. I’m getting prepared to turn the risk dial way up.

That’s what I want for everyone. I want everyone to dream big, whether that’s being a columnist or having kids or building a cabin in the woods or genetically altering pigs to grow functional human hearts. I want everyone to know that if things go awry they’ll still be able to survive, and maybe even thrive.

I think it can be done. I think it mostly requires political will.

I want you to start thinking about this by asking yourself, if you haven’t, “What would I do differently, today, if the worst-case scenario meant inconvenience, rather than ruin?” Consider how other people might answer the question. Think about a world in which that was true for everyone. Would the world look better, or worse? In my experience, it would end up looking somewhat different than you imagine. But it would be far, far better than you could have ever dreamed.