How to Decide Between Money and Meaning

2012 was the year of money. I made a lot of it.

Making money is easy, making meaning is hard. Making money is finding it where you can get it, and last year, I found it everywhere. I had six different sources of income (eight, if you’re the IRS), that made me more than six-figures. Mostly from my pajamas at home, sometimes with a sandwich at a coffee shop.

Making money is fantastic. People that tell you otherwise, I don’t get them. Money feels good, and earning money feels real good. There’s something particularly great when you earn it directly, without a middleman, something about proving your worth.

Especially when your main activity prior to bringing in the cash was the torture of “What should I do with my life?”, “I want to do something meaningful!” and “I’m not living up to my potential.”

Making money after a constant wringing-of-the-hands is freedom. At least in the beginning. Making money after a career in non-profits and startups (my first job out of college paid me $26,500), is all the more amazing to me. No background in banking, no experience in sales. Just desire (and if it’s not obvious, a lot of work, positioning and connections, lest I perpetuate the myth of the American Dream).

Salaried jobs have a ceiling. You work, and “get a salary and a status bump with every sideways leap… flightiness is the new aggression,” argues New Yorker’s Nathan Heller. After job-hopping, you work and make more when you do more. And then finally, you work more until you realize you can’t make more. You hit the ceiling. Maybe with some maneuvering you could earn an extra $20K a year. But most people hit the ceiling and then settle.

I hit the ceiling and looked for a window.

It started with a dinner party. I met the owner of a small business, followed his company, and noticed an opening for a full-time marketing professional. I pitched him the idea that I could do everything in his job description for two-thirds of the salary and half the time. The next day, I still had my full-time job, and signed my first client.

“Today, careers consist of piecing together various types of work, juggling multiple clients, learning to be marketing and accounting experts, and creating offices in bedrooms/coffee shops/coworking spaces,” argues the Atlantic.

Creating a portfolio career, where we have more than one job/employer/client at a time is not for the feint of heart. Many of us have employers, precisely because we don’t like what we do. It’s easier to shift personal responsibility to the organization. It’s easier to play a pre-defined role instead of create your own. And despite being the most entrepreneurial generation, for many Gen Yer’s it hasn’t sunk in yet that a salaried job carries just as much risk as a do-it-yourself career.

Regular emails from young graduates land in my inbox, frustrated by their Starbucks career, anxious for “real work.” Their search for the elusive dream job lacks any real direction or enthusiasm, except for an insistence that they don’t want to be part of the sixty percent of America who can’t put a finger on what’s holding them back from their goals. Not knowing our purpose in life, it’s unbearable. “My insatiable desire for more money, knowledge, time and freedom leaves me perpetually unsatisfied,” argues blogger Ryan Stephens.

Gen Y’s overwhelming anxiety began long before the recession, and has only deepened after being forced into jobs we should feel grateful for, but instead only make us feel claustrophobic. Pile on the generation’s massive debt and unconscionable unemployment rate, and we’re at a loss to do anything but ask, “Now, what?”

I chose money, at least for the short-term. I paid off my student loans, maxed out my Roth IRA, built a six-month emergency fund, bought a new wardrobe twice, nested our new place, and paid for a two-week European vacation (with real beds and adult dinners). I chose money over settling. But I also chose it over meaning.

It’s here I’d like to say I proved my hypothesis – that you should make money, and do what you love on the side. But jobs that pay well require your full attention. And insatiable desires to change the world don’t just go away (darn it).

So 2012 closes how it started, between making money and creating meaning, a rock and a hard place. I’m relieved to have my finances in better order. I’m proud to have proved “my worth.” And I’m still desperate to do something with my life.

How do you reconcile your dreams with a paycheck?