What happens after you design the life of your own making? What then?

Boomers will be our ruin, was our constant refrain in the late 90s. This was a time when we actively practiced our apathy, regarded the internet with a mixture of interest and suspicion, and carried cellular phones the size of small bricks. We survived grunge (barely), witnessed a 70s comeback (no thanks), and shirked off our over-generalized Gen-X moniker. We weren’t fragile unique snowflakes, but we didn’t aspire to be our parents either, and it would take a new generation of upstarts to fix the mistakes we initially made with the internet (remember the epic implosion of 2001? My unemployment checks sure do) and show us that everything we were taught to believe about work, success, and life, was far from gospel.

For seventeen years, I worked in an office. I did what I’d been told to do or mimicked generations past — I worked hard and paid my dues, knew my place in the hierarchy and adhered to it, and believed an Odyssean commute and a matching 401K were the “only way”. I never conceived of a career outside the confines of a cubicle until I learned that corporations couldn’t guarantee a safety net or protect you from market and industry volatility, and even though you were constantly reminded of your value and worth during the annual corporate retreats and holiday potlucks, your livelihood was predicated on a P&L. You were only as valuable and indisposable as a company was profitable. You existed for as long as a company could bear the weight of you.

In 1997, I graduated college with a plan: work in finance for 10–15 years, get married, have kids — the whole whitewashed nine-yard. Just stick to the plan, I told myself because this singular version of a dream, one that had been photocopied by multitudes, was the only way. Right?

Until I learned that I loathed finance. You could be good at something and still cry in bathroom stalls. My work didn’t challenge me, the dress code (yes, back then we had a suit dress code with only Fridays as a reprieve) was daunting, my coworkers all hailed from the same Northeast schools, and I became curious about this “Internet thing”. I spent nights and weekends navigating AOL and dial-up service (remember when no one could reach you because you were online? Good times.) and using my financial and accounting skills, I launched a small business where I bought designer clothes and accessories from outlets and samples sales in New York and sold them online. I did this successfully for two years, but still didn’t believe in the safety of going out on my own. I’d relegated my business to a side project, that thing that would steer me away from finance and I could mail my paper resumes to new companies in new industries. During this time, I managed to fit in getting my master’s degree in Fine Arts — the antithesis of my “safe” Bachelor’s of Science degree.

My plan in 1997 was a graft that didn’t take, an implanted organ rejected by its host. My views on marriage shifted — I cared less about the white dress and the fanfare and confetti and instead wanted a partner, regardless of the paperwork. I also realized that I didn’t want children, which made marriage at the time a trickier proposition. Instead, I wanted my career and my novels. I worried less about the whitewashed life and figured that a partner would eventually materialize.

By 2013, most of my views of success were usurped. Millennials annoyed me initially with their impatience toward hierarchy and their seemingly abnormal professional velocity. There seemed to be an urgency in this generation that hadn’t existed previously. I kept thinking know your place until I began to wonder what is “your place”? I was reminded of how I hated being silenced in the room when I had good ideas simply for the fact that I was under 30. I wanted to work hard, true, but I also wanted to contribute and be respected even if I hadn’t yet gone gray. I’d spent time around smart and creative millennials, who had great ideas and worked hard, but believed one could take control of one’s success, that one’s identity was not inextricably bound to their title. I saw them leave and start their own ventures and at first, I was shocked (though mostly afraid), but that fear turned into envy because I thought: I could do this too. So I left a job that made me unhappy to venture out on my own.

At first, I thought, oh, I’ll probably consult for a few months and get a job. Fast forward three and half years later.

There are hundreds, if not thousands, of articles that will instruct you on how to be successful as a freelancer. I’m not here to add to that noise, other than to say yes, it’s important to discern if this kind of work is right for you as opposed to being seduced by the glamour of working from home (it’s not glamorous, rather, it’s often isolating), getting experts like bookkeepers and lawyers are tantamount, and being smart about your offering and value proposition (i.e. what you do and why you do it better or differently than the freelancer down the block), know you have to have multiple projects going as a hedge and you have to always be pitching, closing, etc — these are all important and elucidated elsewhere in excruciating (and necessary) detail.

I turn 41 this weekend and it took me a really long time to be okay with not having a plan, of playing the days as they lay. That I’m not a failure because I didn’t cleave to what I had thought defined one’s personal and financial success and realized that definitions aren’t binary. That you can fail and fail better.

Sometimes I look at my peers or those who are younger than me and I think: they have it together. They bought a house, they live debt-free, and their life isn’t an artful navigation of student loan officers, creditors, and creative accounting. And for a moment I step into that comparison trap and before the claws snap I fall back. That’s their life, their definition of happiness, their path — not mine.

Would I love to be out of debt? Absolutely. Do I regret going to a fancy Ivy League school for a graduate degree when I could’ve saved money and gone somewhere equally good and local? Sure. But right now, right this moment, I have a business that makes me jump out of bed in the morning, I write the books I dream of writing, and I’m healthy (finally), sane, and the things I want will come…eventually. Right now, I focus less on a “plan” and more on living the best and most mindful life I can live. Right now, I focus on giving back and using my privilege to help others. Right now, I focus on living.

I read this quote today (I’m not a fan of Kerouac, but felt it appropriate):

And I will die, and you will die, and we all will die, and even the stars will fade out one after another in time.

You could look at it and think, that’s morbid, or you can view it as a call to live.