I have a problem. One that is entirely First World in its privilege, but challenging all the same.

I’ve been a personal blogger longer than I’ve been any other kind of writer. It was the easiest place to start on a campaign that began in 2009 (however unwittingly) to finally figure out my truths and learn to live them. Then as now, blogging platforms were democratically accessible and mostly free. In addition, I was in such a bad place nine years ago – personally and professionally – there was no want of material for such a creative endeavor. I was so lost in life, so inexperienced with the craft, I didn’t know enough to feel self-conscious – about fledgling skills or the nakedly intimate topics doubling as cries for self-help.

I actually went looking for my first-ever blog post on Which End Is Up Today?, a brief project on which my sister and I collaborated. It was a fun union of two close, but distinct voices – Jenny’s suburban mom with a broadcasting career; I the childless, urban dwelling, semi-starving artist. However the platform has been dormant for so many years, Google stopped indexing the site. That’s probably for the best.

My early work, while charmingly guileless, is fairly cringe worthy in form, structure and content. For one, I wrote under a pseudonym, a handy metaphor for the near-complete lack of self-awareness with which I was stumbling through life at the time. For example, if you dare, just gaze upon the hackneyed, uninteresting and fundamentally dishonest bit of autobiography on display here in early 2009. There are reasons beyond artistic self-flagellation for keeping these early efforts alive. I have always believed that the road to self-improvement is paved with recycled asphalt from wrong turns and dead ends.

Back to my present problem. While I remain an unmalleable square peg, with the help of abundant group and personal therapy, as well as hard labor, I’ve found the holes where I fit. I’m not only comfortable in these spaces, I luxuriate in them. Although it’s taken years of repeating empowering mantras until the syllables lose meaning, I deserve this recent comfort in my skin, this confidence about my place in the world, at home, at work and in Chicago’s literary community.

But though it’s an amazing feeling to discover one’s own version of equilibrium, it’s taking a while for new order to jibe with the fight or flight panic that characterized 36 years. Sometimes I’m still unsure what to do without the consistent, existential burn caused by fear, lack and overwhelming envy.

So it was that during a moment of unattached boredom, I found myself Googling, in vague search of answers to a question I never thought I’d ask.

“What’s next after achieving all your goals?”

The precursor to this interrogation of the World Wide Web was wrestling with a few philosophical queries on my own:

• What’s next after marrying the love of my life last year, my true spiritual partner in all things, the one who respects and supports my complicated past and present quirks of character? I chased the wrong men for three decades. This self-defeating past-time consumed a great deal of energy. Three years into a more healthy and balanced love, how do I channel old frenzy into the new, healthy maintenance habits our marriage deserves?
• Bob and I have a beautiful home that is fully representative of us. We’ve spent three years converting his divorced guy bachelor pad into our mortgaged happy place – paint, furniture, linens, multiple rounds of decluttering, infrastructure repairs. Our condo is clean, everything works as it should and I’ve had ample time to let go of old fears that I could be dumped/evicted/foreclosed upon, forced to rebuild alone. What’s next after achieving hard won domestic security? Am I supposed to set goals higher than what’s already more than enough?
• After years of toiling as a poorly paid freelancer, working temporary or otherwise unstable jobs to make ends meet as I waited for my “real career” to begin, I recently confronted a truth. “One day” has fully arrived. Once certain I’d never find fulfillment in a corporate setting, I work for a publicly traded company that entrusts me with challenging work matching passion and skill set. My day job provides me with the financial stability to underwrite riskier, less remunerative creative efforts to which I’m no less committed. Like say, teaching an adjunct English class at my alma mater that’s designed to help students turn liberal arts degrees into jobs. Or publishing a once-in-a-lifetime charity book project about the Chicago Cubs’ 2016 World Series with a friend and colleague. I sit on the boards of two vitally important Chicago-based communications organizations that put me in regular networking contact with brilliant creatives. As a whole, my career is more well-wounded and rewarding than ever seemed possible. But I am a born striver. Do I even know how to stop wanting more than I need?
• After sustained efforts at breaking toxic, co-dependent relationship habits, I’m blessed with healthy, supportive friendships and good relationships with the family members I choose to include in my life. For the most part, I’ve given over obsessing about the estranged, broken and bizarre bonds with my parents that used to make me feel ritual, low-grade shame and discomfort. Is it ok to let go?

If you’re are wondering why the hell one would overthink success and contentment, I couldn’t agree with you more. But I suspect this quote from a recent article on the Lifehack website gets at the heart of the real issue. It’s about fear – of losing what I’ve gained, rather than failing to accrue addition:

“What do you do once you achieve your big goal and make it to the top? This can become a big problem if it looks like the only way you can go is down…The problem can be one of maintaining the position [if this is what you want], or figuring out where to go next while avoiding a big letdown.”

I’ve worked so hard to get to this place, I don’t want to disappoint anyone, myself most urgently of all.  After a life of operating (correctly) like I had nothing to lose, I’m somewhat confounded by today’s emotional, physical and spiritual plenty.