Why Aren’t You Making a Career of Writing Again?

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Why aren’t you making a career with your writing?  It’s a question I’ve been asked what seems like an inordinate amount as of late.  It’s as if the universe is converging on me from all angles to remind me, you would think unnecessarily, of that thing I love and why I should be pursuing it.  It all started with a text conversation with my best friend Meg.   She was walking down the steps at the train station on her daily commute and suddenly found herself thinking of all the playwriting I did in college. Random. “I swear, I did!” She promised me.  “You were so into writing then.” She continued.  Oof.  Total gut punch.

It’s not that Meg intended to zing me or say anything remotely hurtful.  It was just one of those off the cuff comments that gets to the heart of the matter and cuts right through you. And as a result I thought about it. A lot.  Arguably it’s much easier to be “into writing” when you’re in college and you have no real responsibilities outside of class.  Typically, you’re not paying a mortgage, a car payment, or worrying about your health insurance.  Your biggest worry is usually a hangover or cranking out that 20 page term paper overnight.  It’s much easier in that environment to devote a lazy afternoon to working on your “masterpiece”.  As an adult, it can be much harder to motivate yourself.  You get up early, work all day, and when you come home, often you just want to veg out and turn your brain off.  For me, even as a huge movie nerd, sometimes watching a new film is even more than I can stand because I want to avoid thinking just that much.



Ben Schwartz speaks the truth.


But still, I love writing.  It’s something I can comfortably say that I am good at. And so, theoretically it shouldn’t be so hard for me to make time for.  At times, I’ve beaten myself up for not writing and wondered if maybe my lack of production and motivation was a sign that I didn’t love it “enough” to make a go of it.  Ultimately I think that’s bullshit. Success and a career isn’t guaranteed to even those who want it the most.  It’s not a movie magic twist of fate.  If I’m honest with myself, it’s mostly a flaw in my own DNA, not a lack of love or desire, that makes it hard for me to motivate myself.  It’s something that bleeds into all aspects of my life.  It’s perhaps my fatal flaw.  This is going to make me sound like a real douche but bear with me.  I’m pretty good at most things I try.  I tend to be a fast learner and while I’m by no means an expert at anything, I can usually pick up on something pretty quickly and be average or a little above right way.  And so, when things are hard for me, when they require some real blood, sweat, and tears, sometimes (ok a lot of the time) (ok almost always) I have a tendency to bail.  Poor me, right?  I know. I’m coming off as a real asshole right now.

And so, here we are back at the original question I’ve been asked so much lately – why aren’t you making a career with your writing? Because I’m being an asshole, I guess is the most direct answer.  Because I’m getting in my own way and wasting my own time, is probably the more specific one.  But the silver lining to that brutal honesty is that I can fix it.  I’m the master of my own destiny.  It’s probably the biggest, most obvious lesson I’ve learned in my late 20s and early 30s. There’s a lot we can’t control in this world – the list seems to be getting longer by the day.  But we can always control ourselves, our perspective, and our approach.  I could have looked at all these inquiries about my writing as a downer, and I definitely let myself have a pity party for a hot minute or two.  But ultimately, I’ve looked at them as a chance to reevaluate my approach to writing and reassess my priorities.  It’s never too late to start over.  Hopefully ten years from now Meg with have another random thought and texting me about this time in my life will say something like, “that’s when you got so into writing again.”


A Little Perspective, A Lot Re-Energized

Self-awareness can be a great thing.  If you’re aware of your behaviors, shortcomings, moods, it can do wonders for your ability to manage yourself, interpersonal relationships, and navigate life in general.  But no matter how well we may know ourselves, there’s nothing like an outside perspective to shine a light through our dustiest windows, exposing truths we have left forgotten to decay in the recesses of our brains.


I am aware I am a rabbit.

At 31 I took a leap.  I felt myself stuck in the same gear, on the same path, chugging along from administrative position to administrative position, never advancing, only moving on to what I always perceived as “better jobs” because of…well, pay mostly.  I found myself making the most I had made in the almost ten years since I graduated college and I was completely unfulfilled and utterly miserable. And so, when I saw an opening I took it.  I make donuts for a living now. I make roughly half what I was, and yet, overall my quality of life has improved drastically.  It has thrown my brain into complete chaos, adapting to my new lifestyle with its ever changing schedule and sheer physical demands.  And while that can be stressful and anxiety inducing for the part of me that has spent my whole life organized and planned, it’s exactly what I needed – like a reboot for my life.

And still, as of late, I’ve felt a little as though I’m treading mud in lead boots.  My motivation and momentum has gone on holiday and I’ve been moody, depressed, and feeling rather lost.  And so, in a moment I cannot assign quite the correct adjective or characteristic to, I reached out to an old friend, someone I had not seen in quite some time, someone I cannot recall having ever spent time one on one with, and I set up a date for a chat. And that is why I find myself here writing this now; because I find myself energized, motivated, and inspired.  Because an outside perspective – and I really mean outside, not your partner, your bestie, or your work wife/husband – can hit you like a bolt of lightning.

I sat across from this self-assured, successful, put together woman for two hours tonight and while we did catch up on life, we mostly talked a lot about intentions, skills, fulfillment, and how much we’ve learned from failures and jobs that weren’t right for us.  She talked a lot about myself to me.  She spoke plainly about how she perceived me, the skills I had, my value professionally, and the steps I should be taking to achieve my goals.  When I confessed that I sometimes doubted my decision to take the leap I did, that I sometimes wonder what the hell I had gotten myself into, she reminded me that doubts are very human and at the very least it makes my life, and the book I will someday write, way more interesting.

Talking with my friend for the first time in months, very possibly over a year, during which time we had both evolved so much, I was reminded why I made the choice I did 7 months ago.  I was reminded of all the ways it was infinitely better for me than not.  And most importantly, I was reminded that momentum can begin with a single breath, step, word, or giant leap. Momentum is always lost only momentarily and it’s up to you how long that moment will be.  I’ve always considered myself very self-aware, certainly to a fault, as I love to torture myself with my shortcomings.  But someone else’s perspective has helped to reorganize my awareness – a little mental feng shui if you will. A message leads to a conversation to an idea to a blog and onwards.  I think I’ve shed the boots and I’m crawling forwards out of the mud.