The Surprising Things That Happened Once I Won at Everything


In May of 2013, I got drunk and fell off of a bench, and without any credentials or anything of a plan, declared myself an artist. With incredible tenacity, I have persisted in pursuing my dream and my craft since that moment.

It sounded like a good idea at the time. There was no way of knowing what my life would look like, what it looks like, today.

For the first thirty or so years of my life, I launched myself full tilt at all sorts of windmills. I knew what I wanted. I always knew what I wanted. At the age of twenty, I thought I knew how the world worked and I thought I could see my place in it. I may have doubted whether I could do what I had set out to do, but I rarely lacked confidence in my dreams.

I knew I was supposed to go to college, so I could get a good education, so I could establish a career, and I thought that was what I wanted. I knew I desperately wanted to find a good husband, get married, have children, buy a house, and eventually, to own my own business.

I graduated from college, a herculean effort. I got married, launched a career, had children (at the same time!) and purchased a condo. I had a spreadsheet. I had a plan. I was going to go to law school at night, become a lawyer, buy a bigger house, send my kids to a good college so that they could do it all over again.

It turned out, winning at all the things was nothing like what I wanted, and it was pretty awful. Undoing it all was even more awful. I left my career, got divorced, sold my house, and pretty much lost almost everything I had worked for over ten years to build.

Almost everything, but not all. Afterward, what I had left was my children, my family and friends, the indelible changes left on my intellect by my education and work experience, a boatload of debt, plenty of shame, and absolutely nothing else left to lose.

I found out what was actually important to me, and it turned out not to be the career, the marriage, the house, or the story in my head.

It was time to build a new life, with what I did have left. I still had my children. I still had my parents. I still had my friends. I still had a car, and a computer, and the skills and the wherewithal to use them to take me places, literally and figuratively.

Since the great unravelling of 2011, I have frequently found myself sitting amidst the wreckage of the life I once had and wondering what EVER possessed me to pursue this new life, where instead of returning to the safety of convention and the land of “should,” I flounder in the bizarre space of “could.”

Friends and misfits with me on this journey told me it would get easier. I would get better at being fully myself. I would learn new skills and new habits, and life would get better. I still knew what I wanted, I just didn’t know how to make it happen.

Then, better started to happen, for real. For almost three years, I have worked consistently as an artist. I built up a business slowly, surely. I started to charge more. I found a team of amazing supporters and friends. I started to be more selective about the commissions I took on. I started to make actual money.

I started winning at all the things. At first, I was ecstatic. But then a strange thing happened: I found myself terrified. Why? My projects are succeeding. My clients are happy. My work is fulfilling, interesting, meaningful. I have structured my entire life around myself and my children, my family, my friends and lovers, my various communities. Everything is going well, and moving in the right direction, and the seemingly impossible contradictions of my needs and wants and desires are growing together into a beautifully integrated whole.

In short, I’m succeeding. Yet, frequently at the end of these long, hardworking, difficult days, I weep from the sheer pain of having successfully built the life I have always dreamed of. I thought something was wrong with this. Why would being happy feel so much like being broken into pieces? Maybe I was doing it wrong?

I don’t think I am. There’s a surprising dark side to success, you see, one I have seen many people speak of, but only now begun to understand, as I experience it firsthand. When things are difficult, it’s not pleasant, but all feelings can be put on hold, pushed aside, because the need to address the crisis at hand is foremost. I was busy fighting fires. I didn’t have time to feel.

But once the crisis is past and I find myself in a new place of relative security and emotional safe harbor, there’s nothing to keep all of that pain from flooding back in. I lost a life I didn’t love, and I gained one that I do, one that is in many ways much more complicated and much harder than before, but infinitely more satisfying in its truth and complexity.

As my life comes back together and I rebuild, I have to learn to allow myself to truly feel again. I can’t simply put aside all the doubt and fears and grief of the past few years and walk on. I don’t want to ignore my anxiety that things will all come apart again, that all that I’ve worked so hard for will blow up in my face a second, or a third, time. It might. I refuse to live in nothing but that fear. Instead, I celebrate my own uncomfortable growing pains, my griefs and sorrows, my overwhelm. I accept that I can be succeeding without faking or forcing a false ecstasy.

I AM happy to be succeeding. I AM happy to be healing. Most of all, I am happy to be surprised by the funny things that happen, when I start to win at everything.



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