Asking Not Asking #2:
TINA ESSMAKER / Creative Coach
I have had many achievements that I never imagined I would have as a professional photographer over my years practicing my craft. But now as a mid-career artist, I am looking on the horizon at my life as a freelancer and I ask, “Did I choose the wrong life?”
When I started out as a photographer’s assistant many many years ago, I could see that the life I was choosing was one of a freelancer, and I embraced the independence and uncertainty. For years, I was okay with not having a dependable income—I always got by somehow. The phone always rang or some cool project came in the nick of time. I even got to publish two books of my passion project work, which was a great achievement and dream come true (from years of hard work!). Especially after the books were published, I thought that my successes would put me on a new level, help me get more recognition, better clients, and make more money with the big juicy jobs and a phone that wouldn’t stop ringing. Instead, I am in debt and barely working, with no real prospects on the horizon.
I continue to be inspired to do work I love, but I’m not getting the work that pays the bills. I am forty-five and thinking, “Will it get better than this?” I suffered two losses in the last two years—my father and brother—so it’s a time of reflection and grief. I am looking towards the future and I try to imagine the life I want to have as I grow older: not being poor, being able to do my creative work, mentor others, and enjoy life. And freelancing scares the shit out of me. How do I build a sustainable future? I’ve never been a conventional person, so I am open to an unconventional life. I think a lot of creative freelancers are thinking the same thing: How am I going to “retire” and grow older without being destitute?
Dear Mid-Life Freelancer,
My hand is raised. Why? Because I can relate. When I flew to Atlanta for my coach training—which I paid for with a credit card—I wondered, How am I qualified to help other people? I’m a broke 36-year-old who is starting from the bottom. I had left my decade-long marriage with $4,000, which I used to move into a new apartment one block away—with a roommate. Over the next year, I transitioned out of the business I had cofounded with my former partner and, even though I was tempted to take a full-time job because a sense of security and a 401K were enticing, I decided to remain a free agent. I, too, have chosen a life of freedom and uncertainty.
My coaching business is nearly a year old. People pay to work with me and they are seeing results, but sometimes I feel unqualified, like when I read your letter. I thought back to the first day of class when our instructor, Pamela, told us our clients don’t expect us to be perfect because the best coaches are in process, too. We’re in this together, Mid-Life Freelancer. I also sometimes look back and wonder, Did I choose the wrong life? And I digress from there: Why did I spend years thinking the future would never arrive? Why the hell was I not more involved with managing finances in my marriage and business? I wish I wasn’t starting over at this age. But it’s a moot point now, because there’s no changing the past.
We’re all tempted to play the What if? game from time to time. In Cory Taylor’s beautifully heart-wrenching book, Dying: A Memoir, which she penned while facing terminal brain cancer, she explains why reverie is unhelpful:
“The problem with reverie is that you always assume you know how the unlived life turns out. And it is always a better version of the life you’ve actually lived. The other life is more significant and more purposeful. It is impossibly free of setbacks and mishaps. This split between the dream and reality can be the cause of intense dissatisfaction at times. But I am no longer plagued by restlessness. Now I see the life I’ve lived as the only life, a singularity, saturated with its own oneness.”
You don’t know how the unlived life plays out because you will never live it. But you also don’t know how the future plays out because you haven’t lived it yet. You could remain in debt and retire destitute, but you could also make a living, pay off your debt, save money and invest, and experience a retirement rich in a multitude of ways that goes beyond money.
This week I began reading The Subtle Art of Not Giving A F*ck by Mark Manson. He challenges readers to think about the metrics by which they evaluate their lives. Financial success is one metric, but it is only one. Last night I met up with two financially successful friends at a bar on Bowery. By the time I arrived stone-cold sober, they were more than a few drinks in and reminiscing about the “good old days” when work felt more satisfying and their colleagues were more deeply engaged in the process.
Years ago, they had dreamt of being where they are now, but the reality isn’t as fulfilling as they thought it would be. I view my friends as successful—they make substantial salaries, are awarded in their field, speak around the world, and are respected by colleagues. But they longed for earlier years, which were full of struggle but somehow felt more meaningful. In the future, you might look back and feel differently about this period as Mark Manson suggests in his book:
“As Freud once said, ‘One day, in retrospect, the years of struggle will strike you as the most beautiful.’ This is why these values—pleasure, material success, being right, staying positive—are poor ideals for a person’s life. Some of the greatest moments of one’s life are not pleasant, not successful, not known, and not positive.”
So here we are. We’ve cracked ourselves wide open with the weight of existential questions. Now, let’s get practical and tactical. It is hard to be in debt. It is hard to not have enough income to pay your bills. It is hard to lose and grieve and question your entire path. No, you can’t control everything that happens to you. Some things were your choice and some weren’t. But you do get to decide how to respond as you move forward.
If you play your life backwards, what do you want it to look like? You mentioned a few things: You want to be debt-free. You want to financially sustain yourself with your work and be able to pay your bills. You want to mentor others. You want to do your creative work. And you want to enjoy life. I would ask you to consider whether or not you could do some of those things now, regardless of your financial situation. What can you do with the resources you already have?
Now let’s talk about money as that seems to be the crux of this crisis. I am still figuring this out, too, but I’ve come across a few resources in my own journey that might be helpful for you. First, my friend Sara says, “You’re going to have to do certain things to make money and certain things to fulfill yourself creatively and they’re not always the same thing.” What are all of the ways you could make money right now? List them. What are all of the things that fulfill you creatively? List them. Where do the two overlap? Start there.
Today I listened to this interview with Sharon Salzberg on WSJ Secrets of Wealthy Women podcast. At the end, she asks listeners to picture themselves in a room filled with piles of money. Picture that—tons of crisp, inked paper in your hands. What would you do with it? Buy a house, pay off debt, take a road trip across the country, donate it to charity? Meditate on how your answers reveal what you really want. Perhaps a house represents security, paying off debt gives you the freedom to make personal projects, a road trip offers new experiences, and donating means being part of something bigger than yourself. Are there ways to have the things you want independent of money?
When you ask, Did I choose the wrong life?, what I really hear you asking is, Will I regret this path? In college I trained as a social worker and did a year-long internship with patients who were in palliative care with terminal diagnoses. Oh, the stories they told. Whether they were full of contentment or regret had little to do with money, material items, or success—it had to do with the way they spent their time, the quality of their relationships, and how they had chosen, or not chosen, to pursue what they really wanted.
I know I haven’t fully answered your question, but I don’t have an answer. I am still living into it, as are you. Money is necessary. We need a certain amount to live, but having unlimited amounts of money does not guarantee success, happiness, or the ability to look back at our lives without regret. I’ve left resources in the postscript so you can roll up your sleeves and get to work, but as you do, consider the ways your life may already be overflowing with richness.
To being debt-free and regret-free,
P.S. Here are some additional money-related resources to check out. A client recommended the Financial Gym, which works with you to make a financial plan based on your goals. Ladies Get Paid is an awesome organization with events in cities across the US to help women get paid what they’re worth (I know you’re a woman because you revealed that in your email, even though your identity is anonymous). I use the budgeting app, EveryDollar, because it helps me plan for every cent I bring in and it’s easy to use (even though I don’t agree with everything Dave Ramsey preaches). And, finally, here’s a list of podcasts all about money.
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Asking Not Asking is a bi-monthly column written by Tina Essmaker, a New York City-based coach, speaker, and writer who helps others live into their possibility. To be considered for the column, send an email to firstname.lastname@example.org with a short note about where you're at and where you want to be, and make sure to include the following:
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