Encore: The Price Of Our Dreams

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The Sugars, along with fiction writer George Saunders, field letters from people who are chasing their creative dreams but frightened by the practical and financial risks that come with that pursuit.

This episode was originally released August 5th, 2017.

Dear Sugars,

I'm a 29 year old mother of five amazing souls. I started my "Mom journey" at sixteen. When I found out I was pregnant, I took myself out of high school and got my GED. I started beauty school at 17 and finished at 18. By 21, I had moved out of my parents house, had another baby, gotten married and bought a house. Life has been a beautiful chaos with my wonderful husband.

I stopped working at a salon before baby number five was born. My plan was to go back to work when she started school in two years but now, I want to go to college. To many, this question might seem like a no-brainer. They'd say, "Just go! It will be hard but you can do it." Can I? No one gets how hard five kids are. I don't have help from family in terms of childcare. If I go to college it will have to be evening classes. My husband works two jobs and goes to bed early since he's up at 2 am seven days a week with no days off. My going to college will mean he'll miss precious sleep time.

There's also the question of money: I just paid off my student loan from beauty school. And what if I don't have the endurance to finish? All that money for nothing. But the alternative is a minimum wage job that I'll be fighting tooth and nail to keep. I can't go back to a salon: the pay, plus the weekends and after hours are too difficult. The thought of going back makes me cry. What do I do? Do I make our lives hell for four or more years so I can feel like I've finally achieved something and add to my family's financial stability? Or do I continue treading water financially but keep this flow we've gotten used to? My marriage is great, but will it suffer if I go to college? Please, tell me what to do. I'm so confused with this life-changing decision.

Uneducated and Confused

Cheryl Strayed: Uneducated and Confused, I think that you should think about going. You know you don't want to go back to working in a salon and you deserve this moment to step into a pursuit that sparks your interest. You want a college degree, so go get one. Why not sign up for one or two online courses, maybe take one class at your local community college, get some college credits before you step in all the way? That will really be helpful for you in terms of keeping that sense of balance and harmony and flow in your family, and it will also get your family used to the idea of Mom being a college student.

Steve Almond: You write "I can finally feel like I've achieved something,” and I just want you to recognize that you have five kids, you've done this with a husband but without family support. You got yourself a GED. You bought a house. You built a marriage. I don't think you're recognizing how much you've already achieved. And you're now saying to yourself “I want to get an education, I want to do something more.” In a short term way, it's going to mean you’re not around as much for the kids or your husband. It's going to mean that you're exhausted. Cheryl and I are not in the business of saying "go, chase your dreams like they're butterflies" that's not it. You have to recognize that you've achieved an incredible amount to build the life you have. That is what's going to provide you the power and the confidence to destabilize your life in the short term so you can ultimately have a bigger and more meaningful life.

Dear Sugars,

I'm an entrepreneur working two full time jobs to get my career off the ground. I'm hopeful that my long term success is inevitable and then I'll be able to quit my day jobs. However, it's a grind and I'm exhausted.

My partner, who I adore, graduated from one of the top drama conservatories in the country. He's a struggling actor. He has worked a restaurant job for years, but ever since we got together, he's been trying to find more work acting, or to find a steadier job. We both feel strongly that we're a great match, and we feel lucky to have found one another. We're in it for the long haul.

There's only one major problem that I foresee: How the f#%$ do people pay for children? How? Every time I do the math in my head, it hurts. Sugars, I love this man. I don't want to ask him to give up his dream. He's incredibly talented. I believe in him. But how do we have a thriving financial situation without his art suffering?

Broke Potential Mother


Steve: The thing you need to do most centrally with your partner is do a self inventory and talk about what your needs are and what your wants are. When you talk about needing a thriving financial situation, that might mean that you see financial security as this "we own our own home, we want to be able to go on vacation," whatever it is for you. Don't lie to yourself and don't squint at it. If you have started your business and you're an entrepreneur because you want to eventually have a thriving financial life, then be honest about it and ask your husband what would constitute success for him.

Cheryl: This is a hard question to answer, so I'm going to try to be really practical, BPM. You don't have to worry about how to pay for kids yet because you don't have kids yet. I want to try to tell you that you are not going to succeed as an entrepreneur unless you take some financial risk. Your partner is not going to succeed as an actor unless he takes some financial risk, and now is the time to do it.

George Saunders: There's a crossroads moment where you say to yourself, “okay, either I'm going to do the starving artist route and make these kids suffer or I'm going to suck it up and find in myself the potential to go into a job that I wouldn't have dreamed of taking a year ago.” And what I found was that actually that was great. To go in and say I have to give up my image of myself as this scrappy, cool young guy and put on a tie and go into this job. So maybe as a way of gaming myself I said "Ok, look, if you're a writer you should be able to find material even here, everywhere." Since these are human beings gathered together, this must be percolating into my artistic machinery, therefore it's not a waste.

Dear Sugars,

I'm a major people-pleaser, so much so that I feel as though I've lived the first twenty-five years of my life for everyone else and their expectations. I've been waking up to this over the last few years and trying to correct my life.

My career path has been shaped by fear and expectation. I took the safe route in school and got my CPA. I left journalism school to do this because my mother was going through bankruptcy at the time from her second divorce and I began to understand the idea of financial insecurity. I had a fortunate upbringing and was sheltered from financial struggles until that point. Seeing what my mom went through the year of her divorce, the same year I finalized my major, scared me. Along the way I convinced myself that accounting was the path I wanted.

Isn't it funny, how when we are so miserable the only way to see the silver lining is to trick ourselves? Although now, I am not tricking myself anymore. I am awake to how miserable I am at my job. It feels as though parts of myself have been obliterated. My creativity, my genuineness, my passion. I know my job is just a job, but I am a romantic when it comes to work and I want to put something out in the world that I truly believe in and that aligns with every fiber in my body. To do less than that feels like I am robbing myself of my core purpose.

The problem is, I feel like I've lost the ability to know what I really want to do. I started asking the question "What am I most curious about in life?" I found the answer was people and their stories and histories. That's all I know right now. I don't know if I should quit my job and go back to school. Should I tack on all this debt if I don't have a vision of what I want to do afterwards? I don't know if I can stay in this job or industry much longer. I feel like I'm losing parts of myself.

My question is how do I get one step closer to what's next? Do I quit my mediocre job with benefits to work as a barista and figure it out? Do I stay in this job and hope that I can unravel what's next even though this job is depleting necessary resources? Do I find a way to care less about work?

Career Purgatory

George: It's wonderful that you have that idea, now make it real. This resonates with me because I was in this phase for 3 or 4 years. I was so afraid to start writing because I thought if I started and was no good at it, that would be the end of the dream. I would just do anything I could to justify not actually sitting down and writing. When you're working full time it's so hard to get even a bad book finished, but if you're really serious about this, keep your day job and do it at night. See how it goes.

Cheryl: I relate to that first sentence "I'm a major people-pleaser" and many people are bound up in that. Some people, like you, Career Purgatory, make career choices based on this societal idea of what is success or what is a real job. I would say: begin writing and begin working on undoing some of those things that have led you down the wrong path.

George: I love this idea that we take these traits and we can turn them a bit and make them advantages. So in this letter, the people-pleaser idea has been a disadvantage, but I would say as a major people-pleaser myself, if you turn that just a bit, that's how you write. I want to please people so instead of pleasing people by my job choice or performance, I want to please them with this literary performance that I'm going to do.

Cheryl: Career Purgatory, I want you to sign up for a class or take your vacation and go sign up for a workshop in some beautiful place with some writer who's a great teacher, and I promise that stepping into creative life will change your life.

Steve: The fact that you're a CPA is awesome. In any creative work, it's not the quality of the life that matters. It's the quality of the attention that's paid to that life.

George: The path that lies between you and the book you dreamed of is actually not a different day to day life except the addition of some writing time. The magic that's going to make you published and beloved is yet to be found. When I was working a day job and writing my first book, I noticed that you can get a lot done in 15 minutes. In some ways, writing at work or writing when you're tired has a way of focusing your mind. I like to gently say to anybody who wants to be an artist, it doesn't always work. Your worth as a human being is not tied to your productivity as an artist, those are wildly divergent things. The pure artistic path is the one that's not too tied to the outcome but is tied to the transformation that happens.


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