How to Fulfill Your Dreams When the Magic-Wand Fairy is Late

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The Sweet Spot

The “Dear Sugars” podcast is an advice program hosted by Steve Almond and Cheryl Strayed. The audio contains more letters; submissions are welcome at If you’re reading this on desktop, click the play button below to listen. Mobile readers can find “Dear Sugars” on the Podcasts app (iPhone and iPad) or Radio Public (Android and tablet).

Dear Sugars,

I’m stuck and I have no idea what to do. I’m 21 and I work as a waitress. I have no education past a high school diploma. I feel so trapped in my small town. I want my life to change. It’s like I can see it already playing out. I work seven days a week and still earn just enough to pay the bills. I want to go to school but have always had trouble in that area. I never had a chance to see the world. I can’t stand this routine.

I spend about twenty percent of my day picturing my life across the country. I know I’m going to get there one day, but it’s almost unbearable waiting because the money seems like it’s never going to be there. My question is how do I make the steps to get there? I’m so incredibly uninspired. I want to wake up and feel energy and love. I want to feel that I know I’m where I’m supposed to be. But I’m scared that I’ll be stuck waitressing forever.


Cheryl Strayed: You’ll only be stuck waitressing forever if you decide to be, Broke. Your life is up to you. You’re not trapped in anything but your own despair. You hold the key. Stop telling yourself you don’t have the power to open the door. Everything about the language you use in describing your circumstances tells me you’re not aware of that. You write: “I want my life to change” rather than “I’m going to change my life.” The former is a passive expression of a desire; the later is an active decision. You can’t do the things you hope to do until you believe you have the capacity to do them. So that’s where to begin: by having a word with the inner voices of doom in your head and telling them to hush up. I understand why you might have those voices in your head (as someone who grew up poor in a small town and worked as a waitress, I really do), but the story you’ve told yourself about being “stuck forever” isn’t true and it doesn’t serve you. It’s time to tell yourself a different story instead.

Steve Almond: One way to begin telling that new story is to focus on the sort of life you want to lead. What emerges from your letter is mostly a desire to get out of town. But an exit plan isn’t the same thing as a destination. I love that you spend a lot of time picturing your life across the country. It tells me you’re ambitious and imaginative. What I want to know is what you envision yourself doing over there. How exactly do you want to spend your precious time on this earth? This may seem like a grandiose question, given how hard you’re working just to pay the bills on time. But it’s really not. Your new life begins the moment you start focusing on what you want, not just what you want to escape.

CS: So let’s get practical. Make a list of the things you want to do. The three you’ve cited in your letter are: move to a different part of the country, work a different job, and get an education, so let’s start there. Beneath each item on your list, make another list composed of the steps you need to take to achieve that thing. To get a new job you have to apply for one, for example. Be as specific as you can be with each item on your list and then start doing them, one by one. Some steps may require money, but others won’t. Perhaps one item beneath “get an education” is to study for college entrance exams. To do that, you can check out books from your local library. Another might be “research schools and financial aid.” That can be done online. You don’t have to do everything at once. You need only do one thing at a time. But the point is you have to do them, Broke. Each thing you do will bring you closer to the things you seek.

SA: Taking one step at a time is vital, because our popular culture is lousy with fairy tales of overnight transformation: paupers who ascend to the penthouse in the space of one Hollywood montage. This is our designated mythos, as Americans: that all you need to claim your destiny is a little pluck and luck. But more than anything, what you need is patience and humility and self-forgiveness. If you don’t have these attributes, you’re going to get discouraged. And then you’re going to get stuck. Because real change is rarely quick, and even more rarely glamorous. It resides in the small steps Cheryl speaks of, in the daily work of converting anguish into action. Fate did not deal you a hand of privilege. You have very real obstacles to overcome — of class, gender, and opportunity. Most of all, Broke, you have to be able to outlast your doubt.

CS: One of the most valuable lessons of my life has been to understand that one truth does not cross out another, contradictory truth. We have the capacity to hold opposing truths in one hand. There is no question that it will be more difficult for you to travel, attend college, and find more compelling employment than it is for those who have more economic privilege than you, Broke. But it’s also true that you can do all of those things. Your situation is one I know intimately. I was in it. The way I got out of it was to decide I could and I would. The barriers were real. So was my determination to climb over them. You have that determination too — it’s what moved you to write to us. Keep moving.