The Art of Failing Your Way to Your Dream Life
Learn to Follow Your Desire All the Way to Fulfillment.
We have things we love to do. Are they the things we’ll love to do once we start doing them every day? We want to attract good things into our life, but we work within the limits of our finances, opportunities, and the prescribed roles others often put on us.
This is why pursuing your desire is so powerful.
On the road to fulfillment, we are faced with choice after choice and not all the choices are well-marked. People talk about listing goals, but get overwhelming fast, and you don’t connect with lists on an emotional level. Goals are only as effective as the processes we put in place to achieve them.
That’s why you need to tap into the primal and emotional level of what your desire can and will lead you to.
Start With Aspirational Goals
If the primary objective of pursuing desire is to feel good, you can’t feel burdened and stressed by the big ambitious goals you set for yourself. Think of goals as giving you a vision toward where you want to be, but don’t give yourself hard deadlines. Not yet. Be aspirational at first.
The idea is to get to clarity, something I didn’t have in my early 20s when I was earnestly searching for what I was supposed to do with my life. What you do want is direction. Having an idea of where you want to head gives you clarity, which gives you peace of mind.
First, feeling calmer makes you all the more likely to experience joy on a regular basis even when you grind to achieve your goals. Second, it feels good to take small, consistent steps toward your goal.
And when you start wearing down from time to time — as you inevitably will no matter how accurate your goals and how well-integrated your values — reach out to others. Your peers will encourage you, give you perspective, remind you why you are important and enough already.
But stick toward your signpost and you will change. Believe it. Feel it.
Follow Your Curiosity
Taking small steps toward a much larger goal helps you follow your curiosity, try things out, and fail fast. Not “fail fast” in the macho-minded, startup platitude rhetoric. But in the real world way. You are designing your life. Follow broad interests in specific ways. Try stuff out.
I conduct tests all the time. Ever since I left the house on my 18th birthday, I began to stumble upon self-discoveries. I had never cooked even once to my recollection at home. Cooking was just something Mom did.
But I was hungry a lot in college and the cafeteria wasn’t always open. Over the ensuing years, I found I could get by without a cafeteria by cooking, and save money. Over the years I got better and better at cooking. I enjoyed it. But so what? Did that mean it would be my desire to become a chef or start a restaurant? I set out to find out.
For brief periods, I worked in restaurants. I met people, learned from people in our communities, read books, watched documentaries about chefs. I learned as much as I could about the challenges, joys, and travails of owning a small business.
My experiences are not unusual. The point is there are many ways to funnel your learning when you know — and therefore even obliquely pursue — your curiosity about your desire. Opening a restaurant or becoming a chef is not for me.
A few years ago, I knew I liked all kinds of beer. I also like making things from scratch like fresh bread, homemade pasta, roasting my own coffee beans. So, under lots of instruction and encouragement from my brother who had already been brewing for years, I also started brewing my own beer. At first, I didn’t know why. I was curious and my brother could expedite my exploration.
Over time, through successes and failures, I got more and more serious. My brother and I started to make weekly batches, documenting the process with spreadsheets and videos, getting better and better equipment, trying different storage styles, different approaches to bottling and kegging.
In the process, we learned how ciders were relatively easy to make. We dreamed of what it would entail to own some small rural orchard and open our own cidery or brewery.
But for as fun as it was as a hobby, the idea of turning it into a lifestyle and a business began to feel daunting. It’s a high competition and low margin business. It takes hardcore, boots-on-the-ground work daily combined with incredibly precise scientific recipes with expensive equipment.
By the time I realized I didn’t want it to become a business, I then had to decide if it was worth the continued investment of time and energy and loads and loads of beer that we ended up mostly giving away.
It was a grand experiment, but one I was willing to walk away from with a minimum of investment to learn a lot and have some fun experiments for a couple of years along the way.
I will say that not having a heavy goal kept the process a lot more joyful. I had a vague goal of exploring whether or not I wanted to get into the brewing business while having a good time drinking the results and sharing along the way.
Goals like this keep your attention directed. You know how you are spending your Saturdays. You know where that little bit of extra money is going. You know what to order and when you need supplies.
Finding My Desire
This is about you finding your own desire, but you might want to know more than about my detours. From about the age of ten, I was interested in the possibility of being a writer. I was always fascinated by the experience of a few well-constructed lines having the power to move me on an emotional or intellectual level.
I dabbled with writing poems in high school, but the desire to write poems took years to fully discover and embrace. I took creative writing courses as an undergraduate and during seminary, but it wasn’t until after I’d graduated that I began an intentional discovery to read other poets.
I was casting about, trying to figure out what I really wanted to do next while paying the bills as a substitute teacher in Naperville, Illinois. I was taking blues guitar lessons, playing pick-up basketball with my roommates and their friends, and checking out books of poetry from the public library by the armload. I wrote almost daily.
I had always read fiction and nonfiction, but not much poetry until my early twenties. Yes, I’m an English major and did read a great deal of Shakespeare and the Romantics and such, but that’s not the same. When I began discovering contemporary poets and reading them with my full attention, my growth accelerated.
Poetry is a desire that is almost by definition not going to be a standalone profession, and yet it is also the kind of desire you can pursue all the days of your life. But I had to ask myself, was it going to be like playing guitar and recording a few tunes on my Tascam 4-track? How far was I willing and ready to take my pursuit?
I decided to see if I could specialize in it, become a professor, and make a living at it that way. I studied at Georgia State, started a literary magazine in Atlanta, published in all the literary journals that would take me, and published the poems of others. Eventually, I did become a professor.
For many, at the right institution, teaching the right material under the right conditions, that is as good as it gets. Desire meets identity meets vocation.
After ten years of teaching lots of poetry, fiction, nonfiction, and literature — but mostly freshman composition and research — I followed my desire out the door. My desire was to write, not teach reluctant students how to put a comma in front of a conjunction between two independent clauses.
But how to make a living at writing, and still keep it as my desire?
I tried literary novels; I tried running a nonprofit press; I tried editing; I dabbled in freelancing. Nothing was coming close to making ends meet, and I wasn’t particularly fulfilled with the labor either.
I kept asking myself: What would be fun and challenging and also meet the criteria of making money? If it wasn’t going to be poetry or novels or teaching, what was it?
One day, I stumbled upon my old collection of Choose-Your-Own-Adventures. I remember how much I loved them as a school kid. I did some Google searches, and couldn’t believe that there had never been a serious follow-up. There was no second generation of interactive fiction.
All the talent seemed to have gone to video game design, of which there was a growing trend of games offering multiple narratives through moral-based choices like The Walking Dead, Dishonored, Witcher 3, Fallout 4, and many others. I grew fascinated by the endless possibilities of choice-based fiction. I read book after book on game theory.
I had found my desire again.
We didn’t have much money to put to the new company, but we figured it didn’t matter. Our tenacity, and the sheer dynamism of the idea — the storytelling and illustrations — would stand out on their own. We published the first three without promotion or a strategy we could agree on.
The e-books became a nightmare to make. You had to learn to code to make sure the reader could land at the exact right spot after making a choice. The books didn’t sell, and I had seven others written and partially-illustrated when we ran out of money. It took the better part of a year to come to the painful realization that the project was doomed.
Halfway through that failure, I went from freelancing on parenting and technology to writing supply chain journalism for a freight-tech startup in town. My desire was lost. I was finally making a living as a writer, though, and there was some satisfaction in it.
It was exciting to work for a young, ambitious startup, and I stumbled into podcasting and even broadcasting as a host on SiriusXM. The subject matter wasn’t my passion, but I was learning. I was growing, and for a time that sustained me.
The startup experience lasted a little over two years before I realized I was burning out. I had learned a lot, even a lot I hadn’t expected to learn, but I had lost track of my desire. It was time to take the biggest leap of faith yet, to start the Big Self School with my wife, Shelley Prevost.
Keeping up with your desire keeps you alive. It keeps you busy. It leads you into things you might have to learn the hard way, and it leads you into things you didn’t know you needed — or wanted — to know.
It’s taken the better part of three decades, but I feel like I’ve arrived at a cross-section of strengths, desire, and experience all merging together. The work is only just beginning, but I think it’s safe to say, we’ve never been happier.
Aspirational goals impact your persistence. They prolong your effort, and they will supply you with more information than you would have had otherwise.
Keep trying things out. Every single part of what you do within finding your desire may not be what you want to do, but they might be a means to your end. The important part is that you succeed on your own terms.
No doubt, goals that are too open-ended go nowhere and usually just fade away. But isn’t that better than living less joyously under the oppression of rigid goals? Soldiering on to meet hardcore goals just to prove how tough and amazing you are becomes joyless.
Learn the art of when you’ve gone far enough to know you should abandon ship and when you’re quitting too soon.
You are not your goals. You are in charge of your life. You are in charge of your joy.