NOTE: This essay originally appeared on my Medium page in 2019. Between an unexpected U.S. trip and my son starting school this week, I’ve been a bit behind on writing. I don’t intend to make a habit of recycling content, but I wanted to stay consistent with my three-times-a-week publishing schedule of content. Plus, I don’t think many people saw this post as it first appeared :).
In 2015, I was on a Metro train traveling through a tunnel in Washington D.C. I had just finished an interview for a public radio station to promote my (slowly) developing career as a singer/songwriter, and I was headed to the airport to catch a flight to Chicago to perform at a small local college.
My phone rang.
I picked up to hear the voice of my my fiancé sobbing into the phone. She was in agony. Through her tears, I was able to gather that she had been struck with an overwhelming pain in her stomach that left her unable to walk or even move.
Then the call was dropped. I tried calling back, but I was deep underground in a Metro tunnel with no signal. By the time I got off at the next station, rushed to the surface, and called her back, her misery hadn’t subsided.
Fortunately, she had been staying with some of my family while I was traveling, and they were able to take her to a hospital where she learned an ovarian cyst had burst inside her — incredibly painful, but in her case not life-threatening or dangerous.
I found out all of this via texts while on the other side of the country, in the midst of a weeks-long string of travel from venue to venue. It was then, sitting on the hard plastic seat of the Metro, that I began a process that would change the course of my life.
I started to give up on my career.
Since this event and the period that followed, which saw me leave my label, move out of LA, and begin a career as a freelance writer, I’ve spent a lot of time thinking about failure.
Why? Because I am one, in the purest sense of the world. I failed. I had a goal to become a successful singer-songwriter, a goal that began when I was 12 years old, and I abandoned that goal.
But what surprised me most about giving up on a dream I’d had for years was how profoundly painless it actually was.
Make no mistake: there was a great deal of pacing and sleepless nights as I tried to figure out how to support myself and my future family with no college degree and no professional experience outside of music.
But all of the emotions I expected to accompany the transition — the regret, the feelings of worthlessness, the guilt of facing everyone who had believed in me (and the shame in facing those who hadn’t) — they never came. I felt shockingly at ease regarding my past career and my decision to leave it. This was very confusing to me.
I remember thinking, Shouldn’t this suck more?
It wasn’t until sometime later that the reason for my sense of peace became clear. Those dreams no longer belonged to me. Like all dreams, my dreams were based on an assumption — that whatever I achieved in the end would make all of the struggle along the way worthwhile.
But as I began building the dream, I gathered more data surrounding that assumption. I discovered the parts I thought I’d enjoy but didn’t, like constant travel and performing live night after night. My personal circumstances changed as I met a woman I wanted to marry and with whom I hoped to raise a family. I realized I loved writing far more than everything else that surrounded it as a performing artist.
Based on the new data I had gathered, I changed my dream. I adapted it to what I’d learned about myself and my goals.
I didn’t have a name for this concept until years later, when I was reading a book about entrepreneurship and how to develop successful products. In business, they call what I experienced apivot.
How to Live Your Life Like a Startup
Most new startups follow what’s known as the ‘lean’ or ‘agile’ approach to business. Using this strategy, businesses begin with an assumption that can usually be summed up this way — “Customers will pay X amount of money for a product that solves Y by doing Z.”
Put simply, they believe that they’ve conceived of a product or service that people want.
So, what do they do? They build the product, or at least a version of it, and fill it with the features they think matter most to their target users. Then, they get that product into the hands of as many of those users as possible.
If they’re really, really lucky, their users will say (or show in their behavior), “We really like this product. But we would like it better if you got rid of features A and B and added features C and D.”
Then, the company will immediately start to work on a new version of the product, implementing what they’ve learned and creating the next iteration.
But far more common than that scenario is an outcome where users say, “This product you spent all of this time imagining, designing, building, and releasing… we don’t like it at all. It doesn’t fulfill any of our wants or needs, and it’s definitely not worth the price. It might have met our needs a while ago, but things have changed now.”
In this moment, a company must decide whether to persevere or pivot. They must decide whether they believe in their product enough to continue marketing it as it is, making minor refinements to its core value, or whether they need to take a hard look at what they’ve made and go back to the drawing board with the new knowledge and data they’ve obtained.
The courses of our lives aren’t built on whether we succeed or fail. They’re built on whether we decide to pivot or persevere, and we need to make those decisions way more often than we think. Because the happiness of the person who buys our dream — us — depends on how well our evolving needs are met by the person who builds that dream — also us.
When to Pivot and When to Persevere
Many of us may be on board with the idea of making personal pivots or persevering, but how do we know when the time is right to do one or the other?
First, we have to become more comfortable asking ourselves tough questions about our current path and accepting the answers.When we find ourselves on a trajectory, it can be tempting to avoid considering whether it’s the one we really want to follow. But like startups developing new products, we can’t be precious about our dreams. We have to test them, apply pressure to them, probe them. Is this still what I want? Is the perfect version of my destination worth the cost to get there? Am I the same person who was once willing to give up X for this dream?
That process can be scary. But if your dreams hold up to this personal pressure, you’ll benefit from the renewed confidence that you’re on the right path. If they don’t, you’ll have gathered enough evidence to support yourself as you begin to make changes.
Next, we have to acknowledge and understand our motivations for following a given path. Wanting to be a musician when I was 12 years old is no more valid a motivation today than wanting to be a veterinarian when I was five. Ask yourself whether the You of todaystill wants what you used to want. If not, why are you continuing? Are you reluctant to declare everything you’ve done so far a waste? Are you staying on your current path because you told people it was what you were going to do? Are you afraid of embarrassment or shame?
Some good news — the people in our lives care either too much or too little about us for our life choices to affect their feelings towards us. The ones who love you will love you whether you’re an Oscar-winning actor or a plumbing contractor, and the ones who don’t love you don’t think about you enough to care whatyou do.
If your reasons for continuing in your current path are practical — concerns about how to make a living otherwise, for example — they shouldn’t be discounted. Like a startup developing a product, you should assess all of the risk factors at play before making a decision. There’s nothing dishonorable about deciding that a certain direction might hold great rewards but isn’t worth the personal risk. No one can make that decision but you.
Changing How We Talk About Failure
As a culture, we need to remove shame from conversations about giving up. Even the most positive interpretations of personal and professional failures take the stance that “Sure, it’s a setback, but…”
But failure as we define it isn’t always a setback at all. It’s a pivot. A reassessment. A decision based on new knowledge and data designed to increase our chance at lasting joy and lifelong fulfillment.
And all that time we spent following a path only to ultimately abandon it? It’s never wasted. My time in entertainment led me to London, where I met my wife. Learning to compress complex ideas into three-minute songs taught me to communicate efficiently, a skill that’s been an enormous benefit to my writing career. I learned about who I am, what excites me, what bores me, what’s personally worth sacrificing and what is not.
To be clear, I’m not an advocate for abandoning career goals in the pursuit of a family. I’m an advocate for abandoning the goals of Past You to pursue the goals of Present You. You might find that those goals are one and the same, but you owe it to yourself to find out. It’s not always comfortable and is almost always inconvenient, but it’s always worth it.
Give up on your dreams. You owe it to your new dreams.
AGREED! I feel SEEN!