Why you need to build the wrong company, date the wrong person, and take the wrong job.

We suck at knowing what we want. 
If you ask most people what they really want out of life, the answer is going to be shaped far more by their perception of what they should want than the reality of their interests and desires.

We want what we’re trained and conditioned to want. For some people, that’s been two cars, two kids and a picket fence. For others, it’s a career full of accolades and attention. Our parents program these wants into us, unconsciously, and so do our friends, the media we consume, and our surroundings.

If you’re told that you want to do X, Y and Z your whole life, and never given the space to consider whether you actually wanted to do A, B and C — your path will seem to make sense.

You think you know the kind of company you want to start, the kind of person you want to fuck, date and marry, and the kind of job that will make you happy and lend your life a sense of purpose. You dive into these passions and pursuits with abandon, believing that the only way to know if it works is to give your all, to give everything, to give without reserve.

But how often are we wrong? How often are our careers littered with jobs that we hated after just one week, and felt trapped into? How often do we get deep into a relationship with someone — who might be an entirely decent person — but who isn’t the one we want to grow even a minute older with?

How often do we devote our most precious and guarded resources to companies, ideas and products that won’t, don’t or can’t work, only to realise in hindsight that the true issue at the heart of it was that we weren’t the right fit in the first place?

Psychologist William Berry talks about the trust bias that centres on ourselves.

“At this point, I imagine a collective sigh, and thoughts along the lines of, “other people may not know what they want, but I do.” That is exactly my point. We all believe that. Just like most of us believe we are better than average (a statistical impossibility). The mind is designed to trust itself, but psychology time and time again proves it is unworthy of that reputation.”

We need to actively find what we don’t want, to uncover what we want.

David Cain, the author of Raptitude, says that knowing yourself means knowing your wants as much as your needs — and it can be a life’s work.

“I am convinced that how happy a person becomes in life depends on how much time they spend learning what they want. Just to know what makes you glow inside is the work of a lifetime. Your real, heartfelt wants accumulate over the years, as you stumble into new experiences that electrify you.”

The shortcut here is to just keep fucking up. Repeatedly. Keep getting it wrong, keep failing the test, and keep making the wrong choice. Because every time you do so, you are unlocking a new piece of data that can help you to understand what you don’t want, and by comparison, what you do.

It can become a process of elimination. The more you know about what you’ve tried, what works and what doesn’t, the more you can fill in the empty spaces. The closer you can get to knowing the right path.

Finding out the truth about who we are is what guides us. Finding out the truth depends on learning what doesn’t work.

This is why I think making definitive choices in our teens is a harmful practice.

We raise kids to believe that their entire lives are completely dependent on the decisions they make in their late teens; how well they do in their high school classes, the grades they make that unlock particular academic or vocational career paths, the people they choose as partners. We make them believe that they need to make every decision, and commit to it, and get it right.

When we look at the research about the stress levels in high school leavers, we’re seeing heightened stress and anxiety that should scare the hell out of anyone concerned for the wellbeing of entire generations.

From a study by the UNSW School of Education:

A survey of Year 12 students from a range of schools in Sydney did not paint a happy picture of life for the students. Of the 722 students surveyed, 42% registered high-level anxiety symptoms, high enough to be of clinical concern. This proportion is nearly double the population norm and larger than earlier studies.

Of the total survey group, 16% of students reported extremely severe levels of anxiety, while 37% registered above-average levels of stress. Stress, anxiety and pressure levels were highest amongst girls, and higher still in gifted girls

The problem is that we aren’t allowing these kids to have the freedom and space they need to try a dozen things, fuck up and burn it all down when they need to. If you’ll forgive a Robert Frost reference, when two paths converge in a wood, we tell them that picking the wrong one is the end of the damn world.

They don’t have the data to choose the path that’s right for them, because they aren’t allowed to find out which paths are wrong. And that’s a tragedy. It’s a way to produce people who are dissatisfied with their lives and their work, people who lack a sense of meaning.

My own experiences have taught me that failure is not only inevitable — it’s vital.

I have walked down a dozen different paths.

I have written for music blogs and reviewed live shows, interviewing rock stars like Simple Plan and hanging out at shows with The Prodigy. I have flipped burgers and made coffees, had a record deal and produced for a multi-platinum album. I’ve been engaged and had my heart broken. I’ve been an alcoholic and I’ve recovered. Today, I’m an openly transgender writer, author, founder and investor. And I don’t regret a single moment. I don’t regret a single choice. I don’t regret any of it because — I’m here.

And my experiences are not unique. Many of the people we look up to as sources of inspiration have found their direction only through a process of trial, error and elimination. Often publicly, loudly and unashamedly.

Reshma Saujani, founder and CEO of Girls Who Code, had a path without a clear linear plan. Speaking to The Atlantic, she talks about working the wrong job, following the wrong career path, and even failing in a political bid.

“I [worked] at a law firm and then in finance, at jobs that I hated that paid enough to pay off my loans and to help my parents with their mortgage. I was seriously depressed and miserable because I was not giving back to the world. The money wasn’t making me happy, and I felt more and more beholden to it, more and more scared. And so I quit, and ran for Congress. I lost that race, but I put so much personal savings into my race. I hadn’t had a paycheck in eight months. I was broke. But I wasn’t going back. No longer will I work in a job that I hate for a paycheck.”

If leading creatives, founders, writers and makers can fuck up, learn and grow — there’s no reason the rest of us can’t follow suit.

There is room to do everything wrong the first, second and third time.

Nobody is going to get it all right, and even if they did — it wouldn’t make them happy.

I don’t think there is anything with having a past full of mistakes, as long as you’ve been able to learn from those mistakes with a bias for action.

If you courted, dated, married and divorced the wrong human being, that doesn’t chalk up to a point against you on the big scoreboard; it counts as a search filter, giving you more knowledge and insight into what you want — provided you actually listen.

Joan Westenberg is an award winning Australian contemporary writer, angel investor, communicator and creative director. She is the founder of branding and PR firm Studio Self. Her approach to messaging, communication and semiotics has built her reputation as a writer, and she has been named as one of the leading startup voices in Australia by SmartCompany.

Her writing has appeared in The SF Chronicle, Wired, The AFR, The Observer, ABC, Junkee, SBS, Crikey and over 40+ publications. Her regular work can be found on Pizza Party, a blog about creativity, culture and technology. Joan is the creator of Transgenderinclusion.com, an open-source workplace inclusion hack.