“I should have been promoted to VP like the rest of my MBA class,” a man in an outdated suit lamented. “Had I not moved cities for my wife and took a lesser post.”

“And I should have made Partner by now,” said the woman to his right, head hanging low. “If only I had stuck with one firm.”

“I should have never bartended across Europe. Then I would have gotten a real job instead of trying this startup thing…3 times,” said a man in a t-shirt with an unheard of logo.

Career angst ricocheted off wine glasses at the “Should Have” soiree. We dined on plates of status anxiety and washed it down with fermented peer pressure. While our LinkedIn friends had risen up corporate ladders, we had gone sideways. We had treated life choices like vacation lovers, giving into the seduction of experience, but not always considering career path longevity.

Why did we feel so terrible about prioritizing life over a job?

The problem is that our culture places an over-importance on achievement as measured by title, income, and company name. We chain our self worth to our career instead of the experiences we’ve had or the people we’ve met.

Those that claim to win the achievement game structure a militaristic business plan for their life, tromping stoically past tempting detours with blinders on. We renegades get off track, swayed by love, family, creative pursuits, and adventures. When we compare ourselves to our more disciplined peers, we might feel like we are losing the game. But if we always compare ourselves to others, we will be eternally climbing, never happy with where we are. So what do we do?

We could all pick up a Self Help book. After all, it’s a $11B industry. They promise that if you read them cover to cover, you’ll be propelled up a ladder toward the stars. Help? No thanks. The encouragement to cling to a linear career is contributing to the demise of community, our understanding of the world, and our own personal development. We’re becoming a selfish. And boring.

Instead of reading “What Color is Your Parachute” and picking one hue, let’s view life in technicolor. If I were to write a ‘self help’ book I’d author one called “Space.” It would acknowledge the beautiful, delicious space between one career rung and the next when you don’t know if you are going to make it to the next step or fall through the abyss. Or perhaps you chuck the ladder all together, and dive off into the ocean to wonder at starfish with children. It’s in these moments that we find the space to discover what matters, meet others without agenda, and discover new possibilities. We should celebrate spontaneity and things that have nothing to do with progression but everything to do with getting lost…and found. Stop building a resume and start living life.

Stopping to embrace the world is risky. Society will plant seeds of doubt in your head:

“You may never be employable again.”

“You’ll disappoint your parents.”

“You’ll end up in one one of those homeless tents by the train station.”

However, if you can find the strength to shrug off the naysayers, you’ll find other people, work and lifestyles that support new definitions of achievement. Surround yourselves with them and their stories. As inspiration, a few are below.

1. Space to Find Answers

Nine years ago, my dear friend Alicia decided to ditch her stable career ladder to backpack around Europe for mental clarity. She had been trying to build a startup while working full time, felt stuck, and decided to find the answer through adventure travel. Over drinks in London, a good friend motivated her to turn a social shopping experience into a white label B2B for content monetization. She quit her lucrative job, moved to London, and became full-time penniless entrepreneur at age 30. Risk and dedication gave way to Skimlinks, a company with now $24M in funding and over 80 employees. True to its birth, Skimlinks’ culture has a ‘rumination’ theme that acknowledges answers come when you least expect it. Instead of forcing a conclusion, everyone is encouraged to seek space until creativity and viability dance into place.

2. Space to Reconnect

My other friend David also prioritized experience. After too many 12 hour days, he quit his fast paced advertising agency to become a surf instructor and AirBnB host in San Sebastian, Spain. I asked him if he missed having a ‘real career.’

“Are you kidding?!” he said. “I get to surf every morning, and see my two girls every afternoon when they get home from school. I may not make as much money, but I feel much richer.”

His path may not lead him to Silicon Valley valuations, but it will lead to more time with nature and family. Isn’t that the primary goal of monetary success anyway-to earn enough to afford his lifestyle?

3. Space to Be Ourselves

People often ask how I ended up at IDEO, a human centered design firm. I didn’t have a design background. Nor was I hired right out of an ivy league school. They were interested in two things I had done: 1- I quit a prestigious job to gain more ‘me time’ autonomy with freelance consulting. 2- Part of this “autonomy” led to a three month roadtrip across the United States to interview non traditional women about their life choices. IDEO found risk taking and an interest in others more valuable than any other accolade on my resume. And to me, a company that valued human connection was more important than a loftier title or higher salary someplace else.

Choices to value “space” over “achievement” are what add to our overall worth as human beings. Have you ever considered ditching your job for a season to be a ski bum, travel Vietnam by motorcycle, or spend time with your ill grandmother without ANY idea of what you’ll do when you return? This type of behavior not only makes you a much more interesting dinner party conversationalist, but also exercises your risk muscles. You’ll learn that you can jump off and land. The universe will align itself to catch you, the safety net often woven by the hands of friends and family. You’ll become a better entrepreneur, intrapreneur, and person.

Instead of measuring our self worth by title, income, and company logo, let’s measure it by the places we’ve seen, the people we’ve loved, and the conversations we’ve had. That’s a much better way to structure personal achievement than mere dollars or labels.

Before my Granny died I asked her what she was most grateful for in her life. It was never that she had achieved success in a male dominated industry, balanced a job and kids, or saved enough money to visit Egypt. It was that she had a large loving family and a huge network of friends that played Bridge with her every week, even when dementia ate the corners of her mind.

Perhaps the best way to define “Achievement” in life is by how happy and loved we are when we depart it. Until then, let’s at least enjoy our dinner party conversations a bit more.

In the end, it’s not the years in your life that count. It’s the life in your years. – Abraham Lincoln

***This post originally appeared on Medium.  Follow the conversation here. ***