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The Quarter-Life Breakthrough: Invent Your Own Path, Find Meaningful Work, and Build a Life That Matters by [Adam Smiley Poswolsky]

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The Quarter-Life Breakthrough: Invent Your Own Path, Find Meaningful Work, and Build a Life That Matters Kindle Edition

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Chapter 1

Start Jumping Lily Pads

"Not all those who wander are lost."


Taped above my desk is an article from the Onion with the headline "24-Year-Old Receives Sage Counsel from Venerable 27-Year-Old," and a picture of two twentysomethings in plaid shirts in deep existential conversation over pints of beer at a bar.

When I told my dad I was writing a career advice book, he looked at me like I was crazy and asked, "What qualifies you to be writing a book about careers? You've changed what you wanted to do with your life every other year since you were a kid."

My dad is absolutely right. I've never been able to focus on any one thing for very long, and I still have trouble answering the question "What do you want to be when you grow up?" At first, I wanted to be Big Bird, road-tripping around the country in Follow That Bird. Then I wanted to be Mister Rogers. Once, my family was staying at a hotel, and Fred Rogers was there having breakfast. I ran right up to him and exclaimed, "Excuse me, Mister Rogers, Mister Rogers! How did you get out of the TV?!"

When I was in fourth grade, I wanted to be a play-by-play announcer for the Olympics. In eighth grade, I wanted to be Adam Sandler. In high school, I wanted to be a sports writer. Then I went to a liberal arts college, which is to say I majored in film studies, studied abroad in Cuba, and took intro to dance senior year. Making career choices has proved difficult ever since.

After graduation, I could write a fifteen-page shot-by-shot analysis of David Lynch's Mulholland Drive and tell you the difference between cage-free, free-range, and pasture-raised eggs. But I realized that college had not prepared me for the job-finding process in the slightest. Since I had no idea which "career ladder" to climb, I moved to the city where all my friends were moving (Brooklyn), and got a job that matched my college major (film), which is what I thought I was supposed to do at the time.

In the ten years since graduation, I've had ten drastically different jobs, lived in six cities, and gone down four career paths. I've never once seen this elusive "career ladder" everyone talks about. But I do know that whoever invented the ladder has been freaking twentysomethings out for a long time.

Where do you get on the ladder? Is there one in each city in the world? If you hop off for a detour, do you have to start back from the bottom, or do you get to keep your place in line? Is there music along the way? Is it like Pandora-can I choose my station?

As insufferable as this ladder mind-set can be, twentysomethings are still unfailingly being told to maintain a linear career trajectory. Even my father, who was born in the 1950s, hasn't followed any sort of career path. He has worked in stage management and lighting design for off-off-Broadway shows, then for a rock 'n' roll theater start-up in London, dropped out of NYU's theater school, sailed across the Atlantic, joined Pink Floyd as a roadie doing lighting on their international tours, became disenchanted with life on the road and enrolled in architecture school, worked as an architect, raised kids, spent time in corporate real estate, got his MBA at the age of fifty-three, built dialysis clinics, and managed projects and workplace innovation for a large electronics company. Yet even he was skeptical when I told him I wasn't pursuing a "traditional" career path after college, and instead was headed to New York to freelance on film sets.

If you've struggled with picking a career path, or focusing on one interest or calling, then you're not alone. Only 27 percent of college graduates have a job related to their college major.

In high school and during college, I scooped ice cream at Ben & Jerry's, had a few stints as a barista, and among other things, worked at a garden shop, helping customers pick out shade perennials (pretending that I actually knew what a shade perennial was). To list all of my high school and college jobs would be overwhelming. Here's the eclectic array of jobs I've held since graduating from college.

My Wandering Journey

Age Job + Motivation

18 Student at Wesleyan University (Middletown, CT)

Make friends, protest George W. Bush, gain liberal arts education

22 Move back home with parents (Cambridge, MA)

Unemployed and broke

22 Freelance film location scout (Brooklyn, NY)

Live with best friends in Brooklyn, major in film, love movies

25 Film festival assistant (Buenos Aires, Argentina)

Live in Argentina, learn Spanish, travel

26 Obama 2008 campaign field organizer (Anderson, IN)

Join change movement, support gay marriage, keep John McCain from destroying the world

26 Waiter at Eatonville restaurant (Washington, DC)

Make money to pay rent, love food and people

27 Move back home with parents (Cambridge, MA)

Unemployed and broke

27 Special assistant at US Peace Corps (Washington, DC)

Believe in Peace Corps' mission to promote world peace and friendship

30 Freelance writer & Bold Academy director (San Francisco, CA)

Live in San Francisco, love to write, support social entrepreneurs

32 Author, speaker, and Hive Global Leaders Program facilitator (San Francisco, CA)

Empower millennials to have breakthroughs and find meaningful work

There are two mind-sets through which one could analyze my "career" up to this point. The first is what I'll call the career ladder mind-set, the one we've been taught to follow most of our lives. This mind-set tells us that the more AP classes we take, the better we do on our SATs, the better college we go to, the more money we make, the higher on the ladder we rise, the more successful we are.

Someone with this mind-set would look at my career and say, "This kid Smiley is a hot mess; he lived at his parents' house at the age of twenty-seven! He can't make up his mind. He won't stay in a job for more than two years. He'll never be successful because he's not on a specific career ladder. Think of where he could have been if he had spent the last eight years in film."

Although recent college graduates are often encouraged to adopt a career ladder mind-set, these career ladders have several essential flaws:

Career ladders limit new opportunities, experimentation, and risk taking. What happens if an amazing opportunity presents itself-say, to join the 2008 Obama campaign-and I want to get off the ladder, but I've already spent two years on a different career? Ladders encourage people to avoid new challenges in exchange for safety and "moving up." Avoiding these risks may mean avoiding the very opportunities that provide us the greatest satisfaction in life. If there isn't only one answer, there probably isn't one "top of the ladder," either.

Career ladders define success on someone else's terms. Career ladders lead to promotion potential and higher salary. The theory is, "Pay your dues early, and you'll reap the benefits later." I'm not a huge fan of delayed gratification in general-not many millennials are-but it's especially annoying when I don't even get to define what my gratification is or what success means to me. What happens if I'm not in it for a fancy job title or a big salary? What happens if success for me is not my retirement package at sixty-five, but one person realizing their life potential from a book I write?

Career ladders make me stress about the future, which inhibits me from taking action now. When I was thinking about leaving my job at the Peace Corps, one of the things I was interested in pursuing next was writing. Whenever I brought up the possibility of becoming a freelance writer, all I heard from people was, "Well, it's a hard career ladder to climb. You can't get a staff writing position at a major newspaper anymore. Newspapers don't even exist. The New Yorker receives one hundred thousand submissions an hour."

To some degree, the people warning me not to go into freelance writing at the age of twenty-eight were right: writing is extremely competitive, and it's the opposite of financially lucrative. But stressing about my future career as a writer and about where I'd end up ten or twenty years down the road nearly stopped me from even trying. I hadn't even written a blog post yet, and I was thinking about writing for The New Yorker. I was stressing about the future, instead of taking action now.

The best advice I got about starting a writing career was from my friend Ryan Goldberg, a freelance journalist who lives in Brooklyn and has numerous bylines in The New York Times. At the time we talked, Ryan was also refereeing dodgeball to supplement his income. He told me, "Smiley, if you want to be a writer, write. Start writing today."

Stop Climbing Ladders, Start Jumping Lily Pads

The other way of looking at my career is through what I'll call the lily pad career mind-set. My friend and career strategist Nathaniel Koloc sometimes describes careers as a series of lily pads, extending in all directions. Each lily pad is a job or opportunity that's available, and you can jump in any direction that makes sense for you, given your purpose (how you want to help the world). Nathaniel founded ReWork, a talent firm that places purpose-seeking professionals in social impact jobs, and then served as director of talent for Hillary Clinton's 2016 presidential campaign. He has made it his job to study how people build careers worth having.

Nathaniel says, "There is no clear way 'up' anymore-it's just a series of projects or jobs, one after another. You can move in any direction; the only question is how you're devising your strategy of where to move and where you can 'land,' i.e., what you're competitive for."

Leaping to another lily pad for a new job or opportunity doesn't mean you're going backward. There is no backward. You can't go backward if you're learning. The lily pad career mind-set argues that motivated people who want to align their work with their purpose should consider frequent small career jumps based on their changing purpose and interests. This is especially important in a difficult job market that requires job seekers to constantly evolve and develop new skills to remain competitive.

Which of the following scenarios inspires you to take action?

1. Spending ten to twenty years going in one specific direction, climbing a ladder until someone else tells you that you are "successful."

2. Spending ten to twenty years exploring multiple lily pads, learning and experimenting as you go, seeking fulfillment as defined by the unique contribution you want to make.

Leaping between lily pads means you're getting closer to wherever your roots, your interests, and your learning desires are pulling you. Motivated people who want to align their work with their purpose should embrace flexibility and experimentation when it comes to their careers. This doesn't mean that you have to quit your job every two years, but it does mean that you have to consistently check in to see if what you're working on excites you or is making a valuable contribution.

Instead of one ladder leading straight up, the lily pad career mind-set visualizes your career as a pond of lily pads, a series of interconnecting leaps you've made between different opportunities. What's holding everything together is the roots: what you care about and how you want to help the world. In my case, today my roots are driving me to inspire others through writing, speaking, and helping others to realize their full potential. Your roots may be driving you to do one thing now, but that thing may change in five years.

Your education doesn't stop when you graduate from college; in fact, a whole new aspect of it begins the day you enter the workforce. Rather than simply checking a box for your major at the age of twenty, when you barely know what your university has to offer (let alone what life has to offer), accept that you're going to be a lifelong learner. Instead of climbing a career ladder that might not be around in five or ten years, treat your career like a lifelong experiment. Every job, every experience, every place you travel, is a chance to learn something new about yourself, what interests you (and, importantly, what doesn't), what you're good at, and what type of impact you want to have on the world.

Our new economy is characterized by rapid technological innovation. How we communicate and how we work are constantly changing in an increasingly global job market. The US Department of Labor has noted that 65 percent of today's grade school kids will end up in jobs that haven't been invented yet. Whether they want to or not, fewer and fewer people are staying in one job for a long period of time. According to the Bureau of Labor Statistics, in 2014 the median job tenure for twenty- to twenty-four-year-olds was less than 1.5 years, for twenty-five- to thirty-four-year-olds it was only three years, and for all workers twenty-five and over it was 5.5 years. If the majority of millennials are staying in their jobs for less than three years, that means some will have four jobs by the age of thirty, and as many as fifteen to twenty jobs in their lifetime.

In an article about "generation flux" and how to succeed in this new business climate, Robert Safian, editor of Fast Company, argues that we need a mind-set that embraces instability and recalibrating careers. "Our institutions are out of date," he writes. "The long career is dead; any quest for solid rules is pointless, since we will be constantly rethinking them; you can't rely on an established business model or a corporate ladder to point your way; silos between industries are breaking down; anything settled is vulnerable."

Pay Attention When Your Purpose Changes

The story of my friend Ryan Allis teaches us that it's never too late to adopt a lily pad career mind-set. Ryan became an entrepreneur at the age of eleven when his family moved to Bradenton, Florida, where a large percentage of the neighbors were over the age of sixty-five. Ryan's Uncle Steve sent him one of his old Macintosh computers, and Ryan learned everything he could about the computer, played SimCity for hours, and read PC World cover to cover. He felt as ready as an eleven-year-old could ever be, so he created a flyer that said, "Need computer help? For $5 an hour, a responsible eleven-year-old will come to your house. Call Ryan." His parents even let him get his own landline number to advertise on the flyers, which he posted around the neighborhood, at the library, at the laundromat, at city hall, and in people's mailboxes.

Ryan's first call wasn't from a potential customer, it was from the local postmaster, who asked to speak to his parents. The postmaster general was upset at Ryan's mom for letting her son put flyers in mailboxes without paying for stamps. "That was the first important lesson I learned about entrepreneurship: sometimes you have to act first and ask permission later," recalls Ryan. "It's okay to push the boundaries a little bit."

A few weeks later, Ryan made his first sale. He rode his bike to help an older man named Jim with his computer for an hour. Jim paid him $10 (double his rate), and then told his buddies at the bingo hall about Ryan. Soon Ryan was receiving lots of calls from other senior citizens in the neighborhood, and he began showing them how to set up AOL and send pictures to their grandchildren. Ryan made $400 that summer before seventh grade, and by the end of high school he was making $1,000 a month as a freelance web designer.
--This text refers to the paperback edition.


"The Quarter-Life Breakthrough is chock full of smart, practical, relatable, and timely tips for hungry young meaning-makers of the world who are looking to make a bigger impact in others' lives."
-Jenny Blake, author of Life After College

"This book helps you create a life of meaning and purpose." 
-Christine Hassler, author of 20 Something, 20 Everything and 20 Something Manifesto 

"Smiley offers heaps of illustrations and mounds of inspiration for young people seeking to find a career with passion."
-MeiMei Fox, New York Times bestselling author of Bend, Not Break and Fortytude --This text refers to an out of print or unavailable edition of this title.

Product details

  • ASIN ‏ : ‎ B01BD1STPM
  • Publisher ‏ : ‎ TarcherPerigee (October 4, 2016)
  • Publication date ‏ : ‎ October 4, 2016
  • Language ‏ : ‎ English
  • File size ‏ : ‎ 1745 KB
  • Text-to-Speech ‏ : ‎ Enabled
  • Screen Reader ‏ : ‎ Supported
  • Enhanced typesetting ‏ : ‎ Enabled
  • X-Ray ‏ : ‎ Not Enabled
  • Word Wise ‏ : ‎ Enabled
  • Sticky notes ‏ : ‎ On Kindle Scribe
  • Print length ‏ : ‎ 220 pages
  • Customer Reviews:
    4.7 out of 5 stars 214 ratings

About the author

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ADAM SMILEY POSWOLSKY is a millennial workplace expert, internationally renowned keynote speaker, and author of three books: The Quarter-Life Breakthrough, The Breakthrough Speaker, and Friendship in the Age of Loneliness.

Smiley helps companies attract, retain, and empower the next generation, and he has inspired thousands of professionals to be more connected at work, through speaking at companies like Google, Apple, Facebook, Unilever, Deloitte, and Stanford University Graduate School of Business. Smiley’s TED talk on “the quarter-life crisis” has been viewed over 1.5 million times, and he has spoken in front of 50,000 people in 20 countries. Smiley has advised heads of state and foreign leaders about millennial talent, multigenerational engagement, and fostering belonging in the digital age.

Smiley’s work has been featured in The New Yorker, The New York Times, The Washington Post, Fast Company, CNN, and the World Economic Forum, among many other outlets. Smiley is a 13-time camp counselor at Camp Grounded: Summer Camp for Adults and advisory board member for Digital Detox.

In 2017, Smiley launched The Women, BIPOC and Inclusivity Speaker Initiative, a community that aims to increase the number of women and people of color speaking at conferences and companies, as well as ensure that women and other underrepresented speakers are paid competitively as compared to their colleagues. The group now has over 4,000 members.

Smiley is a proud graduate of Wesleyan University, and can usually be found dancing in San Francisco, California.



Instagram/Twitter: @whatsupsmiley

Customer reviews

4.7 out of 5 stars
4.7 out of 5
214 global ratings

Top reviews from the United States

Reviewed in the United States 🇺🇸 on November 28, 2022
Reviewed in the United States 🇺🇸 on August 9, 2017
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5.0 out of 5 stars An Insightful, Genuine, and Actionable Guide to Aligning WHO you are with WHAT you do
By JeremyJensen on August 9, 2017
The Quarter-Life Breakthrough is a refreshing manifesto for breaking the status quo, by finding work and building a life that matters to you.

I found this book to be very empowering. The dedication in the first few pages says it all:

“This book is for anyone who ever heard, ‘That’s not possible, you can’t do that, you’re not good enough, you don’t have the qualifications, you’re too young or too old, you don’t have the money or the connections, it’s too late,” and took a deep breath, listened to their heart, and went out and did it anyway.”

This really resonated with me right off the bat.

The book was also well-written, genuine, and most important – actionable. It includes dozens of exercises that help moving words on a page into tangible action. I highly recommend not skipping the exercises.

The book is broken into 3 parts:

Part One: Invent Your Own Path
Chapter 1: Start Jumping Lily Pads
Chapter 2: No Mo’ FOMO
Chapter 3: Embrace Fear

Part Two: Find Meaningful Work
Chapter 4: Define Meaningful Work
Chapter 5: Find Alignment
Chapter 6: The Infinite Paths to Meaningful Work
Chapter 7: How to Kick-Start Your Meaningful Job Search
Chapter 8: Is Graduate School Worth It

Part Three: Build A Life That Matters
Chapter 9: What to Do When Someone Tells You You’re Not Ready for Your Dreams
Chapter 10: Get Your Breakthrough Hustle On

Summarized below are a couple of key take-aways. Hopefully these observations are useful in giving you a taste of the material covered, but to get the full benefit you really should read the whole book.

• Social media and comparing yourself to others: “I don’t know much, but I do know that you won’t find the secret to overcoming your quarter-life crisis on Facebook or Instagram; you’ll just waste time and start to feel sorry for yourself. Instead, move beyond worrying what other people are doing, and start figuring out what you want. What is calling you? What mission are you drawn to? What goal is worthy of your time? Finding meaning is about looking within and listening to the voice inside.”
• Overcoming fear and listening to your voice, not the voice of others: “Fear is a sign. Rather than a sign of encouragement or motivation, fear all too often becomes a red light that puts the brakes on the very ideas, goals, and journeys that are right for us. Try shifting your perspective to view fear as a green light, and indicator that you’re moving in the right direction.
• Pursuing your dreams: “Ignore anyone who tells you not to pursue your dreams, and listen to anyone who says you need to hustle harder. Sure almost everything has been done before, but it hasn’t been done by you yet, and that’s all that matters.”
• Finding an accountability buddy: “Find someone who believes in you. When you find believers, you find accountability, and when you find accountability your dreams come true.”
• Dating yourself: “When you start dating yourself, your mind-set shifts. Rather than define your own self-worth based on whether someone else swipes right at your photo or whether someone else wants to go home with you, you determine your own self-worth based on how you’re spending your time. You can commit to personal projects, set aside time for self-reflection and self-care, and discover new career aspirations. Instead of simply going through the motions, you’re in the driver’s seat of your own life.”
• Public speaking and knowing your audience: “Never ever assume that your audience is ‘too young or too old’ or too anything. Never assume that your audience doesn’t understand what you are talking about. Chances are your audience knows more than you think, and they might even know more than you. Never speak down to your audience. Instead, engage them, ask them for feedback, and treat them like equals.”
• Inspire one person: “If you want to make an impact, all you need is one person. If one person shows up, that’s one person who has taken time out of their busy day to come to your event. That’s one life you can change. You don’t need to have a huge platform or a huge audience to be relevant. No one cares how many Twitter followers you have. The only thing that matters is whether you can empower your audience. You never know who’s in the room, and you never know whose life you’re going to touch. Always show up and perform as if the president were sitting in the front row.”

Enjoy the read. I hope you get as much out of the book as I did!
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5.0 out of 5 stars A practical and sensible guidance
Reviewed in the United Kingdom 🇬🇧 on April 9, 2018
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5.0 out of 5 stars Must read for self-development, finding purpose and meaning in your work!
Reviewed in the United Kingdom 🇬🇧 on May 27, 2018
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5.0 out of 5 stars stressed or anxious about the big decisions in your life this is the best thing you can do to help yourself
Reviewed in the United Kingdom 🇬🇧 on September 18, 2017
Sid Ahmed
5.0 out of 5 stars It’s one of best books I’ve purchased so far. Very insightful and changes your thinking.
Reviewed in the United Kingdom 🇬🇧 on December 31, 2018
Connel Valentine
5.0 out of 5 stars Read it twice!
Reviewed in Canada 🇨🇦 on November 26, 2016
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