Smiley’s New Website:

2 Mar
Bye bye Hello

My new website!

Dear Whatsupsmiley readers,

It’s been a minute (okay, a minute and a half) since I last wrote a blog post here. I’ve been busy speaking about The Quarter-Life Breakthrough and hard at work on my proposal for my second book.

Exciting news: I launched my new website! will be the place where I write new blog posts, share information about speaking events, and keep an updated list of resources that can help you get unstuck, find meaningful work, and change the world.

This means that I’ll no longer be using this site, I know, I know, it’s kind of like when Seinfeld went off the air in 1998 (I’m still recovering from that too). Don’t worry, I’m still going to keep blogging. Go to and you’ll never miss a new post or a helpful resource.

I would like to take this moment to express gratitude to those of you who have been reading this blog since I started it three years ago. When I wrote one of my first posts, “Just For Life (Why I Quit My Job),” in May 2012, I had no idea that three years later I’d still be writing (or getting paid to speak) about finding fulfillment in the workplace. There is indeed some magic when you begin something new. There is genius in not knowing what the fuck you are doing. There is boldness in putting yourself out there. There is power in starting. A blog can really be a platform for a dream. So for all of you who have read a post, liked a post, shared a post, and encouraged me to keep writing and keep going these past three years, thank you. You may not realize it, but you have changed my life.

When you have a moment, check out the new site: I think you’ll like it. 

Thank you for your readership, your support, and your inspiration.

The journey continues,


Smiley Poswolsky, Speaking

Come say hi:

5 Things I Learned at Camp Grounded

15 Jul


In June I spent three weeks working as a camp counselor at Camp Grounded, a summer camp for adults in the redwoods of northern California, where we don’t use digital technology, we don’t talk about work, and we call people by camp nicknames instead of their real names. As someone who spends a lot of time on his digital devices and a lot of time using social media for work, the experience was profound and I learned a lot more from watching 700 adults with names like Popcorn, Bubbles, Big Spoon, Shtetl Fabulous, Sea Monkey, and Ladybug, become their best selves, than I could have ever learned from checking my Facebook feed twenty times a day. Here are a few life lessons I learned at camp that I’m trying to incorporate back into my technology-prone daily life in San Francisco.

1. Take time

We’re always moving, we’re always going somewhere, we’re always doing something, we’re always busy. We’re busy being busy but we’re rarely busy just being. At camp I spent a lot of time taking time. I spent a lot of time doing well, nothing, and in turn, saw everything. The tall redwoods towering above me, swaying in the wind. The late afternoon sunlight pouring through the redwoods making my eyes squint and my heart expand. The luminous moon (Oh luminous moon!) smiling down from her throne. The birds chirping love songs to each other. The ice-cold river passing over my feet, leaving me invigorated. The ding a typewriter makes when you finish typing a line, as if to say, “FUCK YOU INNER-CRITIC! Keep writing you incredible warrior, keep writing!” The sound of the piano playing and the guitar being strummed and the beautiful voices singing. The taste of food when you’re considering every bite and how blessed you are to be eating it. The crackling of the fire giving you warmth.

Take time—especially in the moments when you are alone—to breathe. To look at the world around you instead of your phone. It’s these moments when you have nothing to do—when you’re waiting for the bus or waiting in line to buy a coffee—when time sort of stops and says, “Well, you’re alone now, this is kind of awkward, I guess you should check Instagram,”—that make up much of our lives. When you take time to take time you remember why you’re here.

2. Get weird first 

There are people in this life who always do what they are told and there are people who question what they are told and do whatever the fuck they want. I want to be around people who do whatever the fuck they want—who decide not to wear a shirt, who wear a tutu for underwear, who paint their face, who shave lines into their hair, who jump butt-naked into an ice cold frozen river in the morning, who wear onesies to breakfast (and to dinner), who scream when they feel like it, who blow bubbles in the morning, who throw chairs in the sky for no reason, who sing songs even though they don’t know a single word of the song—these people make me feel alive. They make me feel like I belong. When you get weird you inspire others to get weird too—and when everyone is weird, everyone is themselves—and when everyone is themselves, everyone is perfect.

3. Make eye contact

The default way of talking to someone is to look past them and scan the room for someone more interesting or more attractive. This is rude. It’s also unwise since each person we meet may share wisdom that inspires us or changes our perspective on life. When you make eye contact you are actually listening to someone—you are validating their reason for being and they in turn will value yours. When you look down at your phone when you meet someone, you are communicating that the Gmail notification you just received (alerting you that your Bank of America statement is now available online) is more important than a human being’s heart. Treat every person like they’re a beautiful person that has something precious to teach you—because they most definitely are.

4. Your job (however cool or shitty) does not define you

Society likes to box people by their name or ethnicity or where they live or what they do or how much money they make. A person is not a box to be checked off in an annual census. A person cannot be defined by labels or prejudices or guesses or judgements. At camp we don’t call people by their real names, we also don’t talk about what they do for work. So when you meet Uncle Freckles, you are not thinking “Oh, they work at Google, they must be like so and so,” or “They run a startup non-profit, they must be like so and so,” or “They’re unemployed and broke, they must be like so and so.” Starting a conversation with “What do you do?” is a good way to ensure the conversation will be as boring as every other conversation you normally have at happy hour. At camp we ask things like “What’s a fear you’ve overcome recently?” or “If I were to go traveling with you where would we go?” Beyond just asking questions, you have to listen and watch and play with and realize that getting to know someone has nothing to do with their job title.

Greatness is rarely found on a resume; greatness is experienced when we allow people to share their gifts. Gifts can be anything from the way someone hugs to the way they write a poem to the way they dance to the way they listen. Gifts let us see how infinite someone is, which makes us feel infinite too.

5. Validation is power

The role of a camp counselor—similar to that of a good teacher, coach, mentor or friend—is largely undervalued in our society. The role of a camp counselor is to validate their campers. To tell their camper: “you belong and you are awesome.” We don’t get told that enough as kids, and we certainly don’t get told that enough as adults. Rather, we get told things like, “You’re not smart enough, you need to get better at math, you need to dress differently, you need to lose weight, you need to stop being so weird, you need to stop playing, you need to stop making so much noise, you need to pay better attention, you need to buy more of what I’m selling, you need to change your life, you need to change your life NOW!”

The truth is people just don’t need to change as much as they need to be validated for who they really are. You can have a profound impact on the world simply by turning whatever environment you spend your days in—be it an office, a school, a business, or a camp in the woods—into a place where everyone feels validated. When we create this kind of community, people are empowered to fully express themselves and anything is possible.

A version of this post also appeared in Medium

-Smiley Poswolsky

Life Is A Typo

1 Jun

It was the day before the launch of my first book. It was a warm day in San Francisco—over 80 degrees—and even warmer in the East Bay. I had taken a 45-minute BART ride to Berkeley and rode my bike up the seemingly endless hill to the Haas Business School.

I was supposed to speak to an undergraduate class about millennials and meaningful work, and when I arrived, I was sweating balls. Two minutes later, I was told by the professor that there had been a mix-up with the schedule and I couldn’t speak.

I was pissed that I had wasted about an hour and a half each way on the day before my launch.

Then my sister called me and said, “Sorry, Adam, I just wanted to let you know I caught a typo in your book.”

I started freaking out since my launch was the next day and people were already buying the paperback on Amazon.

My sister said matter-of-factly, “Adam: nobody cares.”


She replied, “I mean, nobody cares about the typo. They just want to read your book. They’re not reading it to judge your grammar, they’re reading it because they want to know what you have to say. They’re reading it because they want to be inspired.”

I closed my eyes and took a deep breath. I knew she was right.

We get so caught up in our own heads about the smallest details. We become obsessed with perfection in our work. I sometimes get so obsessed I’ll stare at an email for 45 minutes, tweaking each sentence, bolding some words, italicizing others, making sure the tone is perfect.

But sometimes you just need to press send. If you spend a year on a project and it’s ready for the world to see, it’s time to get it out there, even if it’s not 100% perfect.

Press send. Ship it.

I’m not saying you should release something you haven’t worked hard on. Don’t ship something that’s crap. But if it’s a product that you’ve spent many months or years on; something that will make peoples’ lives better, then get it out there.

Nothing about writing is perfect. Nothing about self-publishing is even close to perfect. I could have spent months, shit, YEARS, getting my book to be just right, and you know what? Inevitably, someone somewhere would catch a typo. Inevitably, the printer will make the gray text box too dark. Inevitably, the formatting will look slightly different on each of the 18 Kindle-friendly devices people can read it on. Inevitably, when someone sets the font to 42-Comic Sans, the book will look weird. Inevitably, I’ll think of a word I wish I had used or the perfect anecdote, two months after the book is published.

Inevitably, your final product won’t be perfect. Inevitably, on the day before your launch, you’ll waste three hours of your day and get really sweaty and feel hopeless.

Making something is embracing its imperfection. If Apple can release a new iOS update every couple of months, then you can make a few revisions too.

Life is a typo. Press send anyway. Press it now.

A version of this post also appeared in Medium.

-Smiley Poswolsky

Stop Asking People ‘What’s Next?’

31 May

I recently returned from my first-ever book tour. True to my book, a guide for twentysomethings to figure out what to do with their lives, the tour was DIY to its core. Many events were planned as I was traveling, and instead of a publicist or a publisher, I relied on my community of friends for marketing. I traveled by Bolt Bus and spoke at the Temple where I got bar mitvah’d to my parents’ friends as they noshed on cinnamon babka, to law students chomping on free pizza as they crammed for finals, and to management consultants on a Friday after they had spent three days perfecting a PowerPoint in a hotel room in Louisville.

There are few things in life more gratifying than having someone read your work, and I cannot really explain in words what it’s like to be standing in front of a room and hear someone say, “So, in Chapter 1, you talk about jumping lily pads instead of climbing a career ladder— I really resonated with that idea.” You’re thinking to yourself: holy shit this person read my book. I don’t even know them and they read my book. Not only did they read it, but they’re quoting it. This is insane.

The most common question I got on my book tour was, “So, Smiley, now that the book is done, what’s next?” I’d usually respond, half-joking, but totally honestly, “Well, I’m not sure exactly—I need to read my own book.” This usually got a few laughs but what I really wanted to say when people asked me ‘what’s next?’ was, “WHAT’S NEXT? WHAT’S NEXT?! Dude, I just wrote a book! A fucking book! It took me an entire year! It came out like three weeks ago! Three weeks son! Does it look like I’m sitting around doing nothing? I’m still on my damn book tour. I’m giving a talk—to YOU! WHAT YOU SEE ME DOING IS WHAT’S NEXT! THIS IS WHAT’S NEXT!”

I know, I know—people don’t intend to pressure you when they ask ‘what’s next?’—they probably just want to know what your next book will be about or what your next business will be; what awesome thing you want to achieve and how they can help. But this question is dangerous. Instead of asking people ‘what’s next?’ we should be asking them, ‘what’s now?’ Otherwise, we ‘finish’ before we’re actually done. We move onto the next thing before we’ve made our mark in the first place. It may be more exciting for me to start thinking about what my next book is going to be about, but what I really should be spending my time on is marketing the book I just wrote.

I kept telling the soon-to-be college graduates I met on my book tour who were freaking out about what to do with their lives (with the disclaimer that they were receiving advice from a 30 year-old who lives with a five roommates in an apartment with a mouse problem, and is still figuring his own life out): don’t succumb to the pressure to always know what’s next. Your parents might be obsessed with what you’re doing next because that’s their job, but the people who create meaning in this world don’t know what they’re doing next because they are too busy doing something meaningful right now. Chances are, living in this moment, instead of thinking about the next one, will give you all the answers you need to get where you’re going.

A version of this post also appeared in Medium

-Smiley Poswolsky

10 Steps to Turn Your Quarter-Life Crisis Into a Breakthrough

15 Apr

The Quarter-Life Breakthrough Visual Workbook Featured on Slideshare

Feeling stuck? Over-dosing on FOMO (Fear of Missing Out)? Tired of climbing the career ladder? Interested in finding meaningful work but not sure how to start? Check out the brand new Quarter-Life Breakthrough Visual Workbook— featured today on the homepage of Slideshare! With practical and fun exercises taken straight from The Quarter-Life Breakthrough and illustrations by Whitney Flight, this workbook is for millennials who want to get paid for who they are and what they believe in. 


The Quarter-Life Breakthrough: Launch Day Highlights

9 Apr

QLB_launch day photo_Smiley Poswolsky

Yesterday was a very special day. Posts, tweets, texts, phone calls, and emails came pouring in from friends all around the world and from all parts of my life, dating back to elementary school. I truly could not be more grateful for your support. Launching a book is the hardest thing I’ve ever done, but all of you made it FUN.


The Quarter-Life Breakthrough had a strong showing opening day on Amazon: 

#1 on Amazon Kindle for Job Hunting/Internships

#3 on Amazon Kindle for Job Hunting

#5 on Amazon Books for Job Hunting

Top 3,000 of Amazon Books overall, and was in the top 7,300 on Amazon Kindle. 

QLB_am_#1 internships

QLB_am 1-3-5

Amazon category rankings’ significance are definitely up for debate, and fluctuate by the hour (this morning the book is at #1, #4, and #8 in those categories, and dropped down to 11,000 in Kindle) and a lot of industry blogs seem to say the category rankings don’t matter (unless it’s the Amazon Top 100 or the New York Times/Wall St. Journal list– and even those lists are sometimes rigged by marketing companies who sell bulk pre-orders to corporate clients), but for a self-published author with a minuscule marketing budget who lives in a tiny bedroom in a apartment with five roommates and a mouse problem, this is definitely a reason to celebrate. I feel very proud of the Quarter-Life Breakthrough movement we’re building together, and I enjoyed a delicious pint of beer last night. Check out what else is happening during book launch week:


RSVP for a free Virtual Conference today (Wednesday, April 9, at 6pm Pacific) to learn how to have your own breakthrough.


Remember: if you buy the book during launch week, I’ll give you a FREE copy of The Quarter-Life Breakthrough Visual Workbook, featuring fun exercises from the book (see below for a sneak peak!). Designed by visual storyteller Whitney Flight, this colorful exercise book is the perfect companion to reading The Quarter-Life Breakthrough.

To get your FREE Workbook: Email me your Amazon receipt (or a screenshot of it) before Saturday, April 12 (, subject line: WORKBOOK). You can buy either the Paperback or Kindle; the Workbook is yours either way!

QLB Workbook screenshot for launch_Smiley Poswolsky


1. SHARE this post with friends, family, co-workers who need to read The Quarter-Life Breakthrough

2. SPREAD the word on Facebook and Twitter. Join our Thunderclap (only takes 5 seconds!) which will automatically send a post for you during launch week.

SAMPLE TWEET: The #QuarterLife Breakthrough! A must-read book about #millennials following their dreams.
3. RSVP for a free Virtual Conference (WEDNESDAY, APRIL 9, at 6pm Pacific) to learn how to have your own breakthrough.

4. ATTEND speaking event or launch party near you. 

With gratitude,

-Smiley Poswolsky


Check out the Advance AcclaimPress, and Amazon Reviews

The Quarter-Life Breakthrough is LIVE!

8 Apr

A Guide for Millennials to Find Meaningful Work 

Now Available on Amazon 

Cover Kindle_The Quarter-Life Breakthrough_April 2014

Today is a day for dreamers. Today is day for hustlers.  

Today is a day two years (actually, more like 30 years) in the making. 

Today is launch day for The Quarter-Life BreakthroughThe Quarter-Life Breakthrough is an inspiring career guide for twentysomethings to get unstuck, pursue work that matters, and change the world. With practical exercises and helpful resources, this book is essential reading for anyone who wants to get paid for who they are and what they believe in. This is the book I wish I had during my own quarter-life crisis. 


Pre-ordered in 38 countries! Available in Paperback and Kindle.
Check out the Advance Acclaim, Press, and reviews on Amazon


Check out these great posts about the book that came out today:

Thought Catalog: 3 Cures For a Quarter-Life Crisis 

Under30CEO:  Most Important Lessons Learned From The Quarter-Life Breakthrough

75 to Go: Millennials: What Does it Mean to Find “Meaningful Work”?


If you buy the book during launch week, I’ll give you a FREE copy of The Quarter-Life Breakthrough Visual Workbook, featuring fun exercises from the book (see below for a sneak peak!). Designed by visual storyteller Whitney Flight, this colorful exercise book is the perfect companion to reading The Quarter-Life Breakthrough.

To get your FREE Workbook: Email me your Amazon receipt (or a screenshot of it) before Saturday, April 12 (, subject line: WORKBOOK). You can buy either the Paperback or Kindle; the Workbook is yours either way!

QLB Workbook screenshot for launch_Smiley Poswolsky

A sneak peak at The Quarter-Life Breakthrough Visual Workbook



1. SHARE this post with friends, family, co-workers who need to read The Quarter-Life Breakthrough

2. SPREAD the word on Facebook and Twitter. Join our Thunderclap (only takes 5 seconds!) which will automatically send a post for you during launch week.

SAMPLE TWEET: The #QuarterLife Breakthrough! A must-read book about #millennials following their dreams.
3. RSVP for a free Virtual Conference to learn how to have your own breakthrough.

4. ATTEND speaking event or launch party near you. 

This book would not have been possible without your support. I cannot express how grateful I am for all of your love and encouragement during this journey. Two years ago, I didn’t even have a blog and now I have a book, and together we’re building a community of millennials that refuse to settle.  

Thank you,

-Smiley Poswolsky

qlb bookshelf


This is a Community, Not a Book — How I’m Marketing The Quarter-Life Breakthrough

26 Feb

After nearly a year of hard work, I finally finished writing my first book. The book launches April 7  on Amazon, and I can’t wait to share it with you. All of you have already been so incredibly supportive of my Indiegogo campaign to raise funds for the book, and I cannot thank you enough. Together, we’ve started to build a community of young people who will support each other in pursuing work that matters.

The Quarter-Life Breakthrough shares the stories of many 20- and 30-somethings who are discovering how to work with purpose (and still pay their rent). I wrote the book I wish I had during my own quarter-life crisis. Two weeks ago, as I was freaking out and stressing about what I was going to do with my life now that the book was coming to an end, I had to force myself to sit down and read my own damn book.

Writing the book over the past year has been the hardest and most fulfilling experience of my life. On the one hand, l have spent many months not returning phone calls or going out with friends, instead passing my days and evenings locked up in the UCSF Library writing with a crew of med students studying for the Boards. On the other hand, I have dedicated my time toward something that will help young people figure out what they want and how they can make a difference in the world. Most importantly, I have tried to lay the foundation for what I hope becomes a community that inspires others to get unstuck, embrace fear, and find meaning in their lives.

Navigating the world of self-publishing sometimes feels more painful than trying to find a job right after college. Before I discuss my marketing plan, I want to emphasize how much I’ve learned from several easy-to-digest and free (or very affordable) resources about writing, publishing, and marketing a book. I’ve read each one about three times, and I currently have all these open on my computer. In fact, Charlie Hoehn’s brilliant post inspired me to write this.

3 essential books about publishing:

APE: Artist- Publisher- Entrepreneur – How to Publish a Book by Guy Kawasaki and Shawn Welch

Your First 1000 Copies by Tim Grahl

The Unconventional Guide to Publishing by David Fugate

3 essential blog posts about book marketing:

How I’m Marketing My Self-Published Book by Charlie Hoehn

How to Self-Publish a Bestseller by James Altucher

How to Write a Bestselling Book This Year – The Definitive Resource List and How-To Guide by Tim Ferriss

With the help of these resources, I’ve learned three essential lessons:

1)    Write a book because you have a story that needs to be told, not because you want to make money. This one should be obvious for anyone who writes for a living, but I spent the better part of the past 12 months making barely enough money to get by, working on a project that may not lead to much income. I did this because I knew others were facing the same questions I was, and that my story could help them.

Whenever someone asks me what will happen if I “fail” and don’t make the bestsellers list, I tell them two things: First, I definitely won’t make the bestsellers list since my book is not in bookstores (at least not yet), so yes, I already failed. I failed! Failure is cool! WOOT WOOT! Second, actual failure is impossible because I’ve already won. I wrote a book. I jumped through the creative vortex. The process of writing my book, running a crowdfunding campaign to build support for my book, and seeing people get excited about their breakthrough, has been worth every single moment of fear about how I’m going to make a living this year (that’s like 365 days worth of fear). Frankly, one reader telling me a few months back that seeing my book’s website inspired her to re-think what she wanted to do with her life, has already made this project worth it. Even if Amazon shuts down tomorrow and I can’t release my book, I’ll still be grateful. 

Screen Shot 2013-07-26 at 1.28.53 PM

I used crowdfunding to give myself an advance.

2)     Whether you self-publish or publish, you are going to do a shit-ton of work. I’ve been inspired by what James Altucher calls “Publishing 3.0” and Guy Kawasaki’s theory that a writer is an author, publisher, and entrepreneur. Your book will be as good as you make it, regardless of whether it’s being published by Random House or 20s & 30s Press (my publishing imprint). Because I decided to self-publish, I ran an Indiegogo campaign to sell pre-orders for The Quarter-Life Breakthrough, and raised $12,800 from 518 supporters in 38 countries around the world. Basically, in addition to demonstrating that a market (a community that spans 38 countries) exists for my book, I gave myself an advance that is probably more than I would have gotten from a publisher as a first-time non-famous author. Now I own all rights to the book, get to keep 70% of the royalties from sales (instead of give 80%+ to a publisher), and I have the ability to sell the rights to a publisher if I gain some traction. 

I used the money I raised from the Indiegogo campaign to pay for developmental and copy editing services, cover photography and professional book design, and printing and marketing costs. In addition to writing something of value and making it look professional (which took me about 11 months), now I need to manage my personal brand, my platform, and this community. After a year of getting more gray hair each day, my real work is just beginning. In the last week I have done everything from write copy for a video trailer to get print quotes to send out review copies to press. I’m essentially running a start-up venture. As Jay-Z puts it, “I’m not a businessman, I’m a businessman!”

3)    Being an author is not really about writing; it’s about connecting with your readers. Tim Grahl stresses the importance of creating a system where you continue to connect with your readers through your email list and your platform, where you can share interesting content and build community. A successful book requires successful community engagement.

In the interest of engaging this community, I’d like to share my marketing plan with all of you. First, sharing this will hold me accountable to the 1,456 thoughts currently running through my brain and help me learn from you what I’m doing right, what I’m missing, and what I’m screwing up. Second, this allows each of you to see where you can best contribute based on your unique talents and connections. Finally, I hope it serves as a resource for other authors marketing their books, or other creatives trying to engage millennials. This marketing plan (like my book itself) is a work in progress. I want to thank my dear friend Sydney Malawer, who helped me begin brainstorming many months ago. I welcome your collaboration, feedback, and suggestions in the comments or by email! 

Marketing Plan for The Quarter-Life Breakthrough

Launching on Amazon, April 7, 2014

Author. Publisher. Entrepreneur.

Author. Publisher. Entrepreneur.

Who is this book for? 20-somethings, 30-somethings, recent college grads, parents of millennials, career changers, any passionate about pursuing meaning and reaching their potential.

What do my readers want? From my interviews with 20-somethings, I’ve learned that most millennials are hungry for the complete opposite of the way the media portrays us. Despite being shackled by debt, recession, and the jobs crisis, millennials want meaning more than money. We want more stories of empathy and empowerment, inspiration and innovation, in a time when society is telling us our dreams are impossible.

Why does it matter? When people have a breakthrough they come alive, find meaning, reach their potential, and change the world. It was other young people that inspired me to have my breakthrough. You can’t have a breakthrough alone, you need help along the way; you need a community.

Marketing goal: To build a supportive community of 20- and 30- somethings who refuse to settle. This is a community, not a book. My goal is to engage this community and provide valuable resources that will inspire everyone to support each other in having breakthroughs.


1.    Email list

Thoughts: According to Your First 1000 Copies, email is the single most effective way to connect with readers and sell your book (25 times more effective than a Facebook post or a Tweet, which is fascinating to me).

Goal: Double number of email list subscribers by June, 2014.

Action Items:

  • add my blog followers, Indiegogo supporters, and additional Gmail contacts to new MailChimp email list (roughly 2,000 people)
  • add email sign-up forms to website and blog
  • engage readers with free content (free pdf of Manifesto, free pdf of preface/intro)
  • get partner organizations I feature in the book to email their subscribers with info about the book

2.    Amazon reviews

Thoughts: Since the majority of my sales will take place on Amazon (e-book through Kindle Direct Publishing and paperback through Lightning Source or CreateSpace), this page is the key hub for all web traffic. Amazon reviews indicate whether your book is being taken seriously, and can lead to increased visibility.

Goal: 100 Amazon reviews posted on launch day, 500 Amazon reviews posted by April 1.

Action Items:

  • give free pdf to all 518 Indiegogo supporters 2-weeks prior to Amazon release so people have time to write reviews
  • give free pdf to Amazon reviewers via Facebook page
  • reach out to top Top Reviewers in my category               

3. Word of Mouth Engagement / Speaking / Workshops

Thoughts: This is by far the most near and dear to my heart since I love people, so this is what I will spend the most time on.

Goal: Spread the word about book through impactful in-person and online events between launch and end of summer. By Fall 2014, get asked to speak at major events/conferences for millennials.

Action items:

  • Request the 19 inspiring millennials I feature in book to email their friends/family/co-workers telling them about the book / also invite them to participate in online forums so it’s not just me telling the story, it’s a community of people who refuse to settle.
  • online forums about The Quarter-Life Breakthrough + finding meaningful work (1 prior to launch via Google Hangout), 2 Reddit AMAs during launch week.
  • In-person “Breakthrough Nights”/ Meet-ups to discuss book and provide support network for people going through career transition (1x/week during March, hosted at a friend’s house)
  • Host Skillshare class about having a quarter-life breakthrough (not sure I can handle putting this together right now, but I will consider for 2 months after book launch—great marketing opportunity that also provides revenue)
  • Speaking/workshops at events through leveraging my network of social change organizations (Hive, StartingBloc, Bold Academy, Camp Grounded, Passion Co.). Use existing network help me build community and share the book via email and social media.
  • East Coast speaking tour, April 20-May 2. Already booked at Wesleyan University and the Association for Journalists and Authors Conference in New York. Trying to book venues/colleges during those dates in Boston, Middletown, New York, Philly, Washington DC.
  • Reach out to prominent partners in meaning/impact space about speaking (General Assembly, GOOD, Indiegogo, Ignite, TEDx, World Domination Summit, SOCAP ’14, SXSW ’15, Freespace, XOXO, HUB, Awesome Foundation, Feast on Good, etc.)
  • Reach out to partner career services organizations (ReWork, JVS, Echoing Green, Net Impact, Idealist, LinkedIn, Monster…) and request cross-promotion initiative 

 4.    College campus engagement

Thoughts: This book will succeed if I can figure out how to break into the college speaking circuit, or market to recent college grads. Please let me know if you can help with this (do you know authors who have run successful college book campaigns? Can you help me organize an event at your school?!)

Goal: Spring 2014 (college graduation season!) speaking tour as a pilot run, speak at Wesleyan University (my alma mater) and 3-4 northeast schools, plan full college tour for Fall 2014.

Action items:

  • Send free copy of the book to college career counselors. Provide discount bulk rate to career services departments at schools.
  • Market to recent college graduates entering the less-than-ideal job market
  • Develop book content into workshop for college seniors (potentially develop pdf workbook and distribute online
  • Secure “campus ambassadors” at schools across country
  • Workshops/events at innovative non-traditional education orgs (Uncollege, Watson University, Experience Institute, Thiel Fellowship, etc.)

 5.   Parent engagement

Thoughts: It has occurred to me that a lot of my friends are broke; I need to get their parents to buy this book as a gift.

Goal: Get parents who are freaked out that their kid went to a liberal arts college, majored in film studies, and won’t get a job, to buy my book.

Action items:

  • Figure out a way to market to parents to buy this book as a gift for their kid.
  • Potentially launch Online Forum or “Breakthrough Book Club for Parents of Millennials.” I envision this being a “support group” of some sort for parents freaking out about how their kids are gonna make it. Would be cool to engage in constructive dialogue with both parents and millennials in an online or in-person forum. Do our parents use Reddit AMAs?

 6.    Press

Thoughts: If I learned anything from my crowdfunding campaign, it was that passionate press is the best press. Seeking out the largest publications is not as effective as finding issue-aligned blogs with small readership but passionate readers. Let me know if you have contacts at any of the publications listed below!

Goal: Focus on small blogs with hardcore followings of millennials + career changers.

Action items:

  • Instead of pitching content, give content. Write content (“5 Things Every 20-Something Needs to Know,” etc…) for value-aligned blogs and sites like GOOD, Elite Daily, Thought Catalog, PolicyMic, Elephant Journal, 99U, Brazen Careerist, Daily Muse, Soul Pancake, etc.
  • Pitch mission-aligned publications (Brain Pickings, Flavorpill, FastCompany, Forbes, etc.)
  • Do interviews with prominent bloggers/thought leaders in the 20-something/coaching space (Penelope Trunk, Danielle Laporte, Amber Rae, Christine Hassler, David Burnstein, Emily Esfahani-Smith, Nona Willis, Scott Dinsmore, Courtney Martin, etc.)
  • Give FREE copy of the book to any blogger interested in reviewing the book or interviewing me
  • 1-2 months after launch, pitch major publications (NPR, The Atlantic, Wired, NY Times, Wall St. Journal, SF Magazine, SF GuardianSF Chronicle, Upworthy, etc). 
  • Get reviews in trade publications (PW, Kirkus, etc.) if possible
  • Pitch TV interview with Pivot (TV channel for millennials); please let me know if you have a contact at Pivot!
  • Press Kit available for download on book website

 7.    Blog-

Goal: Use my blog to engage readers with content and build community.

Action items:

  • Use blog to give free resources, get email sign-ups, ask for Amazon reviews
  • Write 2 short blog posts per week leading up to launch. Cross-post on Medium and Huffington Post.
  • Interview top 20-something coaches on my blog (time permitting)
  • Promote other marketing assets on blog
  • Invite community members to tell their story on my blog 

 8.   Video

Thoughts: Video is an effective way to share my story to a wide audience.

Action items:

  • Finalize 2-minute trailer video. Post on YouTube and Vimeo
  • Film funny 60-second trailer video for YouTube
  • Film interviews about the book and post on YouTube

 9.    Radio & Podcasts

Thoughts: It would be awesome to be on the radio. If you can help me with this, let me know.

Action items:

  • Pitch relevant radio programs (KQED/SF, WBUR/Boston, NPR, Tom Ashbrook) – (I need radio contacts!)
  • Do podcasts with millennial thought leaders (Danielle Laporte, Nate Bagley/Loveumentary)

10. Social Media

Thoughts: Anytime I mention I’m launching a book, people ask me about my social media strategy. From everything I’ve read, social media doesn’t matter that much for book sales. This doesn’t mean I’m going to ignore it (you’ll still see me posting on Facebook and Twitter), but there’s a reason it’s #10 on this list. According to the resources above, people are on social media to take in content, not to buy stuff.  

Action items:

  • Facebook page: post relevant articles to millennials, engage fans, build community
  • Twitter: engage bloggers and followers, reach out to press, foster conversation between Breakthrough-ers around the world
  • Google +: Google Hangouts-on-Air
  • YouTube: post video trailers and interviews
  • LinkedIn: help readers advance careers and connect with others, potential content partnership with LinkedIn (need contact at LinkedIn!)
  • Instagram: post photos of the book/ quotes, potentially Insta videos
  • Pintrest: it just ain’t me (unless any of YOU want to own this?)
  • Goodreads: engage aligned readers with recommendations for similar books.

 11.  Slide Share Deck

Thoughts: Not sure I’ll have time for this, but I’ve noticed some good SlideShare presentations have 100,000+ views, which is crazy!

  • Turn key points from book into deck and post on SlideShare (need someone to design this!)

 12.  Breakthrough Manifesto

Thoughts: This will take some time and design work, but I think it’s a good idea since I already have the content.

  • Turn best 1-liners from book into a 2-3 page Manifesto (a la Holstee). Give Manifesto away for free on website/blog/email list.

13.  Breakthrough Book Club

Thoughts: Book clubs are excellent ways to engage readers (and create communities of support and accountability for people who refuse to settle, which is my main goal).

Action items:

  • Start San Francisco-based Breakthrough Book Club in April to discuss the book in greater detail.
  • Invite readers to join virtual book club. Provide pdf on website with “discussion group questions” for readers to lead book clubs about The Quarter-Life Breakthrough in their community. Time permitting: provide recommended reading list (with suggested questions) of additional books for Breakthrough Book Clubs to discuss.

14. 1-on-1 Breakthrough Coaching Program

Thoughts: This is an excellent opportunity to engage more with readers (as well as an additional revenue stream). 

Action items:

  • Provide 1-on-1 coaching (in-person for Bay Area and via Google Hangout elsewhere) for readers who want additional engagement. Add coaching section with testimonials to blog and website. Limit to 2-3 clients per month for now to focus on client impact.

15. Other fun stuff

Thoughts: Oh you better believe I’m having a book launch party.

Action items:

  • Letterpress poster (I love letterpress!), stickers, postcards for Indiegogo supporters, business cards
  • Book Release Party! Invite all Indiegogo supporters and friends to party in San Francisco. Anticipated party date: March 28, 2014 (if you want to help plan this event or know of a venue that will gift space to me, let me know!)

How you can help

Clearly, the next few weeks are going to be busy. I might not have the bandwidth to do everything on this list. However, I’m going to consider each opportunity, and prioritize as needed. As I’ve mentioned throughout this post, this book is not about me. It’s about building a community of millennials who refuse to settle. To that end, now that my editor and designer have completed their work, my office (that would be me, my Moleskine, and the best chocolate chip cookies San Francisco can offer) is rather quiet. I could really use your help (in-person or virtually). If you are interested in helping me with anything on the above list (or something not mentioned), please do one of three things: 

1)    Let me know which of these 15 initiatives (and 54 action items!) you are uniquely capable of helping with. 

2)    If you live in the Bay Area, and want join Team Breakthrough (my advisory crew of badass entrepreneurs, creative artists, and marketing gurus) for an epic brainstorming session about this marketing plan in San Francisco, sometime next week, please sign-up here. I will provide drinks and snacks!

3)    If you already pre-ordered the book on Indiegogo and want to receive a FREE pdf of the book 2-weeks prior to the book becoming available on Amazon, sign-up here.

Thank you for helping sustain this exponential community,

-Smiley Poswolsky

To learn more, check out To get free resources for your breakthrough, sign-up for my email list. I welcome your collaboration, suggestions, and feedback in the comments or via email:

The Decision to Keep Going

18 Feb

Over the past year, I jumped head first into the creative vortex and somehow made it to the other side. The creative vortex is what separates the “I want to create” from the “I did create,” the “idea” from the “doing of the idea.” For me, this meant going from what was once a far-fetched dream to write a book, to actually writing the book, finalizing the book’s design, and (this past weekend!) pressing ‘send’ to my distributor.

The book tells the story of how I decided to start paying more attention to the voice inside my heart asking, urging, imploring me to live a life where I got paid for who I was and what I believed in. During this time, I quit my comfortable, government job in D.C. and moved to San Francisco with nothing but two suitcases, my newfound optimism, and a lot of energy.

Manuscript. Check.

One year later, the real work begins…

Not a day has gone by where I haven’t had to balance the voice inside my heart telling me to “keep going,” with the far more practical (parental) voice inside my head telling me to “be realistic, and get a real job.” Sometimes the practical voice gets so loud that I can’t even hear myself think and I start emailing every single person I know who works for a tech company to see if they are hiring.

On Friday night, when I told a friend I was considering moving halfway across the country to take a “real job” offer, she told me straight up, “Smiley: you can’t do that.” I replied, “Why not? I need to make some real money. The book is finished. It’s time to move on.”

She shot back, “Move on? You’re going to give birth to something and let it go by the wayside? Writing the book is just the beginning. You can’t stop now.”

I took a deep breath and let out a little scream, knowing she was right. You spend a year crawling through the creative vortex; writing your book, finishing your art installation, making your album, developing your product, launching your start-up. You stop seeing your friends, you don’t go out on the weekends, you give up drinking, you even give up sex (or maybe you just don’t get any); you are totally consumed working on something you believe in.

Finally, you get to a point where you’re work is ready to share with the world. Your initial instinct is one of fear. “Hmmm, some people are definitely going to hate this piece of shit I just made—why the hell did I just waste a year of my life working on this?—I need a back-up plan—I should get a job that pays well and provides me unlimited access to KIND bars and Kombucha.”

At some point you realize that the very instincts telling you to hold back are the same fears that inspired you to jump into the vortex in the first place. You accept that failure is impossible if you see your work through to the end.

The reality is that jumping into the creative vortex, while seemingly impossible, is actually the easy part. The process of sharing your work, of struggling to sustain your work, is far harder and scarier than creating it in the first place. I have to put as much energy into distributing and marketing the book as I did into the days I spent locked in the library writing it. I know that Day 366 requires far more dedication than Day 1.

Learning to balance this tension between the fire that burns within your heart and the practical voice inside your head is what makes you an artist or an entrepreneur. It’s what allows you to make the hardest decision you ever have to make (which you have to make every single day—sometimes two or three times a day): the decision to keep going.

To not get distracted by projects that may fulfill other people’s agendas, but not your own. To realize that if you are going to work in alignment with your purpose, if you are going to believe in yourself, then there is no end date or finish line. To accept that the road to your dreams is more likely to be marked by days spent actually living those dreams, than days spent in pursuit of a paycheck.

A version of this post also appeared in Medium.

Notes From a Facebook Sabbatical

18 Sep

And, we’re back. My apologies for not posting in so long. Between mid-August and mid-September, the entire What’s Up Smiley office (myself, 3 Moleskines, pair of dancing shoes) took a sabbatical from Facebook, Twitter, and Instagram—to get my introvert on, and write the second draft of my book. So, while I missed one wedding, one engagement, 13 inspiring TED talks, 92 YouTube cat videos, 213 Buzzfeed gif-montages, and thousands of pictures of what my friends were eating for brunch; I was able to write 35,000 words (about 95 pages) and give my second draft to my editor, on deadline, with five minutes to spare.

A few things I learned from my Facebook sabbatical—that I will continue to remind myself from time to time, now that I’ve returned to the Blue-and-white Menace.

1.  Facebook is addictive  

Facebook is a drug. It’s not easy to go without Facebook—it’s almost as hard as going without coffee. The first few days I was off, I caught myself clicking on my Facebook bookmark tab, without even realizing it. It had become second nature for me to “check my Facebook,” whenever I opened my computer. I deleted Facebook from my bookmarks tab, so I wasn’t tempted to check my News Feed.

I got the sense that Facebook knew I was trying to get off—it started sending me daily email notifications of “what I was missing”—which I had to turn off. On Day 4, after staring at blank tab for 30 seconds, I realized that the only reason I had even opened my computer was to look at Facebook, and I closed my laptop, and picked up a book to read.

2.  Avoiding Facebook added 2-4 hours to my day

During the month of July, I ran a crowdfunding campaign for my book, relying heavily on Facebook to spread the word about my project. I probably had the Facebook tab open on my computer for about 10 hours a day for nearly four weeks straight; the site was the single largest driver of traffic to my Indiegogo, and a main reason my campaign was successful. However, in August, after my campaign was over, I still found myself on Facebook for over 4 hours a day—except now I wasn’t running a campaign, I was just avoiding the one thing I knew I needed to be doing: actually writing my book.

I used the time I wasn’t spending on Facebook (or consuming the infinite number of blog posts, photos, articles, and videos, I click on via my News Feed), to write.

3.  I felt happier off Facebook

I’d like to pretend that I don’t check my Facebook after I post something to see how many likes it got, but I do. I’d also like to pretend that it doesn’t faze me when I see other people doing cool things on Facebook or Instagram, but it does. My first reaction is, “I’m happy for my friends—that’s so awesome they’re at the beach.” But there is an indirect effect, as well, and maybe it’s just me (but from conversations with numerous friends, I know it isn’t): I get jealous or start doubting my own decisions—“I wish I was at the beach today…” Regardless of the science behind Facebook-induced FOMO; not having to think at all about whether to post something on Facebook, what to post, how people react to my post, and how I react to their posts, is a liberating sensation—you feel empowered to enjoy whatever it is you are doing, wherever you are.

4.  I was more focused, confident, and productive, sans-Facebook

This feeling of being present during my Facebook sabbatical was most noticeable during my writing process this past month. In August, I would alternate between writing a few paragraphs and checking my News Feed—realize that someone had just written an article about exactly what my book was about—in words far more eloquent than I had—and I would feel worthless and self-critical, and think to myself: why am I even bothering writing this stupid book

Instead, during my Facebook sabbatical, I would focus on the task at hand: writing a chapter or a section of a chapter, and without distractions or comparisons, I would judge my day based on the quality of what I wrote, not the quality of what other people were writing for their projects. My own creativity, not my News Feed, became my priority.

5.  Facebook is all about balance

Lord knows, I have posted more than my fair share of captivating New York Times articles, as well as inane YouTube videos, and Seinfeld quotes, but there is nothing happening on Facebook that is more interesting than what’s happening in real life. Over the past four weeks, I spent time with my family, danced with old friends, and had lengthy phone calls with people I hadn’t talked to in months.

Social media is an incredible tool to get the word out about a project, cause, or event (and self-publishing my book would likely be impossible without it), but every now and then—especially during the creative process—it is worth taking a short vacation from listening to what the world is saying, to listen to yourself.  

Smiley's Moleskines   

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