Introduction

If you’re stuck in a job you hate, you’re unfortunately not alone. In fact, astonishingly, more than 80 percent of Americans and 75 percent of Canadians are dissatisfied with their jobs.

I was unhappy with the career path I entered just after graduation from university. I woke up late, went to sleep when I got home at 6:00 p.m., and developed all sorts of aches and pains I had never felt before. It took me a while, but I finally gathered the courage to quit. Like many people, I’d put more thought and effort into getting the job than into figuring out if it was something I actually wanted. There’s plenty of research and advice out there on how to write the perfect résumé and ace that interview. But when it comes to figuring out what you want to do with your life, the strategies aren’t so clear.

I realized that although I could predict and pontificate about a career path that might make me happier, I’d never actually know until I was in the thick of it. I had an idea that I might like to do something related to entrepreneurship but didn’t exactly know what that meant. Did I want to join a startup? Start my own? Try to get into venture capital? Join or start a non-profit? Do international development work abroad?

More importantly, I didn’t know how I could figure it out without a huge investment of time, like starting another full-time job with a new company.

But then I had a different idea. I decided to enter a competition to shadow Dave McClure, who founded the accelerator 500 Startups. Being selected as one of the top six finalists gave me the kick I needed to quit my job, fly down to Silicon Valley, and begin what I call a “self-education program” on something they don’t teach you in school but is arguably the most important thing of all: what I wanted to do with my life.

What is that? I run my own company and make a competitive salary. I control my days and who I spend time with. My company makes a difference in the lives of our customers, staff, and community members — and has strong potential to grow. Sometimes I have bad days, but many are good. Certainly, there are many more good days than I used to have. And the work is fulfilling. I learn new things every day, and I’ve met the most amazing people through my involvement with this business. I can’t think of anywhere I’d rather be. In this book, I share the Career Design Process I created to get to this point, made up of ideas from the quantified self movement (users and makers of self-tracking technological tools), design thinking, lean startup methodologies, and more.

So what did I do during my self-education program? So many things — and I’ll tell you all about them in this book. Over the course of a few months, I began cold emailing anyone I could think of who I was interested in meeting and learning from. To my surprise, I had a shockingly high response rate. I met with the founders of Airbnb, Square, Kiva, Mint, Color, and many more, and also with various investors and professors in the Bay Area. I asked them about their career paths, how they’d come to be where they were now, and what recommendations they had for figuring out my next move.

And I didn’t stop there. I also volunteered at major conferences such as DEMO and Founder Showcase so I could meet more people and attend the talks for free. I checked out various events and lectures in the region, and even sat in on classes at Stanford University, which the professors were kind enough to let me attend. Finally, to get a full holistic experience, I lived in a co-op in Palo Alto, California, and had an amazing time learning about cooking, co-operative living, and various lifestyles.

One of the most important conversations I had was with John Krumboltz, an international career expert who teaches career coaching at Stanford. He advocated an idea that stuck with me: testing out the different career experiences I was interested in, in the most lowcommitment way I could for each option. I had just been introduced to the entrepreneurial concept of “minimum viable product” — an interesting parallel, I thought — so I decided to apply these same principles to deciding what to do next with my career.

I began “prototyping” the different work experiences I was considering — dipping my toe in each, so I could figure out which I liked best. Again, using my favourite tactic of cold emailing, I reached out to and secured “shadow experiences” with companies, including Launchrock (a 500 Startups company), Dojo, Causes (started by Sean Parker), Kiva, the Stanford d.school, and Ashoka (a non-profit that supports entrepreneurship). I spent one to five days with each company, not only learning from them but also assisting them wherever I could. At Causes, I helped produce success reports for clients and sat in on strategy meetings and interviews with potential hires. At Kiva, the then CEO Matt Flannery let me follow him around for the day (the literal definition of a shadow) and experience “a day in the life,” complete with accompanying him on his daily walk in the park to clear his head.

So what did I learn through all of this? I realized that I wanted to pursue my own business as soon as possible. In one of the classes I sat in on at Stanford, the professor asked the students how they wanted the world to be different when they died. I knew then that not only did I want to be passionate about what I was doing — I wanted others to be, too. I wanted my business to do something that helped other people find and pursue career activities they were passionate about, and I’ve worked toward that objective ever since.

But looking back, I’m so happy I took the time to prototype my different career options and am grateful for the fact that it was nearly free to do so — much cheaper than an M.B.A., which many people say they take to figure out what to do with their lives. I learned more in those few months than I had in years.

And whether or not you can spare a few months off work, you can learn like that, too. If you’re not quite sure about your career path, you can pick a few things you think you’d rather be doing and then prototype them yourself by setting up experiences in which you can try out your different options. Find companies you’d like to work for and individuals whose career paths you admire and then reach out to them to see if you can shadow them for an afternoon, a day, or a week. This book will show you how. Try informational interviews, volunteering, internships, and more. And don’t be surprised when they say yes, or even if many of these experiences lead to job offers — without you even asking for them.

One thing that really surprised me during my experience was how easily approachable, open, and helpful most people are. Cold emailing has become perfectly normal, as has saying, “I saw you on Twitter and thought you seemed interesting, so I wanted to reach out.” This is the first time in history that people’s career interests and hobbies are listed online and are easily searchable — and it’s an amazing opportunity to create your own network beyond just the people you meet in person.

Take it from me: if you’re trying to decide on your next step, it’s an opportunity you can — and should — take advantage of.

Now, am I an expert on success? It depends on how you look at it. I’m definitely still in the process of figuring everything out, since I believe everyone is for the entirety of their lives, but so far some people have said I’ve managed to figure out, sort through, and accomplish some pretty amazing things for my age. I was inspired to write this book because of the reaction I got from an article I wrote for Forbes about my Career Design Process.

When I set out to write the piece for a blog called The Daily Muse, my main aim was to get it on Forbes, one of The Daily Muse’s distribution partners. I didn’t expect it to go anywhere or to get much traffic — I just wanted to have an article on Forbes, and that was that. I thought it would be pretty cool. The Daily Muse said it would definitely be able to put the article on its site and would try its best to get the piece on Forbes but couldn’t promise anything.

So the article went up on The Daily Muse’s website, and the next day, imagine my surprise when I got an email from a reader saying, “Hey, I loved your article on Forbes.” I replied, “What article on Forbes? Can you send me the link?” And the emails didn’t stop from then on. In fact, years later, they still haven’t ceased, which has provided me with one of the most remarkable experiences of my life. Either every week or a couple of times a month, I hear from incredible people trying to navigate their next steps in life. Some of them are extremely accomplished — and it’s a real comfort to know that even they don’t have everything figured out. Everyone’s just trying to make the best of what they’ve been given in this world. When you walk down the street, everyone you see along the way is attempting to make life as good as possible for themselves, their families, and in general, the people around them. It’s amazing!

I think the reason the Forbes article got so much traction was because it was something of a unique story. Within a short period of time, the piece had over 250,000 views, was reprinted in New York City’s daily morning newspapers, was featured on LinkedIn Today and the Forbes “Most-Read and Top Trending Stories” lists for more than a week, and resulted in multiple requests for book proposals. Now it’s up to over 1.5 million views. And it’s also led to thousands of emails, tweets, LinkedIn and Skype requests, and even some phone calls.

At first the experience was a bit overwhelming. And to some extent, it still is. But I feel exceptionally privileged to help so many people figure out what to do with their careers, figure out how they can make the biggest impact for themselves and for the world, and figure out how they can be happier than they were when they first got in touch with me.

I’ve been doing career coaching for a number of years. It’s one of my favourite things to do because I’m a strong believer in the power of human potential, especially when it’s aligned with the strengths and desires of the individual and the world. I also believe that what you do in your career has a huge impact on the rest of your life — either positive or negative. So it’s important to make sure it’s positive! The halo effect of your work can affect everything from your family life, friends, physical shape, and spending, to sicknesses, bodily problems, and many other things.

What topics will we cover? We’ll start with a bit of background about me and my career choices so you can get an idea how I came to develop my methodologies. Then I’ll show you how to develop your own ideas of what you might like to do as your next career move, based on what you like, what you’re good at, what the world needs, what you can make money from doing, and a series of experiments I’ll guide you through to set yourself up. We’ll also cover self-education programs and the ability to train yourself to be virtually anything you want to be. Once we’ve begun figuring out what you want your next career move to be, we’ll shift to definitive strategies for getting what you want, dealing with everything from cover letters and résumés to job search tools, online presence, networking, interviewing, and the day-to-day of being in your new position. This book is both for people who want to find a job and for those who want to be entrepreneurs. It will help you figure out what you want to do and then go get it. If you’re unemployed and looking for a job, this book will help you with that, too.

My writing is based on more than 10 years of career counselling, personal career experience, interviews with countless successful people about how they got to where they are today, hundreds of books I’ve read about career choices (plus many more articles), and the education I’ve received in business, marketing, psychology, happiness, and storytelling. I’ve helped my clients land jobs at Google, Procter & Gamble, Kelson, and many others; make investments; sell franchises; and get into prestigious incubators.

Everyone wants to be happy with what they’re doing in the world and how they’re spending their time. I’ve interviewed some amazing people about how they created careers they love — and how you can do that too. Some of the people I spoke with and/or interviewed in preparation for writing this book include Peter Thiel (co-founder and former CEO of PayPal), Dave McClure (angel investor who founded the 500 Startups incubator), and the founders and CEOs of Airbnb (Joe Gebbia), Square (Randy Reddig), and Kiva (Matt Flannery). I also leverage my experience participating in Singularity University’s Graduate Studies Program at the National Aeronautics and Space Administration (NASA) to discuss not just where the market stands today in terms of work and job opportunities but what the future of work will look like — as told to us by Sophie Vandebroek, the chief technology officer of Xerox, and many others — and how you can fit into it.

I’ve written this book with the hope that I inspire others to follow their passions in a way that makes a positive difference in the world. If I do that, I’ll have truly succeeded.

Now, let’s begin.