Introduction: The Question That Started It All

Part 1: Eating Sh!t
(Working in customer service)

Paper or Plastic?—Getting my first job as a bagger at a local grocery store.
The Square Beyond Despair—Setting a record for shortest job ever after seeing how the sausage (pizza) gets made.
TGIF My Life—Serving the post-church crowd at a T.G.I. Friday’s.
Whistle While You Work—Balancing work and life as a teenage lifeguard.
Barnes & Not-So-Noble—Surviving my “dream job” during Black Friday.

Part 2: Studying Hard
(Working through college)

Missions Over Majors—Thinking back to a conversation with my college advisor that would change the rest of my life.
Poppin’ Bottles—Finding my first freelance project as a design student.

Two Birds, One Poster—Working smarter, not harder for a class project and getting a little taste of internet fame.
Golden Showers and Whiskey Sours—Reliving my worst night of bartending while in college.
The Summer of Random—Juggling three summer internships at the same time before graduating college.

Part 3: Flying Solo
(Working as a freelancer)

Lattes and Good Luck—Thinking about a serendipitous, post-college conversation that changed my career.
What’s the PowerPoint?—Taking on my first corporate client while learning the ins and outs of PowerPoint.
How to Fire Your Client Without Going to Hell—Hiring and firing my biggest freelance client.
There’s No Working Like Coworking—Joining a ragtag group of freelancers and entrepreneurs at a local co-working center.
Business Cards and Open Bars—Trying to fix shitty networking events with (you guessed it) an app.
Wasting Time on the Toilet—Writing online for the first time and growing an online following.

Part 4: Teaming Up
(Working with business partners)

Aca-scuse Me?—Turning a passion into a profit with one of my best friends.
Bad Blood—Starting and ending a company with strangers.
Eurovision—Working abroad and making friends from all over the world.
A Tale of Two Cities—Traveling to San Francisco and working there for a month.
Rad Bromance—Finding the right business partner at the right time.

Part 5: $elling Out
(Working in Corporate America)

The Price Is Right—Turning my first public speaking gig into my first full-time job in consulting.
Empire State of Mind—Flying to New York for my first client project outside of St. Louis.
Church and State—Learning a very hard lesson about keeping work and life separate.
Like Mother, Like Son—Experiencing what it feels like to take up less space as the only man in the room.
Follow the Leader—Moving into leadership and navigating a whole new set of challenges at work.

Epilogue