Do Over: Make Today the First Day of Your New Career reprint Edition

1

The Career Savings Account

When you’re a mailman, you shouldn’t ask people if you can use their bathroom.

In hindsight, I probably didn’t need to learn that lesson via personal experience. And yet, there I stood on the front steps with today’s mail and an awkward request.

As a creative writer, I made for a pretty horrible mailman. I was disorganized, fumbling and prone to get pepper spray in my own eyes. One day I switched my morning route with my afternoon route, which meant people who usually got the mail late got it early. A happy homeowner told me I was way better than that other guy, unknowingly referring to me. I agreed, telling her, “He’s the worst. Just a real jerk.”

My career arc would continue through places like “Apple Country,” a convenience store that did not sell apples, and “Maurice the Pants Man,” no Maurice but plenty of pants.

I’d spend sixteen years traveling through corporate America, writing advertising for the Home Depot, branding for Bose and marketing for Staples. I was laid off from one start-up, fired from another, ran my own into the ground and then found and left my dream job. Along the way, I learned one lesson about work.

You control more than you think.

Good job, bad job, dream job, no job, this is true.

It’s on us. Though we often prefer to blame others or the economy or a boss who doesn’t “get us,” the reality is that a better job begins with building a better you.

Work is not the enemy.

Work does not have to be a miserable bar-free prison we voluntarily serve time in until the parole of retirement. On the contrary, work can be great.

Work can be wonderful.

If we rescue Monday. If we dare to reinvent it. If we refuse to get stuck.

This book isn’t about quitting a job. (I already wrote that one, it’s called Quitter because I’m creative like that.)

This book isn’t about starting something. (I already wrote that one too; it’s called Start.)

This book is about intentionally building a career using the four investments every extraordinary career has in common.

The investments are so obvious you just might miss them. The balloon animal guy certainly did with me that night in the field.

Lest you fear I spend the weirdest Craigslist-initiated weekends ever, let me back up a second. I assure you I can explain my moonlit rendezvous with the man in the rainbow suspenders.

I was waiting in line with my wife and kids at Family Fun Night at our local elementary school. It was Friday night and next to the face-painting lady, the balloon guy is whom you visit immediately at events like that.

While twisting and pulling at the colorful balloons, this craftsman of inflated rubber looked down at me from the stool he was standing on.

“I love your books,” he said, recognizing me and smiling, but then some other thought dimmed his otherwise bright eyes.

“Sorry about today,” he added in a more serious tone. “I wish you the best in your future endeavors.”

The balloon animal guy was encouraging me because he believed I lost a lot.

And he was right, I did lose something. We always do when we leave old places for new adventures.

That morning, I left my dream job.

In the process, I left behind products, money and the craziest opportunities I’d ever had.

If you tallied the day, it might be my most loserish day of all time. Even reading about what I left behind made me feel a little like I was going to scream Phil Collins lyrics at the balloon animal guy: “Take a look at me now, oh there’s just an empty space.”

I don’t blame the guy wearing a fanny pack of balloons for worrying about the future of my career.

But I had something he didn’t know about.

A tool kit I would have never jumped without.

A tool kit you probably already have too.

A tool kit my friend Nate was about to need.

■ The Day Everything Changed

My neighbor Nate lost his job on a Friday.

If you are ever invited to a late Friday afternoon meeting with your boss, that’s not a meeting, that’s a booby trap.

Nate’s career quickly changed that day.

He was suddenly afloat and not by his own choice.

I met with him the next week for coffee.

With a dazed expression he told me how he felt losing a job he’d had for eight years.

He was good at it. He always hit his numbers. People liked him. Clients texted their condolences to him days after it had happened. He was and still is a great guy.

But he was in trouble.

Cocooned for eight years inside a big, safe company, he unexpectedly found himself out on the streets. The career home he had constructed didn’t exist any longer and the rest of the world had changed dramatically since he entered the bio dome of that job.

With a great sense of exasperation he said, “I don’t even know how to use LinkedIn.”

No one expects a sudden job change; that’s why they are sudden. And if you’ve been employed for longer than a year, you’ve seen one happen—either to you or to someone you know. A corporate rogue wave caught some boat completely off guard.

In between the massive waves of drastic career change, there are other, less pressing problems that also threaten our work. Things like Career Ceilings.

A Career Ceiling is the lid on top of your career ladder. It’s the top height any particular job path is going to take you. I ran into one when I was a senior content designer at a software company.

I started working there as a contractor. Over time, I earned a real position within the company and in a few years I was given a senior content designer title. That’s when I had effectively come to the end of my career path.

I was making the most money I would ever make in that role and there were no other writing roles available at that company. Nor would there ever be. The only way up was to become a creative director, which meant managing designers and copywriters. That’s a great option for some people but for me it meant doing a whole lot less of what I actually liked doing: writing.

I was thirty-two and my life had already gently rolled to a place of inertia. I might get small raises over the years to come and slightly more responsibility, but for the most part that was it.

My wife would later tell me she was deeply concerned. With two young kids, a mortgage and a fairly new marriage, it was intimidating to stare down thirty years of possible career monotony. I might not be that adventurous, but being “done” careerwise at thirty-two was a jagged little pill to swallow.

When you hit a Career Ceiling, you used to have only a few options. You could:

1. Get a job at another company.

2. Do a job you didn’t want to do, like being a creative director.

3. Suck it up and die inside over a period of roughly thirty years.

The first option doesn’t fix things, it just delays them. You might get a different title and more money. That other company might have a “senior senior writer” position but eventually you’ll face the same ceiling you faced at your previous job.

In the second option you just trade your ladder for a different one. This plan doesn’t work well because you end up doing more of something you didn’t want to do in the first place. If you didn’t want to be a creative director, progressing up that ladder wouldn’t feel like a promotion, it would feel like punishment. You would just be going deeper into the wrong career.

The third option is...