Do Over: Make Today the First Day of Your New Career - Softcover

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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 definitely the most depressing but it’s also the most popular. That’s why in a 2013 Gallup survey, 70 percent of Americans said they hated their jobs or felt disengaged.1 As a culture we’ve collectively bought into the lie that work has to be miserable. Dilbert books didn’t sell millions of copies because people are happy at work. We eat at TGI Fridays not TGI Mondays. We live for the weekends because we’ve accepted that the weekdays are where dreams go to die. Poke your head up if you’re reading this book at work. Seven of the ten people you can see hate being there. No one wants to stay at a job they don’t like.

What if it didn’t have to be that way? What if having the job we wanted to have was about being the person we needed to be first? What if it wasn’t about trying to avoid career transitions but instead embracing them? Because they are coming, for all of us. Every one of us will experience a Career Jump, a Career Bump, Career Ceiling or Career Opportunity.

How do we make wise Career Jumps?

How do we navigate the Career Bumps?

How do we break through the Career Ceilings?

How do we make the most of unexpected Career Opportunities?

Turns out the solution to all four questions is the same: We build a Career Savings Account.

■ Opening the Vault

Within twenty-four hours of leaving my last job one hundred different friends had reached out to me.

Within a week, I had a team helping me build a new blog.

Within a month I had new writing projects lined up.

This did not happen because I am amazing or have a thick, commanding head of hair. It happened because for five years I’d been making deposits into the tool kit I call my Career Savings Account.™ Since I’m bad at math, I came up with a very simple formula to explain the Career Savings Account (CSA).™

Put more Twittery:

(Gang + Awesome + Nice) × Grind = Career Savings Account

What does each investment mean? Here’s how we’ll define them:

Relationships = Who you know. The gang you lock arms with during your career.

Skills = What you do. The tools you use to build your career.

Character = Who you are. The mortar that holds the entire CSA together.

Hustle = How you work. The fuel that pushes you to do the things other people don’t, so you can enjoy the results other people won’t.

You’re already familiar with every part of the Career Savings Account. Regardless of your current job situation, you weren’t surprised to hear that you need anything on that list. No one read it and thought, “Character? I’ve never thought to have that!”

You’ve also already applied aspects of the CSA to other parts of your life. You’ve worked on the skills of your golf game to get better. You hustled when you and your wife were dating to convince her you were the one. You’ve built relationships with sorority sisters who you still keep in touch with long after college ended.

The items aren’t new, but the direction we focus them is. You already have most of the things you need for a Career Jump, Bump, Ceiling or Opportunity; you’ve just likely never applied them to your job.

Or, like me in the first seven years of my career, you haven’t combined all four investments before. Maybe you’re amazing at relationships and skills, but haven’t mastered the art of hustle yet. Or you’ve got the type of character people write folk songs about but have never honed a set of skills. It’s not that you have a bad career, but in the absence of one investment, the other three never reach their full potential.

Here’s what happens if you only have three pieces of a Career Savings Account:

Relationships + Skills + Character – Hustle = Wasted Potential, NFL Draft Busts, One-Hit-Wonder Bands

Skills + Character + Hustle – Relationships = The Career Version of the Emperor’s New Clothes

Character + Hustle + Relationships – Skills = Me in the NBA or Michael Jordan in Baseball

Relationships + Hustle + Skills – Character = Tiger Woods, Enron, Guns N’ Roses

I didn’t really even know I had been building a CSA until I saw how I was handling my jump and how people thought I should be handling it.

People would approach me with sad looks on their face, as if I had lost a limb. With quiet, concerned voices that sounded like chamomile tea they would ask me questions like,

“Are you guys going to move?”

“Is there anything we can do?”

“Could we just hold you awkwardly and cry together for a while?”

These were all nice questions, but they revealed an interesting belief: Someone who is in career transition should be devastated.

The reason most people think this is that they don’t have anything to fall back on. An unexpected Career Do Over forces them to swing wide the doors of their vault and for the first time they are horrified at how empty it is. They’ve never created a Career Savings Account and didn’t even know they needed one until they were desperate.

Why is that the case?

Because we were taught to work jobs, not build careers.

■ Why We Ignore Our Careers

People often say it’s not what you know, it’s who you know. When I have a problem with my cable, I call the Comcast guy. When I have a problem with my computer system, I call my IT guy. When I have a problem with my money, I call my financial adviser.

In almost every single situation in life that you will face, there’s someone you can call or e-mail for help.

Except for your career.

Except for the thing you do at least forty hours each week.

Except for that thing you’re going to do in order to pay off a $100,000 student loan.

That area has few experts or counselors. It is by and large left vulnerable and unprotected. It is not because we are bad at seeking advice. And it’s not that we’re bad planners. Look at the way we approach saving for college.

If you haven’t started a college fund for your child by the time you leave the maternity ward with that wrinkled raisin of a human, you are already behind. And probably a pretty lousy parent.

The second they emerge from the womb you have a great sense of dread that college is almost here. Every parent on the planet just makes you feel worse as they tell you constantly at dinner parties, “It goes by so fast. Kids grow up so fast! Dust in the wind.”

You call your financial adviser and set up some sort of upside-down Roth IRA. (I’m sketchy on the specifics but I’m pretty sure my guy Jeff has used those words around me.) You start saving and paying off debt in preparation for college.

But that’s not all. You also have to get your kids signed up for the right activities. When I was a kid, I spent my entire elementary school career just trying to jump my bike off of angled piles of dirt in the woods. Now though, each year the need to get a kid good activities for a college application starts earlier and earlier. My daughter spent one Saturday participating in the math Olympics. She’s on a competitive math track, one that will prepare her for the future and hopefully college.

She was also in the fourth grade at the time.

We pull the college slingshot back so far until finally high school graduation comes and we release it. We head off to four or five amazing years. Our parents needed eighteen years to prepare for those and it is all worth it.

We graduate college, eventually find a job and then wait for the next career transition we’ll prepare for, which turns out is retirement.

From the age of twenty-two to sixty-two this is the only thing we are taught to get ready for. We have conversations about our 401(k). We start paying for our house so we have somewhere to live when our jobs are ...