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 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 over and our bones are brittle. We get disability insurance just in case we get hurt and can’t work. We write living wills and get ready for the great beyond.

And we completely and utterly ignore the years between college and retirement.

We have a forty-year gap where we just get by.

We save for rainy days when it comes to our bank accounts but don’t do anything to protect our careers from the storm.

Sure, there are some professions that have continuing education. I know real estate agents and financial advisers who work with life coaches and gurus. But for the vast majority of us, we have nowhere to turn if we feel stuck or have a career itch.

If you’re a thirty-four-year-old Web developer right now and you feel like maybe you’re in the wrong place careerwise, who are you going to call?

Although I’m a huge fan of personal counseling, I know for a lot of people that’s not an option. There’s a significant emotional span to cross if you think you’ll just pick up the phone and ring up someone who tends to deal with personal crises.

Maybe you could call your friends. After all, they get it. They probably hate their jobs too. Maybe over coffee you can commiserate about the state of things. Misery loves company, but company often multiplies your misery. Quiet coffees in hipster spots usually change very little.

Perhaps you could just get on Twitter or Facebook and complain about your job as if public social media platforms are private. Ignore the fact that there are entire companies that exist to build background checks on employees, scraping everything you’ve done online. Right now, 80 percent of employers Google you before they bring you in for an interview.2 Though whining online might provide temporary relief, you’re also building a pretty good argument that you deserve to be underappreciated at the current job and not hired at the next one.

Maybe you go online and search “Career Help.” The good news is, there are two billion results. The bad news is, there are two billion results. Where would you start? CareerBuilder, a site for posting your resume? An article on the Huffington Post about unconventional things you should be doing to get your dream career? A career coach? The first one I found charged $1.99 per minute, which seemed less like a career coach and more like a . . . racquetball instructor. You could always polish off a few skills you haven’t thought about since the last time you looked at your resume and throw your hat in the ring. Only there are a lot of hats in there already.

So you hang up all the phones and go off-line and decide to suck it up for one more day. Or one more week or one more year.

You feel better, comforted by the fact that at least you tried. A deliberate Career Do Over is too complicated. It’s just too fuzzy. It’s just too hard to figure out.

It’s not, though. The Career Savings Account makes a Do Over incredibly simple. All you have to do is combine things you already understand, like relationships and skills, and amplify them. You won’t even have to face that many different types of career transitions either. There are actually only four.

■ The Four Types of Career Transition Everyone Faces

Have you ever felt overwhelmed at the very thought of having a Do Over? Maybe the idea of improving your career feels like entering a jungle full of thick vines, dangerous pitfalls and battling a resume you’ve done a pretty horrible job of updating. Fear not, our careers are not that complicated. In fact, there are only four career transitions you have to deal with and this illustration shows each one.

Sometimes, in your career, you will make voluntary decisions, like applying to a new job. At other times, forces outside your control, like an unexpected layoff, will impact your work in an involuntary way. Drawn north to south, this line captures every type of career action you’ll experience. But not every voluntary action is good; you might willingly stay at the wrong job out of fear. We all make bad decisions. We all have friends who voluntarily dated idiots much longer than they should have. Not every involuntary action is bad either. You might get an unexpected promotion at work.

In addition to the vertical line, representing voluntary to involuntary, there is a second line going horizontally from negative to positive. These two simple lines create four boxes, representing the four major career transitions you’ll experience in life.

In the upper-left box, between 9 and 12 o’clock, is a “Career Ceiling.” When you willingly go to a job where you know you are stuck you are experiencing a “voluntary, negative experience.” Unless someone is holding a gun to your head throughout the day, you are choosing to be stuck and therefore can choose to be unstuck! Your entire CSA will help you with whatever transition you’re in, but there will be one of the four investments that shines brightest in each. When you hit a ceiling it is your skills that will be the hammer that helps you break through.

Going clockwise, the next type of transition is a “Career Jump,” shown in the upper right box between 12 and 3 o’clock. When you decide to change companies, start your own company, or take a continuing education class to get better at your current job, you have made a voluntary, positive decision. “Character,” is the investment in the CSA that will most greatly impact your ability to have a successful Career Jump.

In the bottom righthand box between 3 and 6 o’clock, we run into the “Career Opportunity.” When something awesome that is out of your control happens, you’ve experienced an involuntary, positive moment. A friend you haven’t talked to in years calls with a job offer or your boss falls in love with someone and moves to Hawaii vacating a position you’ve always wanted at your company. “Hustle” is the investment that will help you make the most of these unexpected moments.

In the bottom lefthand box between 6 and 9 o’clock is the “Career Bump.” You got fired, lost your job in a layoff or graduated into an economy where approximately nineteen positions are available. It’s an involuntary experience all right, but it’s certainly not a positive one. “Relationships” are critical here because community is what will carry us through challenges like this.

Are the lines between these four transitions as neat as they were drawn in the illustration? Of course not; life is messier than that and the borders between something like a Career Jump and a Career Opportunity can feel murky. With a well-funded CSA, though, you’ll be ready for any of the career shifts you experience.

That’s the best part of the Career Savings Account: You have the freedom to apply it to your unique situation. It isn’t a tool for certain types of people with certain types of career aspirations. It’s a tool to reinvent your work, no matter how you choose to personally define that goal.

■ Two Things That Will Ruin Your Career Do Over

Fear does not fight alone.

I used to think it kicked down the doors or slid through the keyhole by itself. I spent years working with people around the country to help them face their fears. To the best of my abilities, I taught them some tricks about defeating the fear we all feel. We wrote them down. We responded to them with truth. We punched them in the face.

Unfortunately, fear has a friend. While I was feeling smug about defeating fear, something else was kicking people in the ribs. Something quieter and far subtler than the neon monster of fear.

The moment fear gave up the ghost, it tagged in its partner and something even more insidious stepped in the ring. Complacency.

And it starts so subtly, too.

Early on, we fight our fears. We get full of motivation. We read that book. Go to that event. Drink that brightly colored energy drink and jump into the air full of excitement. As our feet hit the ground though, we are promptly slapped in the mouth by the question “What next?”

We land on our feet after our celebratory fear-beating jump and don’t really know where to begin. The fear might have subsided but very rarely is a plan left in its wake.

If we knew what to do next, exactly what to do, we would do it. You’d be amazed at what we would do. Our fury and fire would rival the sun. But, what? What next? What now?

We don’t have a perfect plan. Nobody does, but we think everybody does. And we don’t want to make a mistake. You don’t want to waste this moment on the wrong thing.

We pause for a minute, just to get our bearings, mind you. Just for the moment, to perhaps catch a breath. All the while we are completely unaware of how fast inertia sets in. Becoming stuck is never dramatic, because then we would wake up. Complacency is a slow gas leak, not a bomb blast. Like being robbed by a thief in the night who only steals a penny at a time, we awake to find the days have all gone somewhere.

Things aren’t bad. We don’t hate our jobs. They’re OK.

They’re fine, even.

Our job is fine.

Our boss is fine.

Our life is fine.

A fine life is fine.

We are fine with fine.

And so we grow comfortable.

This is not a bad thing. I like comfortable. But great lives are very rarely created in great comfort. You’ll never hear a musician say, “Life finally got so comfortable and easy that I was able to create my best music.”

The distance between comfortable and comatose is surprisingly short.

The bright light of our bravery dims.

Our hope congeals.

We become stuck.

We will have Career Bumps. Someone will take the option to be stuck out of our hands, for the moment, catapulting us into a brave new world when they fire us or lay us off. For a brief moment we will consider doing something different. Maybe that Career Bump was a gift in disguise. But finding a job like the job you just had is a lot easier than anything else right now. Bumps are no time to dream. We return to center.

New job. New business card. New title. Same fine. Eventually the same stuck.

Other times we will shake off the rust ourselves, spurred on by something louder than our complacency. We watch our parents retire into a world they were promised would exist at the end of their fine job, only it doesn’t. Our kids drop a comment grenade about how we’re never around because we travel so much for work. A coworker makes an offhand comment about being a “lifer” and for a fleeting moment we see the thin shackle we have applied to ourselves. We become aware of our own career mortality, determined to do something more meaningful. We get focused and work. We clean our room and do mental push-ups.

We go for it, believing that with our leap into something new we have finally beaten our fear forever.

Day one of our new adventure behind us, we are shocked to learn the hardest lesson of chasing a dream. When you go for it, you don’t escape fear, you land in it. Fear is not a dragon to be slain once, it’s an ocean to be swum daily.

When you were stuck at that job, fear felt simply like a pond you had to cross. It was dark and perhaps mysterious, but you could see the other side. Having sworn you were made for something more, sworn you’d never let fear defeat you, you jumped believing your single act of boldness left the deep waters behind. Only to land in the Mariana Trench.

On the other side of a Career Jump is more fear than you’ve ever known before. And I swear, no one tells you this. Not your friends. Not your family. Not books. They sell you on the before, maybe the moment of beating that fear, but never the after.

The after doesn’t sell books. Nobody wants the promise of deep water, they want sunsets and sailboats.

So you think you’ve made a mistake. If you’d made the right decision and chased the right dream, shouldn’t you feel less fear, not more?

In those moments of doubt, fear launches an ad campaign for fine. Your fine life was easier. It wasn’t this hard. It’s always available. What would the harm be in going back on the shore? It wouldn’t be giving up. You’d just be taking a break.

Complacency rolls its sluggish head and wakes back up, ready for its shift.

Most of us will spend most of our lives walking that same circle.

We are afraid of the unknown.

We grow stuck in the known.

If we fight fear and become brave, fear will concede the loss but mutter under its breath as we pass, “It’s going to be really hard, maybe you should be complacent.”

If we fight our inertia and hustle, complacency will concede the loss but mutter under its breath as we pass, “It’s going to be really scary, maybe you should be afraid.”

These two enemies hot potato us back and forth until we finally give up. We accept that Monday must be miserable. We buy the myth that there’s a perfect job out there and quit a dozen great jobs in search of it the wrong way.

It wasn’t always this way, though.

As kids we believed we had the power to declare “Do over!” when something didn’t turn out the right way.

We’d stand in the street and boot a second attempt at kickball. We’d crumple up a piece of paper when the dog’s head ended up lopsided and scribble all over on a new one.

We were not afraid to try again.

Somewhere along the way to adulthood we forgot we still have permission to do that.

And not just with art or neighborhood sports, but something much larger. Something that often owns our days and haunts our weekends. Our careers.

The good news is it’s never too late to declare a Do Over.

All you need is a Career Savings Account.

With these four investments: relationships, skills, character and hustle, a Career Savings Account will help you rescue, reinvent and reenergize your work.

Sound like an overpromise? It’s not, because now you know there are only four types of career change you have to face in life. Whether you’re a thirteen-year-old with a paper route or a forty-three-year-old with a hedge fund we will all deal with the same handful of situations from our illustration.

You will hit a Career Ceiling and get stuck, requiring sharp skills to free yourself.

You will lose a job unexpectedly, requiring strong relationships to survive.

You will make a job jump, requiring solid character to push through the chaos stepping out always stirs up.

You will get a surprise opportunity you didn’t see coming, requiring dedicated hustle to take advantage of it.