Most of us will change careers at least three times in our lives. And most of us will be nervous at one point or another in the process.

Invariably, you’re giving up the known to pursue the unknown. So, even if you hate your current career, it’s still scary to give it up.

Five Steps to a New Life

I have a lot of experience in this arena. I’ve changed careers a lot, going from professional beach volleyball player to software marketer to entrepreneur to freelance writer. While I was doing that, my husband changed careers three times in five years.

Each change was different and difficult in its own way for both of us. But I’ve learned some tricks along the way to make career changes easier.

Here are five ideas to consider in your own career change:

1. Test things out before you make the leap.

You don’t need to quit your current job to get started in a new career. Give yourself a chance to test things out. Try it on vacation or on the weekend. Try an internship — there’s no rule that says an intern has to be 19 years old.

It’s very hard to predict what you’ll like. Once you admit this and really try things out, you’re much more likely to be accurate about what you’re well-suited to do next.

The most effective way to make the very serious move of changing careers is to try out that career in a not-so-serious way. I’ve done this in the past, and I once discovered that I didn’t end up liking the new career. This tactic can save you a lot of large missteps.

2. Talk about your change in a way that will make it happen.

When people ask you what you do — or, even better, what you want to do — you need an effective answer. Tell people what you’re aiming to do and why it makes sense. This little speech is what will allow people to help you make that career change.

Laura Allen, co-founder of 15 Second Pitch, helps people figure out what to say when they want to make a career change. The key to answering the question “what do you do” is knowing yourself and knowing why you want to change. Once you know that, the pitch will come more easily.

3. Keep your significant other in the loop.

A career change is so emotionally and financially profound that it’s practically a joint decision if you’re living with a significant other. I learned this the hard way, when my husband changed careers.

As a career advisor, I had a lot of opinions about what he should be doing, but I didn’t want to step on his toes so I tried to leave him alone to make the decisions himself. But I started getting nervous about the instability his choices might create.

There’s a definite balance you need to strike between wanting to support your partner in chasing his or her career dreams, and wanting to maintain sanity in the relationship while the chase is on. Keeping your partner in the loop, not just about what you’re doing but also what you’re thinking, can go a long way toward creating a team feeling.

4. Make the change before you go nuts.

Most people hold out in a career until it’s clear that it’s not for them. All change is hard. We like to be stimulated and interested, but most of us don’t like constant change. It’s too stressful, so we find ways to avoid it.

The problem is that if you put off change for too long you compromise your ability to orchestrate it. I spent a lot of my career with the bad habit of letting myself bottom out before I made a big change, so take it from me — the change is much harder to manage when you’re operating from a place of desperation and exhaustion.

5. Downplay financial issues.

I write a lot about how you don’t need a lot of money to be happy. In fact, research shows that you only need $40,000 to be happy, and that the rest of the money you earn has little impact on your happiness.

But Tim Ferriss takes this one step further. In his book, “The 4-Hour Workweek,” he starts with the idea that time and flexibility are worth more in life than money. So when you think about if you can afford to make the change, think in terms of your net gain in time and flexibility rather than in money.

Anticipating the Risk

Career change is always risky. But if you have a good understanding of why you’re leaving your current career and choosing the new one, the clarity can give you the strength to endure instability and uncertainty.

At some point, your self-awareness will make the career change your only viable alternative. Then it’ll seem like a relatively low-risk move.

Quitting is not what it used to be. When a job was the sign of security, quitting meant you had a self-destructive streak. And when long-term employment was the only acceptable format for a resume, a string of quit jobs was a sign of an inability to get along with other people. Not so today.

Now, people have a new job almost every year before they turn 32. And with all the management-training courses about how to retain young employees, you can bet those young people are not getting fired. They’re quitting.

Today quitting is part of the process of finding your dream job, finding synergy between your home and work lives, and finding where you fit in. Young people have different expectations for work than older generations. A job today should feed one’s soul, ego, and sooner than later, family. It’s no surprise that you have to quit a lot of jobs to find the one that meets such lofty goals.

Yet with all the advice about how to get your dream job, there is a dearth of information on how to quit a job first. In a world where people change jobs constantly, and their network is the key to success, you have to quit as well as you hunt. Here’s a list of ways to quit a job well:

1. Go before things get bad.
Lynn recently left her accounting job. “I’ve been really good about quitting jobs amicably,” she says. “I realized I was hitting a point where I was going to start acting out.” Like Lynn, you need to know yourself and be honest about how you’re feeling on the job so you don’t let your emotions get out of hand.

2. Make a good first step.
“The very first person that you should tell you’re leaving is your boss,” says Alexandra Levit, author of They Don’t Teach Corporate in College. “Your boss will be insulted to hear it from someone else.” Also, get your story right the first time and tell the same, optimistic plan to everyone. Lynn, for example, explained that she wanted to give freelancing a try, which shows positive vision for her career.

3. Leave the door open a crack.
If you’ve done good work, there is no reason you couldn’t come back later, when things for you and for the company might have changed. Especially as you begin to specialize in your career and lay down roots, the pool of possible companies gets smaller. So don’t close any doors definitively.

“It’s very tempting to spill your guts or rant about the people you work with, but be careful what you say because you never know when you’ll want to come back,” says Levit.

4. Beware of the exit interview.
“If you trash the company during an exit interview, it will follow you everywhere. In fact, don’t even bother to do one,” says David Perry, a recruiter and author of Guerrilla Marketing for Job Hunters. “Just leave on good terms and let them know you had a wonderful time.” Even if you didn’t.

5. Resignation letter.
Try to get out of it if you can. But if you really need to write one for legal reasons, make it short and gracious. You are not the president of the United States. The world does not need a public record of why you quit or what your aspirations are. Just a simple end date and a thank you will be fine.

6. Trust that the company can continue without you.
“People think the world is going to end if they quit their job,” says Lynn. “In my last job, everyone who quit thought everything would go wrong, but it’s easily fixed and everyone’s replaceable.”

7. Set yourself up for a good reference.
Perry is adamant that any negative parting will haunt your job hunts forever. “You want to be sure the trail you leave is a positive one,” he says. And although the law discourages past employers from dissing you to future employers, Perry says a recruiter can circumvent this hurdle. “I have never, in my 20 years of recruiting, had someone not answer questions about references.”

8. Manage the in-between time carefully.
“Burn no bridges,” warns Brendon Connelly, author of the popular blog Slacker Manager. Sometimes quitting a job is as loaded as dumping a lover. “I have quit a few jobs and there has been tension because it’s always been for something else,” says Connelly. “You need to lay the groundwork ahead of time for the transition.” Tie up loose ends at the old job and get your files organized to pass on to someone else. “You don’t want to give the old people the shaft.”

9. Be conscious of the shift in the balance of power.
The moment you quit is when you go from being your boss’s underling to your boss’s equal. After all, you are no longer beholden to your boss for a job. At the point of quitting, any more work you do for your boss is out of kindness and respect for the custom of giving notice.

This is one of those times we tend not to see ourselves clearly, writes Daniel Ames, professor at Columbia Business School. Hitting the right note of assertiveness — not too much and not too little — is hard to do. We notice poor balance in our colleagues but rarely notice it in ourselves. So keep in mind that the bottom line of quitting well is assertiveness. Have enough to leave when you need to, but tone down your assertiveness enough to keep your friends and colleagues on your side even as you’re walking out the door.

 

On some level, it’s fun to quit a job. It’s fun to remind people that they don’t own you. It’s fun to feel that burst of freedom as you walk out the door. But it’s no fun if you don’t quit right.

Before you quit, you need a semi-plan for what you’ll do next: You will either work or play. Pick one. You cannot pick sitting in front of the TV because it is lame and you will be sorry.

If you pick work, then get another job lined up before you quit, because getting a job while you have a job means that your company paid you to job hunt.

If you choose to play, make sure you have enough money to play in a way that will actually be fun. One of my most misguided attempts at play was when I took a trip to France and ended up earning room and board by chopping off chicken heads.

Before you quit you also need to make sure the job is the problem. Maybe you are the problem and you are blaming everything on the job so you don’t have to look at yourself. The Occupational Adventure offers a good way to take a look at your life to see what’s really holding you back. Do an honest assessment. If your job is not holding you back, then deal with what is, while you’re gainfully employed. Self-examination is always easier to do when you can pay your rent.

If you really do think quitting is the right decision, here’s how to tell your boss:

1. Be kind, even if you hate your boss, because your boss is not your boss anymore. She is part of your network. And some people who are jerks to work for are actually nice and fun outside of work. You don’t know until you try. So hedge your bets and be gracious on the way out, even if you don’t feel that way.

2. Make sure your boss knows that this is a good move for you. Even if you’re not sure if it’s a good move, tell your boss that it is. We all need to believe in ourselves, or else who will?

3. Put it in writing. Why are there six thousand examples of resignation letters on the Internet? You are not Winston Churchill. You can write one sentence: “I’m leaving this company on [date].” If you want to tell your boss how much you hate her, see rule number one. If you want to nail your boss for illegal behavior, see a lawyer. Don’t tell the company how to fix itself. You are leaving. If they care about your input so much they can pay you as a consultant. Which they will not, because they do not care.

4. If you want a counter-offer, give your boss enough notice to come up with one before you leave. A counter-offer is much less likely to come after you’re gone.

5. Show gratitude for what your boss has done for you. A personal thank you note is a good way to leave because your boss can reread it all the time and remember only the good things about you. This will help when you call your boss for a favor — like when you need a reference.

Also, people who express gratitude are happier than those who don’t. The National Institute of Healthcare Research reports, “People who regularly practice grateful thinking reap emotional, physical and interpersonal benefits.” So find something nice to say about your boss and you’ll feel great as you walk out the door.

 

How to tell when you should leave your job is actually very simple: If your boss loves you, stay. If your boss does not love you, assess where you went wrong, and decide if you can fix it. If not, it’s quitting time.

The problem is that most people take very little responsibility for making their boss love them. Which, in turn complicates the decision about staying or leaving. Your number one task in a job is to get your boss to love you.

This means that you find out what your boss cares about, how your boss likes to communicate, what scares your boss, and how you can help. Of course, your career goal is not to help your boss. But if you boss loves you then he or she will help you to meet your career goals.

Here are common problems people have at work: Boring assignments, inflexible schedules, no recognition, too much red tape, no upward mobility. But these are all problems that disappear when your boss loves you. When your boss loves you she helps you figure out how to get around this stuff. When your boss loves you she’s like a teammate, trying to help you get what you want for your career.

But this should come as no surprise because the way to get your boss to love you is to worry about your boss’ career. See your boss’ roadblocks and get them out of the way. Understand your boss’ dreams and make it your job to facilitate them. Put aside your idea of your job description and just focus on what will help your boss.

How do you do this? Here are six steps:

1. Attend to detail. The details of your boss. You should be sure to learn something about your boss from every exchange you have. If you do not learn from the exchanges then there is probably little depth to your conversations, and that is the first step to a vacuous relationship.

2. Make each conversation meaningful. You can infuse meaning into your conversations with your boss by probing a little bit each time about what your boss cares about. Why is he or she rushed today? Or, by the way, what is the big deadline that consumed all of last week? Even something as basic as “How was your weekend?” is a fine way to learn something about the boss.

3. Listen to gossip. You can learn about your boss from watching him deal with other employees. Listen carefully to what co-workers say about your boss. Whether it’s true or not is secondary to how your boss is perceived in the ranks. The more you know about your boss the more you can cater to her.

4. Express gratitude. If you let your boss know what you appreciate about her, she’ll open up to you more because you will feel safe. For example, you can thank her for steering you away from a mine field in the marketing department. Or you can tell her you appreciate how well she did during a difficult moment in a meeting. Be specific and she will be flattered and touched. That will create a connection you need to understand your boss better.

5. Get over your shyness. Because if you are too timid to initiate conversation then you will not get to know your boss enough to make your boss love you. To get yourself talking, remind yourself that everyone wants to feel cared about. It’s hard to manage people because it means caring a lot about other people and it’s pretty one-sided. A manager will be thrilled to hear that a direct report cares about him.

6. Identify the culprit. Take a look at your track record. Have most of your bosses loved you but one doesn’t? Then it’s probably not all your fault. But most people who are not loved by their bosses were never loved by their bosses. And most people who are a pain are a pain in similar ways in all of their jobs.

So instead of focusing on why your boss is difficult, focus on what is keeping you from being loveable. It’ll be worth it. But you will find that the rewards of being loved by a boss are almost endless. Most importantly, you will like yourself better and you will love your job.