in: Career, Career & Wealth, Featured

• Last updated: June 30, 2023

30+ Questions to Ask Yourself Before Leaving a Job

Edward whitehead getting off airplane illustration.

Editor’s note: The following excerpt comes from How to Live the Good Life by Commander Edward Whitehead. A British Royal Navy Officer, WWII veteran, and the president of Schweppes (USA), Whitehead accumulated a bevy of wisdom on how to live better (he articulated the idea of there being 3 characteristics of an educated man) and find success in one’s career.

Make Your Job Pay Off For You

If your job doesn’t give you pleasure, if your heart sinks on Sunday night at the thought of going to work the next morning, do something about it. Consider the questions: Is it the job itself? The hours? The pay? The circumstances? Incompatibility of aims? Lack of prospects or scope for development? Or personality clash with your employer?

Make a list of every task you tackle during the normal day. If your workload varies, keep the list for a week. You may find that you’re working too hard, or that you are doing too little, or that you have insufficient activity and responsibility — and you’re probably bored. Sort out the tasks you enjoy and the ones you dislike. You may be giving inadequate attention to work you don’t care for. Perhaps someone better equipped than you would do better at those tasks?

What would you like to do within the company that at that moment is not included in your job description? If it’s a bigger job and you are confident you can do it, go to your boss and tell him so. Even if there is no opening at that time, it will do no harm to let him know that you have your eye on bigger things. If he doesn’t think you’re up to it, he’ll tell you so.

If the problem lies with your employer, see if you can find ways to minimize contact with him. All of us are susceptible to being made miserable by somebody else if they’re in a position of power over us. No matter how confident we are, we’ll be worn down by a superior who is constantly thwarting us and frustrating our best efforts. Your boss may find you just as difficult as you find him, and may be glad to see less of you, so see if you can find legitimate ways to get around him. I have been in that position and found a way out, more than once.

Sometimes a lateral move provides the solution. When I first joined Schweppes in London, I worked directly under the head of the company as Advertising Manager — a subject I knew nothing about. (“Never mind,” said he, when I protested to this effect, “you soon will.”)

For a number of reasons, my boss and I did not get along. He was charming, amusing, bluff in manner, Falstaffian in size and in his sense of humor, and all this endeared me to him when I met him socially or shared platforms with him at conferences. But working under him was another matter. It was impossible for both of us. I felt that I was on my way to doing the right job with the right company, but I was working with the wrong man.

I also knew that I needed a better grounding of the basics of running a business, so I requested, and got, a lesser job, a demotion. I became London Sales Manager. I gained in two ways from the change. I “got out from under” and out into the field with my thirty-six salesmen, calling on customers, learning something of their problems and those of my salesmen which, until then, had been a closed book to me. This experience proved invaluable and stood me in a good stead a year or so later.

As it happened, this new job ended after only six months. My old boss had apparently forgotten our differences, or decided to overlook them, in the short time that I’d been out of his sight. He called me to his office and asked me if I would take on the job of General Manager of Schweppes Overseas — a post I’d joined the company to fill two years earlier. A year later, I moved my headquarters from London to New York for some of the same reasons.

If all such internal efforts fail for you, face facts and find another job. To choose more wisely the next time around, read the next chapter and take heart. It’s not as difficult as you might think to find a job in which you will do well and which will do well for you.

Or Find Yourself a Better Job

Before you think how to put in your two weeks, do your homework. It pays off to take the time to think through just what you want to do next, what kind of job you want and, if possible, what kind of boss. An ancient military axiom declares that “Time spent in reconnaissance is seldom wasted.” If you quit first and plan later, fewer choices may be open to you. You are no longer dealing from a position of strength.

Even if you don’t like what you’re doing now, you can make it a means to an end before you move. If you reserve part of your paycheck for future job training, or ask people you meet in the course of your day’s work to suggest other employment opportunities, you are making your job work for you, and you should keep at it.

But first you should ask yourself some vital questions. Do I really want to make a move to a new career altogether? Or am I just feeling restless — perhaps because I’ve been easing up and not making the most of the opportunities where I am? Only you can answer that one, and it deserves long and careful consideration.

If the result of your deliberation is in favor of a change, take the plunge. You’ve only got one life and you’d better see that it offers you opportunities for self-fulfillment, for success, and for happiness (they all mean the same thing).

With pencil and paper, draw up your personal balance sheet, for your own use only. Nobody else can do this for you. Only you know, exactly, where your strengths and weaknesses lie. List your skills, the concrete experience gained from each job, your upward curve of earnings. (If it isn’t an upward curve, all the more reason for you to be evaluating your job patterns.) List your total personal resources, including skills, qualifications, talents and abilities, used and unused. What have you done in your community? Do you have latent abilities — writing, inventing, entertaining, public speaking — that you could develop? Do you have hobbies? Are you athletic? Be realistic, but be thorough. What do you like best to do in your leisure time? Is there a job that would incorporate some of the qualities that you use or seek out in recreation?

On your list of work debits, what are your limitations of knowledge, education, experience, and ability? Your list might include a complete lack of interest in your present job, a loathing for figures or paperwork, an inability to delegate responsibility, resentment of even constructive criticism — you know better than anyone what situation or personal limitations make you anxious, flustered, depressed, indecisive, dissatisfied with yourself and your performance. And unless you own up to what those limitations are, you won’t cope with them any better in the future than you have in the past.

Like people who walk out of divorce court only to marry again — to a virtual duplicate of their previous mate — many people go from one job that doesn’t suit them to another just like it. They rationalize that at least the problems are familiar. But they pay a heavy price for this kind of “familiar” stress. If you would prefer not to remake your character from the inside out, you can at least put yourself in a job that brings out the best in you rather than the worst. If you can’t stand criticism, putting yourself under the sharp eye of a finicky boss is going to give you ulcers or get you fired; you may be better off self-employed, or at least working in a more autonomous situation than in the close quarters of an office.

How do you function best? With the mind or with the hands? Are you a frustrated gym teacher trapped behind a desk? A weekend chef who should be running a restaurant? Are you happiest with figures, facts, or words? With people or things? With details or with broad concepts?

At this point your balance sheet should suggest general goals. You will see whether you wish to work with a large company, a small company, or none at all. Or maybe start your own. You will look over your off-the-job activities and see that you have both the skill and the desire to work outdoors — or with children, or older people.

If you have worked in an office all your life, and assumed from the start that you will work only in offices until you retire with your gold watch, toss out that assumption. What seemed true to you at eighteen need not be true at thirty or fifty.

Sociologists tell us about the growing phenomenon of the two-career worker — the person who quits or retires early from one line of work, only to take up a completely different career for the second half of his working life. A buyer in a large merchandising company who quit at forty-five to go back to college, earned his B.A. and did graduate work at Stanford to become an English teacher, and a stockbroker who pulled out during the last recession to become a landscape architect — are only two such men who have crossed my path, happier in their second career than they ever were in their first.

Once you have a general sense of the field in which you would like to work, consider the specific job. If the area is new to you, will you have to start at the bottom? Would it be to your advantage to work your way up? Or can you enter at a higher level? Are your skills and experience transferable from your present field to a new one? Will on-the-job training be enough, or should you be taking a course to prepare you for the move? What about going back to school or college to earn whatever credits you lack toward a diploma or a degree? Do you need graduate work for the job you want? Or do you simply need some time off, a few weeks or even months to consolidate whatever gains you made on your last job, or understand and accept its setbacks?

The bigger your career change, the more time you should give yourself to sort out your future choices.

Be sure to listen to our podcast with career coach Joseph Liu for even more insight: 

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