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A Career Changer's Checklist - 12 Common Sense Questions to Find Your Career: How Willing Are You to Change? (Flexibility!)

📄 Contents

  1. Top 10 Questions to Assess Your Attitude, Willingness, and Flexibility
  2. Top 5 Strategies for Improving your Attitude
  3. Conclusion
In this tenth question in the Career Changers’ Checklist, Warren Wyrostek examines your flexibility, willingness, and attitude when you change careers. If you set out to change careers with a "defeatist" attitude, you will fail. If you set out to change careers with an "optimistic" attitude, you will in all likelihood succeed. This article presents the top 10 questions to assess your attitude, willingness, and flexibility as you prepare to make a change.
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Here we are at question 10 in this series of career-oriented diagnostic questions titled the Career Changer's Checklist.

We have covered a lot of territory over the last 10 weeks. Everything from what you want to do to how to get started. You have taken a lot of notes, and hopefully with all these diagnostic questions you have a pretty good idea, at this point in the discussion, of what direction you want to take.

This week we have to look at an aspect that is often overlooked. The assumption that you and I are making (by me writing this series and you reading it) is that you are interested in changing careers. That is a given!

But how willing are you to change careers? With everything that I have asked you, are you still willing to take the plunge?

Change is difficult. The title of this series is focused on changing careers. That means that there will be change. You may want to get into a better career, but how willing are you to tackle all of challenges that we have discussed so far?

How flexible are you? How willing are you to change?

Flexibility! Willingness! This all comes down to attitude! This week we'll look at your attitude about changing careers.

In this article, I will ask you the top 10 questions to assess your attitude, willingness, and flexibility as you prepare to change careers.

I will then present you with the top five strategies for improving your attitude as you make the change.

It is often said by the truly wise, "attitude is everything." With a good attitude you can overcome even the toughest obstacles.

When you set out on a journey like changing careers, you have to have a good attitude if you want to reach your destination.

You have to be willing to take the chance necessary to succeed and you have to be flexible to adapt to changing circumstances.

So as you embark on this journey, it is necessary to also diagnose your attitude, your willingness and your flexibility. Are you up to this?

Many of you at this point might be getting a bit pessimistic and think that what I am asking this week has no bearing on your career change.

But if you set out to change careers with a "defeatist" attitude, you will fail. If you set out to change careers with an "optimistic" attitude, you will in all likelihood succeed.

Which do you want to do?

Succeed? So let's ask some questions about your attitude!

Top 10 Questions to Assess Your Attitude, Willingness, and Flexibility

First some generic, rapid-fire questions:

  • How is your attitude?
  • Do you have a positive attitude or a negative attitude?
  • Are you someone who sees the glass half full or half empty?
  • Are you a pragmatist, an optimist, a realist, or a pessimist?
  • Are you desperate? Are you at the end of your rope?
  • Do you feel in these tough economic times like you have to make a career change or you will not survive?
  • Are you willingly making a career change, or are you doing it because someone else told you to or is coercing you to?
  • Are you flexible or inflexible? If I asked your spouse, or best friend this same question about you, or any of these questions, about you, what would they say?
  • How realistic are you when it comes to changing careers? Have you seriously looked at all of the questions I have asked?
  • What has been your history with change? Do you resist it or embrace it?

I want you to succeed but with realistic expectations, which means you have to explore your willingness to change. Your flexibility and your attitude!

Had enough?

As I wrote earlier in this series, I am going along with all of you as I face a major career change. I have had some real awakenings when I look at my attitude. There are days I am very optimistic and days when pessimism rules.

I have been very willing to change (I think) but understanding that there are some things that I will not change. I have days when I am very flexible as I approach the change, but others where I become downright stubborn.

Is that good or bad? Neither—just real! There are things I am willing to do to get the right job and things I am not willing to do.

What about you? So far, in this encounter you should be writing down some of your responses and thoughts about your attitude.

What is driving your attitude and how willing are you to jump into the deep end of this career pool?

Now let's look at the 10 important questions that you need to consider.

  1. How willing are you to explore your limitations?

    We all have limitations and we all have to one day face up to those limitations. When changing careers, and looking for the ideal job, it is so easy to overadvertise your skills and accomplishments, to oversell yourself. And that is okay, but it is also necessary to quietly, reflectively, and introspectively assess your limitations.

    The way to assess this is with the following two questions:

    • Do you know your strengths and weaknesses and are you willing to admit to them?
    • Do you know what you are willing to do and not do?

    Every job, career you pursue, will cause you to be honest when it comes to strengths and weaknesses and what you are willing to do and not do.

    I was in an interview a few months ago. I had a very positive telephone interview with an agency that was interested in me. Things were really going well. I was asked to come in for a face-to-face interview, which I was glad to do.

    In that interview, the chemistry was excellent. I was able to respond to their questions in an acceptable way and I was very relaxed. I felt no stress. At the end of the interview, one of the interviewers asked me what I considered my strengths and weaknesses.

    I listed three strengths that were pertinent to the job and three weaknesses. One of my weaknesses, as I noted earlier in this series, is that I am not a political person. I do not function well in a political environment.

    Well this was a highly charged political environment, which I did not know at the outset. As we talked about it, it was clear that this was not a good fit. And I moved on.

    Even though I was strong technically, knowing that I did not like politics caused the interviewer some concern (and caused me some concern when we spoke about it).

    There were no hard feelings and we each moved on. This was all possible because I could honestly and openly identify my weaknesses with a positive attitude.

    What are your limitations, strengths, and weaknesses? Write them down! Identify them. Do so with a positive attitude.

    If you are not willing to face your limitations and weaknesses, you will in all likelihood find yourself in a situation that will not be a good fit, will not be comfortable, and cause you a good bit of angst.

    Remember that you want to find the ideal career that will make you happy. In order to do that you have to face up to what you are good at and not so good at.

    Think about. It is worth the time.

  2. How willing are you to change careers?

    This question is the key to this whole series. We have been talking about changing careers. But are you really willing to make a change? Consider the following ideas and questions:

    • Should you consider changing careers at this time? Maybe you should not be changing careers! Maybe you should stay where you are and gain some additional skills? Maybe you should ask your boss for a transfer to a new location.
    • Is location causing dissatisfaction? Or is there something else that you could change without changing careers? Be honest.
    • Is this just a phase? Are you just going through a bad time and you are looking to throw out the baby with the bath water? If this is a phase, what would make it easier to deal with?
    • Are you just looking to move up the ladder? As opposed to changing careers, are you looking to be promoted or to move horizontally in your current environment?
    • Do you like the looks of someone else's job as opposed to your own? Is the grass really greener?

    How willing are you to think outside the box? As opposed to changing careers, could you change something or someone to make your current career what you want it to be?

    My mom used to work with a woman who tried everything in her power to make my mother's work life horrible. She wanted my mom to quit. She was threatened by my mother's capabilities. She just annoyed my mother eight hours a day. My mom got angrier and angrier which just made the environment fester.

    Then one day, my dad asked her why she doesn't go to work and be nice to her coworker Every time she does something to annoy you, he said, do something to make her day pleasant.

    My mother thought my dad was nuts. But she tried it. Guess what? It worked and her time at work became fabulous. And best of all, my mother and this woman became the best of friends. It took time and it took thinking outside of the box.

    My mom wanted to change careers because of the situation. But instead she tried something unnatural and it changed the environment completely. All for the better.

    Do you really want to change careers or do you want to change something about your current career? Write it down.

  3. How willing are you to change locations?

    What is your attitude about changing locations? Are you really willing to move? How flexible are you?

    We have mulled this over in a number of previous articles. But when it comes to attitude, you really have to be honest about how you feel about relocating.

    Do you want to leave your home and environment for a new career and job? Be honest and write it down.

  4. How willing are you to accept less than your ideal job?

    We are talking change now. When you change, things can get better or worse. What if your new ideal career is a turkey? Change can be good or bad.

    Here is a real cliché that works: Is the devil you know better than the devil you don't know?

    When you are planning a change, a career change, are you willing to accept a job that is less than perfect? A step or two down from the ideal job that you dream about!

    This is where flexibility comes in along with reality.

    Is your attitude driven by the need for the ideal job, or is it driven by needing a change? How flexible are you in your expectations?

    Write down your thoughts.

  5. How flexible are you when it comes to salary demands?

    This takes off from the last question. What are your expectations when it comes to money? What is your attitude? Do you need X dollars to be satisfied in your new job or will you accept less?

    Are you open to fewer benefits, a smaller signing bonus, or fewer incentives to just land the ideal job?

    What are your expectations when it comes to money? What is your attitude when it comes to salary, benefits, bonuses, and incentives?

    How tied to more money is your need to change careers? Are your expectations based on an unrealistic assessment of the current market, your skill set, or a combination? Here you have to be honest with yourself. Not with me. But with yourself.

    If you have inflated your value, you will not be as flexible when it comes to salary and benefits and the like.

    Could you take a second job, stay in your current position and simply supplement your salary and be satisfied?

    If money is the key, maybe a second job is all that is needed to satisfy your needs, your expectations and improve your attitude?

    Be honest and write down your thoughts?

  6. How open are you to negotiations?

    When you change careers, be prepared to negotiate. Everything from salary, to benefits, to hours, to needs, to terms and conditions. Are you open to negotiating these?

    What is your attitude concerning negotiations? What is your history of negotiating?

    What are your expectations? Are you willing to give and take?

    Remember that not all negotiations are like those portrayed on television. Not all negotiations are like those done in major labor negotiations where everyone puts on a show.

    Many are simply realizing what you want and what is offered and seeing how much flexibility each side has.

    I have learned that, depending on the tone of the discussions, I can either be very flexible or completely inflexible and stubborn when it comes to negotiating rates, salaries, terms, and so on.

    A lot of negotiating is attitude and presentation. If you go in anticipating the worst you will probably get the worst. If you expect the best, you may not get the best, but you may be able to negotiate close to the best.

    So, how do you feel about negotiating?

  7. How willing are you to change life styles?

    When you are changing careers, what is your attitude concerning your lifestyle? Are you used to being able to do certain things and purchase products without thinking?

    If you have to relocate, if you have to take a cut in pay to get started, you may have to change your life style.

    When I moved from NYC in 1988 to a rural town in north Florida, I was moving with high expectations. I fully expected that my life style would not change.

    For the first few years things were great. Then I started to see how my life and style of life had to and did change.

    Many would joke with me that I experienced culture shock. I did, but it was not an obvious shock. It took time to settle in. I loved the change.

    I had to go from getting groceries, medicine, and other essential services around the corner, to driving everywhere and having to allot time for commuting. This was a major change for me.

    My life style changed and so did I. Was I willing to change? Yes. As I go through a career change now, am I willing to change? Absolutely!

    As part of my career change, I am selling my home. It has been a wonderful place to live for 20 years. But with the passing of my parents and the market changing, I have had to come to grips that as part of the change I have to sell a beautiful piece of property and what I have worked for.

    When I have showed my property to interested parties from urban areas, some become very interested while others are not flexible enough to really want to change their life style. They think they know what they want but do they? It is personal preference. Some folks like a lot of action; others like a quiet, peaceful, serene environment. Different strokes for different folks, as they used to say on television.

    The point is this: Are you willing to change your life style? What is your attitude, what are your expectations?

    Do you realize that this change will be long term? This is not a vacation type of change. Many of us, when we are on vacation, wish that our lives could be just like they are when we are away. But when faced with this vacation life style long term, we find that we miss those things we have grown comfortable with in our daily lives and need to get back to them.

    Be honest. How flexible are you when it comes to changing life style?

    Write down your thoughts, attitudes, and expectations.

  8. How flexible are you in your thinking?

    This question underlies this whole article. Whether it comes to changing careers, life styles, locations, or salaries, you have to come to grips with what you are thinking and feeling.

    If you are stubborn you will have a difficult time with change of any kind. If you are flexible and have lower expectations, change will be a lot easier to deal with and accept.

    If you are stubborn but still want to change, ask yourself why you are so stubborn. What has generated this type of response from you?

    The only way to have a smooth ride is to identify where the potholes are and avoid them. If your potholes center on your attitude, you have to identify them and find out what caused them.

    You don't want to have to keep filling in potholes.

    How flexible are you when you think about this whole idea of change? Does your back stiffen up? Or do you relax a bit and get a smile on your face?

    Be honest with yourself and write down your thoughts. Your answers to this question alone will help you decide how much you really want to change careers.

  9. How willing are you to be retrained?

    What is your attitude about learning new skills and maybe going back to school? A lot of people resist change based on this question alone. The old axiom that it is tough to teach old dogs new tricks has to be dealt with.

    A big part of the trick is attitude. What is your attitude about learning new skills? My mom, who turned 90 just before she passed away, was still trying to learn new things and skills up to her passing. She had a great attitude about learning.

    I bought her a laptop so that she could learn to surf the Web, send e-mail to friends and family, and design graphics for her embroidery machine.

    What is your attitude about retraining? Are you open to keeping up with all the changes in IT? If you are not, maybe you need to look at another field. IT is changing very fast and every one of us in it has to continually be retrained on the latest technologies. The same is true in every sector.

    So it is important for you to decide whether you are open to retraining. Write down your answers and thoughts.

  10. How willing are you to fail?

    This is without question the toughest question you have to face. Are you willing to fail? Is failure an option? Have you even considered that this career change might not work out? How do you deal with failure?

    Are you free to fail? What is your attitude about failure?

    Is there a chance you can fail if you don't change your attitude or some aspect of your credentials?

    One thing that I have learned through my life and career in IT is that some things just don't work out. Whether it is programming code, an infrastructure design, or a working relationship does not matter. Some things don't work and fail. Is that bad? Nope! It's just the way things are.

    My attitude about failure changes regularly. There are times when failure is not an option; other times when it is just part of the process.

    There are some careers/jobs I have looked at where failure is a real possibility. Others where failure is not an option.

    At the stage of life I am in now, failure still exists, but it can be managed. How? With a positive attitude.

    I was recently asked if I regretted not becoming a doctor. The answer is no. I failed to be accepted to medical school some time ago. I was very upset at the time, but in retrospect, it worked out very well. How can I say this? Easy!

    If I had been accepted I would not have been free to take care of my parents when they needed me to—in the later stages of their lives. So I failed to be admitted to medical school, but I took care of my folks and was able to have a good career in IT.

    It was a win/win situation. Why? Because I failed.

    I had to adjust my attitude about this and it took some time, but all in all it worked out for the best.

    So what is your attitude, your history with failure? Is failure an option?

    Write down your thoughts and feelings.

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