Exploring Career Transition: How to Discover Your ‘Point B’

By Guest Blogger Catherine Morgan

Some people actively court change. They seek it out and embrace it. I’m not one of those people. Circumstances had to slap me upside the head a few times before I could take the leap and make a major career transition.

Exploring Career Transition: How to Discover Your 'Point B'

I started my career on the trading floor of the Chicago Board Options Exchange. It was the mid 80’s. Times were good. The work hard/play hard lifestyle worked well for me. Heck, I was in my 20’s! What better time than your 20’s to work and play hard? The job was a perfect transition from college into the workforce.

My career path took me through the trading technology and market data side of the financial service industry. Then I read a book titled The Mind of the Strategist. The author had worked for McKinsey and the braininess of consulting was all of a sudden hugely appealing to me. I was told that I would have to get a MBA if I wanted to work for a company like that. That was *not* appealing – but somehow a few years later I ended up being brought into a major consulting organization by a former client. Perfect! I loved working with incredibly smart people and moved through a few of the global consulting organizations.

My last position was a very difficult role at one of The Big Four (top four firms). Being on call 24/7 and extreme deadlines started to take a toll on me. My body told me it was time to make a move before my mind caught up. The effects of stress are well documented, and I had most of them. I also stopped doing the things that made me really happy. I blurted out during my mid-year review, “I can’t believe this stupid job is interfering with my dance classes!” My boss was sympathetic, but something had to change.

Exploring Career Transition: How to Discover Your 'Point B'

One of the wonderful things about working there, was that I had the opportunity to work with a coach. I couldn’t take advantage of that fast enough. Initially we worked together to help me transfer to another group within the organization (and hopefully to a job that was a better fit). The coach asked me questions that really gave me insight into myself, my likes and dislikes, and what could be the next right move for my career. Wow, I was finally making strategic decisions for the first time in my life, and based on a plan. I felt confident and in control.

Well, today, I am that same coach helping people transition from career A to career B- be it to another job, another company, another industry, or your very own business! Whether you are looking to make a change voluntarily or have been forced to make one due to a layoff, there are some questions you need to think through in order to discover your Step B.

Exploring options. How to determine the right next job.

When you are looking to make a career change because you want a new challenge or a new job situation, there are some questions that you need to ask yourself:

  • How could you present your value to other groups within the organization?
  • Who could you network with to learn about different groups within the organization?
  • What groups within the organization seem to be growing?
  • What groups within the organization seem to be doing interesting work?

If you decide that you want to leave your current company, make sure you consider:

  • Do you want to stay in your industry and go to work for a competitor?
  • Do you want to do a job function similar to your last position or try something a little different?
  • Do you want to work for a big company or a small company?

Exploring Career Transition: How to Discover Your 'Point B'

Or you can get creative and try some career envisioning. Give yourself some time and write down your thoughts around each of these questions over the course of a few days or even a week. Just keep some paper handy and write down the first things that come to mind:

  • What skills have you used in this job and previous jobs that you enjoyed?
  • What were some peak experiences for you in your career?
  • What other industries are interesting to you?
  • What skills have you always wished that you could use in your job?

Be creative and have fun with these questions. Don’t censor yourself in any way! Outrageous answers (or ones you don’t initially understand) often lead to creative ideas that you can then translate into other job titles and job functions that might be a better fit. If you like these kinds of exercises, I highly recommend you pick up a copy of Do More Great Work by Michael Bungay Stanier.

Or, finally, maybe this…

I want to work for myself. I want to start a business!

Exploring Career Transition: How to Discover Your 'Point B'

Starting a business is really hard work and it isn’t for everyone. Here are some of the things you might want to think through if you are contemplating starting your own business:

  • Is now a good time in your life to do this? (Do you have big overhead? Do you know that you will have big expenses in the near term? If so, maybe this isn’t the right time.)
  • Do you like being in charge and making your own decisions? (If you don’t, maybe you should consider a different position in corporate.)
  • Are you prepared for the emotional roller coaster of entrepreneurship? (If not, owning your own business may not be right for you.)
  • Are you in a financial position where you can afford to take this kind of risk? (Most entrepreneurs will have to self-fund at first. And you need to plan that it will much longer and cost much more than you think it will.)
  • Is your partner/family supportive of this idea? (If you are in a relationship or have kids this can be a big one.)

I am very happy with my decision. It was the right decision for me. I was prepared emotionally and financially for the risk of being an entrepreneur, and I love what I do today. Your Point B may be very different. Don’t be afraid to explore different options. I highly recommend asking yourself the tough questions or even working with someone before making any type of career transition. You may find a wonderful job option that you had never previously considered.

One thing’s for sure. If you’ve been unhappily sitting on the fence about your Point A, it might be your time to jump off the fence and go discover your Point B. You never know unless you try.


Have you recently or are you currently going through a career transition? What questions have you been thinking through? How are you evaluating your options? I would love to hear from you in the comments below.



Exploring Career Transition: How to Discover Your 'Point B'

Catherine Morgan is a Transition and Entrepreneur Coach, and the founder of Point A to Point B Transitions Inc. The company is a virtual provider of coaching services and info products to individuals who are in career transition or are looking to establish and grow their own successful services businesses. http://PointAToPointBTransitions.com/

  1. Having been laid off last week, I really needed to read this. I have been thinking about starting a cleaning and organizing buisness, and being laid off gives me sometime to work on that. I am a single mother, I help take care of my grandmother who is in poor health, and my mother who is not in the best of health either. Although I know that this is not the best economy to be doing this in, it seems like the universe is pushing me towards doing this. Thank you for being such an inspiration and role model for women everywhere, and of all ages.

    1. Hi Theresa, thank you so much for your nice comments. Sorry to hear that you were laid off. It is very difficult and is happening to so many people these days. Having been through it myself, all I can say is sometimes better things happen as a result. While you may want/need the flexibility of working for yourself as a single mom and to take care of your grandmother, it may be a tough time for you not have predictable income such as a salary. You have a lot of things to think through. I wish you great success.


  2. Great article and very useful questions to ask yourself when trying to figure out your next move. I am currently in career transition. I was laid off 3 months ago and have been trying to figure out what I enjoy doing. It’s a scary time but an exciting time at the same time. I need the stable income so starting my own business wouldn’t be an option for me. NOw i just have to figure out what job to chase. That’s the million dollar question.

    1. Hi Patty, so glad the questions were helpful. I like your attitude. It is good to think of this as a time of opportunity – a time to reassess and figure out what you really want to do next. Have you tried setting up informational interviews? Sometimes talking with people about what they do and what their typical day looks like can be helpful. Also, I can’t recommend Michael Bungay Stanier’s book enough. Here’s the link http://www.domoregreatwork.com/


  3. Part of that decision, as you know Catherine, is how much control do you want to have over your own life. Granted, in the early stages of going out on your own, you’re at the mercy of every potential client, deadline, vendor, and whim of the market. But once you’re established … and have structured your business, client base and target market carefully … you’re as close to being the master (mistress?) of your destiny as is possible. And for some of us, it’s the only way to live! Thanks for an invaluable inside look at the decision-making process!

    1. Thanks, Susan. Just a start on the questions as there are so many more. I work with people every day to help them create clarity and confidence. An outsider’s perspective can sometimes be helpful.


  4. Catherine, I think the only way to learn whether you’re ready to make the big transition is by gathering years of wisdom and experience. I talked and talked for years about leaving my government and PR agency jobs to start my own firm, and like you, circumstances forced me to do it.
    I’ve had my own business for 5 years and am now confronted with challenges of juggling clients, finding new business, and deciding to hire or not to hire part-time help. It’s a different world than having a 9 to 5 job, but I love being in control and charting my own destiny.
    You also learn about the generosity of others when you become an independent person. I am continually amazed at how people are willing to help, if you are willing to admit that you don’t have all the answers.

    Thanks for the great post Catherine. Best of luck to you on your business journey.

    1. Hi Michelle, I too love controlling my own destiny, and it was a primary motivator for starting my own business. The juggling sometime feels like juggling fire sticks or chainsaws – but it is part of being an entrepreneur and can be quite a rush too! Thank you for the point about people being willing to help. I am constantly amazing by the support I get from colleagues and even from total strangers.


  5. With so many people in transition today, voluntary and involuntary, what a great resource to help them get grounded, gain clarity and prepare to move forward.

  6. With so many people in transition today, voluntary and involuntary, what a great resource to help them get grounded, gain clarity and prepare to move forward. (oops on the previous anonymous)

  7. As a self employed professional, I wholeheartedly agree with your questions Catherine. There’s a mindset that comes with being self employed and for those who have been in the corporate world their entire careers, may find it difficult to make the transition. BUT! That’s where you come in! Your company Point A To Point B Transitions is a lifeline for anyone struggling with these questions.

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