Most people make several significant career transitions over their work life. If you are thinking of changing focus within a field, of changing career fields, or are leaving the military or federal government, recognize this transition will take lots of preparation and time. Research shows that most successful transitions involve many small changes and testing of assumptions along the path to the next career move.

The first step is NOT to jump into active job searching.

If you are retiring from the military or federal government, you may think mainly in terms of doing the same work – for a different level of government or via a government contractor. That alone is a big change.  Is that really what you want to do?

If you are changing careers in your 30s-40s, the process and questions about next steps are similar. Most career changes are a search for work that is more fulfilling or interesting. Those in one’s 40s-50s often are in part about one’s legacy or contribution to the greater good.

You need to consider what you want to do and how your past work achievements can be used to support your future. You need to learn enough to be realistic about the need for new skills and the probability of lower income for a few years.

Stage 1 – Self-Assessment and Career Exploration

A. The ‘blue ocean’ exercise
Start with a blank page and write down those things you have done which you most enjoyed. Be sure to include both paid work and volunteer roles. Add in any hobbies or other interests. Add to this several times over a week or two.
Once you have a full list, look for patterns which can provide ideas for your next career step. What are some skills you really enjoy using and what other careers may call for these skills? What roles were most satisfying and how could these influence your next step? What have you wanted to learn and apply but have not?

B. Personal Career Advisors

Consider developing an advisory group to help you make good decisions. This can be very useful in most career transitions. Whether you ever host them as a group or just work individually with them, having an informal set of supporters is a key to successful transitions. Here you want people who know you fairly well. Those who will help you with your self-assessment and the process of deciding what you want to do next. Start by thinking of those people you can trust to be honest with you and to give you solid advice based on their expertise. Invite them to assist you and explain the process you are using. If they agree to help, set up a few regular meetings – preferably over coffee or lunch as a thanks for their support.

These people should be non-judgmental but willing to help you understand your strengths and weaknesses. They can be family, friends, coworkers, past bosses, mentors, or other people you know and trust. Each will serve as a sounding-board during this process so that you have trusted sources to talk with about your ideas, concerns, or issues. Consider these categories to select your advisors – pick one from each category or add your own:

  • known for seeing the ‘big picture’
  • knows your skills well
  • knows your temperament well
  • is very creative
  • has private sector business experience
  • has a broad range of experience
  • has experience in the general career area(s) you are considering
  • a “devil’s advocate”

As you begin to clarify the picture of who you are and what future options most interest you, you will expand your discussions beyond these advisors. But keep these first advisors in the loop to help you understand and assess what you are learning from other connections.

In expanding your discussions, you will start with your existing network. Your goals are to learn more about successful career change or transitions and to figure out what you might want to do next in more detail. Seek out:

  • peers you worked with who can assess/recommend some of your best attributes and skills to add to your self-assessment
  • people who know you well and can assist as you debate varying career options
  • people you know who have already made the transition to a new career and can tell you what they did that worked well and what mistakes they made
  • people in your community who can offer information or contacts in career fields you are assessing.

Sample Questions to Ask

  • Based on our work together, what do you think my best skills and interests are?
  • Based on your knowledge or me, what private sector work/new career options do you think I might want to consider?
  • I am thinking of making a new move into “X” field – how did you make that transition?
  • I am thinking of making a new move into “X” field, do you know people in that field I might talk with to learn more about it?
  • You have already made this transition, what do you think was the smartest thing you did in the process?
  • Based on your transition, what would you have done earlier in the process? What did you waste time on?


Stage 2. Focusing on a Critical Few Career Choices

As you finish your self-analysis and focus on possible career choices, begin to expand your connections. Find those who can help you understand more about the work and your target employers or how to translate your skills effectively.

Talk to people you know in the community.

Look for local groups of people in each field to meet. Some may be chapters of professional or trade associations. Others could be found searching,, other social media, and local business calendars for relevant events.

A local job club will offer a range of useful information and connections.

If you are not in the U.S. or are far from the location you intend to move to, you can also build a network at your desired location by starting to connect using social media.

Online you can join networks on the specific field and groups on social media, such as LinkedIn. Look for the relevant professional or trade associations and their social media efforts too. Reach out to those whose advice or articles you read regularly online or in professional journals and see value in.

Talk to a range of people at each event you attend and learn about them. Follow-up with those who seem the best matches to your goals. As you build a relationship with each one, ask for their recommendations on other people who might be able to help you.


All these actions will help you narrow your potential career choice down to one or two real options. This is critical so you can focus effectively on what you need to learn. As you learn more about the field and its needs and requirements, you can begin to assess the value you offer an employer in your chosen field and how you will demonstrate that.

Taking the time early in your career transition process to assess your interests, to create realistic goals, and to help you learn how to make an effective transition. Too often, people in the change mode jump into the actions before they have a useful plan. This results in longer job searches or several jumps in rapid succession. You can create the conditions for your transition to be successful – and to make the process easier and more effective.