Assessing yourself and your next career

As many of us baby boomers are settling into the middle part of our lives, we are not thinking about retirement or stopping work. Whether for financial reasons or wanting to do something different than the traditional modes of retirement, most of us are not planning on stopping work anytime soon.

This is a great time to look at a second or third career that really excites and enlivens us. Some say we originally had to work doing whatever we did for a living to meet the definition of success we were given or to support the family. Now it’s time to do work that is fulfilling and rewarding for us.

Where to start?

Many think the place to start is designing the future. I disagree. I have found it’s better to start with where you are right now. What got you here? In other words, take an inventory of all that you have learned and accomplished. Knowing that will help inform the creative process of what is next. You can take all this information and find creative ways to harness it in going in a new direction.

Do you know your strengths, your skills and competencies? Probably some. Do you know how much wisdom you have attained? Probably not. This is the biggest mystery for most. We tend to take for granted how much we actually know about things. I find it very challenging to sit down and capture all of what I know and can do. To me, that would fell pretty dry and even hard.

Here is a creative way to uncover this important information.

Be interviewed by someone.

Yes, just like on NPR or Oprah. Doing it yourself isn’t all that easy and you might miss some important things.

Have your wife, a friend or someone else who knows you conduct the interview. Both of you can sit down and create the questions and plan the interview if you like. But let them come up with the main ones. That way you will be surprised and stretched a bit. Some examples of thought provoking questions like:

What are you most proud of in your career?

Tell me a time when you loved what you did – what were you doing? What was the work environment like? What happened?

What kinds of things do you find yourself having an opinion about (this taps into how much you might know about something)?

When you look back at your career, what are you most proud of? Why?

What was important to you in your career that kept you overcoming cynicism, burn out or even putting up with stupid bosses and terrible commutes?

I asked a client some these questions and we were both surprised how much information surfaced that we didn’t think we would have uncovered any other way. He had a lot to say about opinions on how a start-up tech business should be reorganized after it moves from initial start up to the next phase of development. To his surprise, he had a lot of passion about this. He ended up realizing he was a subject matter expert on this and began offering consulting services. He is successful and loves his work.

Then, when you are done, switch roles. You interview that person – about you. You ask them what they see as your strengths, competencies, skills, and most importantly what is your wisdom? What do you know that would be valuable?

This should be a long interview – not a quick answering of 5 questions. Really spend some time on this. I recommend recording the interviews. There will be a lot of very valuable information that surfaces.

Next, repeat the above with other people in your life. If you were to do this, say 5-6 times, you would have a huge amount of vary valuable data to work with.

Keep a journal tracking what you learn from the interviews. Once you are done, read through the journal and develop themes from answers each of the questions. Answer these questions:

1. What themes did you uncover?
2. What did you already know?
3. What surprised you?
4. What new thoughts are emerging about what you might want to do next?

We’ll explore what you can do with that data and what to do next in upcoming articles. Have fun doing these interviews. You will be amazed at what you will learn about yourself. And the people in your life will have a ball doing it.

Let me know how it goes – leave comments below.

This post is part of LifeTwo's Midlife Career Change FAQ covering all aspects of changing careers in middle age.