Bottom Line/Personal: Have you had enough of the job you’ve had for years or maybe decades, and you are kind of ready for a reinvented you? But what does that mean? Where do you start? You know you’re done with what you were, but you’re not sure of what you want to be. So how do you reinvent yourself?

I’m Sarah Hiner, President of Bottom Line Publications, and this is our Conversation with the Experts, where we get the answers to your tough questions from our leading experts.

Today I’m talking to Nancy Collamer, a leading career coach, speaker, and author of Second-Act Careers: 50+ Ways to Profit from Your Passions During Semi-Retirement. Welcome, Nancy.

Nancy Collamer: Thanks, Sarah.

Bottom Line: So reinvention. They know they’re not happy, but they don’t quite know – it’s so hard to figure out what you want to go into. How do you start?

Collamer: There are lots of different ways that you can approach this. There are assessments that you can take. Clearly you can go speak with a career coach; lots of books out there that address this issue.

But, you know, I’ve been a career coach since ’96, and one of the things I’ve learned over time is one of the best ways to get at what’s next is by asking some really, really weird questions. Let me share some of those with you.

Bottom Line: Okay.

Collamer: One of my favorite questions is – and this really gets to your inner dreams and things that you can’t imagine even thinking about – what would you do if you could not fail? I love that question, because what it does, it takes people out of the realm of reality, to some degree, and it just opens up what is that deepest inner ambition that you have?

Bottom Line: So it could be anything. Again, because it’s so hard to even fathom. It could be, “If I could not fail; I would be a tap dancer on Broadway.” That’s really where you’re going to.

Collamer: Right, right, because fear plays such a role in career change. If you – again, hypothetically, remove the fear, it at least allows people to get in touch with –

Bottom Line: “I wish I were a…”

Collamer: “I wish.” Yeah, exactly. So that’s one question. Another question is what are you the go-to person for? Think about that in terms of both work and personal. What do people come to you for? It’s interesting, because a lot of times at work, you may be the accountant, but everyone comes to you to help them with their technical problems.

Or in your personal life, you may be the person that everyone comes to ask questions about, “Where should I go on vacation?” because you love doing research about travel plans. So think about that. What are you the go-to person for?

Bottom Line: It’s funny, because we take so much of that for granted. You don’t even think about it. “Oh, I always have the restaurant answer. That’s just what I do.” No, it really is something that other people are interested in.

Collamer: Yeah, and oftentimes what comes most naturally to you is the thing that you find it the hardest to say, “Oh yeah, I guess I am really good at that,” because it’s just so easy for you.

Another question that I really like is – and it sounds so basic, but what do you like to talk about? I love in What Color Is Your Parachute, which is probably the most classic career development book of all time, when Richard Bolles asks you to think about what type of language you like to speak every day. And he doesn’t mean Russian or English; what he means is, what are the subjects that you enjoy speaking about? Is it food? Is it theater? Is it sports? What do you like to talk about? And that’ll give you some clues about your interests. So I like that question.

Another one that I like that can sometimes make people feel a little uncomfortable is, “What are your weaknesses?” We get asked that question when you go in for job interviews, and everyone knows you get coached to take a strength and turn it around. That’s not what I’m talking about. I’m talking about what are the things that just drain you and take energy away from you, which when you have to do them, you just think, “Ugh.”

Bottom Line: That is so important. I ask that all the time in interviews, actually. What don’t they want to do? While they’re reinventing themselves, they have to think about what can’t they stand doing all day long?

Collamer: Yeah, yeah, I think that’s a really important question to ask. And then probably the single most important question that you need to ask once you answer any of these questions is, why? If you say what could you do if you couldn’t fail and your answer is, “I’d really love to be an actress on Broadway,” okay, why? What is it about being an actress on Broadway that is so compelling to you?

For one person, it may be being on stage and being the center of attention; for somebody else, it may be a love of the literature and the opportunity to do Shakespeare. Well, those are two entirely different motivators, and so you want to take that and say okay, if you’re someone who loves Shakespeare, there could be all sorts of paths outside being a Broadway actress that will help fulfill that interest. Or if you’re someone who loves being the center of attention, teaching might be for you.

So it’s a way of expanding the options that are available to you. So ask, “why?”

Bottom Line: Interesting. Do you by chance have worksheets? Because as I’m listening to it, you want to build a grid of it, right? You have the questions, and then you have your answers. I’m such a gridding kind of person. Do you have any worksheets or anything on your website that has any of this, or maybe in your book?

Collamer: Yeah, and on the website I have a lot of other questions. Because as I said, I think these questions are great to help you open up the possibilities. By the way, these questions can be really fun. Talk with other people at a dinner party. Go to the website, write down 10 questions, hand them out to people, and it can be a great way to start a discussion. Don’t feel that you have to just sit and look at a test or go see a career counselor; have some fun with it.

 Bottom Line: That’s great. Give me your website again?

Collamer: It’s

 Bottom Line: All right, that’s great. Thank you so much, Nancy Collamer.

 Collamer: You’re welcome.

Bottom Line: The bottom line is if you’re ready to reinvent yourself and reinvent your career, there are a few questions that you can ask to help you figure that out because you don’t necessarily know. What would you do if you didn’t want to fail? If you knew that you couldn’t fail? What’s your fantasy, what are your dreams? What kind of things do you talk about every day? What do you like to talk about, what’s interesting to you?

Why do you want to do that? The important thing, when you ask these questions, is why? Why would you want to tap dance on Broadway, for example? What does that lead to? Because all of those help lead you to a surprising answer that can help you find what the characteristics are of what you want to do. And what don’t you want to do? What are your weaknesses? What is it that you can’t fathom spending your next career doing?

For the questions that we talked about and lots more of them, find a whole bunch of questions on Nancy’s website at This is Sarah Hiner with Bottom Line.