Everyone feels stuck sometimes. Being stuck feels like you’re waiting, and it seems we are always waiting. We put plans on hold until kids are grown, the mortgage is paid, our parents pass…and that usually results in feeling like you are living sort of in between. You may even wonder to yourself “when is it going to be my turn?”

Another kind of stuck is the “not knowing stuck.” What am I supposed to do next? Why am I here? Is this all there is? Sometimes this stuck has to do with purpose and often it has to with career. You may feel miscast in your profession, even if you’re a “success” in the eyes of others. Or maybe you’ve outgrown a significant role in your life, or simply met your original objective.

And even if your stuckness isn’t career-related—let’s say you’re not working, or you’ve retired—a good tool to help gain clarity is the informational interview. It is helpful for simply gaining momentum and a perspective, as well as helping you to see other possibilities. Next to creating a vision board, the informational interview is my favorite tool for helping me to get back on track when I am feeling lost.


I was feeling unfulfilled in my career. The irony is, I owned the business I was working in. It was an ad agency, and I was feeling really one dimensional. I felt like I was working too much and doing the same sorts of things too often. My life felt like a never-ending cycle of new business pitches, client meetings, staff meetings, employee reviews and putting out fires. I felt I had lost touch with my own creativity. So I scheduled a series of informational interviews with fellow entrepreneurs. I picked women who owned businesses. The only thing they had in common was that I really respected them, even though some I had never met in person. One of my interviews was with the publisher of a local business newspaper: a fabulous lady who is probably 20 years my senior.


We had our meeting over lunch and I told her, candidly, about my inner feelings. I told her I was hoping she might shed some light. I asked her what she thought my skill sets and offerings were and where I might be able to plug the gaps. Her feedback? She said she had always thought of me as a teacher and a coach. She said she saw me as an articulate, smart and capable, (which in itself is nice to hear, especially coming from someone you admire). And then she offered up a casual suggestion. She said “You’ve always had a way with words. Why don’t you write a column for a publication in your industry or some area of your life that brings you joy.” Well, that was an idea that resonated, and if nothing else was worth seeing if I could make happen.


I went back to my office and sent a query letter to the editor of a graphic design magazine I had written for once or twice before and asked if they were looking for writers. Within an hour my phone rang. It was the editor himself. His words nearly knocked me off my chair. He said “Wow, what timing! We are starting a business advice column in the next quarter, wanna write it?” I ended up writing that column for five years. Not only did it help scratch an itch I was feeling, I made some extra money in the process. Now, I am not saying you’ll have such epic results. But I do know that I have never had an informational interview without a payoff, even if it was just that I got to know somebody a little better.


Be clear about what an informational interview is and isn’t. It’s not a thinly veiled job interview. It’s not a counseling session. It’s a conversation with someone you respect where you learn about their path and then ask for possible guidance about your own.


I typically make my invitations by email or over the phone. I keep it short, and I might say something like, “I am calling you because you are someone I admire and look up to. I have been feeling a little stale in certain areas of my life and I would like to meet with you. I am hoping you will be willing to share with me some of your own life’s paths. I promise to only take a half hour of your time, and I will even pay for the coffee.”


Have some questions ready to ask, but be careful to not make your conversation sound like an interrogation. I’ve never once gotten to ask all the questions I had prepared, because a good conversation really flows naturally.

Before you start with your questions, tell the person briefly what your purpose and intent is. This may involve a little vulnerability on your part. If your interview is work related, you might say for example “I am feeling a little unsettled in my career right now and am even toying with the idea of a change. It is not my intent to ask you for a job or anything. I am just looking to you for help in finding a little clarity.”

Then, you can ask question such as:

  • Can you tell me about your own path?
  • Where did you start and how did you get where you are now?
  • Looking back, did you ever have a time where you felt like I do now? How did you handle it?
  • Is there anything about your past you would do over, if given the chance?
  • Might I ask how you perceive me? What would you say my assets are?
  • If you were in my shoes, what would you do?
  • Is there anyone else you might recommend I talk with who might shed a little light?

Of course, you will tailor the questions to fit your own situation but notice that much of the interview is centered around the other person. You are seeking to learn from a person you respect.


It is essential to thank the interviewee for their time, whether they were helpful to you or not. My preferred method is a handwritten note, and sometimes I might even include a small gift, if it feels right. I’ve given a $10 coffee shop gift card, a small stone with the word “gratitude” etched into it, a beautiful bookmark. This gesture positions you as someone who values connection, and in the end, that is what this entire exercise is all about.


The list of possibilities for interviewees is limitless. Don’t be constrained by your own insecurities about bothering someone or taking up time. Most people love to help others, and I can honestly say I have never had anyone decline to meet with me. Also keep in mind that while the best interviews will be in person, Zoom or telephone are also possibilities if geography is an issue. Consider reaching out to:

  • Your professional advisors: accountant, lawyer, financial advisor
  • Your spiritual community: leaders and members of the congregation or shul
  • People you have done business with
  • People you see in passing rather often, but don’t generally speak to
  • Those who are in your local news
  • Your friends, especially those you have not seen in a while

Sheree Clark is a Midlife Courage Coach, television show host, inspiring speaker and accomplished author. Sheree has written and presented on topics ranging from finding your passion to overcoming career burnout. Her Fork in the Road coaching practice keeps her busy working with clients one-on-one and in groups on creating an authentically fulfilling life. In her personal time, Sheree and her cat Lotus work on their yoga poses.

To learn more about Sheree, visit www.fork-road.com.