Photo by Aron Visuals on Unsplash


Mary was unhappy with her job. There was an urgency in her voice as she asked me whether I could help her. She was a senior partner at a VC, but she felt something was wrong in her career.“The problem is that I do not know what I want to do,” she said. “I know I do not want to be here. But I cannot think of what else I would like to do. I am stuck.”She wanted to start coaching immediately. For a moment, I felt the desperation and the anxiety of someone who does not know what they want next. What if it was as hard to figure it out as she said it was? What if I could not help her?And then, I relaxed as I remembered… I had yet to meet a client who did not get clarity about what they wanted through coaching. What’s more, most of my clients figured it out within the first two sessions.

Realizing what you want is not hard. Acting upon it is the real challenge.

I came to believe that deep down, we always know what we want. We are just too afraid to admit it to ourselves because pursuing it may require change. Or we are so busy running around that our mind is like a snowglobe. The pause that coaching invites allows the snow to settle down. Then, the scenery of the snowglobe reveals itself.I am going to share with you the exercises and questions I have used to help my coaching clients figure out what they want in life. I am hoping that you can use them to get clarity about your own desires for the future. Are you ready?


Remove the limitations

Many times you sabotage yourself from finding out what you want. A reason is your fear that it might be impossible to get. You are afraid that you will get depressed if you want something you cannot have.

The problem is that unless you get clear on what you want, you cannot assess the feasibility of getting it. And by avoiding clarity, you are missing out on some great opportunities.

Here are the most common questions I ask when I want to remove limitations and unlock new ideas.

  • If you had a magic wand, what would you do?
  • If you had unlimited resources and you knew you would be successful, what would you do?
  • If you knew everyone would be supportive, what would you do?

I learned the importance of “removing limitations” questions when I first started coaching. Sarah had a successful career in finance, and she had taken a break after the birth of her child. She hired me to help her figure our her next career step.

In the beginning, she shared with me that she wanted to explore consulting, the third sector, and utilities. We agreed that she should talk to people from those industries. The discussions would help her get a feeling about which one of those would work better for her.

Sarah was a networking machine. She managed to get countless meetings with influential people in those sectors. People were offering her opportunities, but she was hesitant to get into any formal recruitment process. I explored whether Sarah wanted to go back to work at all. She was ambivalent. I knew something was blocking her. She finally got two offers, but both of them fell through.

In the following session, I asked her what she would do if she knew she would be successful, and everyone was supportive. She took some time to think and then she answered that she would go into politics. But of course, she had pushed this option to the back of her mind. It did not look like a reasonable career path for someone who had her business acumen.

Once this was out in the open, what she needed to do next became clear. She would pave her way towards a political career. The mental block was gone. I learned to remove limitations with my questioning a lot earlier in the coaching process.

Visualize success

You can use one of the following visualization exercises to help you get a clearer picture of what you want.

  • Imagine you go to sleep, and a miracle happens and the problem you are having is resolved. You go back to work tomorrow, and you do not know the miracle happened. How would you find out? What would be different?
  • Imagine that in the next three years, everything goes in the best possible way. Describe your ideal workday three years from now.

Laura did the “miracle” exercise. In her vision, her team high-fived among themselves after a good meeting with a client. She realized that a sense of community was what she was missing in her current role. She looked and found that in her next move.

When John did the “ideal workday” exercise, he had an “aha” moment. He wanted to explore whether he needed to leave his comfortable corporate job. I asked John to draw images of his ideal day on the whiteboard we had in the room. As I observed his pictures, I noticed that they looked similar to what his life was in the present. He was surprised, but he agreed. His current job with a few minor tweaks was allowing him to live his ideal day. There was no need to leave.

Think about your legacy

The first time I tried to get a client to think about their legacy, it was a disaster. I asked Sonia what she would like written on her tombstone. She freaked out. She did not want to think about her death at all. Paralyzing her was not the effect I was going for.

I quickly changed my question to “Imagine that a magazine of your choice does a special on your career. What’s the magazine, and what would it say?” This question worked better. Sonia chose Forbes.

She then realized that what she wanted to be known for was “building people.” This was a massive insight as she always thought she needed to be in manufacturing. She now realized that her interests had shifted. She did not need to build products anymore to feel fulfilled. She wanted to “build” people.

The version of the question I use now and I recommend for you is: “Imagine you are receiving a lifetime achievement award. What would you want the announcer to say as she invites you to the stage?” This question helps focus the conversation on your legacy and get the airplane view on your career.

Identify your values

I love sharing with my clients a list of 90 values or so and ask them to circle their top five values. This is always a challenging exercise as they want to circle more than five. Once they do it, though, the clarity that comes is uplifting.

My client George’s top values were freedom, fun, family, love, and learning. Once he selected them, it became clear to him what was missing from his current role and what he needs in the next: freedom, fun, and learning.

Another way to identify your values is to look at what produces intense emotions to you. Many times when we are upset with someone at work is because we feel they do not share one of our values. Fairness, for example. Or respect.

Once you know what your values are, you can make sure to look for people who share them in your next step.

Look at your hobbies

After Larry had established that he wanted to move into a startup, I needed to help him decide on the industry.

I asked him about his hobbies, and he was surprised. He could not see why this would be relevant, but he went along with it. His hobbies included sports and music. “So, why don’t you look at cool tech startups in the music or sports space?” I asked. He smiled. He had never thought that he had the power to choose an industry that he considered fun.

What do your hobbies tell you about what you want to do in the future? I am not arguing here that you should turn your hobby into a job. But you can use them as information about what type of things you like.

Remember what you enjoyed as a child

Another place where you can get insights about what you want to do is your childhood. What did you want to be when you grew up?

I was taken aback when I remembered what I wanted to do when I was a child. I wanted to have a column on a magazine answering readers’ letters asking for advice on personal or work issues. At the core of it, I wanted to do what I do now, coaching people 80’s style.

What about you? What did you enjoy or dream before society put on its expectations on you?

Design experiments

A common myth that gets people stuck is that they need to discover their passion. Stanford scholars argue that this advice is not helpful. Our interests are not fixed; they are fluid.

Rather than looking for something that you are passionate about, look for some things you are interested in. Or things that pique your curiosity. Then design some experiments to see whether you would like to pursue them or not.

Experiments could be anything that would give you more exposure to that option. The most common is to speak to someone already doing what you would like to do. Or do a project in that area. Volunteer. Anything that can provide you more information without taking huge risks.

My goal when I coach clients is to help them narrow down their options to three. Then we design experiments to help them get more information on whether they indeed like those options. It is difficult to figure out what you want by being in a room on your own. You need to get out there and expose yourself to things.

Use the purpose diagram


Source: Wikimedia Commons

The Japanese call it “ikigai.” It is the overlap among what you are good at, what the world needs, what you can be paid for, and what you love.

I did this exercise with a creative agency executive, John. A new CEO joined the company and was thinking of a re-org. The CEO asked John what role did he want in the new organization. We adapted the Ikigai diagram slightly. Rather than what the world needs, I asked him what the company needs. When he filled in the diagram, there was something that was in all categories. — pitching for new business. John decided to suggest that his role got extended to include the new-business department.

Avoid getting into specifics too early

You need to explore what you want at a high-level at the beginning of your quest. Do not ask yourself whether you wish to be a COO or a venture capitalist. It might be too early for this type of specificity. You might get yourself stuck.

Start with more general questions. Do you want to be mostly with people or have uninterrupted work time? Do you prefer a big or a small organization? Would you like to travel with the job? Are you open to relocation? This type of generic questions will help you narrow down your options.

Another question I have found useful is: “Who would you like to serve?” This line of exploration helped Nigel have a breakthrough. He had a senior corporate job and was exploring two business ideas as he wanted to be an entrepreneur. I noticed that Nigel did not look too excited about any of the two business ideas. As he was talking about his life outside work, he mentioned that he had paid to create a portfolio for a voice actor. He had sponsored a poor painter as well.

When I asked him who does he like to serve, he said: “people, I like to help people.” I shared the observation that he particularly wants to help creative people. “Oh,” he said. “You are right. Also, all my girlfriends are creatives. I feel creativity is something that I am missing. I like to nurture it and protect it when I see it.”

We discussed this interest. He soon started considering launching a talent management agency. This possibility had never occurred to him before, but he started smiling just thinking about it. We designed some experiments to explore this idea further.

Flip a coin

If you are torn between two options, let’s say two job offers, try flipping a coin. Not because you want to leave your decision to luck. But because this exercise may help you access your more instinctive gut-feeling emotions. Most probably, the moment you throw the coin, you already wish for it to fall a certain way. Or, if you see the side of the coin and you feel rejoiced or disappointed, you have your answer.

I have done this a couple of times with clients, even though it becomes more and more difficult for any of us to have a coin on us nowadays. A client suggested using a coin app once, but I was not sure it would have the same effect. You can try it.


Mary, who we met in the beginning, changed jobs after two coaching sessions. She moved to a different VC. She realized that it was the company rather than the industry that she did not like. Sometimes, the change we need is smaller than we think when we are unhappy.

There you have it, friends. A selection of the most successful exercises and questions I use with my clients to help them achieve clarity about what they want in life. You can do them on your own by journaling. Even better, get a friend to ask the questions to you, as they will observe patterns that you miss. Or, hire a professional coach.

There is no need to stay stuck. Most decisions in life are less important than you think they are. You can try things out and change your mind later. Take the pressure off. Take tiny steps towards what feels like the right direction. Or many little steps in 2–3 directions until you develop a clear preference. What matters is to keep learning more about you and the world around you.

Happy exploring.

This article was originally published on Medium.

Leave a Reply