How Do You Reach for the Top Again?

What tools do you need for your new climb?

What tools do you need for your new climb?

How do you decide what you want in life? I find many of my clients are facing changes they couldn’t imagine in their careers. It doesn’t matter how old they are or what they are involved in, many are going through major life transitions. Some are as young as 30 and some are older, in their mid 60’s, but this extended, uncertain economy has given them a chance to reexamine what they do with their lives. I thought it might be helpful to share several questions I use to help these people reconnect with their passion and purpose in new ways. I use these three questions as an assessment with people to see what’s going on in their lives when they seem listless or just don’t seem like themselves. I use many different assessments in my role as strategic advisor. Most people enjoy them and I find they increase learning velocity versus more traditional methods used in the coaching and counseling profession.

The first question I ask is, “What do you want?” I then listen attentively and allow them to share what they want. Sometimes I ask them to write out their answers and really think about what they want. For my younger clients, this seems to be easier than with my older clients. When I talk to young adults, they are buzzing with passion and energy. I let them share the hopes and dreams. It’s as if this is the first time anyone has ever asked them what they want. Many times, they go on for 30 minutes about what they want. When dealing with older clients, they sometimes struggle with this question. It makes them vacillate as if they’ve never really thought about what they want. They sometimes say, ” I don’t know,” or “I don’t really feel I have choices at this stage of life.” In many cases, I have them think about it for several days and then send me their best answers. The act of writing it down sometimes frees them to say what they want. I also think some of their answers are uncomfortable. They feel that they don’t have the right skills, strong network, or any plans to move ahead on.

The second question I ask is designed to help put focus into your think. The second question is, “What don’t you want?” Now this question really gets people thinking about their lives. Some people can tell me a hundred things in a very short time. For older people, it seems easier to say what they don’t want than what they do. There are as many different answers to this question as there are people. My standard follow up question is, “Why?” A quick head nod and affirmative body language all go together to allow people to share without any judgment. The more people say the clearer they become. After sharing twenty different answers, people are very focused on what they don’t want and why. For many women entrepreneurs, it’s the first time they’ve been asked this question and, more importantly, have been heard without judgment.

For business owners selling their businesses, these answers can be emotionally charged. I hear answers from “I can’t imagine life without my business” or “I’m afraid I die if I don’t go to work” to “You know only lazy people don’t work.” Because it’s easier to say what you don’t want, it’s easier to understand what you might want, but not always. The opposite of a negative isn’t always a positive. It can be a neutral, and in my experience, neutrals do not give you the power you need to move forward. To put this another way, many people do more to avoid pain than they do to find joy.

The third question I use has evolved over my professional career. When I first started working with clients I would use a metaphor to describe it, but today since most of my clients are involved in emerging technologies I use a more direct question. The third question is, “If we took a time machine out three years into future and then looked back over the past three years, what would you need to see to consider your time invested in this new direction to be worth your investment both personally and professionally? How would your life have changed for the better?” Then I shut up. Let me tell you this can be very challenging for me. I don’t say anything until after they have spoken and have begun seeing their potential future.

I bet you’re thinking, It can’t be this easy. It has to be harder than just three questions to change my life.” Here’s a pop quiz, try it out on someone else. Focus your attention on listening and supporting their answers. Help them share with you by being a great listener. Now, when you’re done ask them how they feel. Ask them, “Do you feel closer to your hopes and dreams?” Then ask how they feel about what they learned from this exercise. Many of my relationships go back over forty years. Whenever I get together with people I do this check in. In my whole career, I’ve never had a person not get back to me when I’ve called if I’ve done this exercise with them, ever. Next week, I’ll give you the final two questions that make anyone virtually unstoppable when they answer these additional questions. So I guess it actually takes five questions to turn your life around. See you then.

About the Author

Tripp Braden partners with individuals, families, and businesses on getting rid of all their debt, including their mortgages, in less than 9 years. We do this while supporting wealth creation and transfer. My goal is ensuring that your money outlives you and your family for generations to come.

My practice focuses on midlife entrepreneurs, technology professionals, and engineers. I develop a wealth creation strategy that fits who you are and what you want to achieve. Think of it as growing your wealth, your way. It’s a street-smart way of managing your priorities and goals to help you achieve financial independence.

If you’re interested in learning more, contact me at tbraden@marketleadership.net or send me an invite on LinkedIn. You can find Tripp’s business growth blog at Market Leadership Journal.

Tripp Braden – who has written posts on Empowering Serving Leaders.


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