Photo of mentoring checklist that supports casting off the tyranny of should

By Steve Richards, CEO & President

I do a fair amount of mentoring, usually on the topics of work and career path. My career has followed more of a zig and zag pattern, than a straight line (much to my late father’s dismay, and then amusement), and this has given me some useful insights on the topics at hand.

It is a fact that many people, at the end of their life, have some regret about their work life. The most common regret I hear is that their chosen work was meant to meet another person’s expectations, rather than the work they would have preferred.

In my mentoring sessions, I try to discover what my client would really like to do for work. This process can be hard work as we navigate influences such as parental expectations and financial worries. It usually takes two one-hour sessions to get to the point: what the client would “ideally” like to be doing for work. There is a sense of accomplishment for both of us at this point. But more work remains, and more courage will be required from the client.

Seek flow

As we discuss what the client would really like to be doing for work, I try to weave in factors to corroborate or fine tune the client’s thinking.

One factor is “flow.” A person is “in flow” when they are doing work that draws them in, brings their full attention, and often makes them lose track of time. When one is in flow, time seems to fly by. Typically, the state of flow comes when the person is doing something at which they are good. It is not a struggle to pay attention. The person may feel that they have a gift for such work.

When Warren Buffett says he has never worked a day in his life, it is because he chose work that suits his temperament and allows him to focus on what interests him. Buffett once said that a key to his choice was that he wanted a work calendar that included few if any meetings. He knew that he preferred introverted work and deep learning. His choice has served him well financially, and given him a long, happy life, free of addictions and chronic illness.

In his book, Working, Studs Terkel writes about his interviews of hundreds of people concerning their work lives. One of his findings: people who work with their hands tend to be happy. When you read about his interviews of the hands-on people, the artisans, you can tell that they worked in flow much of the time. There seems to be something intrinsically satisfying about creating a handmade work product.

Warren Buffett’s work and the artisan’s work, on the face of it, could not be more different. But they both share the magic of flow in their daily work.

Utilize tools

In addition to our discussion of flow states and work, I use a few tools to help my clients with self-awareness and further progress our discussion. I find that personality and temperament matter a lot in the context of flow and “ideal” work. My three go-to tools are:

  • The book, Please Understand Me II, by David Kiersey, based on the Myers Briggs methodology. The book includes a survey that is like the Myers Briggs tool. You see your results and then read about your type in the context of work and relationships.
  • The online tool developed by Ray Dalio found at This tool is free and generates a particularly useful report on your propensities and your relative strengths and weaknesses. We use this tool extensively at my company.
  • The book StrengthsFinder 2.0 by Tom Rath. This tool poses a questionnaire that helps you identify your “strengths.” I have used it extensively and think that the tool certainly identifies your favorite types of work – your “themes” – if not exactly your strengths. That said, you are more likely to be strong at the types of work you like most.

These three tools yield a composite of results that helps my clients with self-awareness, which I think is crucial to the whole conversation about what career and types of work is best for them. They also create useful substance for a profound conversation about life and work. Often the client gains a better understanding of why they thrived in previous education and work scenarios and struggled in others.

Find meaning

The outcome we seek from these mentoring sessions is the identity of the client’s “highest and best” work life. This concept pulls together the client’s talents, skill sets, personality, temperament, values, and desired lifestyle. Earlier I mentioned the need for courage in these sessions. Courage is required throughout this entire process because it is easy to compromise any of these key factors to meet others’ expectations and to be “practical” in the face of life’s challenges. I am more likely to empathize with the latter, while I press my clients to simply drop the baggage of others’ expectations. I want the client to live the life of their choice. It is essential that that the client casts off the “Tyranny of the Should.” (A phrase coined by the Karen Horney, M.D.)

When it is necessary to weave in practical concerns, like personal debt, into the conversation, I try to work with the client to create a phased approach to the promised land – the highest and best work life. This kind of pragmatism will avoid the anxiety that a client may feel if they were to put the practical concerns wholly to the side. To be useful, it is important for the phased approach to be specific and timebound.

Self-awareness is essential to making good choices in one’s chosen work and career. Self-awareness also promotes adaptability. The client must stay in an athletic position, responding to, not merely reacting to, changes driven by technology and other strong influences on what is deemed “useful” in the marketplace. We should all strive to choose the work of our choice and, indeed, the life of our choice. Before it is too late.

Headshot of Garnet River CEO and President Steve Richards

Steve Richards is CEO, Principal, and Board of Director Member for Garnet River. He can be reached at

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